Trips

October 11 - 25, 2026



Join Wheel & Anchor for a two-week sojourn through southern Italy, staying in just three places: the Bay of Naples, the Valle d’Itria, and Lecce. From private boats to ancient ruins, limestone villages to mozzarella farms, we explore a slower Italy, one that often gets hurried past on the way to shinier objects.

October 13 to November 1, 2026



Join Wheel & Anchor for an adventure through the Silk Road, immersing ourselves in urban Kazakhstan, nomadic Kyrgyzstan and diving deep into the old imperial and trade capitals of Uzbekistan.

October 16 to 30, 2026



Join Wheel & Anchor for an in-depth journey through Andalusia, Spain’s southern crossroads of culture, faith, and design. From Seville to Córdoba and Málaga, explore Moorish palaces, Roman ruins, and whitewashed towns. This immersive two-week itinerary includes sherry tastings, flamenco, and time to absorb the region’s complex, layered history.

October 16 to 31, 2026



Join Wheel & Anchor as we explore cultures ancient and modern, sailing from from Sai Gon to Siem Reap, stopping at fishing villages and orchard groves, and visiting temples and pagodas, markets and workshops before getting to see one of the true wonders of the world, the temple of Angkor Wat at sunrise.

October 19 to November 7, 2026



Join Wheel & Anchor for an adventure through the Silk Road, immersing ourselves in urban Kazakhstan, nomadic Kyrgyzstan and diving deep into the old imperial and trade capitals of Uzbekistan.

October 19 to November 2, 2026



Join Wheel & Anchor for a two-week sojourn through southern Italy, staying in just three places: the Bay of Naples, the Valle d’Itria, and Lecce. From private boats to ancient ruins, limestone villages to mozzarella farms, we explore a slower Italy, one that often gets hurried past on the way to shinier objects.

October 20 to 30, 2026



Join Wheel & Anchor for a quiet journey through Belgium by barge, exploring canal towns, historic squares, and centuries-old brewing and distilling traditions. From Brussels to Bruges to Ghent, we’ll travel at a slower pace to see a side of Belgium few Canadian travellers experience.

October 27 to November 11, 2026



Join Wheel & Anchor as we explore cultures ancient and modern, sailing from from Sai Gon to Siem Reap, stopping at fishing villages and orchard groves, and visiting temples and pagodas, markets and workshops before getting to see one of the true wonders of the world, the temple of Angkor Wat at sunrise.

November 1 to 15, 2026



Join Wheel & Anchor for a vibrant adventure through Morocco that begins in Casablanca and winds through the blue-washed streets of Chefchaouen, the artisan quarters of Fes, and the shifting sands of the Sahara Desert. Continue through the kasbahs and gardens of the Draa Valley before culminating in Marrakesh, where tiled courtyards, calls to prayer, and palm-shaded riads offer a final, lasting impression of this remarkable country.

November 6 to 19, 2026



Hard to get to, impossible to forget. Join the Wheel & Anchor community as we set sail aboard the Aranui, a working ship whose crew will take us along for the ride from port to lagoon to beach as they deliver supplies and we get an indelible look into the life and beauty of Tahiti and the Marquesas islands of French Polynesia, thousands of kilometres from any mainland, but self sufficient for thousands of years through the sheer abundance of flora and sealife. Rarely visited beaches, remote volcanic peaks, and days on bright waters that will live in your memories forever. From the Tahitian capital of Papeete, around the six inhabited islands and back again, we'll get a taste of island life as it's lived no place else on earth.

November 11 to 22, 2026



Join Wheel & Anchor for a journey through Egypt guided by our resident Egyptologist, Younes. Spend three days in Cairo exploring its museums, mosques, and historic districts, followed by seven days sailing the Nile on our private dahabiya with stops at Luxor, Edfu, Aswan, and more. One final night in Cairo concludes the trip.

November 25 to December 6, 2026



Join Wheel & Anchor for a journey through Egypt guided by our resident Egyptologist, Younes. Spend three days in Cairo exploring its museums, mosques, and historic districts, followed by seven days sailing the Nile on our private dahabiya with stops at Luxor, Edfu, Aswan, and more. One final night in Cairo concludes the trip.

November 29 to December 12, 2026



Embark on a captivating 13-night Christmas market trip, immersing yourself in the festive charm of European cities. Begin with 2 nights in Frankfurt at the Römerplatz market, then travel to Düsseldorf for 3 nights, including a side trip to historic Cologne. Continue with 4 nights in Ghent, exploring medieval markets, and take a detour to Brussels and Bruges for Belgian holiday traditions. Conclude your adventure with 4 nights in Vienna, exploring the imperial beauty, and a day in Bratislava's charming markets, completing your magical holiday experience.

January 13 to 24, 2027



Join Wheel & Anchor for an immersive journey through Costa Rica’s cloud forests, coffee highlands, and Caribbean waterways. From spotting quetzals in misty reserves to drifting along jungle canals, we’ll experience the country’s extraordinary biodiversity, vibrant culture, and natural beauty in a way that goes far beyond the typical tropical escape.

January 25 to February 10, 2027



Join Wheel & Anchor for a coastal immersion in Costa Rica, split between Montezuma and Sámara. You’ll explore wildlife refuges, quiet beaches, and offshore islands, with opportunities for snorkelling, kayaking, and encounters with macaws and sea turtles. The journey balances guided nature experiences with free time by the ocean, giving a fuller sense of daily life along the Pacific. It ends with a night in San José before the flight home.

January 26 to February 9, 2027



Join Wheel & Anchor for a two-week journey through the Canary Islands, a region shaped by volcanic forces and a deep maritime history. We’ll start with seven nights in Tenerife, where Mount Teide dominates the skyline, coastal towns offer markets, cafés, and a mix of old and new influences. Then, we’ll spend a week on La Palma, home to dense forests, volcanic ridges, and some of the world’s clearest night skies. With time to explore and ponder, this trip provides the opportunity to really get to know the landscapes and cultures of the Canaries.

February 1 to 15, 2027



Join Wheel & Anchor as we head to Koh Samui, an island that has evolved from a quiet fishing community into a place where Thailand’s traditions and modern comforts meet. Set in the Gulf of Thailand, it’s a place of palm-fringed beaches, Buddhist temples, and waters that shift between deep blue and turquoise. We’ll have time to explore at our own pace—whether that means wandering through night markets, discovering the flavours of Thai cooking, or drifting into the calm of a hidden cove. It’s Thailand island life, with both guided adventures and the time and space to take it all in.

February 6 to 20, 2027



Join Wheel & Anchor for a two-week exploration of Colombia, from Bogotá’s high-altitude markets to the coffee farms of Quindío, the hills of Medellín, and the Caribbean streets of Cartagena. We’ll meet growers, artists, and guides who show us the country through their eyes. This journey offers a grounded, thoughtful view of Colombia—one that rewards curiosity and time spent wandering and wondering.

February 9 to March 2, 2027



Join Wheel & Anchor for a three-week Australian journey with full weeks in Melbourne, Hobart, and Sydney. Settle into Melbourne's café culture between day trips to coastal limestone stacks and misty mountain railways. In Tasmania, explore Port Arthur's prison ruins and meet wombats and Tasmanian devils at wildlife sanctuaries. Finish in Sydney, where you'll be able to see the Opera House from land and water, before venturing to the eucalyptus-scented Blue Mountains

February 10 to 24, 2027



Join Wheel & Anchor on a trip to two islands you’ll never forget. Part of that special North Atlantic breed of the island, they’ve got culture to spare alongside golden sand beaches, homegrown drinks, and a cuisine that has benefited from centuries of just enough isolation from Europe to make it unlike anything you’ve tried before. Take the time to get to know the place, relax, and take in the sights, sounds, and scents as you soak up the sun. Madeira and Porto Santo are the kind of places our LiveAway program was built for, so please, come spend some time with us.

February 17 to March 3, 2027



Join Wheel & Anchor for a two-week stay in both of Bali’s cultural heart and its coastal retreats, with an optional extension to the wild landscapes of Komodo. From Ubud’s timeless temples and artisan traditions to Sanur’s oceanfront tranquillity, we’ll explore beyond the usual tourist trail. Optional excursions include rice terraces, ancient water temples, and snorkelling in pristine waters. For those who venture to Komodo, encounters with legendary dragons and vibrant coral reefs await.

February 26 to March 4, 2027



Join Wheel & Anchor for a week of discovery in Malta. Based in Valletta, we’ll explore the island’s storied past, from temples older than the pyramids to the Renaissance fortresses of the Knights of St. John. We’ll ferry to Gozo for a glimpse of rural island life, wander the quiet streets of the Three Cities, and take in sweeping Mediterranean views. Along the way, we’ll try Maltese cuisine, uncover hidden corners of this tiny nation, and soak up the charm of this endlessly fascinating slice of the Mediterranean.

March 1 to 15, 2027



Join Wheel & Anchor for two weeks in Cyprus, where we’ll split our time between Larnaca and Paphos—two coastal towns where archaeology, politics, and daily life all share the same streets. This is a chance to explore slowly, walk often, and stay long enough to notice what doesn’t announce itself.

March 5 to 20, 2027



Join Wheel & Anchor for a two-week journey through Sicily, staying in three distinct regions: Ortigia, Trapani, and Cefalù. Rather than rushing from site to site, we’ll slow down and take the time to understand the island’s complex history, layered cultures, and varied landscapes. With visits to ancient ruins, coastal towns, mountain villages, and neighbourhood markets, this is a grounded exploration of Sicily from the inside out.

March 8 to 29, 2027



Join Wheel & Anchor for a three-week stay in New Zealand, with time in Auckland, Rotorua, and Queenstown. We’ll trace volcanic slopes, visit geothermal fields, and travel through Fjordland by land and water. With fewer stops and longer stays, this LiveAway offers a clearer view of a place many only pass through.

March 12 to 27, 2027



Join Wheel & Anchor for a two-week journey through Sicily, staying in three distinct regions: Ortigia, Trapani, and Cefalù. Rather than rushing from site to site, we’ll slow down and take the time to understand the island’s complex history, layered cultures, and varied landscapes. With visits to ancient ruins, coastal towns, mountain villages, and neighbourhood markets, this is a grounded exploration of Sicily from the inside out.

March 15 to 29, 2027



Join Wheel & Anchor for a vibrant adventure through Morocco that begins in Casablanca and winds through the blue-washed streets of Chefchaouen, the artisan quarters of Fes, and the shifting sands of the Sahara Desert. Continue through the kasbahs and gardens of the Draa Valley before culminating in Marrakesh, where tiled courtyards, calls to prayer, and palm-shaded riads offer a final, lasting impression of this remarkable country.

March 16 to 30, 2027



Join Wheel & Anchor for a two-week exploration of Mallorca, dividing our stay between the island’s historic capital and a quieter beach town in the north. Discover vintage trains, hilltop villages, and coastal walks, with opportunities to try local wines and learn regional cooking. This journey blends guided excursions with unstructured days, offering a deeper experience than a typical visit.

March 18 to 31, 2027



Join Wheel & Anchor for a journey through Argentina and Chile that’s equal parts breathtaking scenery, rich history, and culinary discovery. Wander the streets of Buenos Aires, sip Malbec straight from the source in the vineyards of Mendoza, and take in the landscapes of the Andes as you cross into Chile. In Santiago, experience the rhythm of daily life before heading to the eclectic port city of Valparaíso, where colourful streets and Pacific breezes add the perfect finishing touch to this South American adventure.

March 22 to April 5, 2027



Join Wheel & Anchor for a two-week sojourn through southern Italy, staying in just three places: the Bay of Naples, the Valle d’Itria, and Lecce. From private boats to ancient ruins, limestone villages to mozzarella farms, we explore a slower Italy, one that often gets hurried past on the way to shinier objects.

March 29 to April 12, 2027



Join Wheel & Anchor for a two-week sojourn through southern Italy, staying in just three places: the Bay of Naples, the Valle d’Itria, and Lecce. From private boats to ancient ruins, limestone villages to mozzarella farms, we explore a slower Italy, one that often gets hurried past on the way to shinier objects.

April 1 to 15, 2027



Join Wheel & Anchor for an in-depth journey through Andalusia, Spain’s southern crossroads of culture, faith, and design. From Seville to Córdoba and Málaga, explore Moorish palaces, Roman ruins, and whitewashed towns. This immersive two-week itinerary includes sherry tastings, flamenco, and time to absorb the region’s complex, layered history.

April 7 to 20, 2027



Join Wheel & Anchor for a two-week exploration of Tuscany and San Marino, from Florence’s cathedrals and galleries to the hill towns of Montepulciano and Pienza. We’ll visit smaller cities like Arezzo and Cortona, walk through San Gimignano and Siena, and spend time in a winery where the cheeses and wines come from the same estate. The trip finishes in the tiny country of San Marino and the town of Santarcangelo, with a hands-on pasta-making class and views across the Adriatic.

April 14 to 28, 2027



Join Wheel & Anchor to explore Japan’s gardens, castles, shrines, and markets from Tokyo to Kyoto, with stops in Hakone, Takayama, Kanazawa, and Hiroshima. This journey brings meaningful encounters and a deeper look at traditions.

May 4 to 19, 2027



Join Wheel & Anchor for a journey across the Greek islands, from Crete to Santorini, Naxos, Paros, and Syros. While many travellers rush through Greece, we’ll take our time, moving by ferry and exploring historic towns, ancient sites, and traditional villages. Along the way, we’ll discover the rich food, wine, and culture that give each island its character.

May 7 to 24, 2027



Join Wheel & Anchor for a journey through the Adriatic, where history, culture, and stunning landscapes converge. From the ancient walls of Dubrovnik to the coastal charm of Cavtat and the serene islands beyond, we’ll explore the region’s rich heritage and maritime traditions. Along the way, savour the distinct flavours of Dalmatian cuisine and uncover hidden gems that reveal the Adriatic’s timeless allure.

May 29 to June 9, 2027



Join Wheel & Anchor for a journey through Norway’s fjords and coastal towns. From Bergen to Oslo, we’ll travel by train, boat, and scenic highways, staying in places like Flåm, Ålesund, and Trondheim. Experience dramatic landscapes, historic cities, and the quieter side of Norway, far from the cruise ship crowds.

June 11 to 23, 2027



Join Wheel & Anchor to explore the capitals of Scandinavia during the season of the midnight sun. We’ll walk historic harbours, cross the Baltic by ferry, and follow the solstice to Helsinki. Optional days in Estonia bring time to explore Lahemaa’s forests and Tallinn’s market stalls.

September 1 to 17, 2027



Join Wheel & Anchor for seventeen days across China's most storied cities — Beijing, Chengdu, Xi'an, and Shanghai — with four nights on the Yangtze River through the Three Gorges in between. From the Great Wall and the Terracotta Army to giant pandas in the mountains above Chengdu and a farewell dinner on the Bund, this is China's full sweep of history, landscape, and food.

September 2 to 16, 2027



Join Wheel & Anchor to explore the misty magic of the Emerald Isle. Take in stunning landscapes like Connemara, the Cliffs of Moher, the Ring of Kerry, and more. We'll stay a few nights in Dublin, Killarney, and Galway with lots of time to soak up the atmosphere of this charming country.

September 7 to 22, 2027



Join Wheel & Anchor for a journey across the Greek islands, from Crete to Santorini, Naxos, Paros, and Syros. While many travellers rush through Greece, we’ll take our time, moving by ferry and exploring historic towns, ancient sites, and traditional villages. Along the way, we’ll discover the rich food, wine, and culture that give each island its character.

September 13 to 30, 2027



Join Wheel & Anchor to explore Poland through its castles and historic towns. At the heart of Europe, this country has been shaped by centuries of shifting borders and rulers. Come with us to discover Gothic fortresses, Renaissance palaces, and medieval cities that reveal Poland’s complex history and enduring culture.

September 15 to 27, 2027



Join Wheel & Anchor for two weeks along the southeastern edge of the Aegean, where the Greek islands sit within sight of Turkey. We'll begin with four nights on Rhodes, walking the medieval old town and climbing the acropolis at Lindos. Then we'll board a traditional wooden gulet and sail a quiet circuit of the smaller Dodecanese: Symi, Panormitis, Tilos, Nisyros, and Kos, swimming in empty bays and walking down into a live volcanic crater. The voyage ends in Bodrum, the ancient Halicarnassus. By the last night at anchor, the rhythm of the boat will feel like your own.

September 18 to October 4, 2027



Join Wheel & Anchor for seventeen days in Mongolia, a country of almost unimaginable scale and one of the last places on earth where the herding life of the steppe is still being lived as it has been for centuries. We'll start in the granite-and-larch landscapes of Terelj National Park, spend time in Ulaanbaatar, and then strike out west across the open steppe to the wild horses of Khustai, the dunes of Elsen Tasarkhai, the ancient Mongol capital at Karakorum before turning north into the river country, where pace slows and the days are spent walking, fishing, and watching the light change. With nights in good hotels, traditional ger camps, and remote river lodges, this is a trip designed to give you Mongolia at the speed it should be experienced: slowly, with the windows down.

September 24 to October 10, 2027



Join Wheel & Anchor on a special trip to the hardly-known, yet amazing vibrant cities of Tbilisi and Yerevan, which have a whole lot of spectacular countryside and rich history in between.

September 25 to October 9, 2027



Join Wheel & Anchor to explore Japan’s gardens, castles, shrines, and markets from Tokyo to Kyoto, with stops in Hakone, Takayama, Kanazawa, and Hiroshima. This journey brings meaningful encounters and a deeper look at traditions.

September 25 to October 11, 2027



Join Wheel & Anchor to explore the coastlines and inland villages of western Turkey, from the domes of Istanbul to cute seaside villages. We’ll spend time on foot, on the road, and aboard a private gulet as we sail from Bodrum to Göcek. Along the way, we’ll meet winemakers, walk through ancient ruins, and visit quiet harbours that rarely see visitors. This journey offers a deeper look at daily life and long traditions across one of the Mediterranean’s most layered landscapes.

September 25 to October 4, 2027



Join Wheel & Anchor for a 10-day culinary journey through Burgundy and Lyon, two of France’s most storied gastronomic regions. From the markets of Dijon to the vineyards of the Côte de Nuits and the bouchons of Lyon, this experience blends history, flavour, and craftsmanship. Along the way, meet passionate producers, learn classic recipes, and savour regional specialties, gaining a deeper understanding of France’s culinary traditions than one could achieve on their own.

September 26 to October 9, 2027



Join Wheel & Anchor to explore Portugal beyond the usual trail—from the tiled streets of Porto to the terraced vineyards of the Douro Valley and the volcanic beauty of the Azores. This journey blends wine, history, and exquisite Atlantic nature for a rich experience on both land and sea.

October 4 to 17, 2027



Join Wheel & Anchor for a two-week exploration of Tuscany and San Marino, from Florence’s cathedrals and galleries to the hill towns of Montepulciano and Pienza. We’ll visit smaller cities like Arezzo and Cortona, walk through San Gimignano and Siena, and spend time in a winery where the cheeses and wines come from the same estate. The trip finishes in the tiny country of San Marino and the town of Santarcangelo, with a hands-on pasta-making class and views across the Adriatic.

October 5 to 15, 2027



Join Wheel & Anchor for a quiet journey through Belgium by barge, exploring canal towns, historic squares, and centuries-old brewing and distilling traditions. From Brussels to Bruges to Ghent, we’ll travel at a slower pace to see a side of Belgium few Canadian travellers experience.

October 6 to 25, 2027



Join Wheel & Anchor for an adventure through the Silk Road, immersing ourselves in urban Kazakhstan, nomadic Kyrgyzstan and diving deep into the old imperial and trade capitals of Uzbekistan.

October 6 to 22, 2027



Join Wheel & Anchor for seventeen days across China's most storied cities — Beijing, Chengdu, Xi'an, and Shanghai — with four nights on the Yangtze River through the Three Gorges in between. From the Great Wall and the Terracotta Army to giant pandas in the mountains above Chengdu and a farewell dinner on the Bund, this is China's full sweep of history, landscape, and food.

October 16 to 29, 2027



Join Wheel & Anchor for an in-depth journey through Andalusia, Spain’s southern crossroads of culture, faith, and design. From Seville to Córdoba and Málaga, explore Moorish palaces, Roman ruins, and whitewashed towns. This immersive two-week itinerary includes sherry tastings, flamenco, and time to absorb the region’s complex, layered history.

October 16 to November 4, 2027



Join Wheel & Anchor for an adventure through the Silk Road, immersing ourselves in urban Kazakhstan, nomadic Kyrgyzstan and diving deep into the old imperial and trade capitals of Uzbekistan.

October 16 to November 5, 2027



Join Wheel & Anchor for a remarkable journey through eastern India, with time in Kolkata, Bodh Gaya, and Varanasi, and two weeks sailing the Ganges River aboard a privately chartered ship. From riverside villages to historic cities, we’ll explore temples, markets, and monuments across Bengal and Bihar with insight and ease.

October 18 to November 5, 2027



Join Wheel & Anchor for the trip that will not only show us but also help us get a handle on this immensely popular but still ill-understood part of the world. We'll go beneath the surface to discover not only how the nations differ from each other, but how the regions within these nations have developed differently to offer the panoply of food, clothing, architecture, and street life that they do.

October 19 to November 2, 2027



Join Wheel & Anchor for a two-week sojourn through southern Italy, staying in just three places: the Bay of Naples, the Valle d’Itria, and Lecce. From private boats to ancient ruins, limestone villages to mozzarella farms, we explore a slower Italy, one that often gets hurried past on the way to shinier objects.

October 19 to 29, 2027



Join Wheel & Anchor for a quiet journey through Belgium by barge, exploring canal towns, historic squares, and centuries-old brewing and distilling traditions. From Brussels to Bruges to Ghent, we’ll travel at a slower pace to see a side of Belgium few Canadian travellers experience.

October 20 to 31, 2027



Join Wheel & Anchor for a journey through Egypt guided by our resident Egyptologist, Younes. Spend three days in Cairo exploring its museums, mosques, and historic districts, followed by seven days sailing the Nile on our private dahabiya with stops at Luxor, Edfu, Aswan, and more. One final night in Cairo concludes the trip.

October 26 to November 10, 2027



Join Wheel & Anchor as we explore cultures ancient and modern, sailing from from Sai Gon to Siem Reap, stopping at fishing villages and orchard groves, and visiting temples and pagodas, markets and workshops before getting to see one of the true wonders of the world, the temple of Angkor Wat at sunrise.

October 27 to November 14, 2027



Join Wheel & Anchor for an unforgettable rail journey across Africa, beginning in Dar es Salaam and winding through Tanzania, Zambia, Zimbabwe, and Botswana before arriving in South Africa. Along the way, we’ll explore Nyerere National Park, admire the cascading waters of Victoria Falls, and spend time in Madikwe Game Reserve on safari. The adventure culminates in Cape Town, surrounded by vineyards and mountain scenery.

October 29 to November 7, 2027



"Join Wheel & Anchor to explore Ecuador, where the Amazon rainforest, the Andes, and historic cities meet. This journey takes us from jungle lodges to highland markets and colonial centres, revealing one of South America’s most diverse countries. "

November 1 to 15, 2027



Join Wheel & Anchor for a vibrant adventure through Morocco that begins in Casablanca and winds through the blue-washed streets of Chefchaouen, the artisan quarters of Fes, and the shifting sands of the Sahara Desert. Continue through the kasbahs and gardens of the Draa Valley before culminating in Marrakesh, where tiled courtyards, calls to prayer, and palm-shaded riads offer a final, lasting impression of this remarkable country.

November 5 to 19, 2027



Hard to get to, impossible to forget. Join the Wheel & Anchor community as we set sail aboard the Aranui, a working ship whose crew will take us along for the ride from port to lagoon to beach as they deliver supplies and we get an indelible look into the life and beauty of Tahiti and the Marquesas islands of French Polynesia, thousands of kilometres from any mainland, but self sufficient for thousands of years through the sheer abundance of flora and sealife. Rarely visited beaches, remote volcanic peaks, and days on bright waters that will live in your memories forever. From the Tahitian capital of Papeete, around the six inhabited islands and back again, we'll get a taste of island life as it's lived no place else on earth.

November 6 to 15, 2027



Join Wheel & Anchor for a journey through the Galapagos aboard a private yacht chartered exclusively for us. Santa Cruz, Isabela, Fernandina, and Floreana provide volcanic coasts, rare wildlife, and quiet anchorages in one of the world’s most distinctive natural environments.

November 7 to 22, 2027



Join Wheel & Anchor for sixteen days across Sri Lanka, an island roughly the size of Nova Scotia holding eight UNESCO World Heritage Sites. We'll begin in Colombo, then head north to the old royal capitals of the Cultural Triangle, where a fig tree grown from a cutting planted in 288 BC still stands. We'll climb into the hills to Kandy and its tooth relic, walk the rows of a working Ceylon tea estate, and ride the mountain railway to Ella. From there we drop down to Yala for leopards, then follow the Sri Lankan beaches of the south coast west to the Dutch ramparts of Galle. Along the way we'll share a farmer's lunch of thirty curries beside the rice paddies and watch for elephants at dusk. It's an island small enough to cross in a fortnight, and layered enough to stay with you long after.

November 7 to 20, 2027



Join Wheel & Anchor for a journey through Argentina and Chile that’s equal parts breathtaking scenery, rich history, and culinary discovery. Wander the streets of Buenos Aires, sip Malbec straight from the source in the vineyards of Mendoza, and take in the landscapes of the Andes as you cross into Chile. In Santiago, experience the rhythm of daily life before heading to the eclectic port city of Valparaíso, where colourful streets and Pacific breezes add the perfect finishing touch to this South American adventure.

November 7 to 19, 2027



Join Wheel & Anchor for thirteen days in Bhutan — a country roughly the size of Switzerland with a population just over 800,000, the only nation in the world that measures progress by Gross National Happiness, and the only one that is, on balance, carbon negative. We'll fly into Paro and onward to the temple valleys of Bumthang, then work our way slowly westward by road through Trongsa's hilltop fortress, the glacial Phobjikha Valley where black-necked cranes return each November from the Tibetan Plateau, the rice country around Punakha, and over the prayer-flagged Dochula Pass into Thimphu. We'll close with a morning's hike up to Tiger's Nest, the cliff-clinging monastery 900 metres above the Paro Valley floor. Along the way: yathra weavers, monastic kitchens, a candlelight dinner by the river, and an unhurried pace the country itself seems to insist on.

November 10 to 21, 2027



Join Wheel & Anchor for a journey through Egypt guided by our resident Egyptologist, Younes. Spend three days in Cairo exploring its museums, mosques, and historic districts, followed by seven days sailing the Nile on our private dahabiya with stops at Luxor, Edfu, Aswan, and more. One final night in Cairo concludes the trip.

November 1 to 9, 2027



Join Wheel & Anchor to experience the deep stillness and layered history of Jordan. From carved sandstone cities to desert silence and hilltop ruins, this is a place shaped by passage and permanence. We’ll explore the traces left behind — and meet the people who continue to live among them.

November 20 to 28, 2027



Join Wheel & Anchor for an extraordinary nine-day safari through Botswana’s most celebrated wilderness regions. From the salt pans of Makgadikgadi to the waterways of the Okavango Delta and the elephant herds of Chobe National Park, this journey reveals the country’s remarkable diversity. Along the way, we’ll stay in remote lodges, experience game drives, and encounter wildlife in its natural environment.

November 21 to December 12, 2027



Join Wheel & Anchor for a three-week stay in New Zealand, with time in Auckland, Rotorua, and Queenstown. We’ll trace volcanic slopes, visit geothermal fields, and travel through Fjordland by land and water. With fewer stops and longer stays, this LiveAway offers a clearer view of a place many only pass through.

November 24 to December 5, 2027



Join Wheel & Anchor for a journey through Egypt guided by our resident Egyptologist, Younes. Spend three days in Cairo exploring its museums, mosques, and historic districts, followed by seven days sailing the Nile on our private dahabiya with stops at Luxor, Edfu, Aswan, and more. One final night in Cairo concludes the trip.

November 28 to December 11, 2027



Embark on a captivating 13-night Christmas market trip, immersing yourself in the festive charm of European cities. Begin with 2 nights in Frankfurt at the Römerplatz market, then travel to Düsseldorf for 3 nights, including a side trip to historic Cologne. Continue with 4 nights in Ghent, exploring medieval markets, and take a detour to Brussels and Bruges for Belgian holiday traditions. Conclude your adventure with 4 nights in Vienna, exploring the imperial beauty, and a day in Bratislava's charming markets, completing your magical holiday experience.

January 9 to 27, 2028



Join Wheel & Anchor for an unforgettable rail journey across Africa, beginning in Dar es Salaam and winding through Tanzania, Zambia, Zimbabwe, and Botswana before arriving in South Africa. Along the way, we’ll explore Nyerere National Park, admire the cascading waters of Victoria Falls, and spend time in Madikwe Game Reserve on safari. The adventure culminates in Cape Town, surrounded by vineyards and mountain scenery.

January 9 to 26, 2028



Join Wheel & Anchor on an eighteen-day journey down the Upper Mekong, from the temple cities of northern Thailand into Laos. We'll board a small ship at the Golden Triangle, travelling downstream past whisky distilleries, Luang Prabang's 328 steps at dusk, and Asia's most argued-over dam. The trip ends in Vientiane, a capital so low and quiet it barely feels like one. There are few better ways to understand a country than to travel its founding river, slowly.

January 12 to 23, 2028



Join Wheel & Anchor for an immersive journey through Costa Rica’s cloud forests, coffee highlands, and Caribbean waterways. From spotting quetzals in misty reserves to drifting along jungle canals, we’ll experience the country’s extraordinary biodiversity, vibrant culture, and natural beauty in a way that goes far beyond the typical tropical escape.

January 19 to February 2, 2028



Join Wheel & Anchor as we head to Koh Samui, an island that has evolved from a quiet fishing community into a place where Thailand’s traditions and modern comforts meet. Set in the Gulf of Thailand, it’s a place of palm-fringed beaches, Buddhist temples, and waters that shift between deep blue and turquoise. We’ll have time to explore at our own pace—whether that means wandering through night markets, discovering the flavours of Thai cooking, or drifting into the calm of a hidden cove. It’s Thailand island life, with both guided adventures and the time and space to take it all in.

January 24 to February 9, 2028



Join Wheel & Anchor for a coastal immersion in Costa Rica, split between Montezuma and Sámara. You’ll explore wildlife refuges, quiet beaches, and offshore islands, with opportunities for snorkelling, kayaking, and encounters with macaws and sea turtles. The journey balances guided nature experiences with free time by the ocean, giving a fuller sense of daily life along the Pacific. It ends with a night in San José before the flight home.

January 27 to February 10, 2028



Join Wheel & Anchor for a two-week exploration of Colombia, from Bogotá’s high-altitude markets to the coffee farms of Quindío, the hills of Medellín, and the Caribbean streets of Cartagena. We’ll meet growers, artists, and guides who show us the country through their eyes. This journey offers a grounded, thoughtful view of Colombia—one that rewards curiosity and time spent wandering and wondering.

January 31 to February 14, 2028



Join Wheel & Anchor for a two-week journey through the Canary Islands, a region shaped by volcanic forces and a deep maritime history. We’ll start with seven nights in Tenerife, where Mount Teide dominates the skyline, coastal towns offer markets, cafés, and a mix of old and new influences. Then, we’ll spend a week on La Palma, home to dense forests, volcanic ridges, and some of the world’s clearest night skies. With time to explore and ponder, this trip provides the opportunity to really get to know the landscapes and cultures of the Canaries.

January 31 to February 14, 2028



Join Wheel & Anchor for a two-week journey through the Canary Islands, a region shaped by volcanic forces and a deep maritime history. We’ll start a week on La Palma, home to dense forests, volcanic ridges, and some of the world’s clearest night skies. Then, we’ll spend with seven nights in Tenerife, where Mount Teide dominates the skyline, coastal towns offer markets, cafés, and a mix of old and new influences. With time to explore and ponder, this trip provides the opportunity to really get to know the landscapes and cultures of the Canaries.

February 3 to 17, 2028



Join Wheel & Anchor as we head to Koh Samui, an island that has evolved from a quiet fishing community into a place where Thailand’s traditions and modern comforts meet. Set in the Gulf of Thailand, it’s a place of palm-fringed beaches, Buddhist temples, and waters that shift between deep blue and turquoise. We’ll have time to explore at our own pace—whether that means wandering through night markets, discovering the flavours of Thai cooking, or drifting into the calm of a hidden cove. It’s Thailand island life, with both guided adventures and the time and space to take it all in.

February 8 to 29, 2028



Join Wheel & Anchor for a three-week Australian journey with full weeks in Melbourne, Hobart, and Sydney. Settle into Melbourne's café culture between day trips to coastal limestone stacks and misty mountain railways. In Tasmania, explore Port Arthur's prison ruins and meet wombats and Tasmanian devils at wildlife sanctuaries. Finish in Sydney, where you'll be able to see the Opera House from land and water, before venturing to the eucalyptus-scented Blue Mountains

February 15 to 29, 2028



Join Wheel & Anchor on a trip to two islands you’ll never forget. Part of that special North Atlantic breed of the island, they’ve got culture to spare alongside golden sand beaches, homegrown drinks, and a cuisine that has benefited from centuries of just enough isolation from Europe to make it unlike anything you’ve tried before. Take the time to get to know the place, relax, and take in the sights, sounds, and scents as you soak up the sun. Madeira and Porto Santo are the kind of places our LiveAway program was built for, so please, come spend some time with us.

February 19 to March 4, 2028



Join Wheel & Anchor for a two-week stay in both of Bali’s cultural heart and its coastal retreats, with an optional extension to the wild landscapes of Komodo. From Ubud’s timeless temples and artisan traditions to Sanur’s oceanfront tranquillity, we’ll explore beyond the usual tourist trail. Optional excursions include rice terraces, ancient water temples, and snorkelling in pristine waters. For those who venture to Komodo, encounters with legendary dragons and vibrant coral reefs await.

March 1 to 7, 2028



Join Wheel & Anchor for a week of discovery in Malta. Based in Valletta, we’ll explore the island’s storied past, from temples older than the pyramids to the Renaissance fortresses of the Knights of St. John. We’ll ferry to Gozo for a glimpse of rural island life, wander the quiet streets of the Three Cities, and take in sweeping Mediterranean views. Along the way, we’ll try Maltese cuisine, uncover hidden corners of this tiny nation, and soak up the charm of this endlessly fascinating slice of the Mediterranean.

March 1 to 15, 2028



Join Wheel & Anchor on a trip to two islands you’ll never forget. Part of that special North Atlantic breed of the island, they’ve got culture to spare alongside golden sand beaches, homegrown drinks, and a cuisine that has benefited from centuries of just enough isolation from Europe to make it unlike anything you’ve tried before. Take the time to get to know the place, relax, and take in the sights, sounds, and scents as you soak up the sun. Madeira and Porto Santo are the kind of places our LiveAway program was built for, so please, come spend some time with us.

March 6 to 27, 2028



Join Wheel & Anchor for a three-week stay in New Zealand, with time in Auckland, Rotorua, and Queenstown. We’ll trace volcanic slopes, visit geothermal fields, and travel through Fiordland by land and water. With fewer stops and longer stays, this LiveAway offers a clearer view of a place many only pass through.

March 8 to 19, 2028



Join Wheel & Anchor for a journey through Egypt guided by our resident Egyptologist, Younes. Spend three days in Cairo exploring its museums, mosques, and historic districts, followed by seven days sailing the Nile on our private dahabiya with stops at Luxor, Edfu, Aswan, and more. One final night in Cairo concludes the trip.

March 8 to 23, 2028



Join Wheel & Anchor for a two-week journey through Sicily, staying in three distinct regions: Ortigia, Trapani, and Cefalù. Rather than rushing from site to site, we’ll slow down and take the time to understand the island’s complex history, layered cultures, and varied landscapes. With visits to ancient ruins, coastal towns, mountain villages, and neighbourhood markets, this is a grounded exploration of Sicily from the inside out.

March 10 to 23, 2028



Join Wheel & Anchor for a journey through Argentina and Chile that’s equal parts breathtaking scenery, rich history, and culinary discovery. Wander the streets of Buenos Aires, sip Malbec straight from the source in the vineyards of Mendoza, and take in the landscapes of the Andes as you cross into Chile. In Santiago, experience the rhythm of daily life before heading to the eclectic port city of Valparaíso, where colourful streets and Pacific breezes add the perfect finishing touch to this South American adventure.

March 11 to 25, 2028



Join Wheel & Anchor for a vibrant adventure through Morocco that begins in Casablanca and winds through the blue-washed streets of Chefchaouen, the artisan quarters of Fes, and the shifting sands of the Sahara Desert. Continue through the kasbahs and gardens of the Draa Valley before culminating in Marrakesh, where tiled courtyards, calls to prayer, and palm-shaded riads offer a final, lasting impression of this remarkable country.

March 13 to April 3, 2028



Join Wheel & Anchor for a three-week stay in New Zealand, with time in Auckland, Rotorua, and Queenstown. We’ll trace volcanic slopes, visit geothermal fields, and travel through Fiordland by land and water. With fewer stops and longer stays, this LiveAway offers a clearer view of a place many only pass through.

March 16 to 30, 2028



Join Wheel & Anchor for a two-week exploration of Mallorca, dividing our stay between the island’s historic capital and a quieter beach town in the north. Discover vintage trains, hilltop villages, and coastal walks, with opportunities to try local wines and learn regional cooking. This journey blends guided excursions with unstructured days, offering a deeper experience than a typical visit.

March 24 to April 7, 2028



Join Wheel & Anchor for a two-week sojourn through southern Italy, staying in just three places: the Bay of Naples, the Valle d’Itria, and Lecce. From private boats to ancient ruins, limestone villages to mozzarella farms, we explore a slower Italy, one that often gets hurried past on the way to shinier objects.

March 26 to April 8, 2028



Join Wheel & Anchor for an in-depth journey through Andalusia, Spain’s southern crossroads of culture, faith, and design. From Seville to Córdoba and Málaga, explore Moorish palaces, Roman ruins, and whitewashed towns. This immersive two-week itinerary includes sherry tastings, flamenco, and time to absorb the region’s complex, layered history.

March 13 to April 3, 2028



Join Wheel & Anchor for a two-week sojourn through southern Italy, staying in just three places: the Bay of Naples, the Valle d’Itria, and Lecce. From private boats to ancient ruins, limestone villages to mozzarella farms, we explore a slower Italy, one that often gets hurried past on the way to shinier objects.

May 15 to 30, 2028



Join Wheel & Anchor for a journey through the Adriatic, where history, culture, and stunning landscapes converge. From the ancient walls of Dubrovnik to the coastal charm of Cavtat and the serene islands beyond, we’ll explore the region’s rich heritage and maritime traditions. Along the way, savour the distinct flavours of Dalmatian cuisine and uncover hidden gems that reveal the Adriatic’s timeless allure.

September 14 to 28, 2028



Join Wheel & Anchor for fifteen days across Scotland, from Glasgow to Edinburgh by way of its west coast. We'll start over Glen Coe to Skye, then board a small ship with just 18 staterooms and spend seven nights among the sea lochs and islands: Eilean Donan, Tobermory's painted houses, Iona's abbey. Turning inland up the Great Glen, we'll climb Neptune's Staircase and pass Loch Ness before the quiet weight of Culloden. It ends in Edinburgh, below a castle besieged 26 times. A whole country crossed slowly, by road and by water, with the windows open.