LYRA
67FT · SAILING CATAMARAN
Pricing from $55,000/week
10 Guests · 5 Cabins · 3 Crew
St. Martin, Anguilla & St. Barts Yacht Charters
Crewed catamaran and motor yacht charters through the Northern Leeward Islands — Gustavia and St. Barts (St. Barths), Anguilla's headline beaches, and the French and Dutch sides of St. Martin, all in a single week.
Why St. Martin, Anguilla & St. Barts
Why Charter Crewed Through St. Martin, Anguilla & St. Barts?
St. Martin sits at the northern edge of the Leeward Islands chain, anchored by Princess Juliana International Airport (SXM) — one of the best-connected airports in the eastern Caribbean. From there, three distinct islands fall within a single week-long itinerary: French and Dutch St. Martin, the British island of Anguilla seven miles to the north, and the chic French enclave of St. Barts (St. Barths) twenty miles to the southeast. One charter, three flags.
A crewed yacht is the practical way to see all three. Ferries between the islands are slow and infrequent, and the most photographed beaches and harbors — Shoal Bay on Anguilla, Colombier on St. Barts, Tintamarre off the French side — aren't ferry-accessible at all; they're reached by tender from a yacht already at anchor. Each island clears customs separately, but the captain handles the paperwork as part of the standard charter setup, and guests step off in Gustavia for lunch or pull up to a beach club without coordinating a transfer.
What sets the cruising ground apart from the rest of the Caribbean is range without long passages. Inter-island sails run two to four hours — short enough to do most of them under sail and still anchor for an afternoon swim. The result is variety inside a single week: a Marigot market morning, a Grand Case dinner, an Anguilla beach day, a Gustavia sundowner, and a half-day at a private islet anchorage like Île Fourchue or Pinel — without ever spending a full day on passage.
What Makes a St. Martin, Anguilla & St. Barts Charter Special
Four characteristics that distinguish the Northern Leewards from other Caribbean charter grounds.
Three Islands, Three Flags
Few Caribbean charter grounds put as many distinct destinations within a single week's sailing. French and Dutch St. Martin share one island under two governments. Anguilla flies the British flag and trades a low-key luxury identity for the Caribbean's best beaches. St. Barts (St. Barths) is wholly French, distinct in tone from any of the others. Customs clearance at each entry is routine — the captain handles the paperwork — and the inter-island runs are short.
St. Barts: Gustavia & Beyond
St. Barts (St. Barths) is the Caribbean's most concentrated stretch of luxury — superyachts side-tied along the Gustavia quay during the season, designer shopping in the harbor district, and beach clubs at Shell Beach, Saline, and Gouverneur. Past Gustavia, the island opens up: Île Fourchue and Colombier are protected anchorages with no road access and no commercial development, reachable only from the water.
Anguilla's Headline Beaches
Anguilla holds some of the Caribbean's most photographed beaches — Shoal Bay, Meads Bay, Rendezvous Bay, Maundays Bay — long uninterrupted strips of fine white sand backed by low-density resorts and beach restaurants. The typical day rotates between an anchorage off one of the headline beaches, a beach lunch ashore, and a tender hop over to one of Anguilla's offshore cays for an afternoon snorkel.
Grand Case, Marigot & French Cuisine
St. Martin's French side is the dining capital of the eastern Caribbean. Grand Case's harbor strip lines up two dozen restaurants over a single half-mile beach — grilled lobster shacks (the lolos) at one end, white-tablecloth French menus at the other. Marigot adds a Saturday market with French cheeses, Caribbean produce, and pâtisseries, walkable from the marina. The chef on board provisions out of Marigot before departure.
Featured St. Martin, Anguilla & St. Barts Crewed Yachts
A hand-picked selection of catamarans, power catamarans, and motor yachts for St. Martin, Anguilla & St. Barts crewed charters — yachts and crews we know firsthand.
Sample St. Martin, Anguilla & St. Barts Crewed Charter Itinerary
Your week is shaped around your group's interests, the season, and the conditions on the water — your captain tailors the days as they unfold. Treat this itinerary as a starting point for inspiration.
Crewed Itinerary · St. Martin & St. Barts
A Weeklong Escape to St. Martin and St. Barts
A private, crewed yacht charter through Saint Martin, St. Barts, and Anguilla offers the perfect mix of secluded anchorages, world-class snorkeling, vibrant island culture, and endless relaxation. Your professional captain and private chef ensure that every moment is stress-free, allowing you to fully enjoy the Caribbean's most stunning destinations.
With gourmet meals prepared fresh onboard, plenty of opportunities for water sports, and breathtaking sailing between idyllic islands, this itinerary offers an unforgettable blend of adventure and indulgence.
- Duration
- 7 days / 8 nights
- Base
- St. Martin (SXM)
Plan your St. Martin & St. Barts charter
Custom-tailored to your dates and group preferences
1
Day 1 of 7 · SXM → Simpson Bay
Welcome to Saint Martin – Embark in Simpson Bay
Anchorage: Simpson Bay, St. Martin
Your journey begins upon landing at Princess Juliana International Airport (SXM). A private transfer will bring you to IGY Simpson Bay Marina, where your captain and crew warmly welcome you aboard. Settle into your cabin, enjoy a refreshing champagne toast and chef-prepared welcome platter, and take in the first views of your floating home for the week.
Spend the afternoon unwinding as your yacht sets sail for a calm anchorage nearby. If you're up for an adventure, hop on a paddleboard or snorkel the warm waters of Simpson Bay.
As the sun dips below the horizon, enjoy a beautifully curated first dinner aboard, featuring fresh Caribbean seafood and tropical flavors. Those interested in exploring can take the tender ashore for an optional nightcap at Sint Maarten Yacht Club or the lively Soggy Dollar Bar.
Day Highlights
- Private transfer to IGY Simpson Bay Marina.
- Cocktail welcome and chef-prepared meal aboard.
- Relaxing first sail and sunset at anchor.
- Optional post-dinner drinks ashore.
2
Day 2 of 7 · Simpson Bay → St. Barts
Sail to St. Barts – Chic Vibes in Gustavia and St. Jean Beach
Anchorage: St. Jean Beach, St. Barts
Wake up to the scent of fresh coffee and breakfast prepared onboard, then set sail for St. Barts, the Caribbean's most exclusive island. The two-hour sail offers the perfect opportunity to relax on deck or try your hand at deep-sea fishing along the way.
Arriving in Gustavia, take time to explore the chic harbor, browse boutique shops, or enjoy a French pastry from a waterside café. In the afternoon, your yacht anchors off St. Jean Beach, where you can swim, paddleboard, or snorkel in the crystal-clear waters.
Dinner is served aboard under the stars, featuring a gourmet multi-course meal paired with fine wines. Those interested in a night out can take the tender ashore for an optional drink at Shellona Beach Club or the lively Le Ti St. Barth.
Day Highlights
- Sail to St. Barts, relaxing on deck or fishing en route.
- Explore Gustavia's boutique shops and harbor cafés.
- Swim and sip cocktails at St. Jean Beach's Nikki Beach Club.
- Chef-prepared dinner aboard under the stars.
- Optional drinks at Shellona Beach Club.
3
Day 3 of 7 · St. Barts → Colombier
Secluded Snorkeling and Beach Picnic at Colombier Beach
Anchorage: Colombier Beach, St. Barts
Start your morning with a leisurely breakfast on deck, then cruise to Colombier Beach, one of St. Barts' most secluded and breathtaking anchorages. Only accessible by boat or a scenic hiking trail, this pristine bay offers fantastic snorkeling and calm waters for paddleboarding.
Spend the day enjoying the peaceful surroundings, swimming in the turquoise waters, or lounging on the beach with a private picnic prepared by your chef. For those looking to stretch their legs, a short hike rewards you with breathtaking panoramic views of the island.
As the evening sets in, return to your yacht for another incredible meal on board, perfectly paired with a Caribbean sunset.
Day Highlights
- Snorkeling and sea turtle spotting at Colombier Beach.
- Snorkeling, paddleboarding, and beachcombing.
- Chef-prepared beach picnic.
- Sunset cocktails and dinner aboard.
4
Day 4 of 7 · Colombier → Orient Bay
Sailing to Tintamarre – Snorkeling and Serenity
Anchorage: Orient Bay, St. Martin
After breakfast, set sail for Tintamarre, a stunning uninhabited island and part of the St. Martin Marine Reserve. The shallow reefs here are teeming with marine life, making it one of the best snorkeling spots in the region.
Spend the morning snorkeling with sea turtles, stand-up paddleboarding, or exploring the pristine beaches. Enjoy a freshly prepared seafood lunch aboard, then sail to Orient Bay, one of St. Martin's most famous beaches, known for its crystal-clear waters and soft white sand.
Relax on the yacht, take the tender ashore for beachside cocktails, or stay aboard for a quiet evening dining under the stars.
Day Highlights
- Pristine snorkeling and marine encounters at Tintamarre.
- Lunch onboard, prepared with fresh local seafood.
- Beachside cocktails and relaxation at Orient Bay.
5
Day 5 of 7 · Orient Bay → Grand Case
Culinary Indulgence in Grand Case
Anchorage: Grand Case, St. Martin
Sail a short distance to Grand Case, the "Gourmet Capital of the Caribbean." Spend your morning snorkeling at Creole Rock, one of St. Martin's most famous underwater sites, where coral reefs and tropical fish create a stunning dive experience.
Back on board, enjoy a leisurely lunch while taking in the view of the picturesque village. The afternoon is yours to enjoy—kayak along the coastline, take the tender ashore for boutique shopping, or simply unwind on deck.
Dinner is another exquisite meal prepared by your onboard chef, though guests have the option to dine ashore at one of Grand Case's renowned French-Caribbean restaurants.
Day Highlights
- Snorkeling at Creole Rock, a vibrant underwater paradise.
- Afternoon exploring Grand Case or enjoying water sports.
- Gourmet dinner aboard, with an optional meal ashore.
6
Day 6 of 7 · Grand Case → Anguilla
Anguilla – White Sands and Tranquil Cays
Anchorage: Road Bay, Anguilla
After breakfast, set sail for Anguilla, an island famed for its powdery white sand beaches, crystal-clear waters, and laid-back charm. Your captain will anchor at Road Bay, where you can take the tender to Sandy Island or Prickly Pear Cays, two stunning offshore islets perfect for snorkeling and beachcombing.
Spend the afternoon enjoying snorkeling straight from the yacht, stand-up paddleboarding, or simply lounging on deck with a cocktail in hand. For lunch, your chef will prepare a fresh seafood feast, best enjoyed alfresco on the aft deck as you soak in the Caribbean breeze.
As the sun begins to set, return to your private anchorage and enjoy a peaceful dinner aboard under the stars. For those who want to explore a bit of local nightlife, a short tender ride can take you to Elvis' Beach Bar, where the relaxed island vibes and live music make for a fun but easygoing evening ashore.
Day Highlights
- Sail to Anguilla, anchoring at Road Bay.
- Snorkeling and beachcombing at Sandy Island or Prickly Pear Cays.
- Paddleboarding, kayaking, or swimming in the calm waters.
- Freshly prepared seafood lunch aboard.
- Sunset dining on the yacht, with an optional visit to Elvis' Beach Bar.
7
Day 7 of 7 · Anguilla → Marigot
Sail Back to Saint Martin – A Perfect Final Day
Anchorage: Marigot, St. Martin
On your final full day, enjoy a relaxed morning swim and a final breakfast on deck before setting sail back toward Marina Fort Louis in Marigot, Saint Martin. The two-hour sail offers time to reflect on your incredible week while basking in the warm Caribbean sun.
Upon arrival, spend the afternoon at your leisure—explore the charming streets of Marigot, browse French boutiques, or sip coffee at a waterfront café. If you prefer to stay aboard, take advantage of the yacht's water toys for one last snorkel or paddleboarding session in the tranquil waters near the marina.
As the sun begins to set, enjoy one final toast with your crew, followed by a gourmet farewell dinner onboard, showcasing the best flavors of the Caribbean. Your captain will anchor in a peaceful bay, allowing for a final night of relaxation, stargazing, and reminiscing about an unforgettable voyage.
Day Highlights
- Scenic return sail to Saint Martin.
- Explore Marigot's French-inspired shops and cafés.
- One last paddleboard or snorkel session near the marina.
- Final chef-prepared dinner aboard, with sunset cocktails.
8
Day 8 · Departure
Farewell to Paradise
Your final morning aboard begins with a relaxed breakfast and coffee on deck, taking in the last views of the Caribbean waters.
By mid-morning, your crew will handle all final arrangements, ensuring a seamless transfer to Princess Juliana International Airport (SXM) or your next destination. As you step off the yacht, take with you unforgettable memories of a luxurious, adventure-filled week at sea.
Plan Your St. Martin, Anguilla & St. Barts Charter
When to go, what it costs, and how to get there — the practical answers guests ask before booking a St. Martin, Anguilla & St. Barts crewed yacht charter.
When to Charter the Northern Leewards
Peak Season (Dec–Apr)
December through April is the highest-volume booking window. Trade winds run from the east-northeast at 15 to 22 knots, daytime highs sit in the low 80s, and rain is rare. The cruising ground is at its busiest from Christmas through New Year and again over Easter — St. Barts in particular peaks during the New Year holiday, when the Gustavia quay fills with megayachts and the island's restaurants book out weeks in advance. The best yachts and crews go 6 to 12 months early for those weeks.
Best Window (Apr–Jun & Nov)
Late April through June and the back half of November sit between peak season and the heart of hurricane risk. Trade winds soften slightly to 12 to 18 knots, water temperatures climb into the 80s, and rates typically drop 15–25% from peak. Cruising traffic thins as full-time cruisers leave the area; St. Barts in particular reverts to its quieter pre-season rhythm. For guests choosing between windows, this is typically the best value the Northern Leewards offer.
What a St. Martin, Anguilla & St. Barts Crewed Charter Costs
$25,000–$100,000 per week
Crewed yacht charters across St. Martin, Anguilla, and St. Barts typically start around $25,000 per week and scale well past $100,000+ for larger motor yachts and superyachts, depending on yacht size, build year, and crew. Most catamarans charter all-inclusive — the base weekly rate covers yacht, crew, all meals, a standard bar (beer, wine, spirits), fuel for normal cruising, water sports, and customary fees. Larger motor yachts and select sailing yachts run plus-expenses instead, where the base rate covers yacht and crew only and food, beverages, fuel, and dockage are paid through an Advance Provisioning Allowance (APA) — a pre-funded allowance set at 25–35% of the base rate, with itemized accounting and any unused balance refunded at trip end. The cruising ground itself adds modest costs that most other Caribbean grounds do not: marina fees in Gustavia rise sharply in peak season, and each customs clearance carries a small per-island fee. Crew gratuities, customary at 15–20% of the base rate, are paid directly to the captain on disembarkation.
How to get to St. Martin, Anguilla & St. Barts
- Gateway airports
- Princess Juliana International Airport (SXM) on the Dutch side of St. Martin is the primary gateway and one of the best-connected airports in the eastern Caribbean. Non-stop flights operate daily from Atlanta, Charlotte, Miami, Newark, New York (JFK), and Philadelphia, plus seasonal direct service from Boston, Dallas, and Washington-area airports — and from Paris, London, and Amsterdam in Europe. Flights from the US East Coast run four to four-and-a-half hours. St. Barts has its own short STOL airstrip (SBH) reached by 10-minute Tradewind or St. Barth Commuter hops from SXM; some guests fly direct into SBH on a private aircraft.
- Embarkation ports
- Most charters embark at IGY Simpson Bay Marina on the Dutch side of St. Martin — five minutes from SXM by taxi and large enough for any yacht size. Fort Louis Marina in Marigot on the French side is a less common embarkation but a favored mid-charter stop. From either marina, the typical run heads first to St. Barts (a two- to three-hour sail) or up to Anguilla (a one-hour sail), depending on weather and the group's preference. One-way charters that begin in St. Barts are also possible; we walk through the options with you before booking.
- Airport transfers
- From SXM, IGY Simpson Bay Marina is a five-minute taxi ride and Fort Louis Marina is twenty-five minutes. Private transfers are easy to arrange in advance through the broker. For guests arriving direct into St. Barts (SBH), Gustavia harbor is a five-minute drive from the airstrip; the yacht typically anchors at Corossol or Shell Beach to receive the tender.
- Customs & immigration
- Each of the three islands clears customs and immigration separately — the Dutch and French sides of St. Martin, Anguilla, and St. Barts each operate as a port of entry. The captain handles the paperwork at each clearance as part of the standard charter setup. Guests need a valid passport for all three. US, UK, EU, Canadian, and Australian citizens do not require visas. The customs stops are routine for any captain working the cruising ground; they add 30 to 45 minutes per island but no other friction.
Frequently asked questions
About chartering in St. Martin, Anguilla & St. Barts.
How long should our St. Martin charter be?
We recommend a week. The cruising ground covers three distinct islands — French and Dutch St. Martin, Anguilla, and St. Barts (St. Barths) — and seven days gives you time to settle into the Northern Leewards instead of rushing through them. A typical week pairs an embarkation in Simpson Bay with a few days in St. Barts (Gustavia, Colombier, Île Fourchue), an Anguilla beach day or two (Shoal Bay, Sandy Island, Maundays Bay), and a French-side dinner in Grand Case before disembarking.
Shorter trips (4-5 days) work too. For those we typically focus on either St. Barts and Anguilla as a tight loop, or St. Martin and one of the two — the inter-island runs are short enough that even a long weekend covers real ground.
What is included in an all-inclusive St. Martin crewed charter?
Included: a professional crew (typically captain, chef, and stewardess), all meals and a standard bar (beer, wine, and spirits), water sports equipment, fuel for normal cruising, customary mooring fees, linens, and towels.
Not included: crew gratuities (15-20% of the base charter rate), marina dockage in Gustavia (which spikes in peak season and is paid separately), customs and immigration fees at each of the three islands, premium drinks or specialty provisions, onshore dining (Grand Case, Gustavia restaurants, etc.), and transfers to and from the yacht.
What is APA, and how does it work on a Caribbean Leewards crewed charter?
APA stands for Advance Provisioning Allowance — a pre-paid fund (typically 25-35% of the base charter rate) that covers food, beverages, fuel, mooring and marina fees, customs fees, and other running costs during your trip. Your captain keeps an itemized account, and any unused funds are refunded at the end of your charter.
Most catamarans across St. Martin, Anguilla, and St. Barts charter all-inclusive. APA pricing is more common on larger motor yachts and select sailing yachts. In this cruising ground specifically, APA also covers Gustavia dockage (which can rise to several thousand dollars per night during peak holiday weeks), per-island customs clearance fees, and any one-way relocation cost if your itinerary ends at a different marina from where it started.
How far in advance should we book a St. Martin or St. Barts charter?
For peak season (December through April), book 6-12 months ahead — the best yachts and crews go first. The New Year holiday is the highest-demand week of the year in St. Barts; many guests book it 12+ months in advance, and the Gustavia quay fills with megayachts side-tied for the week.
For late-April through June (the best-value window), 4-6 months is typically enough. Last-minute availability comes up too, especially when a charter cancels — we can always check what's open.
Can the chef accommodate dietary restrictions or preferences?
Yes. Your chef can accommodate virtually any dietary need — vegetarian, vegan, gluten-free, kosher, allergies, kids menus, and more. Before your charter, you will complete a preference sheet detailing every guest's dietary requirements, favorite foods, and anything to avoid. Your chef builds the menu around it.
In the Northern Leewards specifically, expect French ingredients alongside your preferences — the chef provisions out of Marigot's Saturday market before departure, which means French cheeses, charcuterie, fresh-caught Caribbean fish, and the kind of pâtisseries you'd expect in a French Caribbean kitchen. It's part of what makes a St. Martin charter feel different from a charter elsewhere in the Caribbean.
Should we start our charter in St. Martin or St. Barts?
Both work, and the right call depends on your trip length and how you're traveling.
St. Martin (SXM) is the more common starting point — direct flights from most US East Coast cities and major European hubs, a five-minute taxi to IGY Simpson Bay Marina, and large enough infrastructure for any yacht size. The trade-off is a two- to three-hour sail to reach St. Barts on the first day.
St. Barts (SBH) starts you in the most exclusive part of the cruising ground from the moment you step on board, but the airport is short-runway STOL only — guests fly in either on a 10-minute Tradewind hop from SXM or direct on a private aircraft. There is sometimes a relocation fee to position the yacht to St. Barts at the start of the charter.
For most guests, embarking in St. Martin and sailing to St. Barts on day one is the right balance. For private-aircraft guests on a shorter trip, starting direct in St. Barts is hard to beat.
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How to Book Your St. Martin, Anguilla & St. Barts Yacht Charter
1
Share Your Vision
Fill out our quick form and we'll dive into your unique preferences — from adventure-packed itineraries to pampered escapes. Whether you're a seasoned sailor or new to charters, we'll tailor recommendations just for you.
2
Choose the Perfect Yacht
With over a decade of experience, we'll guide you to the yacht that matches your style, needs, and group. Having personally chartered many of these yachts, we'll ensure you select the one best suited for your perfect escape.
3
Relax While We Handle the Details
Once your yacht is booked, we'll take care of logistics: paperwork, reminders, and personalized resources to help you plan. From arrival planning to must-visit spots, we'll make your charter as seamless as it is unforgettable.
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