Best Caribbean Islands for Sailing: An Honest Comparison

Choosing where to sail in the Caribbean is one of the best problems a sailor can have. The islands are close together, the trade winds are reliable, the water is warm, and every island offers something different. But “best” depends entirely on what you care about. A sailor looking for protected anchorages and easy navigation will choose differently from one who wants challenging offshore passages. A boat on a tight budget will prioritise different islands than a superyacht looking for nightlife and restaurants.

This comparison covers ten of the most popular Eastern Caribbean islands for cruising sailors. Each one is assessed on six factors that matter most when you are actually on a boat: ease of clearance, marina cost, provisioning quality, safety, walkability from the marina, and the quality of the sailing itself. St Kitts and Port Zante Marina are included because the island sits at the centre of the Leeward chain and offers a combination of practical features that many sailors overlook.

How This Comparison Works

Each island is assessed on six criteria, rated from strong to weak. This is not a scientific ranking. It is based on published marina rates, clearance procedures documented by official sources and cruising guides, and the reported experiences of cruisers who have sailed these islands. No island is best at everything. The point is to help you decide where to spend your time based on what matters to you.

British Virgin Islands

The BVI is the most popular charter destination in the Caribbean and for good reason. The islands are close together (most passages are under 10 nautical miles), the waters are protected, the anchorages are well-charted, and mooring buoys are available almost everywhere. Navigation is easy enough for beginners. The Baths at Virgin Gorda, the caves at Norman Island, and the beach bars of Jost Van Dyke are iconic Caribbean experiences.

The downsides are cost and crowding. Cruising permits start at US$55 for the first visit and can reach US$200 or more for extended stays. Mooring buoys cost US$25 to US$35 per night. Provisioning is expensive and limited compared to larger islands. During peak season (December to April), popular anchorages like the Bight at Norman Island and White Bay at Jost Van Dyke can be packed stern to stern. If you are sailing your own boat rather than chartering, the BVI is beautiful but expensive.

Antigua

Antigua is a serious sailing island. English Harbour and Nelson’s Dockyard are steeped in maritime history, and the island hosts Antigua Sailing Week, one of the premier regattas in the Caribbean. There are multiple marinas: Nelson’s Dockyard in English Harbour (US$0.50 to US$1.00 per foot per night), Jolly Harbour on the west coast (US$0.65 to US$1.00 per foot), and Falmouth Harbour Marina. Provisioning is good at Jolly Harbour’s on-site supermarket and decent in St John’s, though the capital is a taxi ride from the south-coast marinas.

Antigua’s main limitation is that the island itself does not connect naturally to other destinations without a longer passage. Nevis and St Kitts are 40 to 50 nautical miles south. Guadeloupe is 40 miles further. St Martin is 85 miles north. Most passages out of Antigua are half-day or overnight sails, which makes it a better base than a waypoint.

St Martin / Sint Maarten

St Martin is the provisioning and marine services capital of the Eastern Caribbean. The Simpson Bay lagoon on the Dutch side has multiple chandleries, boatyards, riggers, sailmakers, and marine electronics suppliers. The French side (Marigot) has excellent supermarkets with European products at reasonable prices. If you need to fix something on your boat, buy parts, or stock up for a long passage, St Martin is where you go.

Marina rates in Simpson Bay range from US$1.00 to US$1.50 per foot per night depending on the marina. The lagoon is secure in normal conditions but has a complicated bridge opening schedule for entry and exit. The island straddles two jurisdictions (French and Dutch), which means clearance can be confusing for first-time visitors. The Dutch side charges port fees; the French side is free to anchor in most bays. For pure sailing, St Martin is less interesting than many other islands. Its value is entirely in the services and logistics.

St Lucia

St Lucia is where the ARC fleet arrives after crossing the Atlantic. IGY Rodney Bay Marina is a full-service facility with fuel, water, power, laundry, a chandlery, and good provisioning nearby. Rates are approximately US$1.00 to US$1.50 per foot per night. The Pitons on the southwest coast are one of the most dramatic landfalls in the Caribbean, and the anchorage at Marigot Bay is famously beautiful.

The island is well set up for visiting yachts and has a developed tourism infrastructure. The downside is that some areas, particularly around Castries, have higher crime rates than other Eastern Caribbean islands. Most cruisers stay on the south and west coasts where the tourism zones are well-managed. Sailing conditions can be sportier than in the Leeward Islands, with bigger Atlantic swells wrapping around the island’s southern tip.

Grenada

Grenada sits at the southern end of the Windward Islands and is a favourite among long-term cruisers. Port Louis Marina in St George’s (US$0.90 to US$1.30 per foot) and Clarkes Court Bay Marina offer secure berthing. The Grenada Marine boatyard at St David’s is one of the best haul-out facilities in the Eastern Caribbean and a popular choice for hurricane season storage south of the traditional storm belt.

Provisioning in St George’s is good, with a lively market and well-stocked supermarkets. The island is known for its spice production and friendly people. For boats heading to the Grenadines (Carriacou, Union Island, Tobago Cays), Grenada is the natural starting point. Clearance is straightforward. The sailing south of Grenada toward Trinidad is rougher and requires careful timing.

The Grenadines

St Vincent and the Grenadines, particularly the islands of Bequia, Mustique, Mayreau, and the Tobago Cays, offer some of the most beautiful sailing in the Caribbean. The anchorages are uncrowded, the water clarity is exceptional, and the pace of life is genuinely slow. The Tobago Cays Marine Park is one of the highlights of any Caribbean sailing season.

The tradeoff is limited services. There are very few marinas, provisioning is basic outside of Bequia, and you need to be self-sufficient. The passages between the Grenadines can be rough, with strong currents in the channels and significant Atlantic swell. This is not beginner territory, but for experienced cruisers, it is hard to beat.

Martinique

Martinique is a French overseas department, which means European standards of infrastructure, excellent supermarkets, and some of the best food in the Caribbean. Le Marin in the south is the island’s main yachting hub, with multiple marinas, boatyards, and chandleries. Prices are in euros, and rates at Le Marin’s marinas range from roughly EUR 0.50 to EUR 0.80 per foot per night depending on the facility and season.

For provisioning, Martinique is second only to St Martin. The supermarkets carry French products, fresh baguettes, wine, cheese, and produce that you will not find anywhere else in the Eastern Caribbean. The sailing on the west coast is sheltered and pleasant, with dramatic volcanic scenery. The east coast is exposed to the Atlantic and not recommended for cruising.

Guadeloupe and Les Saintes

Guadeloupe is another French island with good infrastructure and provisioning. The main draw for sailors is Les Saintes (Iles des Saintes), a small archipelago just south of the main island. The anchorage at Terre-de-Haut is one of the prettiest in the Caribbean, with a sheltered bay, a hilltop fort, and a charming village with bakeries and restaurants. Many cruisers consider Les Saintes the single most beautiful anchorage in the Eastern Caribbean.

The passage from Guadeloupe to Dominica or south to Martinique is open water with significant swell and wind acceleration between the islands. Plan these passages for early morning when conditions are typically calmer.

Dominica

Dominica is the “Nature Isle of the Caribbean” and offers a completely different experience from the beach-and-bar islands. The interior is mountainous, covered in rainforest, and accessible through guided hikes to boiling lakes, waterfalls, and hot springs. Portsmouth on the northwest coast is the main cruiser stop, with a well-organised boat boy association (PAYS) that provides mooring balls, garbage collection, and guided tours.

Marina infrastructure is minimal. Provisioning is limited to small local shops and a modest market. But if you want to see the Caribbean beyond the coastline, Dominica is essential. Many cruisers cite it as the most memorable island on their entire circuit.

St Kitts

Port Zante in Basseterre sits at the geographic centre of the Leeward Islands, 40 nautical miles from Antigua and 55 from St Barts. Port Zante Marina offers transient dockage at US$0.75 to US$1.50 per foot per night depending on vessel size, with fuel, water, shore power, and 24-hour security. Customs and Immigration clearance is handled on-site at the marina.

What distinguishes St Kitts from many other Leeward Islands stops is walkability. The marina is in the heart of Basseterre. Supermarkets, the public market, banks, ATMs, pharmacies, and restaurants are all within a 10-minute walk. For boats handling crew changes, Robert L. Bradshaw International Airport has direct flights to Miami, New York, London, and Toronto and is a 15-minute taxi ride from the dock.

The island itself is compact (65 square miles) and worth exploring. Brimstone Hill Fortress is a UNESCO World Heritage Site. The southeast peninsula has undeveloped beaches on both the Caribbean and Atlantic sides. The clearing into St Kitts by yacht process is straightforward, and Nevis is just 8 nautical miles across the channel for a day trip or overnight anchor at Pinney’s Beach.

St Kitts is not the most glamorous island in the chain and it does not have the marine services depth of St Martin or the anchorage variety of the Grenadines. Its strength is practical: it is affordable, walkable, well-positioned, and easy to clear. For boats moving through the Leewards, it is one of the most efficient stops available.

How They Compare at a Glance

The BVI offers the easiest sailing and the most protected waters, but at the highest cost. St Martin has the best marine services and provisioning. St Lucia and Grenada are the best-equipped Windward Islands stops. The Grenadines offer the most beautiful anchorages but require self-sufficiency. Martinique and Guadeloupe combine French infrastructure with Caribbean sailing. Dominica is the most rewarding island for land-based exploration. Antigua is the sailing heritage capital. And St Kitts, sitting in the middle of the Leewards, is the practical mid-chain stop where you handle clearance, provisioning, and crew logistics efficiently before continuing on.

The best Caribbean sailing itinerary includes several of these islands. For a detailed route plan covering 2 weeks, 4 weeks, or 3 months, see the Eastern Caribbean sailing itinerary guide.

Frequently Asked Questions

Which Caribbean island is cheapest for sailing?

Grenada, St Kitts, and Dominica offer the most affordable combination of marina fees, provisioning costs, and anchorage fees. The BVI and St Barts are the most expensive. Martinique and St Martin fall in the middle but offer exceptional value for provisioning quality.

Which Caribbean island has the easiest customs clearance?

St Kitts, Grenada, and St Lucia all have straightforward clearance processes with on-site Customs and Immigration at the marina. The BVI charges higher fees. French islands (Martinique, Guadeloupe) use a simple online system but require a stop at the bureau des douanes. St Martin’s dual-jurisdiction status can confuse first-time visitors.

Which Caribbean island is best for beginners?

The BVI is the most forgiving sailing environment: short passages, protected waters, mooring buoys everywhere, and well-charted anchorages. The Leeward Islands (St Martin, St Kitts, Antigua) are a step up with longer passages but still manageable for competent sailors. The Windward Islands and Grenadines are for experienced cruisers.

Can I provision well in the Leeward Islands?

St Martin has the best supermarkets and marine stores in the chain. Antigua and St Kitts have good mid-range provisioning with walkable supermarkets. Smaller islands like Saba, Statia, and Montserrat have very limited supplies. Always stock up at a major island before heading to the smaller ones.

Is St Kitts worth stopping at on a sailing trip?

Yes. St Kitts is centrally located in the Leeward chain, affordable, easy to clear, and has a marina that is genuinely walkable to a capital city. It is not the most famous sailing destination, but cruisers who stop consistently rate it as one of the most practical and pleasant stops in the Leewards. The marina handles fuel, water, clearance, and shore power, and Basseterre is a real town, not a tourist village.

What is the best time of year for Caribbean sailing?

December through April is peak season with the most reliable trade winds, lowest humidity, and best sailing conditions. May is still good with lighter winds. June through November is hurricane season, and most cruising insurance policies restrict navigation during these months.

Last reviewed: April 2026