I’ve spent the past two years sailing in the Caribbean. And my partner, a sailor by profession, has been sailing around Caribbean islands since he was a teenager.
Whether you want to charter a yacht in the Caribbean or are planning to sail on your own boat, I hope this article will give you all the information you need to make it into a great trip!
The Best Places to Sail in the Caribbean
What the best sailing destinations in the Caribbean are depends on what you are looking for. And, it even depends a little bit on where you are coming from.
For example, many North Americans will name the Bahamas as their favorite cruising destination, often followed by the USVI.
British sailors will probably tell you about sailing in the Caribbean islands of Saint Vincent & the Grenadines, the BVI, or Grenada.
And French sailors will almost always include Martinique in their list of best destinations for yachting in the Caribbean.
In this article I’m sharing six of the most popular Caribbean sailing destinations, and I will explain what makes them great and which islands and countries are best for which type of sailor.
1. The Bahamas
The Bahamas are probably the most popular sailing destination in the Caribbean for Americans.
And yes, that’s partially because of its proximity to the USA (it’s only 48 nautical miles from Miami to Bimini) but the Bahamas also has a lot to offer as a sailing destination.
Its crystal clear, turquoise waters are some of the most incredible waters I’ve seen anywhere in the Caribbean.
From a natural point of view, the Bahamas is quite spectacular.
You have hundreds of islands and anchorages to choose from. You could find yourself anchored in front of an island with a great hiking trail today, taking your dinghy through a mangrove tunnel tomorrow, and swim with nurse sharks at yet another anchorage on day three.
There is a large variety of things to see and do in the Bahamas that are only accessible if you have a boat. And that makes the Bahamas one of the best sailing destinations in the Caribbean.
The Exumas are the favorite part of the Bahamas for many sailors with famous anchorages such as Norman’s Cay and Pigs Beach, but also many more serene and remote anchorages.
One major downside to sailing in the Bahamas is just how expensive everything here is. From groceries and restaurants to cruising permits and marina fees. Almost everything in the Bahamas will cost you more than on many other Caribbean islands.
But, if you stock up before you sail to the Bahamas and anchor instead of using marinas, you can have an incredible time even if you are sailing on a budget.
Some other things to note about the Bahamas as a sailing destination is that winds are more variable since you are not in the tradewinds here. Plus many anchorages and approaches to anchorages are shallow. If your boat has a draft of more than six feet (1.8 meters) certain anchorages become very tricky and you wouldn’t be the first boat to run aground around here.
But, don’t let any of this put you off. If you want to sail in the Caribbean, the Bahamas should definitely be high on your list because it is just absolutely beautiful around here!
The Bahamas is also one of the most popular places to charter a yacht in the Caribbean and you can find a wide range of boats to rent.
Tip: I recommend getting a cruising guide for every Caribbean sailing destination you plan to visit, but especially for the Bahamas. With its many shallow areas and some tricky anchorages a cruising guide provides valuable information in addition to your chart plotter.
One of the most popular cruising guides in the Bahamas is the Waterway Guide.
2. The British Virgin Islands (BVI)
The BVI consists of four larger islands and 32 smaller islands and islets.
Like the Bahamas, the BVI is a country best explored by boat, and that’s just one of the reasons why the BVI is such a great sailing destination.
The islands here are located close together, which makes it easy to sail from island to island, and there are plenty of sheltered anchorages to choose from.
Almost all of the popular bays offer mooring buoys. So if you are nervous about anchoring, that’s a great feature not many other Caribbean sailing destinations can offer.
With its beautiful beaches, some great snorkeling and scuba diving, and many lively anchorages, the BVI is very popular as a sailing vacation destination, with many yacht charter options.
The Baths at Virgin Gorda are one of the highlights to visit while sailing here. And most likely you’ve already heard about the famous floating bar Willy T’s and the Soggy Dollar Bar. Yes, the BVI is a lively sailing destination!
A downside to sailing in the BVI is that its popularity does make it crowded, and its reputation as an easy sailing destination attracts a lot of novice sailors, which is something to be aware of. At the same time, if you are a novice sailor, the BVI really is a great place to gain sailing experience.
The islands are beautiful and diverse, navigation is easy, and there is plenty to do in the BVI!
The best cruising guide for sailing in the BVI: Simon Scott’s Cruising Guide to the Virgin Islands
3. Saint Vincent & the Grenadines (SVG)
Part of the Windward Islands, Saint Vincent and the Grenadines make for some of the most beautiful sailing in the Caribbean.
It’s all about the Grenadines really though, with Bequia and the Tobago Cays being some of the most popular sailing destinations here.
In total there are 32 islands and cays in SVG, of which only 9 are inhabited.
I’ve heard it being described as a ‘first taste of the South Pacific’. The natural beauty, the crystal clear waters and the marine life are incredible and remind many sailors of the beautiful unspoiled South Pacific.
With consistent winds, easy anchoring, and generally good holding it’s a great sailing destination. Plus, it’s easier to find less crowded anchorages here than in some of the other popular Caribbean sailing destinations.
Don’t get me wrong though, the SVG is popular, so you definitely won’t be the only boat here!
One downside to sailing in the SVG is that unfortunately, crime rates have increased in recent years. Stolen dinghies and robberies from yachts have become more common.
It’s a truly beautiful part of the world though, and for many who’ve sailed all around the Caribbean it’s one of their highlights.
The best cruising guide for sailing in SVG: Chris Doyle’s Sailors Guide to the Windward Islands
4. Grenada
Grenada is one of those Caribbean sailing destinations where many sailors spend months or even years.
It has a great sailing community, friendly locals, and enough different things to explore to keep you entertained for a long time.
We’ve spent months sailing around Grenada, and I actually created a more detailed article about sailing in Grenada in which I describe all the different anchorages and marinas, and share additional tips.
Grenada is one of those lush, green islands offering good hiking, waterfalls to visit, and several chocolate estates that make for a great excursion inland.
Grenada consists of three main islands, Grenada, Carriacou, and Petite Martinique, plus several smaller islands.
Sandy Island is a beautiful anchorage not to miss, and Tyrell Bay and Woburn Bay are two main anchorages with the most lively cruising communities. But again, I describe all of that in my Sailing in Grenada Guide.
You’re in the tradewinds here and mostly sailing on the leeward side, making Grenada quite an easy sailing destination.
If you’re looking for a beautiful tropical island destination with friendly people, decent boating facilities and a large sailing community, Grenada is one of the best choices!
A good number of cruisers decide to stay here for most, or even all of hurricane season. And although Grenada isn’t completely outside of the Caribbean hurricane area (and got hit badly by hurricane Beryl in July 2024), it does get hit less frequently than other islands.
The best cruising guide for sailing in Grenada: Chris Doyle’s Sailors Guide to the Windward Islands (the same as for sailing in SVG)
5. Panama
You might not have expected Panama to be included in a Caribbean sailing guide, but the Caribbean coast of Panama is actually a great sailing destination and one of my favorites.
And Panama as a whole is a great, diverse country to visit.
From the remote San Blas islands to the modern capital of Panama City. From Bocas del Toro with its lively sailing community to hiking in El Valle de Anton or enjoying the cooler air in Boquete.
Panama gives you a whole country to explore.
Also Read: Interesting Facts About Panama
If you love the idea of combining sailing to diverse anchorages with exploring a country on land, Panama has a lot to offer!
Panama is slightly more expensive than other Central and South American countries, but it’s a lot cheaper than most Caribbean islands. Plus, it’s relatively easy to get boat parts and any other supplies shipped from abroad, which is a great help if you need to do any work on your boat.
Marinas are relatively inexpensive making it easy to leave your boat for a while to explore more of Panama.
As for sailing, the beautiful, remote San Blas Islands can’t be missed!
But I would also recommend sailing to Bocas del Toro. Explore at least a few of its many different islands and meet some other sailors around Bocas Town.
The one downside to sailing in Panama is that the cruising permit is more expensive than in most other Caribbean sailing destinations.
The best cruising guide for sailing in Panama: The Panama Cruising Guide by Eric Bauhaus – although a bit older, it’s still heavily relied on by sailors for navigating shallow waters and reefs.
6. Bonaire
If you love scuba diving, nature, and a more laid-back sailing destination, then you’ll love Bonaire.
Bonaire is known for its great and easy scuba diving, attracting divers from all over the world.
Also Read: The Best Dive Sites in Bonaire
The island is small, not overly developed, and the cruising community is great.
It’s really all about discovering the underwater world here though. If you don’t scuba dive yet, this is a great place to learn.
But even if diving is not your thing, snorkeling here is beautiful too, and the island is popular among bird lovers as well.
Some people jokingly say there are more flamingoes than people in Bonaire!
Bonaire is not a sailing destination where you move from anchorage to anchorage. In fact, to protect the marine environment you aren’t allowed to anchor here. You can either take a mooring buoy or stay in the marina.
One downside to Bonaire as a sailing destination is that the mooring buoys do fill up, so you might end up staying in a marina longer than you would have wanted to. A few years ago though, the fees for using the mooring buoys have gone up substantially. This means that Bonaire isn’t the cheap sailing destination that it was anymore, but it does also mean that you are a lot more likely to find an available mooring buoy when you arrive.
Bonaire is, just about, outside of the hurricane belt which makes it a popular Caribbean sailing destination during hurricane season. I say ‘just about’ because Bonaire can get hit by a hurricane and has been in the past, it’s just very rare.
Because Bonaire isn’t a sailing destination where you go from anchorage to anchorage, a sailing guide isn’t really necessary. Your chart plotter or navigation app will suffice.
Tips for Sailing in the Caribbean
1. The Best Time to Sail in the Caribbean
Most of the Caribbean falls inside the hurricane belt. Hurricane season officially runs from June 1st until November 30th.
Therefore the best time to sail in the Caribbean is between early December and the end of May.
December, especially the time around the holidays, is peak season for most of the Caribbean, making it crowded, and prices for things like rental cars and hotels tend to go up.
Because historically most hurricanes have happened between early August and the end of September, you’ll find many sailors still sailing around the Caribbean in June and July, and again in early November.
There are also plenty of hurricane holes around the Caribbean where you could sail to in the event of a hurricane or storm warning, but my recommendation would be to use this time of year to visit parts of the Caribbean that are outside of the hurricane belt.
Bonaire and Curaçao are popular islands for sailors to spend hurricane season.
Panama is also outside of the hurricane belt but hurricane season coincides with rainy season, making it not the best time to sail in Panama.
2. Navigation While Sailing in the Caribbean
We’ve been using Navionics for the past four years and generally, that has been very accurate to sail around the Caribbean. But, I highly recommend buying a cruising guide for the country or island you plan to sail in.
They provide a lot of useful information about the quality of different anchorages, how to enter, what facilities you can find ashore, etc.
In the list of the best Caribbean sailing destinations I’ve added links to the most popular cruising guides for each destination.
3. Is it Safe to Sail the Caribbean?
Well, this is a difficult question to answer.
Of course during hurricane season it’s not entirely safe to sail in the Caribbean anywhere within the hurricane belt.
But, apart from hurricane season there is also crime. And although violent crimes involving sailors are thankfully very rare, dinghy theft is not. And, occasionally you’ll hear a story about someone’s boat getting broken into.
I’ve anchored in bays in Saint Lucia where I didn’t feel comfortable leaving the boat alone. And our neighbor had their dinghy stolen at night in the Honduran Bay Islands. So yes, things do happen, and I’d lie if I’d say that I never worry about crime in the Caribbean.
That being said, the sailing destinations listed in this article are all considered safe to visit. And with the right preparations, you’ll have a great time.
4. Always Lock Your Dinghy!
Dinghies get stolen from dinghy docks, from beaches, but also right off the boat. Lock your dinghy and, if you can, hoist it out of the water at night.
5. How Big of a Boat Do You Need to Sail the Caribbean?
I’ve been asked this several times. And to be honest, it really is all about what you are comfortable with.
I’ve met people sailing around the Caribbean full-time on a 26-foot monohull, but I also met someone who thought her 48-foot catamaran was a bit small.
You can safely sail any of the Caribbean islands listed above in a small boat, and all these islands have marinas and anchorages suitable for big yachts as well.
Do keep in mind that many marinas in the Caribbean are not cheap and since you generally pay per foot, the bigger the boat, the more expensive it will be for you to use marinas.
And, catamarans often pay 1.5 times the rate of a monohull.
6. Chartering a Boat in the Caribbean
If you’re looking to charter a yacht in the Caribbean, I can highly recommend Click&Boat.
They have a great selection of boats on their website at more reasonable prices than some local charter companies.
Chartering a sailboat in the Caribbean is extremely popular. And, you can choose to charter one with or without a captain.
I know several sailors who now own their own boat, but for whom chartering in the Caribbean is what got them hooked. So be careful, you might not want to go home after your Caribbean sailing trip!
Sailing in the Caribbean – Conclusions
The Caribbean is a popular sailing destination, and for good reasons.
The weather is generally great (outside of hurricane season), the winds are stable, and there are more anchorages to explore than anyone could in a lifetime.
But, some destinations will suit you better than others, depending on your personal interests, your boat, and how much time you have.
I therefore recommend taking some time to plan where you want to go and why.
The sailing destinations I’ve listed above are all absolutely great, but they might not all fit your needs.
For example, we sailed to St Maarten because we had some problems with our engine and St Maarten is a good destination in the Eastern Caribbean for boat maintenance.
Read different Caribbean cruising guides and talk to other sailors about their favorite places and tips.
But enjoy, no matter where you’ll end up sailing in the Caribbean, I’m sure you’ll make incredible memories!
Also Read:
- Sailing in Saint Lucia – Anchorages, Sailing Tips & More
- Sailing in Curaçao – Things to Know
- Anchoring in Mullet Bay, St Maarten
- Sailing Across the Atlantic – My Experiences
- Why Taking Seashells From the Beach is a Bad Idea
- The Best Caribbean Islands to Visit & Why
- 5 Most Romantic Caribbean Islands
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