Marigot · French side
The protected marina opens directly into Marigot Bay, avoiding a Simpson Bay bridge wait on the first and final sailing day.
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The complete charter-planning guide
Sailing
Saint Martin
Two jurisdictions. Three island cultures. Anguilla’s white-sand anchorages just across the channel.
Bareboat · Skippered · CrewedReviewed July 29, 2026
Orient Bay, Saint-Martin · Everything Caribbean
Best seasonDecember–April
Classic charter7–10 nights
Primary baseMarina Fort Louis
ExperienceIntermediate · Level 2
Why this base matters
The sailing is compact. The borders make it interesting.
Saint Martin is one of the Caribbean’s most versatile charter gateways. A single week can combine French dining, Dutch yacht infrastructure and Anguilla’s clear water; ten nights can add St. Barts without turning every day into a delivery. The challenge is not extreme mileage. It is managing open-water swell, reef and reserve rules, bridge times, fleet restrictions and repeated international clearance without letting paperwork eat the trip.
01
Read the contract first
Anguilla, St. Barts, reserve islands and exposed east-coast stops may carry fleet-specific restrictions.
02
Protect daylight
The major fleets prohibit night sailing and require the yacht secured at least an hour before sunset.
03
Treat borders as days
A ten-mile sail can still consume a morning when two jurisdictions and office hours are involved.
04
Let Anguilla breathe
Use Road Bay as the base for beaches, restaurants and permitted cay days.
Moorings & Sunsail base
Marina Fort Louis puts the fleet outside the bridge.
Level 2
The Moorings lists at least ten days or 200 nautical miles as skipper on a comparable yacht. Approval remains operator-specific.
October–August
Both brands publish a September closure tied to hurricane season. Other dates and insurance restrictions can change.
Bareboat · Power · Crewed
The Moorings
Marina Fort Louis · Marigot
A major French-side base with sailing catamarans, monohulls, power yachts and crewed options. The published cruising area includes Saint Martin, Anguilla and St. Barts, subject to contract restrictions and current clearance rules.
Current fleet & terms ↗Bareboat · Skippered
Sunsail
Marina Fort Louis · Marigot
The sailing-focused sister fleet uses the same practical gateway. Compare current résumé requirements, skipper availability, fleet dates, hurricane-season closure and permitted cruising zones before choosing a yacht.
Current fleet & terms ↗Catamaran or monohull?
A catamaran suits shallow swimming platforms, group space and long anchor days, but adds windage in exposed bays. A monohull rewards the channel crossings and often costs less, with deeper draft and less level living.
Skippered is not a compromise
A local skipper is the smart first-charter choice for a crew unfamiliar with international clearance, the lagoon bridges, reserve buoys and Anguilla’s permit system.
Season & sea state
Short passages still meet the open Atlantic.
Prime season
December–April
Drier weather, established trades and the strongest charter, restaurant and ferry season. Northerly swell can still close favorite roadsteads.
Warm shoulder
May–June
Warmer water, fewer boats and softer rates, with rising humidity, squalls and sargassum exposure.
Storm season
July–November
Higher heat, rainfall and hurricane risk. September base closure and changing insurance limits make this a specialist period.
Marina Fort Louis → Grand Caseabout 5–7 nm
A natural first shakedown leg when northerly swell is modest.
Marigot → Road Bay, Anguillaabout 8–10 nm
A short international passage; the paperwork can take longer than the sail.
Road Bay → Crocus Bayabout 2 nm
Very short, but still outside Road Bay’s clearance anchorage and subject to current permit rules.
Road Bay → Prickly Pear Caysabout 5 nm
A day-use marine-park outing with no reason to arrive late.
Grand Case → Gustavia, St. Bartsroughly 16–20 nm
An exposed international leg shaped by trade wind, sea state and the exact clearance plan.
Simpson Bay → Road Bayroughly 14–18 nm
Distance varies with the bridge, departure point and route around the western end.
Planning estimates only. Current charts, notices, forecast, reserve rules, yacht performance and the base briefing control every leg.
Simpson Bay Lagoon
The bridge is a timetable, not a suggestion.
8:30 · 10:30 · 16:00
Current published Simpson Bay bridge openings for vessels leaving the lagoon. Regattas and special operations can alter the schedule.
9:30 · 11:30 · 14:00 · 17:00
Hail the bridge on VHF 12, identify the vessel, direction and intended marina, then keep the fairway clear.
5 mph · no fairway anchoring
The Causeway also opens on a schedule. Wake limits, airport restrictions and IALA-B buoyage matter throughout Dutch waters.
Live rule: use Port St. Maarten’s current schedule on the sailing day. Do not build an airport transfer around a screenshot from months earlier.
Saint Martin anchorage atlas
Choose the jurisdiction, then choose the bay.
French Saint-Martin
The charter base, best food stops and most appealing reserve islands sit on this side. Reserve rules matter offshore.Charter base · fuel · clearance
Marina Fort Louis
The Moorings and Sunsail base sits behind Marigot’s breakwater with water, electricity, restaurants and town provisions nearby. It opens directly to Marigot Bay without using the Simpson Bay bridge.Anchoring · town access
Marigot Bay
A practical first or final anchorage outside the marina. Leave room for ferries, commercial traffic and the harbor approach; use the marina or official process for formalities and services.Anchorage · dining
Grand Case
A beautiful leeward roadstead for calm-weather swimming and dinner ashore. Holding and swell deserve a deliberate check, and the dinghy landing plan should be settled before dark.Day stop · beach
Friar’s Bay
A useful swim and lunch stop near the base. It is less suitable when northerly swell reaches the bay and has fewer yacht services than Marigot or Grand Case.Marina · protected cove
Anse Marcel
A sheltered northern harbor with fuel and shore facilities when operating. Confirm current depth, berth availability, entrance guidance and opening status directly.Weather-dependent anchorage
Orient Bay
A striking but exposed east-coast stop. Trade-wind chop, reef, sargassum and charter-company restrictions make it a daylight-and-conditions choice, not a default overnight.Reserve buoys · day use
Tintamarre & Pinel
Use reserve moorings whenever available and obey the size shown on each buoy. Day use is normally free; overnight stays require advance written authorization from the Réserve Naturelle.Dutch Sint Maarten
The lagoon holds the region’s deepest yacht-service ecosystem, while the outer coast provides more convenient short stops.Marinas · repairs · provisions
Simpson Bay Lagoon
The yacht-services center of the island, reached through the Simpson Bay bridge or the lagoon’s French entrance. It is practical, with extensive repairs, fuel, supermarkets and marina choices.Anchoring · airport access
Simpson Bay outer anchorage
Useful while waiting for a bridge opening or flight connection. Aircraft, swell, traffic and a busy dinghy route keep it functional.Anchoring · town access
Great Bay / Philipsburg
Anchor clear of the cruise and commercial areas in suitable conditions. The boardwalk, shops and restaurants are close, but cruise traffic and exposure shape the experience.Protected stop · resort shore
Little Bay
Often calmer than Great Bay with good swimming in settled weather. Confirm the legal anchoring area, resort access and current local restrictions before treating it as an overnight.Restricted / recovery dependent
Oyster Pond
Do not assume historic facilities or access have returned. Charter companies may restrict it; obtain current base guidance before plotting an approach.Detailed Anguilla sailing guide
Clear at Road Bay. Plan the rest around permits and daylight.
Anguilla is the emotional center of many Saint Martin charters and the administrative trap in just as many rushed itineraries. It is a separate British Overseas Territory. Every arriving yacht must complete current Customs and Immigration formalities, and movement beyond Road Bay can require a cruising or marine-park permit. The exact authorization depends on vessel size, intended bays and duration.
01
Enter at Road Bay
Proceed directly to Sandy Ground, keep the crew aboard until instructed and have passports, vessel registration, charter authorization, crew list and outward clearance ready. The skipper handles the official process. Confirm office hours and after-hours arrangements before departure from Saint Martin.
02
Choose the correct permit
Remaining in Road Bay is different from cruising to Crocus Bay, Sandy Island, Prickly Pear, Little Bay or Shoal Bay. Government forms distinguish cruising permits, while marine-park mooring access is separately regulated. Do not assume a charter fee includes either; obtain the current answer and receipt from the authorized department or agent.
03
Respect day-use limits
Public marine-park moorings at Little Bay, Sandy Island, Prickly Pear Cays and Shoal Bay East are published as day-use facilities. Buoy colors correspond to vessel size, anchoring is restricted to approved sand where permitted and Little Bay prohibits anchoring entirely.
04
Keep Road Bay as the overnight plan
Road Bay is the conservative, serviceable overnight base. Rules and charter guidance for overnighting elsewhere can conflict or change. Treat Crocus Bay or another non-Road-Bay night as unavailable unless Anguilla officials and the charter base explicitly approve it for your dates and vessel.
Road Bay · Sandy Ground
Port of entry · default overnightClear Customs and Immigration here before moving elsewhere. Anchor with generous clearance from the commercial dock and ferry traffic; the bay has good shore access, restaurants, taxis and a dinghy landing but no general visitor mooring field.
Crocus Bay
Permit required · confirm overnightA handsome cliff-backed anchorage roughly two nautical miles from Road Bay. Published charter itineraries use it, but current Anguilla overnight rules can be restrictive—obtain explicit official and charter-base confirmation before relying on it after dark.
Little Bay
Marine-park buoy · day onlyA tiny snorkeling cove beneath colorful cliffs. Anchoring is prohibited; use an authorized buoy of the correct size and leave before the permitted day-use period ends.
Sandy Island
Marine-park buoy · day onlyA classic sand-cay lunch and swim. Carry the correct permit, use a suitable authorized buoy and never improvise an anchor on coral or seagrass.
Prickly Pear Cays
Marine-park buoy · day onlyAbout five nautical miles from Road Bay, with reef snorkeling and seasonal beach service. Arrival is exposed, buoys are first-come and the return to Road Bay should be completed with ample daylight.
Shoal Bay East
Exposed marine-park stopA spectacular beach but not a routine charter stop. East-coast exposure, reef, permit rules and many fleet restrictions mean it belongs only in an approved plan with suitable weather and local guidance.
No coral anchoringUse the correct buoy or an officially approved sandy anchoring zone.
No night assumptionsDay-use moorings do not become overnight moorings because dinner ran long.
No dinghy loopholeLeaving Road Bay by tender can still count as cruising outside the port area.
Clear out properlyObtain departure clearance before returning to Saint Martin or continuing to St. Barts.
Provisioning & yacht services
Stock the boat before the islands become the point.
Marigot & major markets
Use the base’s advance provisioning or shop around Marigot and the larger French-side supermarkets. Specialty food, wine and bakery stops are unusually strong.
Largest service network
Simpson Bay and Cole Bay offer the deepest chandlery, repair, supermarket and technical-service bench, but accessing the lagoon can cost a bridge cycle.
Top up—do not start over
Road Bay can provide dining, taxis and selected supplies. Provision heavily in Saint Martin.
Confirm before moving
Fort Louis and major Dutch-side marinas are the dependable planning points. Anse Marcel and other facilities should be checked directly for current operating status.
Two realistic routes
Give Anguilla a week—or give the triangle ten nights.
Lower-stress week
7 nights · Anguilla focus
Marina Fort Louis
Board, provision and complete the chart and yacht briefings. Sleep aboard.
Marigot → Grand Case
Make a short shakedown sail and anchor for a beach afternoon and dinner ashore.
Grand Case → Road Bay
Complete French departure formalities as required, cross to Anguilla and clear in at Sandy Ground before doing anything clever.
Road Bay & Anguilla ashore
Keep the yacht still. Use a taxi for Shoal Bay East, Meads Bay or an island food day, then return to the secure overnight base.
Prickly Pear or Sandy Island → Road Bay
Use the correct cruising or marine-park permit for a daylight cay visit, then return before the authorized period and before sunset.
Road Bay → Marigot
Clear out of Anguilla, return to French Saint-Martin and complete entry procedures before a final dinner ashore.
Base return
Refuel, meet the contracted return window and leave margin for inspection, bridge traffic on land and the airport transfer.
Full northern triangle
10 nights · three cultures
Saint-Martin
Fort Louis handover, Grand Case and a reserve-island day chosen for the weather.
Anguilla
Road Bay clearance and overnights, one full road-island day and a permitted marine-park outing.
St. Barts
Clear into Gustavia, then use Colombier or another approved anchorage according to swell and local rules.
Sint Maarten
Clear into the Dutch side if the route uses Philipsburg or Simpson Bay; time any lagoon entry to the published bridge schedule.
Marigot
Return to the French base only after completing the formalities required by the base and both jurisdictions.
Navigation note: these routes are editorial frameworks, not sailing plans. The charter contract, current charts, clearance offices, permits, weather, reserve instructions and skipper judgment govern every movement.
The non-negotiables
Small distances do not remove consequences.
01
No night sailing
Major fleet contracts prohibit it. Secure the yacht at least one hour before sunset.
02
Watch northerly swell
Grand Case, Friar’s, Road Bay and exposed roadsteads can change character quickly.
03
Use reserve buoys
Tintamarre, Pinel and Anguilla’s parks have habitat rules that override convenience.
04
Respect fleet limits
A beautiful bay outside the contract is still outside the contract.
05
Track bridge time
Missing the Simpson Bay opening can consume the margin intended for clearance or return.
06
Keep a legal fallback
Every day needs a permitted anchorage reachable before dark in the actual sea state.
Official sources & live checks
Open these before leaving the dock.
Fleet restrictions, bridge schedules, clearance offices, Anguilla fees, reserve buoys and marina services change. Recheck each close to departure.
The Moorings St. Martin base information ↗The Moorings route examples ↗Sunsail St. Martin base information ↗Marina Fort Louis ↗Simpson Bay bridge schedule · Port St. Maarten ↗Saint-Martin reserve night-mooring authorization ↗Anguilla Customs contact · Road Bay ↗Government of Anguilla cruising-permit forms ↗Anguilla marine parks & mooring guidance ↗Caribbean Safety and Security Net ↗