Do something unforgettable

We’ve put together some ideas for some trips for the year. The vision behind Wheel & Anchor LiveAways is to spend a month or two of those winter months in a fascinating place with interesting local people, and to do it with a bunch of friends. This guide is designed to give you a sneak peak at what that could look like in Koh Samui, Madeira, Cyprus, or New Zealand, and the kind of things you could do while there!

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Spend a month on one of Thailand's most famous beach destinations

Bask in an ideal spot for a wellness-focused getaway, where you can get all the massages, fresh coconuts, and vitamin D you desire.

Enjoy optional weekend adventures to Singapore, Bangkok, Khao Sok, and Chiang Mai


Spend a month on the balmy 'Island of Eternal Spring' off the north coast of Africa

Take in the spectacular cliffs and seaviews while walking Madeira's famed hiking trails

Enjoy delectable Portuguese cuisine and fantastic wines, including the locally-produced fortified wine Madeira



Spend a month in one of Europe's most popular holiday destinations - Cyprus, the 'Island of Love'

Explore the rich cultural history of Cyprus, a trading hub for centuries with influences from the Greeks, Arabs, Turks, and more

Enjoy optional weekend adventures to Tel Aviv, Beirut, and Cairo


Spend two weeks on the warmer north island and two weeks amidst the spectacular mountain scenery of the south island of New Zealand

Explore New Zealand's incredible outdoors, including Rotorua Geothermal Park, Fiordland National Park, and some of the country's best hiking and walking tra

Enjoy tasting wines from some of New Zealand's most famous wineries



Spend two weeks on the south coast of Sicily in Syracuse, followed by two weeks on the north coast in Cefalù

Explore Catania, Taormina, Palermo, and more fun excursions

Enjoy a post-program in the beautiful Aeolian Islands, a perfect stop on the way to Amalfi


Spend two weeks in Sorrento, the gateway to the stunning Amalfi Coast

Explore the towns of Amalfi at a relaxed pace, as well as Pompeii, Naples, the Isle of Capri, and more

Enjoy Sorrento's fantastic restaurants and sunset vistas



Spend a month in tropical paradise, either all in Bali or two weeks in Samui followed by Bali

Explore the beautiful landscapes and rich cultural heritage of this unique island

Fully relax and take advantage of the many wellness traditions and healers found here


Begin with two weeks in the Renaissance Capital of Florence, followed by two weeks in Cortona, a charming Tuscan hilltop town

Explore the art and history of Florence, as well as Siena, Bologna, Cinque Terre, and more; from Cortona, visit Montepulciano, Pienza, Tuscan wineries, and more trails

Live as an Italian for a month and indulge in all the spectacular cuisine



Spend a month in one of Europe's sunniest cities, the fortressed marvel that is Malta

From our base in Valletta, we'll explore the fascinating neolithic and medieval history of Malta, as well the Three Cities, Gozo Island, and more

Join us for two weeks in Madeira followed by two weeks in Malta, or perhaps two weeks in Sicily after your two weeks in Malta



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