Which Caribbean Yacht Charter Destination Is Right for You?

When someone says they want to charter a yacht in the Caribbean, they oftentimes don't realize we have the Virgin Islands, Bahamas, Leeward Islands and Windward Islands to choose from — so my first question is usually: What do you actually want the week to feel like?

A yacht charter in the British Virgin Islands is very different from a week cruising the Exumas. And both are completely different from a yacht vacation in St. Martin and St. Barths, or exploring the dramatic landscapes of St. Lucia, St. Vincent and the Grenadines.

Do you want to wake up at a different island every morning? Spend most of your time playing with water toys in turquoise water? Go ashore for beach clubs and great restaurants? Dive incredible reefs? Explore historic towns and UNESCO World Heritage Sites? Or disappear into quiet anchorages where there may be almost nobody else around?

There really isn't one "best" Caribbean yacht charter destination. There is, however, usually a best destination for you.

Here's how the major Caribbean charter regions compare.

British Virgin Islands: The Ultimate Easy Island-Hopping Charter

Best for: First-time charterers, families, active groups, snorkeling and diving, short cruising distances and guests who want to explore a lot without spending hours underway.

The British Virgin Islands are one of the easiest places in the world to charter a yacht.

The biggest advantage is geography. The islands are relatively close together, which means you can have breakfast in one anchorage, snorkel somewhere else before lunch and still be at another island in time for cocktails. It also means you can visit a new island, beach or anchorage every day.

That makes the BVI especially good for families and groups who want the yacht to function as their floating home base rather than spending long stretches underway.

A typical week might include places such as Virgin Gorda, Norman Island, Cooper Island, Peter Island, Jost Van Dyke, Willy T's, Oil Nut Bay, Anegada and several smaller islands and cays.

And there is plenty to do ashore as well. You can explore The Baths on Virgin Gorda, stop at famous beach bars, have lunch or dinner on land, visit small island communities or spend an afternoon at a beach club or shopping before returning to the yacht.

The snorkeling and diving are another major reason to choose the BVI. There are reefs, wrecks, underwater rock formations and dive sites throughout the islands, including the famous RMS Rhone.

What is the water like in the BVI?

One reason the BVI works so well for first-time charterers is that much of the cruising takes place within the relatively protected Sir Francis Drake Channel.

Conditions can certainly vary with the weather and trade winds, but compared with destinations involving longer open-ocean passages, BVI cruising can often feel relatively protected with some of the calmest waters in the Caribbean.

One important BVI water-toy restriction

Jet skis/personal watercraft are prohibited in BVI waters. There is a place you can rent them but even if your yacht has one on board, you can't use it in the BVI. So if jet skis are at the top of your wish list, the BVI probably isn't the right destination.

That doesn't mean you'll be bored. Depending on the yacht, you may have Seabobs, e-foils, paddleboards, kayaks, wakeboards, water skis, towable toys, floating platforms and extensive snorkeling or scuba equipment.

In summary, choose the BVI if: You want an easy, activity-filled week where you can see a lot without traveling very far.

The Bahamas: Abacos & Exumas — It's All About the Water

Best for: Water-toy lovers, superyachts, incredible beaches, fishing, shallow turquoise water, privacy and guests who want to spend most of their charter on or in the water.

The Bahamas can look deceptively similar to the BVI in photographs.

Turquoise water? Check. White beaches? Absolutely. Lots of islands? More than 700!

But the actual charter experience is very different.

In the Exumas, the water itself is the destination. This is where I would send someone who says: "Give me the yacht, the water toys, an incredible crew, a phenomenal chef, deserted beaches and the most ridiculous blue water you've ever seen."

The Exumas are particularly spectacular for larger motor yachts and superyachts carrying extensive toy inventories. Depending on the yacht, that could mean jet skis, Seabobs, e-foils, inflatable slides, floating beach clubs, paddleboards, kayaks, wakeboards, towables and more.

Unlike the BVI, jet skis can be used in the Bahamas — and some yachts have multiple on board!

Why I prefer the Bahamas for a full-week charter

One of the most important things people don't realize about an Exumas charter is that you generally aren't stepping off a plane in Nassau and immediately cruising among the famous Exuma cays.

You have to get from Nassau to the Exumas, and depending on the yacht, weather, cruising speed and exact destination, getting from Nassau toward the Exumas can mean approximately five to eight hours underway.

That matters especially on a charter less than 5 nights, because you are spending a significant portion of your first and last day repositioning — which doesn't make much sense on a 3 or 4 night charter. For shorter Bahamas charters, we may recommend staying closer to Nassau, Paradise Island, Rose Island and nearby cays instead.

For an Exumas itinerary, I generally suggest having a full week so you have time to get out there and actually enjoy it.

What do you do in the Exumas?

This isn't necessarily the destination where you're going ashore every night to choose between 15 restaurants. You might visit the swimming pigs, see nurse sharks, stop at a yacht club, have lunch at one of the handful of well-known restaurants or explore a small settlement.

But much of the magic happens away from developed areas: deserted sandbars, beach picnics set up by your crew, snorkeling, diving, fishing, tender explorations, jet skis, Seabobs, and floating behind the yacht in water so clear you can see the bottom — beaches where your footprints may be the only ones in the sand.

Fishing in the Bahamas

For guests who love fishing, the Bahamas can be particularly attractive. Depending on where you're cruising, the season and applicable fishing regulations, opportunities can include reef fishing, deep-sea fishing and other styles of sport fishing.

Tell your broker in advance if fishing is important, because yacht equipment and captain experience/interest varies.

What is the water like?

The protected waters within the Exuma chain can be extraordinarily calm and shallow, but getting there from Nassau may involve crossing more exposed water.

This is another reason yacht selection matters. A fast motor yacht may handle the Nassau-to-Exumas transition very differently than a slower yacht.

Choose the Bahamas if: The yacht and the water are the vacation. You want incredible toys, fishing, beaches, privacy and long days outside rather than an itinerary centered around sightseeing and nightlife.

The Leeward Islands: St. Martin, Anguilla & St. Barths

Best for: Foodies, nightlife, shopping, beach clubs, luxury travelers and guests who want to combine yachting with a sophisticated shoreside experience.

The Leeward Islands is the opposite experience compared to the Exumas. Here, you can combine beautiful Caribbean anchorages with some of the region's best dining, shopping and nightlife.

A popular charter can combine St. Martin/Sint Maarten, Anguilla and St. Barths, and each feels completely different. St. Martin gives you French and Dutch influences, restaurants, beaches and easy international access.

Anguilla is known for spectacular beaches, resorts and a more laid-back atmosphere.

Then there is St. Barths. For guests who want designer shopping, beautiful restaurants, beach clubs, nightlife and superyacht energy, St. Barths is difficult to beat.

You can spend the morning swimming off the yacht, have lunch at a beach club, shop in Gustavia and be back aboard for sunset cocktails — a very different Caribbean vacation from anchoring beside an uninhabited cay in the Exumas.

What is the water like in the Leewards?

This itinerary can involve more exposed passages between islands than a BVI itinerary. The trade winds and Atlantic swells can create rougher conditions, particularly on certain crossings and at certain times of year.

If anyone in your group is especially sensitive to motion, tell your broker. We can look carefully at yacht type, stabilizers underway and an itinerary that makes sense.

Water toys

The Leewards can be great for water toys, although rules vary by island and jurisdiction. Because you're potentially moving between French, Dutch, British and independent territories, your crew will determine where specific toys can legally and safely be used.

Choose the Leewards if: You want Caribbean water and beaches but don't want to give up restaurants, shopping, beach clubs and nightlife.

The Windward Islands: For Adventure and Dramatic Scenery

Best for: Experienced charterers, nature lovers, adventurous travelers, dramatic scenery, culture, diving and guests who want to venture farther off the traditional Caribbean charter circuit.

As you move farther south through islands such as Martinique, St. Lucia, St. Vincent and the Grenadines and Grenada, the Caribbean begins to feel very different.

This isn't just about beaches. You'll find volcanic landscapes, rainforests, waterfalls, historic communities, hiking and some of the Caribbean's most dramatic scenery.

St. Lucia's Pitons, for example, are part of a UNESCO World Heritage Site and create one of the most recognizable landscapes in the Caribbean.

Farther south, the Grenadines offer a wonderful combination of inhabited islands and remote anchorages. You can visit places such as St. Lucia, Bequia, Mustique, Canouan, Mayreau and the Tobago Cays.

The Tobago Cays are particularly spectacular for snorkeling, turtles and clear water. This is where the yacht becomes a way of reaching places that aren't always easy for traditional tourists to access.

The trade-off: longer and potentially rougher passages

The Windwards aren't as geographically compact as the BVI. You may travel farther between islands, and some passages cross more exposed Caribbean or Atlantic waters.

The trade winds can make certain passages lively. For guests who love cruising and adventure, that's part of the experience. For someone who wants to move ten minutes each morning and anchor again, it may not be.

More than beaches

This is also one of my favorite regions for clients who tell me they don't want to spend seven days simply sitting on beaches.

You can incorporate hiking, waterfalls, local markets, historic sites, villages, restaurants, snorkeling, diving and cultural experiences.

Choose the Windwards if: You want your yacht charter to feel like an adventure and you're willing to travel farther between destinations to experience dramatic landscapes, culture and more remote islands.

Which Caribbean Destination Has the Best Scuba Diving?

You can dive throughout the Caribbean, but the experience varies significantly.

The BVI is particularly convenient because good snorkeling and diving can easily be incorporated into an island-hopping itinerary.

The Windwards and Grenadines can also offer excellent diving with reefs, walls, marine life and volcanic underwater landscapes. The Bahamas offers fantastic diving as well, including reefs, walls, wrecks and shark encounters, depending on the area. The Leeward Islands offer a little bit of everything, from water experiences and activities to dining, beach clubs and shopping.

But there is another important question: Does your yacht actually offer scuba diving? Not every charter yacht does.

Some yachts have dive instructors aboard and carry tanks, compressors and full equipment. Others offer rendezvous diving, where a local dive operator meets the yacht.

If scuba is one of the main reasons you're chartering, tell us before we choose the yacht rather than after. You can learn more about the best dive destinations.

Which Caribbean Destination Is Best for Water Toys?

If you want to build your vacation around the yacht's toy garage, I'd look particularly closely at the Bahamas. The shallow, clear water and enormous superyacht inventory make it an incredible playground.

The Leewards and Windwards can also be excellent, but local regulations change as you move between jurisdictions. The BVI is fantastic for almost every water activity except jet skis, which are prohibited.

And remember: the yacht matters just as much as the destination. One yacht might have two jet skis, four Seabobs, e-foils, a slide and a huge inflatable platform. The yacht anchored beside it might have two paddleboards and a kayak. That's why we don't choose yachts based on photos alone.

Which Destination Lets You See the Most?

If your goal is to wake up somewhere different every morning, the BVI is hard to beat. You can cover numerous islands without spending your vacation underway.

The Leewards also work well for multi-island itineraries, but the passages can be longer and more exposed.

In the Windwards, you're generally covering greater distances as you travel down the island chain. The reward is dramatically different scenery and culture as you go.

In the Exumas, you're technically surrounded by an enormous number of cays, but the experience isn't necessarily about checking islands off a list. It's about discovering anchorages, sandbars, beaches and stretches of water that feel completely removed from civilization.

Which Destination Is Easiest to Reach?

This is something people often forget to consider when choosing a yacht charter destination.

The BVI usually requires flying into either the British Virgin Islands or a nearby Caribbean gateway and potentially connecting by ferry or private transfer depending on your arrival plan.

For the Bahamas, Nassau is extremely accessible from many U.S. gateways, which makes reaching your embarkation point relatively easy. The trade-off is that the Exumas themselves are farther from Nassau by yacht.

St. Martin is one of the most convenient gateways for a Leeward Islands charter because its international airport makes it relatively easy to begin an itinerary encompassing St. Martin, Anguilla and St. Barths.

Windward itineraries require more planning. Where you fly depends heavily on where the charter begins and ends, and one-way itineraries can sometimes make the most sense.

This is why we look at the entire trip, not simply the yacht. Sometimes the yacht that appears perfect creates terrible flight logistics. Another yacht may allow you to spend an extra half-day actually enjoying your vacation.

Quick Caribbean Yacht Charter Comparison

So Where Should You Charter?

Here's the simplest way I explain it to clients.

Choose the BVI if you want easy cruising, a different island every day, snorkeling, diving and lots of things to do without spending hours underway.

Choose the Bahamas and Exumas if your dream vacation revolves around the yacht itself: incredible water toys, deserted beaches, fishing, sandbars, beach picnics and spending almost every waking hour on or in impossibly blue water.

Choose the Leeward Islands if you want to combine yachting with great restaurants, beach clubs, shopping and nightlife, especially if St. Barths is on your bucket list.

Choose the Windward Islands if you want adventure, dramatic scenery, culture, UNESCO sites, diving and more remote destinations and don't mind longer passages to get there.

And if you're still not sure? That's exactly why working with a yacht charter broker matters. At Sanderson Yachting, we don't start by asking which yacht you like best. We start by asking how you want to spend your vacation.

Then we match the destination, itinerary, yacht and crew to that experience, because the right yacht in the wrong destination can still be the wrong vacation.