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Secure your yacht in The Leeward Islands
Trade Winds, Chic Harbours
Luxury Yacht Charters in the Leeward Islands
A Leeward Islands yacht charter brings together the Caribbean‘s most stylish ports, from the chic harbor of St Barts to the long white beaches of Anguilla and the sailing heritage of Antigua. Passages between islands are short, the trade winds are steady, and every landfall has its own character, French, Dutch or British, so a single week can feel like several holidays. Crewed catamarans, sailing yachts and superyachts all suit this compact cruising ground, and the winter season, from December to April, brings the best weather and the liveliest calendar.
Explore our curated collection of luxury yachts and crewed catamarans. Our independent brokers can also introduce you to exclusive yachts beyond the published selection.
SAMURAI
Built 2016
· Refit 2022
60.3 mLength12Guests6Cabins15Crew
From / week
USD
+ VAT, APA & expenses
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Just Enough
Built 2012
· Refit 2024
42.98 mLength11Guests5Cabins9Crew
From / week
USD
+ VAT, APA & expenses
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NALANI
Built 2024
23.87 mLength10Guests5Cabins4Crew
From / week
EUR
+ VAT, APA & expenses
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LADY ROSE
Built 2026
20.55 mLength8Guests4Cabins3Crew
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EUR
+ VAT, APA & expenses
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MARIA THERESE
Built 2024
20.57 mLength8Guests4Cabins4Crew
From / week
USD
+ VAT, APA & expenses
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INDABLUE
Built 2017
· Refit 2023
22.56 mLength7Guests3Cabins4Crew
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+ VAT, APA & expenses
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REVE BLEU
Built 2023
20.55 mLength8Guests4Cabins4Crew
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EUR
+ VAT, APA & expenses
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LUNA
Built 2018
· Refit 2024
90 mLength12Guests7Cabins30Crew
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+ VAT, APA & expenses
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PLAN B
Built 2012
73.07 mLength12Guests8Cabins20Crew
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+ VAT, APA & expenses
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GRAND OCEAN
Built
· Refit 2025
85 mLength24Guests14Cabins28Crew
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+ VAT, APA & expenses
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CHRISTINA O
Built 1943
· Refit 2022
99.13 mLength34Guests17Cabins40Crew
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+ VAT, APA & expenses
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Q 72
Built 2012
· Refit 2025
72.45 mLength12Guests8Cabins18Crew
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+ VAT, APA & expenses
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Beyond the collection
The right yacht isn't always listed.
Our independent brokers work across the wider charter market, including yachts that are never publicly advertised. Tell us what you have in mind and we'll put together a selection for you.
CHARTER EXPERTISE
Your First Yacht Charter
A thoughtful introduction to yacht chartering, from choosing the right yacht to life on board.
READ THE GUIDE ↗
DESTINATIONS & EXPERIENCES
Discover Extraordinary Itineraries
Explore remarkable destinations and cruising routes, thoughtfully curated by our charter specialists.
GET INSPIRED ↗
THE destination advantage
Island-Hopping, Leeward Style
The Leewards are among the easiest places in the world to cruise: distances are short, islands are close together, and the trade winds are reliable. Here is what stands out:
✔ Calm sailing conditions and protected anchorages
✔ Short distances between islands, ideal for relaxed itineraries
✔ Excellent marinas for luxury yachts and superyachts
✔ Blend of glamour, culture and laid-back island life
✔ Outstanding dining, beach clubs and nightlife ashore
✔ Well-suited to both motor yachts and sailing yachts
A Leeward Islands superyacht charter is ideal for guests seeking variety, comfort and a polished Caribbean experience.
Insider Tip: “If you want St Barts at Christmas, New Year or the Bucket Regatta, ask us about your dates as early as you can, because Gustavia has limited berths and the best yachts fill first. Plan Colombier for the morning, when the bay is calm and the moorings are free, and keep Anguilla’s Prickly Pear Cays for a long lunch day. Clearance between islands is routine, but it adds time, so we build it into the plan.” Giulia Di Leo, CEO, MYBA and CYBA Broker
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Four Islands, Four Moods
Each island on this route has a distinct character, and most charters combine two or three of them. Antigua brings sailing heritage and long beaches, St. Barts offers the most stylish harbor in the Caribbean, St. Martin adds lively marinas and a French and Dutch table, and Guadeloupe is greener and more tranquil. Choose a base for the week and let the crew plan the rest, with short sails between each stop and time to linger where you like.
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Antigua and Barbuda
Sailing heritage, English Harbor, and the white beaches of Barbuda’s west coast:
✔ Numerous sheltered bays and anchorages
✔ Historic harbors and lively sailing culture
✔ Ideal starting point for Leeward itineraries
St Barts
The Caribbean’s most glamorous harbor, with Gustavia’s boutiques, restaurants, and New Year’s celebrations:
✔ High-end beach clubs and fine dining
✔ Stylish ports and exclusive anchorages
✔ Popular with superyachts and luxury motor yachts
St Martin
A French and Dutch island with lively marinas, Grand Case’s dining, and an easy gateway to Anguilla and St Barts:
✔ Excellent provisioning and marina facilities
✔ Lively ports balanced with quiet anchorages
✔ Gateway to neighbouring islands
Guadeloupe
A greener, quieter island with volcanic landscapes, marine parks and French Creole cuisine:
✔ National parks and volcanic landscapes
✔ Excellent snorkeling and nature-focused itineraries
✔ Ideal for guests seeking a quieter Caribbean experience
THE CHARTER JOURNEY
Popular Leeward Itineraries
The most popular routes in the northern Caribbean combine a handful of islands over a week or two. The 14-day St Maarten itinerary gives you time to explore the island’s marinas and beaches, plus neighboring islands; the 7-day route through Antigua and St Martin links the two ends of the Leewards in a single week, and the 14-day Antigua itinerary explores its bays and neighboring islands at a slower pace. Each can be adapted to your yacht, dates, and season.
Classic Leeward Islands (7 days)
Antigua – Barbuda – St Barts – St Martin
Luxury Lifestyle Charter
Focus on St. Barts, St. Martin, and high-end beach clubs
Nature & Culture Itinerary
Guadeloupe and surrounding islands
(All itineraries are fully customized based on yacht selection, cruising pace, and guest preferences.)
YOUR JOURNEY, DAY BY DAY
A Week Between St Martin and St Barts
This week starts in St Martin, crosses to Anguilla’s beaches and Prickly Pear Cays, then moves on to Gustavia and the quiet beaches of St Barts before returning via Tintamarre. Each day is adapted to the weather and the size of the yacht, and several stops carry notes on clearance, moorings and marine protection. Treat it as a model: we adjust it to your dates and group.
DAY 1
Welcome to St Martin
Begin your luxury yacht charter in St Martin, one of the Caribbean’s principal superyacht gateways. Meet your captain and crew at the confirmed marina before settling into your beautiful surroundings. Depending on your arrival time, cruise toward Grand Case on the French side of the island, celebrated for its beautiful bay and exceptional dining. Enjoy your first swim in turquoise Caribbean waters before a relaxed evening aboard or dinner ashore.
YBH note: Embarkation may take place in Simpson Bay, the lagoon or another confirmed marina. Large-yacht access depends on draft, bridge operations and marina availability. Grand Case anchoring is subject to conditions, and international clearance must be arranged as required.
DAY 2
Anguilla's White-Sand Beaches
Cruise north toward Anguilla, where long stretches of powder-white sand and extraordinary turquoise waters create one of the Caribbean’s most beautiful coastal landscapes. After completing the required arrival formalities at Road Bay, discover the spectacular shoreline of Rendezvous Bay. Enjoy swimming, a beautifully prepared lunch aboard and time to experience the island’s peaceful atmosphere before returning to a suitable overnight anchorage.
YBH note: Anguilla requires customs and immigration clearance and appropriate cruising permissions. Road Bay is the principal yacht clearance point. Beach stops and anchoring depend on weather, local rules and the yacht's dimensions.
DAY 3
Prickly Pear Cays & Meads Bay
Spend another beautiful day exploring Anguilla’s remarkable coastline. Cruise toward the Prickly Pear Cays, where uninhabited islands, clear waters and pale sand create an idyllic Caribbean setting. Enjoy swimming and snorkelling in permitted areas before continuing toward Meads Bay, famous for its beautiful beach and sophisticated waterfront resorts. Spend the afternoon relaxing aboard or arrange a memorable lunch ashore.
YBH note: The Prickly Pear Cays are sensitive marine environments. Access, anchoring and water activities must comply with Anguilla's applicable regulations. Exposed reefs and seasonal swell require careful navigation.
DAY 4
Arrive in St Barts
Cruise southeast toward St Barts, one of the Caribbean’s most celebrated luxury yacht charter destinations. Arrive near Gustavia, where elegant waterfront restaurants, designer boutiques and visiting superyachts create a sophisticated island atmosphere. Spend the afternoon discovering the town, enjoying a leisurely lunch ashore or relaxing aboard with beautiful harbour views. In the evening, experience the island’s exceptional dining and nightlife.
YBH note: The passage from Anguilla to St Barts crosses open water and requires a suitable forecast. Customs formalities must be completed. Gustavia berthing is limited, particularly during major events and the festive season; anchoring and tender arrangements may be necessary.
DAY 5
Colombier & Secluded Beaches
Discover the beautiful northwestern coastline of St Barts, beginning with the spectacular bay of Colombier. Surrounded by green hillsides and clear turquoise waters, this remarkable anchorage offers an exceptional setting for swimming, snorkelling and relaxation aboard your private yacht. Continue toward Anse des Flamands for scenic cruising and beautiful coastal views before enjoying another memorable evening on the island.
YBH note: Colombier forms part of the Saint-Barthélemy Nature Reserve. Anchoring and mooring are regulated, and some areas are prohibited. The captain must use permitted locations and respect protected seabed habitats.
DAY 6
Tintamarre & the French Caribbean
Cruise northwest toward St Martin, stopping near the beautiful uninhabited island of Tintamarre. Discover a remarkable natural setting with turquoise waters, sandy beaches and beautiful coastal scenery. Enjoy swimming and snorkelling in a permitted area before continuing toward Grand Case or another suitable anchorage along St Martin’s northern coastline. Celebrate your final evening with an exceptional dinner aboard or ashore.
YBH note: Tintamarre is within the Saint-Martin Nature Reserve, with restrictions on anchoring, navigation and water activities. The yacht must use authorised areas. Return to the confirmed embarkation marina on Day 6 if early disembarkation is scheduled.
DAY 7
Return to St Martin
Enjoy your final morning cruising along St Martin’s beautiful coastline, with views of turquoise bays, green hillsides and neighbouring Caribbean islands. Depending on your agreed disembarkation schedule, enjoy breakfast aboard or a final scenic cruise before returning to the confirmed marina. Conclude your seven-day Leeward Islands yacht charter with unforgettable memories of Anguilla’s beautiful beaches, the sophistication of St Barts and the relaxed atmosphere of St Martin.
YBH note: Final arrival must follow the charter agreement. Allow sufficient time for marina access, immigration procedures and onward airport transfers. For early departures, the yacht should return to its confirmed marina the previous evening.
DISCOVER ALONG THE WAY
Best Harbours, Beaches and Marinas
These eight places shape most Leeward charters, from Gustavia and Simpson Bay to the beaches of Anguilla, Nevis and Barbuda. Some harbours have limited berths and some bays are protected, so your crew confirms access and moorings well before you arrive.
Port
Gustavia · St Barts
Gustavia Harbour
Discover Gustavia, the sophisticated maritime heart of St Barts and one of the Caribbean’s most celebrated superyacht destinations. Its picturesque harbour is surrounded by elegant restaurants, designer boutiques and beautiful island scenery. Arriving aboard a private yacht offers an exceptional introduction to the island’s distinctive combination of French sophistication and Caribbean charm. Berthing is highly sought after during major events, with offshore anchoring and tender transfers often necessary.
Protected Area
Northwestern St Barts
Colombier Bay
Explore Colombier Bay, one of St Barts’ most beautiful natural destinations, where undeveloped hillsides surround a spectacular stretch of turquoise Caribbean water. This peaceful setting is ideal for swimming, snorkelling and relaxing aboard a private yacht in suitable conditions. As part of the Saint-Barthélemy Nature Reserve, the bay is subject to marine protection rules, including restrictions on anchoring and designated permitted areas.
Beach
Western Anguilla
Meads Bay
Discover Meads Bay, one of Anguilla’s most beautiful beaches, where powder-white sand and remarkably clear waters create a memorable setting for a private yacht charter. The surrounding coastline is home to sophisticated resorts and waterfront dining experiences, making it an excellent destination for guests seeking a balance of relaxation and refined Caribbean hospitality. Offshore anchoring and tender access depend on local conditions and applicable regulations.
Island
Northwest of Anguilla
Prickly Pear Cays
Cruise toward the Prickly Pear Cays, a remarkable pair of uninhabited islands off Anguilla’s northwestern coastline. Their beautiful beaches, clear waters and natural surroundings create an idyllic setting for scenic cruising, swimming and snorkelling where permitted. The surrounding reefs and sensitive habitats require careful navigation and compliance with local marine protection rules.
Marina
Sint Maarten · St Martin
Simpson Bay & Yacht Marinas
Simpson Bay is one of the principal yacht charter gateways in the northeastern Caribbean, offering convenient access to Princess Juliana International Airport and established marine services. The surrounding lagoon and waterfront accommodate a variety of yacht operations, while the island’s location provides excellent access to St Barts, Anguilla and the wider Leeward Islands. Larger yacht access depends on draft, bridge schedules and the selected marina.
Marina
Southern Antigua
English Harbour & Nelson's Dockyard
Discover English Harbour, one of the Caribbean’s most important historic yachting destinations. Home to Nelson’s Dockyard and surrounded by beautiful natural scenery, the harbour combines maritime heritage with established yacht services, waterfront restaurants and a lively international sailing community. It is an excellent embarkation point for charters exploring Antigua, Barbuda and the southern Leeward Islands.
Beach
Western Barbuda · Antigua and Barbuda
Barbuda's Western Beaches
Explore Barbuda’s remarkable western coastline, celebrated for its long, lightly developed beaches and extraordinary shades of turquoise water. The island offers a beautiful contrast to the more cosmopolitan destinations of the northern Leewards, with opportunities for scenic cruising, secluded beach experiences and peaceful days aboard. Shallow approaches, reefs and exposed coastal conditions require careful route planning and suitable yacht positioning.
Beach
Western Nevis · St Kitts and Nevis
Pinney's Beach
Discover the beautiful coastline of Nevis, where tropical vegetation and the dramatic volcanic landscape create a distinctive Caribbean setting. Pinney’s Beach offers a long stretch of golden sand, relaxed waterfront dining and beautiful views across the surrounding waters. It is an attractive destination for extended Leeward Islands yacht charters connecting St Barts, St Kitts and Nevis with Antigua.
destination insights
The Details That Make the Difference
Expert perspectives and practical guidance for planning your yacht charter.
Leeward Islands Yacht Charter Weather & Best Time to Visit
The best time for a Leeward Islands yacht charter is generally December through April, when warm tropical temperatures, beautiful swimming conditions and more settled dry-season weather create an exceptional setting for Caribbean island-hopping. January, February and March are especially appealing for exploring St Barts, Anguilla, St Martin and Antigua, although the northeast trade winds can bring lively sailing conditions and occasional swell. April often offers a rewarding balance of warm seas, pleasant weather and a relaxed atmosphere. The Atlantic hurricane season runs from June through November, with the greatest tropical cyclone risk typically between August and October. Your Boat Holiday tailors every itinerary to seasonal conditions, the yacht and your preferred destinations.
✔ December – April: Peak charter season with ideal conditions
✔ January – February: High demand, especially around St Barts events
✔ March – April: Excellent weather with fewer crowds, apart from the Bucket Regatta week in St Barts
✔ May – August: Limited availability in select destinations
✔ September – October: Low season due to hurricane risk
The Leeward Islands are primarily a winter charter destination, with many yachts relocating to the Mediterranean in summer.
January
Excellent
23–29°C
Air
27°C
Sea
8 h
Sunshine
14 kn
Wind
YBH note: A prime Caribbean yacht charter month, with warm temperatures, beautiful swimming waters and generally favourable dry-season conditions. Northeast trade winds and occasional winter swell require thoughtful anchorage selection.
Days Under the Trade Winds
Days in the Leewards move easily between sea and shore. A typical day includes:
✔ Cruising between lively ports and peaceful anchorages
✔ Anchoring off white-sand beaches and turquoise bays
✔ Dining ashore at renowned restaurants and beach clubs
✔ Enjoying a blend of cultural, culinary, and social experiences
✔ Flexible itineraries shaped by guest preferences
The Leeward Islands combine Caribbean ease with a refined, international atmosphere. Your crew plans each day around the weather and the events you want to see.
Shape My Days
Reading the Leeward Seasons
The best season runs from December to April, when the weather is dry, the trade winds are steady, and the calendar is full: Christmas and New Year in St. Barts, the Antigua Charter Yacht Show in December, and the Bucket Regatta in the spring. Hurricane season runs from June to November, with the highest risk between August and October. Popular weeks fill up early, so we recommend booking well in advance.
✔ December to April: Excellent. Dry, sunny weather and steady trade winds, with air temperatures of 27 to 29°C and sea temperatures around 27°C. This is peak season, with Christmas, New Year, and the spring regattas, so book early.
✔ May to June: Very good to good. Hotter and calmer, with warm swimming water, fewer yachts and more availability. Hurricane season starts in June, so we watch the forecast.
✔ July to August: Good to limited. Hot and humid, with a rising chance of tropical weather and only a few yachts cruising.
✔ September to October: Not recommended. This is peak hurricane season, and many yachts and restaurants close.
✔ November: Limited. The weather settles as the season ends, and yachts begin arriving for the winter.
The best months for a Leeward charter run from December to April, and popular weeks fill up early.
Time the Winds
Types of Yachts Available in the Leeward Islands
The Leeward Islands suit almost every kind of charter yacht, so the right choice depends on your group and the style of week you want. A sailing catamaran or power catamaran is most popular: it offers wide decks, a shallow draft for beach anchorages, easy water access, and suits families and groups. A sailing yacht or motor sailer is ideal for guests who love sailing between islands in steady trade winds.
For more space, speed, and comfort, a motor yacht is a natural fit. Larger motor yachts and superyachts are especially at home in St Barts and St Martin, where marinas and anchorages accommodate them, and a bigger yacht brings a spa, a beach club, tenders, and a larger crew.
The Leewards suit both ends of the charter market, so we propose yachts ranging from agile catamarans to superyachts built for Gustavia and Simpson Bay. At the top is Q 72, a 72-meter explorer superyacht refitted in 2025, with a helipad, spa, gym, and snow room, plus a large crew for up to twelve guests. Moskito is a 55-meter Heesen from 2021 with a lower-deck beach club, spa and sauna, and a jet tender and foils for days ashore at Anguilla or St Barts.
For guests who prefer a lighter touch, Reve Bleu is a 2023 Lagoon Sixty5 sailing catamaran with a French chef and a good range of water toys, and Arktos, a brand-new Lagoon Eighty2, joins the Caribbean this winter with an inflatable sea pool and an eFoil. Viva la Vida is a Sunreef 80 sailing catamaran with solar panels and a wellness focus, while Mattea is a new Sunreef 80 Power, with a flybridge, a jacuzzi and a Sea-Doo for exploring the bays between islands.
Compare Types
THE GUEST BOOK
Handwritten Thanks
Guests often leave a few written words for the crew at the end of the week.
"To whom it may concern, This was a trip of a lifetime. The crew was amazing! They treated us like family. We could not have asked for more! They have expert knowledge, service and care. We always felt well cared for, safe and in the best hands. They went above and beyond! The food was the BEST! By the time we left the boat we could not eat another bite ♥ So yummy, every meal was beautiful. They are the very very best crew we have ever had and would be blessed to have them again. We leave in tears of joy. Thank you very much, All our love and appreciation, The Chandlers"Robert C.Guest aboard 30m motor yacht, 7-night charter from/to St Maarten-
"We loved every moment of our time with our wonderful very special crew. They were so kind & loving with us, seeing to our every need. I’ve never felt so pampered in my life! Seven days of heaven! The sights & activities they introduced us to were amazing! They’re amazing! Thank you & much love from my heart to yours!"Nancy F.Guest aboard 21m catamaran, 9-night charter from/to Antigua
Questions & Answers
Before You Sail the Leewards
Answers to what guests ask most before chartering in the Leeward Islands.
PRIVATE YACHT CHARTER ADVISORY
The right yacht changes everything. The right people make it yours.
Independent yacht selection, firsthand knowledge and personal assistance — from your first enquiry to your return home.
Your journey, our expertise.
Independent selection. Explore publicly listed and off-market yachts through our international brokerage network, without fleet bias.
Firsthand knowledge. We inspect yachts, meet crews and help tailor every detail to your cruising plans.
Professional credentials. Our team is active in established yacht brokerage associations, including MYBA, IYBA and CYBA.
Planning a yacht charter in The Leeward Islands? Tell us your preferred dates, guests and expectations — our brokers will prepare a considered proposal.
Request Your Private Yacht Proposal
Share a few details about your plans. A YBH charter broker will personally review your request and recommend suitable yachts.
