A St Barts yacht charter is the kind of trip that people plan a full year ahead, and once you understand the northern Leewards you see why. This corner of the eastern Caribbean packs four very different islands into a triangle you can cover comfortably in a week under sail: St Barts with its French polish and celebrity harbour, St Maarten and St Martin split between two countries and joined by one enormous lagoon, Anguilla with the best beaches in the region and almost nothing built on them, and Antigua with three hundred sixty-five sand-lined bays and the working history of Nelson's Dockyard. The sailing distances are short, the water is warm all winter, and the anchorages change character every few hours of coastline.
This guide is written for people who actually plan to spend time here, whether you are a guest weighing a charter, a deckhand or chef trying to work the season, or an owner deciding whether to put your boat into charter management. We will cover the island-hopping route, the real 2026 costs, the customs paperwork that trips up first-timers, the two peak weeks that drive prices, and the hurricane window you want to avoid. Real prices, real place names, honest tradeoffs.
Most people picture the British Virgin Islands when they think Caribbean sailing, and the BVI earns that reputation with its short hops and calm Sir Francis Drake Channel. The Leewards ask a little more of you. The passages are open water, the swell rolls in from the Atlantic, and a couple of the crossings will have the boat working. In exchange you get variety that the Virgins simply cannot match. Within forty nautical miles you move between a French port that feels like a slice of the Riviera, a Dutch and French island with the best provisioning and yard services east of Puerto Rico, an island whose beaches are genuinely world-class, and a former Royal Navy base that is now a UNESCO World Heritage Site with megayachts stern-to along the eighteenth-century quay.
The season runs December to April, dry and breezy, with the trade winds settling into a reliable easterly of fifteen to twenty-two knots. The two events that define the calendar sit at opposite ends of that window. New Year in St Barts turns Gustavia into the densest gathering of superyachts anywhere on earth, and Antigua Sailing Week in late April closes the season with a regatta that has run since 1967. Between those bookends the islands are quieter, the anchorages more forgiving, and the charter rates a notch softer.
Work the winter season in the Leewards
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Create your free crew profileSaint Barthelemy, called St Barts or St Barth, is eight square miles of hills, red-roofed villas, and a handful of beaches that draw a wealthy French and international crowd all winter. The island has no natural fresh water and almost no agriculture, so everything arrives by boat or plane, and that scarcity shows up in the prices. A modest lunch ashore runs sixty to eighty euros a head before wine. None of that stops the harbour filling, because St Barts is the social centre of the Caribbean yachting season and everyone with a boat wants to be seen there.
Gustavia, the capital, wraps around a small harbour lined with boutiques, brokerage offices, and restaurants that spill onto the quay. The inner harbour holds roughly sixty yachts up to two hundred feet stern-to along the wall, and demand runs far ahead of supply. For the peak dates you are not choosing a berth so much as being allocated one months in advance. Outside the harbour, moorings and anchorages ring the coast at Corossol, Public, and Colombier to the west, and Grand Cul-de-Sac and Marigot to the east. Colombier is the classic overnight spot, a protected bay you reach by boat or a short hike, with turtles in the shallows and no road access to spoil it.
The anchoring rules matter here, and they are enforced. St Barts is a nature reserve in parts, and anchoring on seagrass or coral is prohibited across marked zones. Much of the popular water is now moorings only, and you take a ball rather than drop the hook. The harbour master's office in Gustavia handles clearance and berth allocation, and you call the Capitainerie on VHF channel 12 or 16 on arrival. Overnight rates in the inner harbour scale steeply with length, and a fifty-metre yacht can pay several thousand euros a night at peak. Anchoring off Colombier or Public is free where permitted, which is why so many boats base there and tender into town.
The last week of December is the single most concentrated superyacht event in the world. For the 2025 to 2026 New Year, a record two hundred twenty-six superyachts gathered off Gustavia, with more than one hundred fifty of them available for charter. The fireworks over the harbour on New Year's Eve are the centrepiece, and boats jostle for a sightline. Because berthing inside is so limited, most yachts anchor in the outer roads or take moorings at Grand Cul-de-Sac, which offers calmer water and a quieter scene for families. If you want a boat for this week, brokers advise locking it in six to twelve months ahead. Yachts confirm their St Barts New Year positions earlier than for almost any other Caribbean date, and rates carry a heavy holiday premium on top of the already high winter pricing.
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List your yacht freeTwelve nautical miles northwest of St Barts sits the island shared by two nations, Dutch Sint Maarten in the south and French Saint-Martin in the north. It is the practical heart of the northern Leewards. If St Barts is where you go to be seen, St Maarten is where the boat gets fixed, fuelled, provisioned, and crewed. The island is the yard and chandlery hub for the whole region, and any charter operation running here leans on it.
The centre of it all is the Simpson Bay Lagoon, a large enclosed body of water straddling the border. Two lifting bridges give access, the Simpson Bay bridge on the Dutch side and the Sandy Ground bridge on the French side at Marigot. Inside the lagoon you find IGY Simpson Bay Marina, Isle de Sol, Port de Plaisance, and a cluster of marine services in Cole Bay: riggers, engineers, sailmakers, refrigeration specialists, and provisioning warehouses. On the French side, Marina Fort Louis and the Marigot waterfront add more berths and a customs office. This is the one place in the northern Leewards where a big yacht can haul out, take on serious spares, and rebuild a crew roster in a single stop.
The bridges run to a published timetable, and you plan your day around it because missing an opening can cost you hours. On the Dutch side the Simpson Bay bridge opens several times daily, with outbound and inbound slots alternating through the morning and afternoon. Recent times have run roughly at 8:30, 9:30, 10:30, and 11:30 in the morning, then early and mid-afternoon, and around 4:00 and 5:00 in the evening, with the exact minutes adjusted from time to time. Always confirm the current schedule with the bridge operator on VHF channel 12 before you commit, and call ahead for permission to transit. The channel is about seventeen metres wide with a controlling depth near six metres, so deep-draft yachts watch the tide.
Provisioning is the other reason boats come. Cole Bay on the Dutch side has the large marine stores and the wholesale-style food warehouses that stock a charter galley for a week. Marigot on the French side brings French supermarkets, a morning market, and better wine and cheese than anywhere else in the eastern Caribbean. Many crews split the run, buying dry goods and hardware Dutch-side and fresh produce, bread, and wine French-side. For an owner or captain building a season here, that combination of yard, chandlery, and provisioning under one lagoon is the reason St Maarten anchors the whole route.
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Get hired this seasonFifteen nautical miles north of St Martin lies Anguilla, a low coral island with almost no relief and the finest beaches in the Leewards. Where St Barts is built up and social, Anguilla is deliberately empty. The government protects it with high fees and firm rules, and the result is water that stays clear and beaches that stay uncrowded. Shoal Bay East regularly appears on lists of the best beaches in the world, and Meads Bay and Rendezvous Bay run it close.
You clear in at Road Bay on the north coast, and from there the paperwork governs everything. Sailing anywhere outside Road Bay, even in a tender, requires a cruising permit, and Anguilla's fees are among the highest in the eastern Caribbean. The permit covers daily anchoring and mooring at the offshore cays, and it is priced by vessel size, running from around eighty US dollars a day for a small catamaran up to well over one hundred dollars a day for larger boats. Overnight mooring outside Road Bay is not permitted, so the offshore cays are day stops only. If you plan to visit for less than twenty-four hours you can clear in and out in one visit.
The day anchorages are the reward. Sandy Island is a tiny spit of sand with a beach bar, a few palms, and a snorkeling reef, reached by a short hop from Road Bay. Prickly Pear Cays offer more of the same with reefs on the leeward side, and Little Bay is a sheltered snorkeling stop under the cliffs. Because the fees keep the numbers down, these cays are often nearly empty even in high season. It is the clearest tradeoff in the northern Leewards: you pay to keep other boats away, and the money buys genuine solitude.
Antigua sits about ninety nautical miles south-southeast of St Barts, which makes it the one leg of the route that is a proper passage rather than a hop. It is worth every mile. Antigua is the southern anchor of the northern Leewards and arguably the most complete sailing island in the Caribbean, with hundreds of protected bays and a yachting culture that runs deep.
English Harbour and the adjoining Falmouth Harbour form the centre of it. English Harbour is home to Nelson's Dockyard, the only working Georgian-era naval dockyard left in the world and now a UNESCO World Heritage Site. Megayachts moor stern-to along stone quays that Royal Navy ships used in the eighteenth century, and the old sail lofts and officers' quarters are now restaurants, a hotel, and marine businesses. Falmouth Harbour next door is larger and holds the big marina berths, the sailmakers, and the crew bars. Between them, this is the winter base for a large slice of the world's superyacht fleet and the crews that run them.
Beyond the harbours, Antigua rewards a slow cruise. Green Island on the east coast gives you reef-protected anchoring with almost nothing ashore. Nonsuch Bay is a wide protected lagoon. Deep Bay on the west coast has a wreck you can snorkel over in the middle of the anchorage. Jolly Harbour on the west side is a full-service marina and provisioning stop with an easier, more relaxed feel than English Harbour. For a charter guest, Antigua alone could fill a week; as the end point of a Leewards run it is the strongest possible finish.
The season closes with Antigua Sailing Week, running April 22 to 26 in 2026, its fifty-seventh edition. The regatta has been reworked into a shorter destination-style format, with point-to-point courses that finish each day at a different anchorage around the island, aimed at cruisers and rally sailors as much as hardcore racers. On average the week draws around one hundred yachts, fifteen hundred participants, and thousands of spectators to English and Falmouth Harbours. If you charter for this week, expect the harbours full and the shoreside social scene at full tilt. It is the best time of the season to be in Antigua and the busiest, so book early and expect a premium.
Antigua is where crews get hired for the season
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Build your free profileA classic northern Leewards charter runs the triangle in a week, and there are two directions. Starting in Antigua and working north means your longest and most exposed passage comes first while you are fresh, with the wind more on the beam. Starting in St Maarten, where most charter fleets are based and where the airport has the most connections, keeps the logistics simple and saves Antigua as a grand finale. Which you choose often comes down to where the boat is based and which airport suits your flights.
Here is a workable seven-day plan running north from St Maarten, though a good captain will flex it around the weather and the swell:
| Day | From and to | Distance | What you get |
|---|---|---|---|
| 1 | Board in Simpson Bay, St Maarten | Provisioning | Yard hub, lagoon, easy airport access |
| 2 | St Maarten to Anguilla | 15 nm | Road Bay clearance, Sandy Island day stop |
| 3 | Anguilla cays | Short hops | Prickly Pear, Shoal Bay, empty beaches |
| 4 | Anguilla to St Barts | 25 nm | Gustavia, Colombier overnight |
| 5 | St Barts | Local | Gustavia town, beaches, restaurants |
| 6 | St Barts to St Maarten | 15 nm | French-side lunch, Marigot provisioning |
| 7 | Depart St Maarten | Return | Or extend south to Antigua, 90 nm |
Adding Antigua turns the week into a ten-day or two-week trip, because the ninety-mile leg each way needs a weather window and usually an overnight or a dawn start. Many charters treat Antigua as a one-way itinerary instead, boarding in St Maarten and finishing at English Harbour, or the reverse, with a repositioning fee to cover the crew bringing the boat back. If Antigua Sailing Week or the St Barts New Year is your target, plan the whole route around that fixed date and let everything else move.
The charter season in the Leewards is a winter season. December to April is the sweet spot: steady trade winds, low humidity, little rain, and water temperatures around twenty-six to twenty-seven degrees Celsius. The two peak weeks are the St Barts New Year at the turn of the year and Antigua Sailing Week in late April, and both carry premium pricing and demand early booking. The quieter shoulders in early December, mid-January, and March offer the same fine sailing at softer rates and with emptier anchorages.
The hurricane window is the flip side. The official Atlantic hurricane season runs June 1 to November 30, and the Leewards sit squarely in the track. August, September, and October are the highest-risk months, and most crewed charter operations shut down or reposition their boats out of the region during that stretch. St Maarten and the surrounding islands were hit hard by Irma in 2017, and the memory shapes how insurers and managers treat the summer. If you want to charter here, aim for the December to April window and treat anything from July to October as off-season with real weather risk.
| Period | Conditions | Crowds and price | Notes |
|---|---|---|---|
| Mid-Dec to Christmas | Trades building, dry | Rising, book ahead | Good shoulder before the holiday spike |
| Christmas and New Year | Peak trades, dry | Highest of the year | St Barts New Year, book 6 to 12 months out |
| January to March | Reliable 15 to 22 kt | Steady, best value in high season | Emptier anchorages, prime sailing |
| April | Warm, steady trades | Spikes for Sailing Week | Antigua Sailing Week Apr 22 to 26, 2026 |
| May to early June | Lighter, warmer | Low, deals appear | Late season, watch early storm risk |
| July to November | Hot, humid, storm risk | Mostly closed | Hurricane season, fleets reposition |
Charter pricing in the Caribbean for 2026 spans a wide range, and the northern Leewards sit at the higher end because of positioning, permits, and the pull of St Barts. A fully crewed week runs from roughly twenty thousand US dollars at the small end to well past two hundred thousand for a large superyacht. Most family groups on a crewed catamaran that sleeps six to ten land somewhere between thirty thousand and seventy thousand dollars for the week, with a private captain and chef included.
The pricing model matters. Many Caribbean crewed catamarans use an all-inclusive rate under a CYBA-style contract, where the fee covers crew, meals, bar, fuel, water, and water toys, and you add only dockage, national-park and cruising-permit fees, and the crew gratuity. Larger yachts more often run on a plus-expenses basis, where you pay the base fee and then an Advance Provisioning Allowance, the APA, of typically twenty-five to thirty percent of the charter fee. The captain draws fuel, food, drink, and dockage from the APA and reconciles the balance at the end, refunding what is left or asking for a top-up. Gratuity for the crew is customary at roughly ten to fifteen percent of the base fee on top.
| Yacht type and size | Guests | Model | Approx. weekly base 2026 |
|---|---|---|---|
| Crewed sailing catamaran, 45 to 50 ft | 6 to 8 | All-inclusive | $22,000 to $35,000 |
| Crewed catamaran, 50 to 60 ft | 8 to 10 | All-inclusive | $35,000 to $60,000 |
| Power catamaran, 60 to 75 ft | 8 to 10 | All-inclusive or plus APA | $55,000 to $110,000 |
| Motor or sailing yacht, 100 to 130 ft | 8 to 12 | Plus expenses, APA 25 to 30% | $90,000 to $180,000 |
| Superyacht, 130 ft and up | 10 to 12 | Plus expenses, APA 25 to 30% | $200,000 and up |
On top of the base rate, budget for the region's fees. Anguilla's cruising permits run eighty to one hundred ten dollars a day depending on size. St Barts harbour and mooring fees scale steeply with length, from modest for a catamaran on a mooring to several thousand euros a night for a large yacht stern-to in Gustavia at peak. Antigua charges national-park and Dockyard fees at English Harbour. Fuel across the region is not cheap, and the St Barts New Year and Antigua Sailing Week weeks add a holiday premium of anywhere from twenty to fifty percent over standard high-season rates. Power catamarans generally cost ten to fifteen percent more than sailing cats of the same length because of higher fuel and engine costs.
The northern Leewards look compact on the chart, but you cross several international borders in a week, and each one wants clearing in and out. This is the single thing first-time charterers underestimate. A crewed charter with an experienced captain handles all of it, which is one of the strongest arguments for going crewed here rather than bareboat.
St Barts and French Saint-Martin are France, so moving between them and to French customs is straightforward, and clearance is often a quick computer terminal at the harbour office in Gustavia or Marigot. Dutch Sint Maarten is a separate jurisdiction with its own clearance at the Simpson Bay or Philipsburg offices. Anguilla is British Overseas Territory and requires clearing in at Road Bay plus the cruising permit before you touch any other anchorage. Antigua and Barbuda is an independent nation with its own customs and immigration at English Harbour or Jolly Harbour, and it charges cruising and park fees. Each clearance means the captain visiting customs and immigration, sometimes both in separate offices, with the crew and guest list, passports, and the boat's papers.
Practical points that save grief: bring your actual passport, not a copy, because immigration checks it. Do not plan to arrive anywhere after office hours expecting to clear, since overtime fees apply and some offices simply close. Keep the guest manifest accurate, because mismatched numbers cause delays. And remember that the fees are per boat and per clearance, so a week that touches all four jurisdictions carries a real stack of customs, immigration, and permit charges that a good broker will itemise up front. This complexity is exactly why crewed charters dominate the Leewards: guests want the borders handled for them.
Owners: understand charter management before you sign
Running a boat through the Leewards season means crew, permits, maintenance, and a management company you trust. Connect with managers and captains on Yacht Service Network and compare your options first.
Explore charter managementFor crew, the northern Leewards are one of the best places in the world to work a winter and to break in. St Maarten and Antigua are the two hiring centres. St Maarten's lagoon and Antigua's English and Falmouth Harbours fill every autumn with boats hiring deckhands, stewardesses, chefs, engineers, and mates for the December to April season, and dockwalking those two ports in November is a proven way onto a boat. Many crews arrive with a green STCW certificate and an ENG1 medical, hand out CVs along the docks, and pick up daywork that turns into a season.
The pay is real. A green deckhand or junior steward on a mid-size charter yacht can expect roughly two thousand five hundred to three thousand five hundred US dollars a month plus food and accommodation aboard, and experienced crew, chefs, and engineers earn considerably more. On top of salary, charter gratuities are shared among the crew and can add meaningfully to a busy season's earnings. The tradeoff is intensity: charter weeks are long, guest-facing, and demanding, and the turnaround days between charters are hard work. But a full Leewards season builds a CV fast and puts you in the middle of the industry's winter hub.
Getting hired is about being findable when a captain has a gap to fill. Agencies exist, but many captains in the Leewards hire directly off the dock and through their own networks, which is where a strong online profile pays off. If you are chasing crew jobs in Antigua or crew jobs in St Maarten, having a complete profile with your certificates, references, and availability listed means a captain can find and message you the moment they need someone, without an agency in between. For a broader picture of how the season hires and what roles pay, our guide to charter yacht crew jobs walks through the whole path from first certificate to full season.
Get found by captains hiring for the Leewards
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Create your crew profileFor owners, the northern Leewards are a strong charter market, and the winter season here can offset a meaningful share of the cost of keeping a boat. The logic is simple: your yacht sits idle most weeks anyway, and a well-run charter program turns those idle winter weeks into revenue while a professional crew keeps the boat maintained and used. St Barts New Year and Antigua Sailing Week alone can book at premium rates that owners of well-positioned boats compete for.
It is not free money, and honesty matters here. Charter yachts take wear, and guests are hard on interiors and toys. A management company takes a commission, typically fifteen to twenty percent of charter revenue, and you carry crew salaries, insurance rated for charter use, dockage, and heavier maintenance. The boat must meet commercial coding and survey standards, which is a real cost to bring an owner's yacht up to charter-ready. Against that, a busy season on a desirable catamaran or motor yacht in the Leewards can gross well into six figures, and the crew and upkeep that charter demands mean your boat is looked after rather than sitting neglected on a mooring.
The decision comes down to how you actually use the boat and how much control you want to keep. Owners who want to use the yacht themselves at Christmas and over the sailing-week window will find those are exactly the weeks that charter best, so there is a genuine tradeoff between personal use and revenue. A good manager, honest crew, and a realistic revenue projection are what separate a program that works from one that just adds hassle. Before committing, it is worth reading our overview of how yacht charter works from the guest side, because understanding what charterers expect tells you what your boat and crew will need to deliver.
The four islands reward different guests, and matching the itinerary to the group is what makes a charter land. St Barts suits people who want restaurants, shopping, a social harbour, and a scene, and it works best for couples and groups who like a night ashore as much as a day on the water. St Maarten is functional rather than a destination, but the French side around Marigot and Grand Case has genuinely good food, and the beaches at Orient Bay are worth a stop. Anguilla is for beach people who value quiet over nightlife and do not mind paying for it. Antigua is the sailor's island, with the best cruising, the deepest history, and enough anchorages to fill a fortnight.
A family with young children often does best basing around calmer water, St Barts's Grand Cul-de-Sac and Anguilla's protected cays, and skipping the longest exposed passages. A group of experienced sailors will want the full triangle with the Antigua leg. A first-time charter party is usually happiest on a shorter St Maarten, Anguilla, St Barts loop that keeps passages under twenty-five miles and touches the best of the region without the ninety-mile Antigua crossing. For the wider Caribbean context, and to see how the Leewards compare with the Virgins, the Grenadines, and the rest of the region, our full Caribbean yacht charter guide lays out the regions side by side.
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Join Yacht Service NetworkA few things make the difference between a good week and a frustrating one in the northern Leewards. Book far ahead for anything touching the peak weeks, because St Barts New Year and Antigua Sailing Week fill their best boats a year out. Build a weather buffer into any plan that includes the Antigua crossing, since the ninety-mile leg needs the right window and a stubborn schedule can force a bad passage. Budget realistically for fees, because the cruising permits, harbour charges, park fees, and clearances across four jurisdictions add up to more than newcomers expect.
Provision in St Maarten if your route allows it, since nothing else in the region matches the lagoon for stocking a galley, and prices ashore in St Barts and Anguilla are steep. Respect the anchoring rules, especially in St Barts's reserve zones and Anguilla's marine park, where fines are real and the moorings are there for a reason. And if you want to keep in touch with the boat, weather, and the wider Caribbean cruising picture between trips, the YSN app puts crew profiles, marine services, and local marine businesses in your pocket; you can grab it from the app download page.
Above all, go crewed for your first Leewards trip. The border-clearing, the bridge timings, the anchoring restrictions, and the exposed passages all reward local knowledge, and a captain and chef who know these waters turn a logistically complex route into an easy week. Bareboat is possible for very experienced sailors comfortable with open-water passages and heavy paperwork, but the crewed option is why most people who charter St Barts and the Leewards come away wanting to do it again.
A fully crewed week in the northern Leewards runs from about twenty thousand US dollars for a small crewed catamaran to over two hundred thousand for a large superyacht. Most groups on a catamaran sleeping six to ten land between thirty thousand and seventy thousand dollars for the week with a captain and chef. St Barts New Year and Antigua Sailing Week carry premiums of twenty to fifty percent over standard high-season rates, and you add fuel, permits, dockage, and a crew gratuity on top.
December to April is the season, with steady trade winds, dry weather, and warm water. January to March offers the best value in high season with reliable sailing and emptier anchorages. The two peak weeks are the St Barts New Year at the turn of the year and Antigua Sailing Week from April 22 to 26 in 2026, both of which demand early booking and cost more.
Very few crewed charters operate in the Leewards from July to November, because the Atlantic hurricane season runs June 1 to November 30 and the islands sit in the track. August through October is the highest-risk stretch, and most fleets shut down or reposition their boats out of the region. Stick to the December to April window for a reliable charter.
Yes. St Barts and French Saint-Martin are France, Dutch Sint Maarten is separate, Anguilla is British, and Antigua and Barbuda is an independent nation, so you clear customs and immigration at each. Anguilla also requires a cruising permit before you visit any anchorage beyond Road Bay. A crewed charter captain handles all of this, which is one of the main reasons to go crewed in the Leewards.
Book six to twelve months ahead through a broker, because St Barts New Year is the densest superyacht gathering in the world and berths are allocated far in advance. The inner harbour holds only about sixty yachts stern-to, so most boats anchor in the outer roads or take moorings at Grand Cul-de-Sac. Berthing and mooring rates carry a heavy holiday premium on top of already high winter pricing.
St Maarten is the practical hub of the northern Leewards, home to the best yards, chandleries, and provisioning in the region around the Simpson Bay Lagoon. It is more functional than scenic, but the French side around Marigot and Grand Case has excellent food and the beaches at Orient Bay are worth a stop. Most charters start or end here because the airport has the best connections and the lagoon has everything a boat needs.
St Maarten and Antigua are the two hiring centres, and boats staff up in autumn for the December to April season. Many captains hire directly off the docks in Simpson Bay and English and Falmouth Harbours, so dockwalking in November works, as does having a complete online profile with certificates and references that captains can find. A green STCW certificate and an ENG1 medical are the usual entry requirements for junior crew.
It can offset a real share of ownership costs, since the winter season books well and premium weeks like St Barts New Year command high rates. Against that, you pay a management commission of fifteen to twenty percent, crew, charter-rated insurance, and the cost of bringing the boat up to commercial coding, and charter guests put wear on the yacht. The best-use weeks are also the ones you might want the boat yourself, so the decision comes down to how you balance personal use against revenue.