Caribbean Sailing Guide 2025

Sailing in the Caribbean is a dream for many – and for good reason. This region consists of over 700 islands, each with its own character and charm. Constant trade winds, warm turquoise waters, and countless idyllic coves make it a sailor’s paradise. In this 2025 Caribbean Sailing Guide, we’ll cover everything you need to know: when to go, what to sail, costs (from charter prices to food and marina fees), and highlights of the top island destinations.

Why Sail the Caribbean in 2025?

The Caribbean offers exceptional sailing with a bit of everything. Steady warm weather, consistent breezes, and beautiful island scenery greet you on each voyage. You can explore white, golden, or even black-sand beaches, vibrant coral reefs teeming with marine life, and unique cultures on every island. Variety is a huge draw – from the calm, family-friendly bays of the north to the more challenging open-water passages in the south, there’s something for every sailing style. After a few quiet years, 2025 finds the Caribbean sailing scene in full swing again, with marinas and charter companies eagerly welcoming sailors.

Americans will also feel right at home here: English is widely spoken across most islands (with Spanish, French, or Creole on some, but tourism areas are very English-friendly), and U.S. dollars are accepted in many destinations or easily exchanged.
Highlights of Caribbean Sailing include constant tradewinds (no engine droning for hours!), short island hops or longer blue-water stretches as you prefer, warm seas perfect for swimming and snorkelling, and the chance to enjoy local music, food, and rum punch in port each night. Once you experience a Caribbean cruise, you’ll understand why many sailors keep coming back season after season.

When Is the Best Time to Sail in the Caribbean?

Winter and spring (December–May) are the prime sailing season in the Caribbean. The weather is warm but not sweltering, and the trade winds blow reliably from the northeast at moderate strength – perfect sailing conditions. The peak months of February to May promise steady winds of ~15 knots, low humidity, and very little rain. By contrast, June through November is the off-season, bringing a higher risk of tropical storms and hurricanes (particularly August–October). Most charter companies shut down during the height of hurricane season. If you do sail in early summer, keep an eye on weather forecasts and consider trip insurance for storm disruptions.

North American holiday timing tip: Early winter (December) can bring the occasional stronger “Christmas winds,” and the weeks around Christmas and New Year’s are extremely popular. It’s a festive time to be in the islands, but you’ll need to book boats and berths well in advance (and expect peak pricing). Many Americans also plan Caribbean charters around school breaks or Thanksgiving; just remember that late November is still the tail end of hurricane season, so weather can be a bit more variable.

Weather & Sailing Conditions in the Caribbean

Trade Winds & Seas: Throughout the season, the Caribbean’s prevailing trade winds blow from the NE or E, providing a consistent push for sailors. These winds are predictable – you won’t often be caught by sudden shifts or gales. Sea conditions vary by area: the Leeward Islands (e.g. BVI, USVI, St. Martin) are relatively sheltered with calmer seas, whereas the Windward Islands (Martinique, St. Lucia, St. Vincent & Grenadines, etc.) see more open Atlantic exposure with bigger swells and brisk winds. If you prefer gentle sailing and short island hops, stick to the northern Leewards; for more sporty sailing with longer passages, the southern routes offer excitement.

Navigation: Many Caribbean islands are surrounded by coral reefs and shallow areas, so eyes-on navigation is important. Even with GPS, you’ll want a crew member on lookout at the bow when entering unfamiliar anchorages – not every reef or rock is marked on charts. Fortunately, most popular areas have well-charted passages and even clearly indicated channels or anchoring spots. Mooring buoys are widely used in marine parks and busy bays (more on that later), simplifying anchoring in tricky spots. Tides are modest (often under 1–2 feet except in certain channels), but be mindful of currents in narrow straits like between islands. Overall, sailing conditions are friendly, especially during the winter months: consistent wind, plenty of daylight, and predictably sunny, warm weather (with occasional brief rain showers to cool things off).

Choosing Your Boat in the Caribbean (Monohull vs Catamaran)

One of the biggest decisions for a Caribbean charter is the type of boat. While both monohulls and catamarans are available, the catamaran reigns supreme in these waters for good reason. Catamarans offer a shallow draft, letting you anchor closer to beaches and venture into lagoons that deeper-keel boats can’t reach. They also provide a stable platform (less heeling and rolling) – great for newcomers or families – and ample deck and cabin space to spread out in the tropical heat. Picture yourself lounging on the wide netting between the hulls, drink in hand, as you glide over crystal-clear water… It’s no wonder cats are popular!

That said, monohull sailboats have their own appeal. They tend to be cheaper to charter and give a more “classic” sailing experience (heeling over in the breeze). Skilled sailors might enjoy the monohull’s responsiveness and upwind performance. But if comfort and easy living are your priority, you’ll appreciate why the catamaran is considered the ideal vessel for Caribbean waters. Many charter companies – including Boataround’s partners – offer a wide range of modern catamarans, from around 38 feet up to 50+ feet, often equipped with AC and watermakers to keep you cool and hydrated. In 2025, 4-cabin catamarans (perfect for 8 people) are the most sought-after boats for groups and families in the Caribbean.

Boataround Tip: Book early if you want a catamaran during peak season – they get reserved fast by repeat customers. If none are available (or within budget), a mid-size monohull (35–45ft) can still be a wonderful way to explore, especially for smaller crews or those who relish true sailing over maximum comfort.

Costs of Sailing in the Caribbean

Sailing the Caribbean is incredibly rewarding, but it does come with costs that you should budget for. Below, we break down the main expenses: charter prices, provisioning (food & drink), and mooring/marina fees. Knowing what to expect will help you plan a fun trip without any unpleasant surprises for your wallet!

Charter and Travel Costs

Boat Charter Prices: The cost to rent a yacht in the Caribbean varies by boat type, size, and season. As a ballpark, a modern 40-foot catamaran might cost around $7,000–$10,000 per week in high season, which often works out to roughly $1000 per person for a two-week trip if you fill all the berths. Monohulls are cheaper – you might find a 40’ monohull for ~$3,000–$5,000 a week in high season. Prices can drop 20-30% in the low (hurricane) season or for last-minute deals, but most sailors stick to peak months for the best weather. One-way charters (starting in one island, ending in another) sometimes incur extra fees, but can be worth it to see more islands in one go.

Flights: Airfare is another significant expense. The good news is the Caribbean is well connected in 2025. For American travelers, direct flights to hubs like St. Thomas (USVI), Sint Maarten (Dutch side of St. Martin), or Antigua are available from major East Coast airports. Major U.S. gateways like Miami, New York, Atlanta, and Charlotte offer frequent nonstop flights to these Caribbean hubs, making it easy to reach paradise from the mainland. Prices range widely (approx $300–$700 round-trip from the US, depending on origin and season). European sailors often fly to Martinique or Guadeloupe (via Paris) or to St. Martin, with typical fares around $700–$1000 from Europe in high season. If you’re chartering in the British Virgin Islands, note there’s no big international airport there – you’ll likely fly into St. Thomas (USVI) or San Juan (Puerto Rico) and take a ferry or puddle-jumper flight to Tortola. Always factor in transfer times and possible overnight stays on land when planning your itinerary start and end. Other Travel Costs: Don’t forget to budget for travel insurance (especially during hurricane months), and any entry fees or visas. Many Caribbean nations are fairly easy: US, Canadian, and EU citizens get visa-free or visa-on-arrival entry to most islands. Customs & cruising fees, however, may apply for charterers. For example, if you sail from the USVI into the BVI, you’ll pay various BVI fees – roughly $20–$40 per person for entry/exit plus a daily cruising tax (currently $16 per person per day in the BVI during high season). French islands (like Martinique, an EU territory) have no visa requirement for EU or US visitors and no entry fee, making them convenient bases. Always check the latest regulations for the specific islands on your route, as fees can change year to year. U.S. citizens should remember that a valid passport is required to fly to most Caribbean destinations (with at least 6 months’ validity recommended), since these are international locations. The U.S. Virgin Islands are an exception – Americans do not need a passport to visit the USVI, but if your itinerary includes the neighboring BVI or other nations, everyone in your crew will need a passport for customs clearance. Skipper’s License: The good news for American charterers is that unlike in Europe, most Caribbean countries do not mandate an official sailing license for bareboat charters. Charter companies will still require a sailing résumé and proof of experience (and they often prefer ASA or US Sailing certifications) to ensure you can safely handle the yacht. If you plan to charter from a French territory like Martinique or Guadeloupe, having an International Certificate of Competence (ICC) or ASA’s International Proficiency Certificate can smooth the process, though it’s usually not a legal requirement in the region.

Provisioning (Food & Drinks)

One great aspect of a sailing vacation is that you can self-cater on board, which helps control costs. Groceries in the Caribbean tend to be pricier than back home, since many items are imported. A common budgeting guideline from charter companies is about $25–$35 per person per day for food if you plan to eat all meals on the boat. This figure includes basics like breakfast, picnic lunches, snacks, and simple dinners aboard (often with some fresh-caught fish – yes, you should bring a fishing rod!). If you’ll mix in restaurant meals on shore, you can provision a bit less; for instance, doing half your dinners ashore might bring provisioning costs down to ~$20/day per person.

Here are a few provisioning tips and facts:

• Stock up on major islands: Prices and availability vary between islands by as much as 200–300%. Large islands like St. Martin, Martinique, or Tortola (BVI) have big supermarkets (e.g. Super U, Carrefour, RiteWay) with better prices and selection. It’s wise to do a big shop at your departure base. In smaller islands (say, Anegada or Bequia), fresh produce might be limited and more expensive.

• Local markets: Don’t miss the local island markets and roadside stands. You can often get tropical fruits, veggies, and fresh bread at reasonable prices. In the French islands, you’ll find baguettes and pastries in even small villages! Martinique in particular “keeps European standards with bakeries and pharmacies on every corner” – your croissant and espresso are never far away.

• Dining out: Restaurants in the Caribbean range from beachside BBQ shacks to upscale dining. In general, French islands have restaurant prices similar to Europe in summer– expect maybe $15 for a lunch plat du jour or $25+ for dinner. In tourist-heavy spots (e.g. St. Barth’s or parts of the BVI), dinner entrees can hit $30–$50 at nicer establishments. Many sailors split their time: cook on board most days and splurge on a few special nights out (perhaps a lobster dinner in Anegada or Creole cuisine in Guadeloupe). Drinks in bars (the ubiquitous rum punch, local beers) will run ~$5-10 each. Keep an eye out for happy hours!

• Provisioning services: If you don’t want to spend vacation time in a grocery store, most charter bases offer online provisioning where you order in advance and have the boat pre-stocked. For example, in the BVI you can order via RiteWay or One Mart online and have it delivered to your yacht. This convenience can be a lifesaver for late arrivals, though the downside is you might not get to hand-pick produce or meats.

Finally, water: Plan to buy drinking water (bottled or in jugs) unless your boat has a watermaker. Tap water is generally safe at marinas but often has a taste. The tropical sun is dehydrating, so budget for plenty of drinking water or juices. And perhaps allocate part of your budget to the essential sailor’s treat – a few bottles of the local Caribbean rum (Martinique’s agricole rums or perhaps some Mount Gay from Barbados) to enjoy sundowners in the cockpit!

Marinas, Moorings & Anchoring Fees

Mooring Balls: In many popular bays, especially in the British Virgin Islands and USVI, you’ll find mooring buoys available for overnight use. These save you the trouble of anchoring and protect reefs from anchor damage. Overnight mooring fees are typically around $30–$40 per night for first-come-first-serve balls, and about $55 per night for reservable moorings in high-demand spots. For instance, the BoatyBall reservation system in the BVI lets you pre-book a mooring for $55, whereas if you just sail in and pick up an open mooring, you’ll often pay ~$30 cash to the local operator. Always check the colour codes or labels on moorings – some are privately owned or day-use only. The National Parks moorings (like those at dive sites or parks) are usually free for day stops, or they may have a nominal fee or require a park permit (e.g. the USVI park moorings around St. John cost $26 per night, payable via self-service). If all moorings are taken, you can always anchor if the bay allows – just be sure to stay clear of coral. Anchoring itself is free nearly everywhere, but some islands (e.g. Bonaire) forbid anchoring to protect reefs, so you must use moorings.

Marina Dockage: Spending an occasional night in a marina is a nice way to recharge (literally, to plug into shore power and fill water tanks) and explore towns. Marina fees in the Caribbean are usually charged by the foot (or meter) of your boat. Typical rates range from about $0.50 to $2.00 per foot per night, depending on the island and the marina’s facilities. In the Eastern Caribbean, a common rate is around $1 per foot per day at mid-range marinas. Upscale marinas or prime locations (say, a luxury marina in St. Thomas or St. Martin) can be 2-3 times higher. For a 40-ft catamaran, expect roughly $40–$80 per night in a typical marina, or more like $120+ at high-end spots or during special events. Note that marinas will also charge for water, electricity, and sometimes a nightly service fee. As an example, Leverick Bay Marina in Virgin Gorda (BVI) lists moorings at $40/night and dock slips around $1.50/ft (so ~$60 for a 40-ft boat), with water and ice available for purchase. Over in St. Maarten, weekly dock rates might be around $12/foot/week (which is ~$1.70/ft/day), giving discounts for longer stays.

Most cruising sailors don’t stay in marinas every night – you might plan for one marina night every 4–5 days to refresh. If you’re on a tight budget, you can actually avoid marinas altogether by using anchorages and the occasional paid mooring, and visit ports/towns via dinghy. “On the hook” (at anchor) is free and offers that unbeatable tranquillity of a starlit bay. Just balance it with your crew’s comfort needs (water, showers, Wi-Fi). Marina reservations are recommended in peak season, especially in places like Christmas in the BVI or regatta weeks.

Other Fees: A few miscellaneous costs to note: If sailing the BVI, you’ll need a National Parks Permit (cost depends on boat size/people, roughly $50–$150 per charter) to use the park moorings (like at The Baths or dives like the Rhone wreck). Many charter companies will arrange this in advance. The Bahamas (if your cruising takes you there) charges an upfront cruising permit fee ($150 for boats under 35ft, $300 for larger, covering customs for crew). Fuel for your yacht is another cost, though sailboats don’t consume much – maybe $100–$150 to refill diesel after a week if you motored a lot. Tipping is customary if you have a paid crew or have hired a skipper (15–20% of the charter fee is standard for crewed charters). For bareboaters, tips might come into play with dockhands or for exceptional service (a few dollars to the helpful marina attendant, for example). Finally, keep some cash on hand in small bills (USD is widely accepted in most of the Caribbean) for things like ice, trash disposal fees, or cute local mooring fields run by enterprising locals.

Top Caribbean Sailing Destinations

One of the joys of Caribbean sailing is island-hopping – you can experience several distinct islands even on a one-week charter. Below, we spotlight four of the most popular sailing areas (BVI, USVI, St. Martin, and Martinique), followed by a quick look at other notable islands. Each destination has its own flavour, attractions, and sailing conditions, so you can choose what suits your crew best (or better yet, plan multiple trips!). We’ve also included links to detailed itineraries and guides where available, so you can dive deeper into route planning for each area.

British Virgin Islands (BVI) – Easy & Idyllic

• Calm, protected sailing: The BVI are a sailor’s haven often called the world’s sailing capital. With short, line-of-sight hops between islands and year-round warm trade winds, this is an ideal spot for beginners and families. The seas are generally gentle here thanks to the protection of islands and reefs.
  
  Compare fleets here: BVI Yacht Charters

• 50+ islands to explore: Four main islands (Tortola, Virgin Gorda, Jost Van Dyke, Anegada) and countless smaller cays offer endless itinerary options. You’re never far from a picture-perfect bay or snorkel stop. Highlights include The Baths (giant boulders and grottos on Virgin Gorda), the shipwreck of RMS Rhone (a famous dive site), and White Bay on Jost Van Dyke – home of the Soggy Dollar Bar (where the Painkiller cocktail was invented 🍹).

• Lively beach bars & chill vibe: BVI mixes laid-back island culture with fun social spots for sailors. Spend days swimming and snorkelling vibrant coral reefs, then dinghy ashore to a beach bar for fresh seafood and reggae music at night. Don’t miss the floating bar “Willy T” at Norman Island for a one-of-a-kind party scene. Despite the popularity, the BVI remain safe, friendly, and relatively unspoiled – there’s a reason sailors return year after year.
  
  

  Beneteau Oceanis 31 | Chilli

  British Virgin Islands, Ritter Marina

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  Beneteau Oceanis 41.1 | Syrma

  6 OK  |  1 Review

  British Virgin Islands, Hodge's Creek Marina

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  Beneteau Oceanis 35 | Big Blue

  British Virgin Islands, Ritter Marina

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Boataround TIP: Check out our 7-day BVI sailing itinerary for a day-by-day plan hitting all the iconic spots. With its gentle conditions and gorgeous scenery, the BVI is often the first Caribbean adventure for new charterers – and an unforgettable one.

U.S. Virgin Islands (USVI) – National Parks & Island Culture

• St. Thomas, St. John, St. Croix: The USVI (just east of Puerto Rico) are a convenient tropical escape, especially for Americans (no passport needed for US citizens to visit). St. Thomas is the bustling hub with a major airport and cruise port, but also rich in history – walk the 99 Steps to Blackbeard’s Castle or explore 17th-century forts in Charlotte Amalie. It’s also known for duty-free shopping and a lively harbour scene. 

  Compare fleets here: USVI Yachts Charters

• Natural beauty in St. John: Sail a short hop to St. John, where 60% of the island is protected as a National Park. You’ll find pristine beaches (Trunk Bay, Cinnamon Bay) and calm mooring fields with turquoise water – perfect for swimming, paddle-boarding, and turtle-spotting. Hiking trails through tropical forests lead to the ruins of sugar mills. The vibe in St. John is quiet and nature-focused (no big resorts or towns, just a few beach bars in Cruz Bay and Coral Bay).
   

• Culture & festivities: The USVI host vibrant cultural events – if you’re around in spring, don’t miss the Carnival on St. Thomas (April–May), the second most popular Caribbean carnival after Trinidad. Colourful parades, calypso music, and delicious street food bring the island to life. Each USVI island has its own character: St. Thomas is energetic, St. John is low-key and wild, and St. Croix (further south, often a separate trip) offers a blend of history, diving, and rum distilleries. Sailing in the USVI is typically within US waters, so you won’t have customs formalities if you stick to these islands – a plus for an easy charter.
   

  Midnight Express 37 | Valkyrie

  U.S. Virgin Islands, Compass Point Marina

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  U.S. Virgin Islands, Frenchtown Harbour Marina

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Boataround Tip: Many charters from the USVI also visit the neighbouring BVI (they’re just a few miles apart). If you plan to do this, remember you’ll need to clear out/in with customs. Otherwise, you can enjoy a full USVI loop. St. Thomas has great marinas and nightlife, while St. John gives you those tranquil park anchorages – the mix makes for a fantastic week. (Boats for charter in the USVI can be found via our site – start from St. Thomas and let the trade winds take you on a U.S. flag island adventure.)

Saint Martin / Sint Maarten – A Two-Nation Sailing Playground

• Dual culture island: St. Martin is famously split into two territories – the northern Saint-Martin (French) and southern Sint Maarten (Dutch). This gives the island a vibrant mix of cultures and cuisines. In French St. Martin, you’ll find chic boutiques, boulangeries, and cafes in places like Marigot (the French capital) – it’s like a slice of France in the tropics. Dutch St. Maarten (capital Philipsburg) offers lively beach bars, casinos, and a cosmopolitan port frequented by cruise ships. The ease of hopping between two countries on one island is part of the fun (no border formalities – you likely won’t even notice when you cross over).

• Sailing & anchorages: St. Martin is often called the “gateway to the Eastern Caribbean.” Many sailors start here because it’s a convenient flight hub and has huge marinas/charter bases (with lots of services for yachts). If you’re comparing fleets, see Yachts in Saint Martin and Yachts in Sint Maarten. The island itself has great anchorages: Simpson Bay (Dutch side) is a large, well-protected lagoon – you can sail under the lifting bridge to enter; Marigot Bay (French side) is another popular anchorage with a European vibe ashore. From St. Martin, it’s easy to take side trips to Anguilla (calm, pristine beaches) or St. Barthélemy (St. Barts) for a taste of luxury. St. Martin’s central location means you can also head south toward Antigua or north to the BVIs on longer voyages.

• Island highlights: Don’t miss Maho Beach, adjacent to Princess Juliana Airport, where gigantic jets roar just overhead as they land – a spectacular (and slightly crazy) sight. For the adventurous, the island boasts the world’s steepest zipline (the Flying Dutchman) and plenty of water sports. If you’re a foodie, you’ll love Grand Case on the French side, known as the gourmet capital of the Caribbean for its fine dining and local “lolo” barbecue joints. St. Martin also has a lively nightlife scene (beach clubs, live music, and yes, a casino or two on the Dutch side). Despite being hit hard by Hurricane Irma in 2017, the island has rebuilt significantly – sailing facilities are fully operational, though you might still see some remnants of the storm here and there.

Jeanneau Sun Loft 47 | Galdor

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Excess 11 | Hegoak

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Overall, St. Martin offers a perfect blend: reliable sailing conditions, lots of nearby islands to explore, and a unique mix of laid-back Caribbean atmosphere with a European twist. (If you plan a trip here, see our St. Martin yacht charter deals and consider a loop including Anguilla and St. Barts for an unforgettable itinerary.)

Martinique – French Flair in the Windwards

• Exotic yet familiar: Martinique is a stunning island that manages to feel like a tropical France. As a French overseas region, it uses the euro and upholds high standards in infrastructure – you’ll find excellent marinas, well-stocked supermarkets, and even Parisian-style boulangeries – all wrapped in lush Caribbean scenery. They call it the “Island of Flowers,” and indeed the landscape is green and dramatic, from rainforest-covered mountains to sugarcane fields and black-sand northern beaches.

• Adventurous sailing: Located in the Windward Islands, Martinique offers more challenging sailing than the gentle BVIs. Passages can be sporty, with brisk trade winds and bigger Atlantic swells, especially on the windward (eastern) side and in channels between islands. This makes it great for those seeking an active sailing experience – you can do longer open-water legs to Dominica northward or St. Lucia southward. Within Martinique’s leeward coast, however, you’ll find plenty of sheltered bays for easier cruising. The main yachting hub is Le Marin in the south, a large marina and charter base for Yachts in Martinique from which most itineraries start.

• Don’t miss experiences: Sail along Martinique’s west coast to visit Anses d’Arlet, a postcard-perfect village with a church right on the beach, or Fort-de-France Bay, one of the safest natural harbours in the world, guarded by an old fort. In the south, Saint-Anne and Les Salines beach offer that quintessential Caribbean paradise feel. Up north, if conditions allow, you can see Mont Pelée, the island’s volcano, and explore black-sand coves. Martinique is also famed for its rum – be sure to tour a distillery (the island produces some of the finest rhum agricole). And foodies will rejoice at the blend of French and Creole cuisine: fresh baguettes and croissants in the morning, accras (cod fritters) and Colombo curry for dinner!
   

  Beneteau First 30 | Ica

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  Martinique, Marina du Marin

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Boataround TIP: Martinique’s mix of European comfort and Caribbean spice makes it a fantastic destination, especially for sailors coming from Europe (daily direct flights from Paris make access easy). It’s also a great jumping-off point to explore the Windward chain. (For a detailed sailing plan, see our Martinique 7-day itinerary, which includes a route to Dominica and back. Martinique truly offers a bit of everything – just be ready for real sailing in real wind!)

Other Notable Islands & Routes

The Caribbean is vast, and part of the allure is that you’ll never run out of places to discover. Once you’ve hit the “big names” above, consider these other sailing gems:

• Antigua & Barbuda – Antigua boasts 365 beaches (one for every day of the year!) and a rich sailing heritage. It’s home to famous regattas (Antigua Sailing Week) and historic Nelson’s Dockyard. Barbuda, its sister island, offers pink-sand beaches and ultra-secluded anchorages. 

• St. Lucia – With its twin Pitons peaks rising from the sea and lush rainforests, St. Lucia is one of the most dramatically beautiful islands. It has upscale marina facilities in Rodney Bay and Marigot Bay, and natural wonders like waterfalls, hot springs, and a “drive-in” volcano to visit. Great stop on a southward Windward Islands itinerary. 

• St. Vincent & The Grenadines – This chain of islands south of St. Lucia is a sailor’s paradise. From the main island, St. Vincent, down through Bequia, Mustique, Canouan, Mayreau, Union and Petit St. Vincent, you’ll encounter quaint fishing villages and unreal turquoise lagoons. Don’t miss the Tobago Cays, an uninhabited marine park of reef islands where you can swim with turtles in a perfectly clear lagoon. The Grenadines offer more off-the-beaten-path cruising and are often the highlight of a one-way charter from Martinique or St. Lucia down to Grenada. 

• Grenada – The “Spice Island” at the southern end of the chain, known for its nutmeg and cocoa, as well as friendly locals. Grenada has become a popular charter base itself. It offers a lovely mix of protected bays on the south coast and adventurous sailing around its satellite islands. Divers will love the underwater sculpture park and wrecks, while others might enjoy the chocolate factories and waterfalls inland. Grenada is also safely below the hurricane belt (for insurance purposes), making it a common spot to keep boats in summer.

• The Bahamas – Though geographically separate (in the Atlantic, north of Cuba), the Bahamas are often included in Caribbean charter talk because of their popularity, especially with North American sailors. The Bahamas offer very shallow, gin-clear waters and thousands of cays to explore, but require careful navigation (shallows everywhere!). They’re ideal for shallow-draft cats. Key areas include the Exumas, Abacos, and Eleuthera. If you crave sandbars, swimming pigs, and watercolours you won’t believe, put the Bahamas on your list for a future trip! 

And that’s just the start – other honorable mentions: Dominica (untouched natural beauty, rainforests and rivers), Guadeloupe (another French island with fantastic food and diverse landscapes), the Turks & Caicos (remote, great diving), and the ABC Islands (Aruba, Bonaire, Curaçao) down near South America (outside the hurricane zone, with world-class diving and windsurfing, though more limited cruising grounds). Every island in the Caribbean has its story, so wherever you sail, you’re sure to find unique treasures.

Key Takeaways: Final Tips for Sailing the Caribbean

• Plan but stay flexible: Itineraries are great, but be ready to adjust based on weather or whims. The Caribbean ethos is “no hurry, no worry.” Perhaps the best advice is to take it slow and savour each destination rather than trying to tick off too many islands. Remember that the Caribbean is meant to be explored “slowly and several times” – you’ll likely be back for more!

• Safety: The sailing itself is straightforward in most of the Caribbean, but always practice good seamanship – keep an eye on the weather (especially if a northerly swell or squall line is forecast), and don’t be shy about reefing the sails at night or in squalls. Ashore, most islands are very welcoming; normal travel common sense applies. Lock your dinghy, don’t leave valuables unattended on the beach, and enjoy the warm hospitality of the locals.

• Booking & Resources: 2025 is gearing up to be a busy charter year, so reserve your boat early for peak dates. Boataround’s platform lets you compare hundreds of yachts in the Caribbean and find the best deals – whether you’re after a luxe catamaran or a budget-friendly monohull. It’s also wise to book any necessary marina slips ahead during holiday weeks.

So, have we convinced you to set sail for the Caribbean?

Beneteau Oceanis 31 | Chilli

Caribbean, Ritter Marina

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Beneteau First 30 | Ica

4 Poor  |  1 Review

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Caribbean, Port de pêche du François

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