Best Sailing Destinations Worldwide, A Liveaboard’s Picks
I have spent more of my adult life on a sailboat than I care to admit, and somewhere along the way I stopped measuring trips in miles and started measuring them in how many nights I slept on the water. Every sailor has a favorite, and mine get picked apart endlessly over dockside beers. So after many thousands of miles across several oceans, here are the sailing destinations I would rank highest, not for pure technical challenge but for the simple combination of wind, water, and the places you can reach under sail. These are the ones that keep calling me back.
Greece: the islands that started it all
The Greek islands remain the best introduction to European sailing, and it is not close. The Cyclades give you that perfect mix of steady summer winds, short hops between islands, and a harbor culture built around sailors for the past few millennia. I have anchored off Santorini, slipped into the protected lagoon of Sifnos, and sat in tavernas where the tables overlook a long line of masts. The meltemi wind can get serious in July and August, so time your passages for the morning, but otherwise this place runs on pure ease and beauty.
Croatia: Adriatic perfection
If Greece is the classic, Croatia is the modern favorite, and I understand the appeal completely. The Dalmatian coast is a maze of over a thousand islands with deep, clear water and medieval towns on bays that seem designed for anchoring. I have tied up in Hvar, Dubrovnik, and a dozen unpronounceable coves where the only sound was the halyard slapping the mast. Croatia mixes easy sailing with a relaxed coastal culture, and the water is so clear I stopped trusting my charts and started trusting my eyes.
The British Virgin Islands: paradise on a budget
For warm water and laid back sailing, the Caribbean is hard to beat, and the British Virgin Islands are the crown jewel. The islands sit close enough that you can raise the anchor and be at your next mooring before lunch, with steady trade winds and sheltered anchorages around every corner. I have spent weeks hopping between the BVIs and never grew tired of it. The anchorages are well charted and lined with simple beach bars, making it the ideal place to introduce a nervous crew to the joy of living afloat. I have handed the wheel to more than one first timer in the BVIs and watched the worry melt off their face by the second afternoon.
The Grenadines: empty water and island character
South of the usual Caribbean circuit, the Grenadines offer emptier waters and a deeper island culture. Stretching between Saint Vincent and Grenada, this chain rewards sailors who want to feel properly away from it all, with anchorages off Tobago Cays and tiny islands that barely appear on a map. I have spent days here seeing sailboats only in the distance, and every quiet anchorage felt like a private reward.
Seychelles: the escape from the crowd
When I want to feel like I am on a different planet, I go to the Seychelles. These granitic islands in the middle of the Indian Ocean offer turquoise water, giant boulder beaches, and a sense of remoteness that most charter grounds cannot touch. The sailing is more open water and less island hopping than the Med, and you need a bit more experience, but the reward is an anchorage off a beach that feels entirely private. I have had mornings there where my boat was the only vessel in sight on a horizon full of color.
New Zealand’s Bay of Islands
For sailors who want scenery that changes constantly, the Bay of Islands in New Zealand is quietly world class. The northeast coast offers sheltered blue waters dotted with over a hundred islands, and behind the beaches rise green hills that feel like sailing through a postcard. The locals are famously friendly, and the sheltered bays make it an ideal place to learn or to shake off the rust. I did one of my favorite moonlit passages there, gliding past dark islands with the glow of the bay town behind me.
How to choose your first charter
My honest advice is to let experience pick the destination. Beginners should start somewhere sheltered and forgiving like the British Virgin Islands or the Greek Saronic Gulf, where wind and weather stay gentle and help is always nearby. More experienced crews can push toward the open water of the Seychelles or the exposed passages of the South Pacific. Whichever you choose, book through a company that knows the local conditions, and give yourself one shakedown day before you commit to a long passage. I have made every mistake a sailor can make, and the good news is the right destination forgives almost all of them. The water will be waiting, and so will a horizon worth chasing.
