7 Small Caribbean Islands You Should Travel or Sail to

There are small Caribbean islands and there are small Caribbean islands. The latter are the places with that extra degree of tranquility (for a region that has some of the most

tranquil places in the world as it is). They are the tiny jewels of Caribbean. I thought I’d suggest some of my favorites for you to check out by sailing or flying to them (if they have an

airport) with one primary criterion: each island has around 2,000 people or less, with the idea being smallness in terms of population, not geography (although these are mostly very

small in that regard, too).

Terre De Haut


It’s no secret that we’re big fans of this tiny, hilly green island in the Les Saintes archipelago of the Guadeloupe Islands, home to beautiful, secluded beaches, mountain views and

some outstanding small restaurants. It may be small, but the town’s main street actually has quite a bit to do. Try the tiny LoBleu Hotel near downtown for an experience right out of

a novel; for a more refined boutique stay,head to Les Petits Saints. The best way to get there is by sailing your vessel there or via ferry from either Grand-Terre or Basse-Terre.



While its far larger neighbor Antigua gets the lion’s share of travel, Barbuda is an oasis. It’s about 38 square miles in area, but with just about 1,700 people, meaning you can

generally enjoy have its spectacular beaches all to yourself. The Lighthouse Bay resort is a great option for a stay, and to get there, you can either sail your vessel there,take the

Barbuda Express ferry or fly SVG Air.



The British Virgin Islands could populate this list all by itself, but Anegada, the only coral island in the BVI, was my pick for this year. Located at the northern tip of the archipelago,

Anegada is home to empty beaches and spectacular reefs. Stay at the Anegada Reef Hotel, the Loblolly Cottages or the Sea Grape Villas are all solid hotel options. Smith’s Ferry

operates three-times weekly service to the island from Tortola. And, it’s the BVI, so if you don’t have your own boat,the options of chartering a boat are endless!!



This Dutch outpost in the Caribbean is almost entirely situated on an active volcano. But it’s also home to terrific diving and a charming, eco-friendly feel. Saba’s hotel sector is largely

comprised of small bed and breakfasts. For a full-fledged hotel stay, try the Queen’s Gardens Resort, or bed and breakfasts like the Selera Dunia Boutique Hotel, Juliana’s Hotel and

the Cottage Club. Sailing out of St Maaten is the best way to get there although Flying Winair from St Maarten by air is an option, and there is a twice-weekly ferry from St Maarten.



If it’s luxury you’re looking for in a small Caribbean island, this is it. Mustique has long been the Caribbean getaway for celebrities looking to keep a low profile, and that remains true

today. When it comes to hotels, there are two top-notch options: the Firefly and the Cotton House. You’ll feel like British royalty at either one. To get there, you can sail out of St

Vincent or fly the very efficient SVG Air.



The party piece on this island in the so-called Spanish Virgin Islands off of Puerto Rico is Flamenco Beach, one of the world’s most universally acclaimed beaches. The 21-square-mile

pearl is also the site of a the Cayo Luis Peña Natural Reserve, a superb sailing destination for snorkeling and diving enthusiasts. For your stay, Club Seabourne and the Casa Resaca

are great bets. Cape Air offers daily flights out of San Juan.



It’s famous for many reasons, from a stay by Dr Martin Luther King, Jr to a chronicle by Ernest Hemingway. But the westernmost island of the Bahamas (just 50 miles from Miami) is

also the Bahamas’ bonefishing capital. Bimini gives new meaning to the term laid-back,its a “must sail” for sailors! For a hotel stay, try Resorts World Bimini or the famous Bimini Big

Game Club. There are daily direct flights to South Bimini International Airport from the US and you can take the Bimini Superfast ferry from Miami.

How Much it Costs to Live on Your Sailboat in the Caribbean

From The Northeast U.S. to South America – A Sailors Guide (Part 6/12)

The Caribbean, Part 2: Captain Gino’s Guide to The Caribbean




Leave a Reply

Your email address will not be published. Required fields are marked *

  • Kevin Wood

    Good selection…..been to all of these but Barbuda….like mountainous islands better than flat ones, and it’s kinda far to windward (from the nearby mountainous ones)!