Discover the Diversity of the Northern Leeward Islands
The northern Leeward Islands offer one of the Caribbean's most varied yacht charter experiences. With St Martin as your starting point, you can explore a fascinating collection of islands, each with its own character, culture and natural attractions. From the beautiful beaches of Anguilla and the French sophistication of St Barts to the volcanic landscapes of St Kitts and Nevis, there is plenty to discover within a relatively compact cruising region.
St Martin itself is an interesting place to begin. Shared between French Saint-Martin in the north and Dutch Sint Maarten in the south, the island combines two distinct European influences with a lively Caribbean atmosphere. It is also a well-established yachting centre, with a selection of charter bases and a good choice of sailing yachts and catamarans.
A Caribbean Sailing Holiday with Plenty of Variety
One of the great attractions of chartering from St Martin is the freedom to choose an itinerary that suits your available time and sailing ambitions. A week allows you to explore the island's own coastline and visit nearby Anguilla and St Barts. With longer, you can venture south to the quieter islands of Saba and Sint Eustatius, then onwards to St Kitts and Nevis.
The contrasts are part of the appeal. Anguilla is renowned for its white-sand beaches and clear turquoise waters, while St Barts offers an unmistakably French atmosphere, with attractive waterfront restaurants, boutiques and sheltered bays. Further south, the volcanic islands introduce a different landscape, with green hillsides, historic settlements and a more traditional Caribbean character.
This is also a destination that rewards those who enjoy sailing. The northeast trade winds provide excellent conditions during the main charter season, with passages between islands offering opportunities for some satisfying open-water sailing. While the shorter crossings are readily manageable for experienced charterers, longer itineraries require more planning than a typical sheltered-water cruise.
Bareboat, Skippered and Crewed Yacht Charters
St Martin is a popular base for bareboat yacht charters, with both monohulls and catamarans available. Experienced sailors can enjoy the independence of planning their own island-hopping adventure, while those who prefer local knowledge or a more relaxed holiday can choose a yacht with a professional skipper.
Fully crewed charters are another attractive option, particularly for visitors seeking a more leisurely experience with time to enjoy the islands ashore.
Whether your priority is rewarding sailing, secluded anchorages, fine dining or simply discovering a different side of the Caribbean, the northern Leeward Islands provide plenty of possibilities.
At Sail Connections we will compare suitable yachts and departure bases to help you make the most of your available charter time.
Sailing the Northern Leeward Islands
St Martin: The Principal Charter Base
St Martin lies towards the northern end of the Leeward Islands and is the main departure point for yacht charters exploring this part of the Caribbean. Charter operations are based around the island's established marine facilities, particularly in the Simpson Bay Lagoon area and on the French side.
The island has two international airports, with Princess Juliana International Airport on the Dutch side providing the principal international gateway. Provisioning facilities are extensive, making St Martin a convenient place to prepare for a sailing holiday.
There are attractive cruising grounds around the island itself, including Grand Case, Anse Marcel and the waters around Tintamarre. Some bays are exposed to the prevailing conditions, however, so anchorage selection needs to take account of wind direction and swell.
Anguilla: Beaches and Clear Caribbean Waters
A short passage north from St Martin brings you to Anguilla, a British Overseas Territory known for its exceptional beaches, low-lying landscape and clear water.
Road Bay is the principal port of entry for visiting yachts. Other attractive cruising areas include Crocus Bay and the waters around Sandy Island and Prickly Pear Cays, subject to local regulations and suitable conditions.
Anguilla is particularly appealing for swimming, snorkelling and relaxing ashore. The island also has a strong sailing tradition, with locally built racing boats playing an important part in community life.
St Barts: French Caribbean Style
Approximately 15 nautical miles southeast of St Martin, St Barthélemy, generally known as St Barts, is one of the Caribbean's most distinctive destinations.
The picturesque harbour of Gustavia is the island's main yachting centre, surrounded by restaurants, boutiques and traditional red-roofed buildings. Its popularity means that berthing and mooring arrangements deserve advance attention, particularly during the busiest holiday periods.
Away from Gustavia, St Barts has beautiful beaches and quieter bays, including Colombier, a popular anchorage within the island's marine reserve. Local anchoring and mooring regulations apply.
St Barts is easily included in a week-long charter from St Martin and combines particularly well with Anguilla.
Saba and Sint Eustatius: Islands Off the Beaten Track
For sailors with more time, the Dutch Caribbean islands of Saba and Sint Eustatius offer a fascinating contrast to their better-known neighbours.
Saba rises dramatically from the sea, its steep volcanic slopes creating one of the most striking island profiles in the Caribbean. With limited sheltered anchorage options, visiting by yacht requires careful attention to conditions and the availability of authorised moorings.
Sint Eustatius, commonly called Statia, has a quieter atmosphere and a rich maritime history. The principal settlement, Oranjestad, overlooks the anchorage on the island's western side. Ashore, historic buildings and the distinctive volcanic landscape provide plenty of interest.
These islands are particularly appealing to experienced sailors seeking something beyond the usual Caribbean charter circuit.
St Kitts and Nevis: History and Tropical Landscapes
Further south, the federation of St Kitts and Nevis introduces a greener, more mountainous landscape.
St Kitts is the larger island, with the capital Basseterre and the impressive Brimstone Hill Fortress, a UNESCO World Heritage Site. The southeastern peninsula offers several bays suitable for visiting yachts, depending on conditions.
Neighbouring Nevis has a quieter character, dominated by the distinctive cone of Nevis Peak. Charlestown, the island's historic capital, is an appealing place to explore, while the western coastline offers opportunities to anchor and enjoy the surroundings.
Allowing sufficient time to visit both islands is worthwhile, particularly if you wish to explore ashore rather than simply sail through.
Charter Itineraries and Passage Planning
A seven-day charter from St Martin is generally best focused on St Martin, Anguilla and St Barts. These islands provide an enjoyable combination of shorter passages, attractive anchorages and time ashore.
With 10 to 14 days, an itinerary can extend south to include Statia, St Kitts and Nevis, with Saba as a possible additional stop in suitable weather.
Longer charters may offer opportunities to sail towards Antigua, or west towards the British Virgin Islands, subject to charter operator permissions and yacht availability. One-way charters may be possible by arrangement.
Although the islands appear close together on a chart, distances, sea conditions and the need to complete customs formalities can make an ambitious itinerary surprisingly time-consuming. It is worth allowing flexibility rather than trying to visit every island.
Sailing Conditions and Best Time to Visit
The principal yacht charter season runs from December through April, when the northeast to easterly trade winds are generally well established and temperatures remain pleasantly warm.
Winds commonly reach 15 to 20 knots during the season, sometimes stronger, particularly during periods of reinforced trades. The open passages between islands can experience Atlantic swell and choppy seas, while acceleration zones around headlands can create more demanding conditions.
The shorter crossings around St Martin, Anguilla and St Barts are suitable for competent bareboat sailors, but longer passages towards St Kitts and Nevis call for greater experience and careful passage planning.
May and early June can also offer enjoyable sailing, often with lighter winds and fewer visitors. The Atlantic hurricane season officially extends from June through November, with the greatest risk generally from August to October. Charter availability during this period is more limited.
Navigation and Local Formalities
The northern Leeward Islands encompass French, Dutch, British and independent Caribbean jurisdictions. Visiting yachts must comply with the applicable customs and immigration procedures when moving between territories.
Entry requirements, clearance arrangements, cruising permits and fees vary by destination. Some marine reserves also have specific rules governing anchoring, mooring, fishing and access.
Your charter operator will provide current guidance before departure. As regulations and conditions can change, it is important to confirm requirements for each island on your proposed itinerary.
The map below has been produced using internet tools and pin placements may not be exact. It is intended as a rough a guide. For further research and preparing itineraries, we suggest you refer to quality on-line maps and charts.
What makes a yacht charter from St Martin particularly appealing?
St Martin offers access to several contrasting Caribbean islands within relatively short sailing distances. You can experience French culture in St Barts, the beaches of Anguilla and the volcanic landscapes of St Kitts and Nevis, combining rewarding sailing with a remarkable variety of destinations.
What are the main highlights of sailing around St Martin, St Barts, Anguilla, St Kitts and Nevis?
The highlights include Anguilla's white-sand beaches, the French atmosphere of St Barts, St Martin's lively coastal communities and the volcanic scenery of St Kitts and Nevis. Each island offers a different experience, making this a particularly rewarding region to explore by yacht.
What sailing conditions should I expect around St Martin and the neighbouring islands?
The northern Leeward Islands offer excellent trade-wind sailing, with winds commonly around 15 to 20 knots during the main season. Passages can be exposed to Atlantic swell and choppy seas, so the region is best suited to sailors comfortable with open-water conditions.
Are there any restrictions on where charter yachts can sail or anchor?
Yes. Marine reserves, protected reefs, designated mooring areas and charter operator cruising limits can affect where yachts may sail or anchor. Some islands also require cruising permits or specific clearance procedures. Check current local regulations and your operator's permitted cruising area before departure.
What is a good seven-day yacht charter itinerary from St Martin?
A seven-day charter from St Martin is best focused on St Martin, Anguilla and St Barts. This provides a varied sailing holiday with manageable passages, beautiful beaches, attractive anchorages and time to explore ashore without trying to cover too much distance.
When is the best time to charter a yacht in the northern Leeward Islands?
The best time to charter a yacht from St Martin is generally December through April, when the trade winds are well established and the weather is usually warm and sunny. May and early June can also be attractive, with fewer visitors and often lighter winds.
When is the best time to charter a yacht in the Leeward Islands?
The peak sailing season in the Caribbean's Leeward Islands runs from December through April, when the weather is reliably sunny, the trade winds are steady, and the risk of storms is low.
Are there any sailing restrictions in the region?
Yes, but they’re mostly straightforward. Marine reserves, particularly in Anguilla and St Barts, may require permits or have anchoring restrictions to protect reef areas. Some areas prohibit fishing or spearfishing. These are usually well-marked on local charts, and your charter company will brief you before departure. It’s all part of helping protect this beautiful sailing region for future generations.
What wildlife and marine life might we see?
This region is home to vibrant marine life. Snorkelling and diving off Anguilla’s reefs and the marine reserve at Colombier in St Barts offer colourful corals, reef fish, and the occasional spotted eagle ray. Sea turtles are commonly seen in bays and around moorings, especially early in the day. During the winter months (January to March), keep an eye out for humpback whales and playful dolphins during open water passages — a special highlight of Caribbean sailing.
What marine life can I expect to see while sailing the northern Leeward Islands?
The waters around St Martin, Anguilla and St Barts support sea turtles, tropical reef fish, rays and other marine life. Dolphins may be encountered offshore, while humpback whales migrate through the wider region during the winter months, although sightings are never guaranteed.
What are the entry and customs requirements when sailing between these islands?
Yachts sailing between St Martin, Anguilla, St Barts, St Kitts and Nevis must comply with the entry and departure procedures of each jurisdiction. Requirements vary, so allow time for customs and immigration clearance, and confirm current procedures with your charter operator before departure.
Is the St Martin cruising region suitable for less experienced sailors?
St Martin and its neighbouring islands can be suitable for less experienced sailors, particularly with a professional skipper. Independent bareboat charterers should be comfortable with trade-wind sailing, exposed passages, anchoring and navigation in unfamiliar waters. This is generally more demanding than sheltered Caribbean cruising.
How long do I need for a charter that includes all these islands?
Allow approximately 10 to 14 days to explore St Martin, Anguilla, St Barts, St Kitts and Nevis without rushing. A week is better spent concentrating on the three northern islands, while two weeks provides more time for longer passages and exploring ashore.
Are there yacht charter bases outside St Martin?
St Martin is the principal yacht charter base for the northern Leeward Islands, with established operations on both its French and Dutch sides. Other islands have more limited charter options, so most bareboat itineraries begin and end in St Martin.
Can I provision easily on St Martin before starting my charter?
Yes. St Martin is one of the better-equipped yacht charter bases in the Caribbean, with supermarkets, specialist food shops and marine suppliers. Both the French and Dutch sides offer good provisioning options, making it convenient to stock your yacht before departure.
Our client reviews about charter sailing in St Martin, St Barts, Anguilla, St Kitts & Nevis
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Rating: ★★★★★Was fun to visit five islands but checking in/out of customs each time and the distance we needed to cover (~220 NM) made for little down time.
The wind blew hard all week and we sailed for more than 5 hours each day (and one 9 hour day). Our allocated skipper was great. The mega yachts in St Barts were fun to ogle and the French culture in St Martin and Guadeloupe was great to experience.
(Sail Connections was) easy to deal with over email and responsive to initial inquiries. Got us a good deal on the boat! Bit of a black hole in comms after payment made and before charter voucher received, which was a bit unnerving, but this all happened over the Christmas holidays, so understandable!
Karl, USA, Feb 28th, 2023
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