St Martin Sailing Itinerary - Your Ultimate Guide to Sailing in the Caribbean

Recommendation: Start with a two-night stay in a beachfront hotel on Simpson Bay and set sail the next morning toward Grand Case to ease into trade winds and currents.

Based in Philipsburg, rent one of the catamarans anchored near Simpson Bay or join a crew aboard a locally operated charter, then cruise to the calm coves around Little Bay for a restful first night. Plan efficient hops of about 12–18 nautical miles each day, with shorter legs on lighter wind days to keep the crew ready and eager for the next stretch along the southern coast.

On day two, cruise to Orient Bay, then follow a path that hugs the coastline where rugged hills meet crystal water. Look for dolphins riding the bow wake, a sign of healthy habitat, and step ashore for a stroll through the streets of Grand Case–where fresh seafood markets and glamorous boutiques give you a taste of local life.

On land, arrange hikes including routes to viewpoints above Marigot and the interior trails that wind through the habitat of seabirds and tropical flora. Although some sections can be difficult after rain, these detours break the routine and keep the rhythm restful, especially after a day on a catamaran.

When you dock for the night, consider a quick stop at a manor-style villa or boutique hotel for a spa break, then chase unforgettable sunsets along the beach. The glamorous evenings on shore, paired with incredible snorkeling moments just offshore, make the itinerary feel based in real Caribbean charm.

whats included in this plan covers route options, recommended harbors, provisioning tips (fresh fruit, water, reef-safe sunscreen), and a packing list that keeps the crew ready for trade winds and occasional showers. Born travelers will appreciate the flexibility to rearrange days around wind, currents, and the dolphins’ playful habitat, so you can enjoy all three skies–sun, sea, and stars–without rushing.

Anse de Colombier to Philipsburg Route Overview

Check-in at your charter base, confirm weather, and trim sails for a southeastern leg along the leewards. Starting from Anse de Colombier, located on the leewards coast, set a friendly pace, keep the bow toward Philipsburg, and favor the lee to dampen seasick-chop. This route keeps legs short and enjoyable, with ample time for snorkelling and side trips.

The distance runs about 12–16 nautical miles, with a typical crossing of 2.5–4 hours under light to moderate trades. Steps to follow: 1) check-in, 2) raise sails, 3) head southeastern along the leewards, 4) monitor wind shifts, 5) adjust course to Philipsburg, and 6) anchor or dock in a public mooring near Front Street. The route traces reefs and shallow bays where you can wade for a quick refresh if needed.

Snorkelling opportunities appear near shallow reefs and around lee-side coves you can reach after a short sail. Drop anchor for 20–30 minutes at a protected spot, don your mask, and enjoy bright tropical fish. Keep an eye on boats approaching the anchorage and respect local regulations.

As you approach Philipsburg, ease into a public dock or anchored mooring near Front Street, which lines a bustling waterfront with shops and eateries. Philipsburg offers ample provisioning options and friendly service, making the stop rewarding. Aside from sailing, you can stroll the street, sample local bites, and plan a next leg with confidence.

Optimal Weather Window: Wind, Seas, and Seasonal Patterns

Choose a 7- to 10-day week in late February through early April to lock in the most reliable conditions: northeast trades around 18–25 knots and seas typically 2–4 ft in lee waters, with occasional 4–6 ft swells along windward routes.

According to latest forecast data for maarten, this window remains favorable, with pinel Island offering calmer micro-patterns and panoramic coastlines that invite relaxed cruising between favorite stops. The route features village charm and a rich selection of places to explore, all within easy reach of sheltered harbors.

Wind direction tends to stay northeast through spring, and orient your route toward protected bays and short hops between places. Average wind speeds run 18–23 knots, with gusts into the mid-20s to high-20s on gusty afternoons. Tropical conditions bring sunny mornings and seas that range from 2–4 ft in sheltered lanes to 4–6 ft along exposed channels, which you can handle with a stable boat and careful planning.

The seasonal pattern is straightforward: December through April provides the most predictable weather for cruising maarten and the surrounding isles. May to November brings higher risk of frontal systems and tropical showers, increasing cancellation risk and making flexible itineraries important.

For a week that features pinel, Grand Case, Orient Bay, and Philipsburg, the loop offers beautiful, panoramic views and a colorful sense of island charm. The path includes savannah coastline segments and a few village stops with delectable dining that’s a favorite for many sailors. Having a plan with multiple anchorages reduces stress if winds rise or seas swell unexpectedly.

Having a flexible schedule helps. If a leg shifts due to weather, shift to a closer harbor and enjoy an extra day at pinel or in a tucked-away cove, with turtle sightings along the beaches. This approach keeps the week enjoyable and minimizes wasted time.

Booking tip: check cancellation policies and fees. Look for options with flexible cancellation terms, typically with lower fees when canceled well in advance and modest reductions if weather forces changes. Confirm terms in writing to avoid surprises during peak season.

Looking ahead, the latest conditions favor a 7- to 10-day week that aligns with northeast winds, tropical days, and manageable seas, letting you look forward to beautiful sailing in maarten and the broader Caribbean, into a week of relaxed cruising and memorable moments.

Navigation Prep: Charts, Plotting, and Safety Gear

Begin with a dual-charting kit: current paper charts and a capable handheld plotter. Ensure coverage for the Saint Martin area and nearby islands, including safe depths, wrecks, and preferred anchorages. If you sail busy harbors or seek untouched coves, set a clear route with one backup and confirm your position every 15 minutes while underway.

Plot waypoints for safe depths, anchor zones, and hazards such as reefs and shoals. Keep a 0.5–1 nm buffer when approaching sandy coves and along the coastline; mark exits toward protected bays or quiet anchors. Use common-sense limits for night entries and maintain a contingency plan in shifting seas.

Safety gear: VHF with DSC, AIS, EPIRB, life jackets for all, a throw line, a first-aid kit, a fire extinguisher, and a waterproof bag for electronics. Test all devices before departure and keep a spare set of fuses, watches, and a whistle at hand. Maintain a simple equipment checklist and review it with your crew before each leg.

Docking and marina planning: verify current mooring options at major ports and prioritize marinas with security, power, water, and reliable access. For coastal visits, bring a compact headlamp and a color map for walking routes, and note access rules for reefs, protected areas, and popular dive spots. If a harbor fills up, switch to a nearby marina with better protection and calmer moorings.

Keep a post-run log of winds, currents, and the performance of each leg. Build a small range of go-to routes to handle sudden squalls, and reserve time for trips to quiet coves when possible. Maintain a clear, lean plan so the crew can adjust quickly as conditions shift.

Anchorages and Mooring Options Between Anse de Colombier and Philipsburg

Base in Simpson Bay Lagoon for effortless access to four locations along the coast, then reach Philipsburg quickly for immigration and restocking. This setup keeps your cruising simple, with relaxed evenings, excellent stress-free navigation, and a range of waterfront dining options within easy reach.

Between Anse de Colombier and Philipsburg, four locations stand out as reliable anchors or mooring bases: Anse de Colombier, Grand Case Bay, Orient Bay/Pinel Island, and Simpson Bay Lagoon. Each offers a distinct coastline feel, easy town access, and ways to tailor your days to favorites like casual eating, beach strolls, and fantastic snorkeling experiences.

Anchor or drop a mooring at Anse de Colombier first: the cove protects from trades blowing from the northwest and presents clear water and good holding in sand and weed bottom. Bring a modest scope and keep well clear of the rocky headlands. Morning arrivals let you beat cruise-ship crowds and set a restful pace for your next leg along the coast.

Grand Case Bay provides a waterfront vibe with a short hill climb to the town. Moorings are available through local operators, or you can anchor to a sheltered lee in the southern part of the bay. After arriving, stroll along the street to the lively waterfront, pick up provisions, and dine on Tropicana’s seafood and creole flavors–great as a base for four days of coastal exploring.

Orient Bay and Pinel Island create a relaxed, casual stretch where you could anchor near the western edge of Orient Bay or take one of the shallow moorings around Pinel Island. The coastline stays shallow enough for comfortable dinghy hops to the beaches, and the week’s experiences often include snorkeling, beachside eating, and a visit to Anguilla across the channel for a quick day trip if you’re sure about border rules.

Simpson Bay Lagoon remains the most versatile base for accessing Philipsburg and the ports along this route. The lagoon hosts a robust mooring field with simple check-in at nearby bases or harbors. It’s ideal for a restful night with easy shore access to towns, groceries, and immigration clearance when you arrive in Philipsburg. The area includes several waterfront options, casual dining, and easy water-taxi connections to the airport area and nearby towns.

When planning arrivals, aim for late afternoon arrivals to minimize crowds, and always establish a plan for immigration checks at Philipsburg if needed. The four locations above offer different flavors of cruising experiences, from the quiet beaches near Anse de Colombier to the bustling waterfronts of Grand Case and Philipsburg. Each makes a solid base for a Caribbean chapter that blends sailing days with flavorful eating, hillside views, and effortless transitions between towns along the coast.

Provisioning, Water, and Fuel: Where to Stock Up Before Crossing

Stock up in the eastern Caribbean hubs before crossing: crowded docks with reliable provisioning shops keep you well supplied. Visit the inner aisles of large supermarkets and dockage-market stalls to load up on water jugs, canned goods, rice, oil, and a range of delicious, shelf-stable items. Call ahead to confirm stock and hours, especially during busy periods, so your attempts to top up don’t end in delays.

Water planning starts with a solid target: plan 60–80 liters per person for a 4–5 day crossing if you lack a desalination option, plus a 25–40 liter reserve. Store the water within protected, well-ventilated lockers to keep it cool and free from sun exposure. Use 20-liter jerrycans for easy handling and fill main tanks at the start; treat any non-potable additions and label containers to avoid mix-ups. Expect a few visits to markets ashore (often in crowded, sunbathing-friendly harbors) and learn where the best tasting tap water comes from in each dockage area.

Propane fuel requires careful planning: carry two 9–kg (20 lb) cylinders, with a spare cylinder as a safety cushion. Keep cylinders in a ventilated, protected area away from heat and fumes, and carry a leak detector and regulator spare. Refill at marina gas docks in the crowded bays, and call ahead to reserve a cylinder exchange during peak season. This form of fuel keeps galley cooking simple and reliable during long passages, particularly when you want to prepare delicious hot meals after a day of bird-watching and gentle sunbathing.

For provisions, choose kinds that mix well with long storage: canned fish, beans, lentils, pasta, rice, tomato products, and sturdy vegetables. Add herbs, olive oil, and spices to elevate meals without adding bulk. When you shop, test a few flavors and taste profiles to avoid dull meals; an occasional tasty snack can make the crossing feel restful. Look for markets near dockage that offer fresh fruit from local farms–delicious options often include tropical juices and island-grown snacks that boost morale after hills hikes or shoreline walks.

Fuel planning also covers auxiliary needs: carry enough diesel for the engine and a small amount of spare fuel for auxiliary systems, keeping the tank inspected and clean. Label all fuel containers clearly and store them away from water access and living quarters. If you don’t have a fuel transfer plan, consult the harbor master during your call to confirm the best exchange points; this minimizes risk and helps you stay on schedule in busy ports.

Garbage and shore duties matter, too. Pack sturdy bags and sort waste ashore at designated points to avoid clutter on deck. Keep the paint-free lines clear and dispose of packaging in proper containers at dockage facilities. A tidy boat improves safety and the taste of every meal, reducing friction with crew and local crews who patrol the sands and piers. By staying disciplined about garbage, you protect the pristine, protected waters you’ll sail through between america and britain’s historic harbors, and you’ll have time to enjoy splendid views and a few quiet moments for restful evening calls with the crew.

Finally, use a simple pre-crossing checklist to learn the unique quirks of each port: dockage forms, local hours, and the kinds of items that are reliably in stock. This practical approach keeps you from rushing through crowded markets and helps you plan a calm, ultimate crossing. The routine you build now will serve you well during future crossings, and you’ll quickly discover the best places to stock up, from the sandy approaches to the prickly scrub along the shoreline–each stop building a stronger provisioning habit that pays off in taste, reliability, and peace of mind.

Day-by-Day Snapshot: Timing, Distances, and Stopover Choices

Plan a 4-day loop: sail from martins toward Grand Case, then Basseterre, then Nevis, and back to the Dutch side for a chill finish. Keep each leg around 18–30 nm to stay relaxed, with plenty of chances for sightseeing and eating along the way.

1. Day 1 – Timing, Distance, Stopover

   Depart martins at 08:00. Distance 15–20 nm to Grand Case, taking 3–4 hours under typical trade winds. Entry into a snug harbor at Grand Case gives you tranquility and easy shore access for a quick stroll and shutters‑facing photos along the waterfront. The area remains popular yet you can dodge crowds by exploring nearby coves. Overnight in Grand Case offers a gorgeous sunset and authentic Creole eating, with numerous options within easy reach. If the dock is crowded, anchor just offshore and use the dinghy to land; this keeps the chill vibe intact for a family or a group renting a boat anywhere along the coast.

2. Day 2 – Timing, Distance, Stopover

   Set sail around 07:30 toward Basseterre, St Kitts. Distance 28–32 nm; expect 5–6 hours of sailing with steady trade winds. Basseterre’s harbor entry is straightforward; you can dock in the inner quay or settle at a protected slip. The town is crowded on market days but remains popular for a mix of history and modern amenities. Take a short excursion to charles Fort for a quick sightseeing moment, then wander through nearby manor‑style estates and the historic waterfront. The dining scene offers numerous eating spots, from casual shacks to nicer restaurants. For families, the walkable streets and calm evenings help everyone stay relaxed and connected to the bay view.

3. Day 3 – Timing, Distance, Stopover

   Depart Basseterre by 08:00 for a short hop to Charlestown, Nevis. Distance 10–12 nm; 2–3 hours of sailing. Anchor or dock near Charlestown, a snug harbor with easy access to shore. From here, visit Montpelier Manor for a half‑day of history and tranquil grounds set against a mountain backdrop. The island’s color is carried by the shutters and white‑washed cottages along the lanes, delivering a laid‑back vibe that suits chill days with family. Eating options are numerous, including beachside grills and local inns, making this a nicest stop for a relaxed pace and an unforgettable contrast to busier ports.

4. Day 4 – Timing, Distance, Stopover

   Head back toward martins with a final stop at Marigot or a quick pass by Simpson Bay. Distance 22–28 nm; 4–5 hours. Marigot offers a modest entry into a vibrant market scene and scenic sightseeing, while Simpson Bay provides convenient dock options and a laid‑back finish to the trip. This last hop is your chance to rent a dinghy for a quick beach landing, stock up on snacks, and enjoy a chill, family‑friendly wrap‑up. The day's pace remains unforced, and the overall route leaves you with an unforgettable sense of serenity and the nicest views to cap off the voyage anywhere along the coast.