Eastern Caribbean Sailing Itinerary: 7 Days to 3 Months, With Distances and Clearances

The Eastern Caribbean is one of the best cruising grounds in the world for a reason. The islands sit close together, the trade winds are reliable, the water is warm, and the cultural variety from one stop to the next is remarkable. Whether you have a week, two weeks for a focused Leeward Islands loop, or three months to work through the full chain from the Virgin Islands to Grenada, the sailing is practical and the planning is straightforward.

This guide lays out five itineraries, from seven days to a full season, each with distances, sailing times, clearance stops and recommended anchorages. It also gives you the three tables most itinerary guides leave out: a leg-by-leg distance matrix, what clearance costs and requires on each island, and what a marina night costs along the route. St Kitts and Port Zante Marina in Basseterre appear in every version because the island sits at the centre of the Leeward chain and is one of the few stops with customs, immigration, fuel and a town all at the dock.

Choosing your base

Where you start decides the shape of your trip. Three things matter: whether a charter company operates there, how easy it is to fly in, and which direction the trade winds will push you.

St Kitts sits between the two strongest charter bases in the Leewards, 40 miles from Antigua and 55 from St Barts on the St Martin side, which is why it appears on every route in this guide. Charter from either base and St Kitts is a daysail away. On your own boat, it is the natural midpoint of the northern chain, with customs, immigration, fuel and a town at the same dock.

Antigua is the most flexible base for a Leewards trip. You can sail north to St Martin or south to Guadeloupe, it has the best UK flights in the Eastern Caribbean, and Jolly Harbour and English Harbour both clear you in on arrival.

How the island chain works

The Eastern Caribbean runs roughly north to south in a 500-nautical-mile arc from the Virgin Islands to Grenada. The northern group is the Leeward Islands: the BVI, USVI, Anguilla, St Martin, St Barts, Saba, Statia, St Kitts and Nevis, Antigua and Barbuda, Montserrat, and Guadeloupe. The southern group is the Windward Islands: Dominica, Martinique, St Lucia, St Vincent and the Grenadines, and Grenada.

Most passages between neighbouring islands are 20 to 50 nautical miles, which translates to 4 to 10 hours of sailing in typical trade wind conditions. The wind blows from the east or northeast at 15 to 25 knots throughout the cruising season, December to May, and the seas are manageable on the leeward, western, side of each island. The windward side and the open channels between islands can be rougher, especially in the Windward Islands where Atlantic swells wrap around the southern islands.

Cruisers moving through the chain almost always travel north to south or south to north, rarely east to west. The standard post-ARC pattern is to arrive in St Lucia or Grenada, cruise the Windwards, then work north through the Leewards. Boats departing the US East Coast typically enter from the north through the Virgin Islands and work south. Either direction works; the trade winds give you a beam reach or broad reach on most legs regardless.

Sailing distances between the islands

Every leg on the routes below, harbour to harbour. Hours assume 5 to 6 knots in trade wind conditions. Where published sources disagree by more than ten per cent we show the range rather than pick a number.

Two legs in the chain are routinely sailed overnight: Antigua to St Martin at 85 miles, and the BVI to St Martin at 85 to 90. Everything else is a daysail if you leave early.

Itinerary 1: Seven days from St Martin

The shortest loop that still feels like a cruise. Start and finish in St Martin, where Sunsail and Horizon have bases and the provisioning is the best in the Leewards.

Total sailing: 140 nautical miles over four sailing days. Three clearances: St Barts, St Kitts, St Martin.

If the St Barts to St Kitts leg is more than you want in a week, swap days 4 and 5 for Saba and Statia. The legs are shorter and the anchorages are quieter, but Saba offers no shelter in a northerly swell, so check the forecast before committing.

Itinerary 2: Ten days from Antigua

Antigua round trip through the heart of the chain. This is the route most charterers from the UK take, because the London flights land at Antigua.

Total sailing: 203 nautical miles over five sailing days. Four clearances: Antigua, St Kitts and Nevis, St Barts, St Martin.

Itinerary 3: Two weeks in the Leeward Islands

A two-week itinerary works best as a focused loop through the central Leeward Islands. This is ideal for charterers, boats on a schedule, or sailors who want to cover the heart of the chain without rushing. Start and finish in Antigua, which has direct flights to the US, UK, and Europe.

Day 1 to 2: Antigua. Clear in at English Harbour or Jolly Harbour. Explore Nelson’s Dockyard, Shirley Heights, and the south coast anchorages. Provision at the well-stocked supermarkets in Jolly Harbour.

Day 3: Sail to Nevis (40 nm, 6 to 8 hours). Anchor off Pinney’s Beach. Visit Charlestown, the birthplace of Alexander Hamilton. A quiet, unhurried island with excellent restaurants.

Day 4 to 5: Sail to St Kitts (8 nm, 1 to 2 hours). Dock at Port Zante Marina in Basseterre. Clear in using the on-site customs and immigration. Walk to the town centre for provisioning at supermarkets, banks, and local markets. Visit Brimstone Hill Fortress, a UNESCO World Heritage Site. Fuel up at the marina before departing. The clearing into St Kitts by yacht guide covers the full process.

Day 6 to 7: Sail to St Barts (55 nm, 8 to 10 hours). Anchor in Gustavia harbour. Explore the shops, restaurants, and beaches. Anse du Gouverneur and Anse de Grande Saline are among the most beautiful in the Caribbean.

Day 8 to 9: Sail to St Martin (15 nm, 2 to 3 hours). Provision at the excellent and affordable supermarkets in Marigot on the French side or Simpson Bay on the Dutch side. St Martin is the best provisioning stop in the Leeward Islands. Pick up any marine supplies you need.

Day 10: Sail to Anguilla (8 nm, 1 to 2 hours). Anchor off Sandy Ground or Meads Bay. Clear in at the customs dock. Stunning beaches with very little development.

Day 11 to 12: Return to St Martin (8 nm). Use the extra days for boat work, a second provisioning run, or simply enjoy the island.

Day 13 to 14: Sail back to Antigua (85 nm, 12 to 16 hours, typically an overnight passage). Clear in and depart.

Itinerary 4: Four weeks through the full Leeward chain

Four weeks allows you to cover the entire Leeward Islands from the Virgin Islands to Guadeloupe, with time to linger at each stop. This is the sweet spot for most cruising sailors: enough time to experience each island without feeling rushed.

Week 1: Start in the BVI or USVI. Spend 3 to 4 days exploring, then sail to Anguilla or St Martin, 85 to 90 nm from the BVI, typically an overnight passage.

Week 2: St Martin for provisioning and marine supplies, St Barts for 2 to 3 days, then south to Statia and Saba if conditions allow. Saba is one of the most dramatic anchorages in the Caribbean but offers no protection in a swell.

Week 3: St Kitts and Nevis, 3 to 4 days. Dock at Port Zante in Basseterre for fuel, water, clearance, and provisioning. Cross to Nevis for a day or two. Then sail south to Montserrat, 45 nm, to see the volcano exclusion zone, and continue to Guadeloupe, 30 to 40 nm, to explore the Saintes and the west coast of Basse-Terre.

Week 4: Guadeloupe and Les Saintes, 3 to 4 days. Then sail back north to Antigua, 41 to 43 nm, to close the loop and fly home, or continue south into the Windward Islands if your schedule allows.

Itinerary 5: Three months from the Virgins to Grenada

Three months gives you the full Eastern Caribbean experience. You can cruise every major island, spend a week or more in the places you love, and still have time for weather days and spontaneous detours. This is the itinerary for ARC arrivals, snowbirds, sabbatical sailors, and anyone living aboard for a season.

Month 1, December to January: Arrive in St Lucia or Grenada after the Atlantic crossing or from the US East Coast. Cruise the Windward Islands: Grenada and the Grenadines, Carriacou, Union Island, Tobago Cays, Bequia, then St Vincent and St Lucia. Spend Christmas in whichever island feels right. Take your time in the Grenadines; the anchorages at Tobago Cays and Mayreau are worth multiple days. Most boats bypass mainland St Vincent on the run from the Pitons to Bequia, which is around 50 miles, and go straight to Admiralty Bay.

Month 2, February to March: Move north through the Windwards and into the Leewards. Martinique, where Le Marin is the cheapest marina in the chain and an excellent provisioning base. Dominica, where Portsmouth is a favourite cruiser stop with organised tours of the rainforest interior. Guadeloupe, where the Saintes are not to be missed. Montserrat for a short stop to see the volcano. Then Antigua for Sailing Week or simply to enjoy English Harbour.

Month 3, March to April: The central and northern Leeward Islands. Nevis, then St Kitts, where you dock at Port Zante for fuel and provisioning, walk to Basseterre, and visit Brimstone Hill. St Barts, St Martin as the major provisioning and marine supply stop, Anguilla, and finish in the BVI or USVI for flights home. Alternatively, leave from St Martin or Antigua, both of which have strong flight connections.

Caribbean sailing routes: which direction, and why

There are three patterns, and which one you follow depends on how you arrived.

Southbound from the Virgins. Boats from the US East Coast enter at the BVI or USVI and work south. The first big leg is the overnight to St Martin, then everything is a daysail until the Windwards. The trades put you on a beam reach for most of it.

Northbound from the ARC. The ARC finishes at Rodney Bay, St Lucia, in early December, and ARC+ at Port Louis, Grenada. Those boats cruise the Grenadines over Christmas and then work north through the Leewards in February and March, which is when Antigua, St Kitts and St Martin are at their busiest. If you are on this route, St Kitts is roughly the midpoint of the Leewards run and a natural place to stop for fuel and a proper provisioning run before the St Barts and St Martin legs.

The Leewards loop. Charterers out of Antigua or St Martin sail a loop and return to base. This is the seven, ten and fourteen-day routes above. You can run it clockwise or anticlockwise; the Antigua to St Martin overnight is the long leg either way, so most people put it at the end when they know the boat.

Whichever pattern you follow, the St Martin to Antigua axis is the spine of the northern Leewards, and St Kitts sits on it.

Clearance on each island: what it costs and what it needs

Each island nation requires its own clearance. Most of the chain now uses an online pre-arrival system, and the French islands have moved to mandatory online declaration with self-service terminals in marinas and chandleries. Fees change without much notice; where we could not confirm a current figure we say so.

Budget 2 to 4 hours per clearance in most islands. The French islands are faster once you have used the online portal once. The BVI is the outlier: since June 2025 a week there costs a 45-footer several hundred dollars in permits alone, which has pushed some cruisers to spend more of the season further south.

What a marina night costs along the route

Anchoring is free almost everywhere in the chain, and most cruisers anchor most nights. You dock to clear in, take on fuel and water, run laundry, provision properly, or leave the boat safely. On a Leewards loop that is typically two to four marina nights in a fortnight.

Berth charge only, for a 45-foot monohull in high season. Electricity, water and tax vary and are set out in full on the marina rates comparison.

Four other marinas on these routes, Nanny Cay, Rodney Bay, Port Louis and Nelson’s Dockyard, publish no rates and quote on request.

Le Marin is the cheapest marina in the Eastern Caribbean and it is not close. Port Zante is the cheapest published rate in the northern Leewards for a short stop. At a full week Lagoon Marina’s weekly tier overtakes it.

Where St Kitts fits in every itinerary

St Kitts sits at the geographic centre of the Leeward Islands, roughly equidistant between Antigua to the south and St Martin to the north. It is 40 nautical miles from Antigua, 55 from St Barts and 8 from Nevis. That positioning makes it a natural mid-chain stop on any Leeward Islands itinerary, and the only one where customs, immigration, fuel and a town are all at the dock.

Port Zante Marina has 36 berths, takes boats to 65 feet and 12 feet of draft, tide dependent, and catamarans to about 25 feet of beam in the catamaran slip or alongside the pier, subject to availability. Rates are US$0.75 per foot per night under 40 feet, US$1.00 at 40 feet and over, and US$1.50 for catamarans, with no tax added and no seasonal increase. Electricity is $0.50 per kWh, water $0.10 a gallon, and the fuel dock runs 06:00 to 18:00.

Customs and immigration are both inside the marina. Basseterre is at the dock: supermarkets, pharmacies and banks are a one to two minute walk, the chandlery is a fifteen to twenty minute walk or a three minute drive, and laundry is by drop-off. For crew changes, Robert L. Bradshaw International Airport is fifteen minutes by taxi, with direct flights to Miami, New York, London and Toronto.

The yacht clearance guide covers SailClear pre-registration, the clearance process and what documents to have ready. The Antigua to St Kitts passage guide and the St Martin to St Kitts passage guide cover the two approaches most boats take, and the harbour approach guide covers the entry into Basseterre.

Enquire about a berth at Port Zante
Tell us your length, beam, draft and dates. Customs and immigration are on site.

Planning notes

The cruising season runs from December to May. By early June, most boats are either heading north to the US, shipping home on a yacht transport, or finding a hurricane season berth. Insurance policies typically require boats to be south of 12.5 degrees north or out of the water between June and November. If you are planning to stay through the summer, research hurricane season options early and read the best time to sail to the Caribbean article for seasonal detail.

Clearance procedures vary by island and the table above gives you the current picture. Carry enough cash in US dollars and local currencies. EC dollars are used across most of the Leeward and Windward Islands, pegged at EC$2.70 to US$1, and euros on the French islands.

Provisioning quality varies dramatically. St Martin and Martinique have the best supermarkets and marine supply stores in the chain. Antigua, St Kitts, and Guadeloupe are good mid-range provisioning stops. Smaller islands like Saba, Statia, Montserrat, and the Grenadines have limited supplies; stock up before arriving.

Frequently asked questions

How far apart are the Eastern Caribbean islands? Most neighbouring islands are 20 to 50 nautical miles apart, which translates to 4 to 10 hours of sailing in trade wind conditions. A few legs, such as the BVI to St Martin or Antigua to St Martin, are 85 to 90 miles and are usually sailed overnight. The full distance table above has every leg.

Which direction should I sail, north to south or south to north? Either direction works. The trade winds blow from the east, so most passages are a beam reach regardless of whether you are heading north or south. Boats arriving from the ARC or transatlantic crossings typically start in St Lucia or Grenada and work north. Boats from the US East Coast usually enter from the north.

How many islands can I visit in a week? In two weeks? Three in a week, five to seven in two. Rushing more islands in means you spend all your time clearing in and out and never really experience any of them.

Do I need to clear in and out at every island? Yes. Each island nation requires its own clearance, even if the passage is only 8 miles, as between St Kitts and Nevis, which share a country but clear separately, or between the French islands. Some groups, like the BVI and USVI, have internal clearance that is simpler but still required.

How much does clearance cost? From nothing in the USVI and Statia, to a few euros on the French islands, to several hundred dollars a week in BVI cruising permits since the June 2025 increase. The clearance table above gives the figure for each island.

Can I stop in St Kitts on a Leeward Islands cruise? Yes, and it is on the standard route between Antigua and St Martin. Port Zante Marina handles clearance, fuel, water and shore power at the dock, Basseterre is a two minute walk, and the island has a UNESCO World Heritage fortress, beaches on both coasts, and direct international flights for crew changes.

What is the best month to start a Caribbean sailing season? December is the traditional start. The trade winds are established, hurricane season has ended, and the islands are at their liveliest. January and February are peak season with the most reliable wind. March and April remain excellent with slightly lighter winds and fewer boats. By May, the season is winding down.

Last reviewed: August 2026. Distances cross-checked against published cruising guides; clearance fees from Noonsite and official sources, dated where given. If you find a figure that has changed, tell us.