Tinkering with the Timing of our Travels

Greetings from Cefalù!

We’re approaching the final few days here of our Sicily LiveAway, and we’ll soon be off for a few nights in the Aeolian Islands en route to Sorrento for our 2-week LiveAway on the Amalfi Coast.

We have been absolutely blessed with gorgeous sunshine and comfortable temperatures while here, and being as early in the season as we are, we’ve also been relatively free of the throngs of tourists that will begin to descend upon the island later this month.

Great weather + fewer tourists is perhaps the Holy Grail of travel in the modern era, and it’s more rare than ever in the still-surging post-pandemic era. In the end it comes down to timing and a bit of luck, and it’s why many of our trips happen in the shoulder or even off-season in the destinations we visit.

It’s a question we regularly get from new members – if you were to google ‘best time to visit x destination,’ you may notice that we don’t have much happening in the months suggested by the search engine.

It’s not that our algorithmic overlords are wrong; they certainly have the data to know when most people want to go…everywhere. The point is that peak season, particularly now, is a brutal time to travel.

Huge crowds, lines to get in the most significant sites, hard to get into the best restaurants; any one of these three issues puts a damper on a great travel experience, and they tend to come as an unwelcome trio.

Now, we as travellers can’t really begrudge other travellers for wanting to go to the same places we do! But the experience of overtourism is a far cry from the ideal we are after…so we aim for those small windows on either side of the peak, and sometimes even the off-season for most of our programs.

Sometimes this planning comes down to a very specific few days that we aim for, without much wiggle room. Here in Sicily, for example, many of the hotels and restaurants only opened a few weeks ago, and we couldn’t have come much earlier than we did.

And while it used to be primarily about avoiding hordes of tourists, now the element of hotel space has become primary, particularly in smaller, boutique hotels that we like to choose.

Indeed the biggest risk in the shoulder or off-season is the weather, and though it’s calculated, it’s a risk nonetheless. In my view though it’s worth taking for a more intimate, less harried travel experience…and that’s why you’ll find most of our trips happening in these spots on the calendar.

Briefly, on new trips – I’m pleased this week to release the 2024 edition of our Namibia & Botswana safari program, just slightly ahead of our first trip there happening right after our Amalfi LiveAway.

As far as safaris go, this one is indeed special, as we’ll be staying at several different lodges in several different ecosystems, including a more water-based safari in the Okavango Delta. As such it is an opportunity to see a huge variety of Africa’s majestic wildlife.

And, just prior to our wildlife adventure is a journey through the Namib Desert, one of the continent’s oldest and most riveting landscapes. Take a look at the full itinerary below and stay tuned for some thoughts on the experience in this newsletter while it’s happening later this month.

I’ll sign off here – lots more to come in the weeks ahead, so much so in fact that we will be slightly shifting our webinar schedule such that the webinar for some trips will after the itinerary is released. Stay tuned for all this and more 🙂


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