Set on the Dutch side of St Maarten, Koolbaai (the lagoon-facing area often associated with Cole Bay and Simpson Bay) is a practical launchpad for exploring St Martin/St Maarten and the surrounding Leeward Islands. Calm, protected waters inside the lagoon, short open-water hops outside, steady trade winds, and a choice of marinas make Koolbaai yacht charters straightforward for first-time skippers and flexible for returning crews. From here you can day-sail to quiet beaches, snorkel coral heads in turquoise bays, and plan longer passages to nearby islands—without long, complex routes.

Koolbaai Yacht Charters: Why This St Maarten Base Works

Trade winds, year-round sunshine, and line-of-sight sailing

The northeasterly trade winds typically deliver manageable breeze and gentle seas, creating reliable conditions for sailing most months of the year. You’ll find year round sunshine, short legs between anchorages, and abundant services around the lagoon and at sea-facing marinas. Navigation is largely line-of-sight: pick a morning swim, make a short hop after lunch, and be ashore for dinner without rushing.

Best time to go and hurricane season

Peak charter months run through winter and spring when humidity is lower and winds are settled. The hurricane season spans June–November; some crews still sail during early summer, but itineraries should stay flexible and weather-led. If you’re planning an October vacation, monitor forecasts closely and keep sheltered options in your pocket.

Yacht Charters St Martin & St Maarten: Easy Leeward Islands Itineraries

Leeward Islands highlights from Koolbaai

Koolbaai sits in the northern Leeward Islands, a compact chain known for secluded anchorages, relaxed beach bars, and varied shore excursions. From St Maarten/St Martin you can:

• Circle St Martin/St Maarten: Grand Case for French bistros, Anse Marcel for a calm anchorage, Orient Bay for watersports, and Marigot for markets.

• Hop to St Barts: Short but lively reach to Gustavia’s harbor and shell-sand coves; plan arrivals early for moorings.

• Angle to Anguilla: Known for long, white beaches and clear reef snorkels (check marine park rules and formalities).

Ambitious crews sometimes add Antigua/Barbuda or Saba, but most week-long charters keep things simple with St Martin, St Barts, and Anguilla.

Windward Islands vs Leeward Islands—what’s realistic in a week?

You’ll see dream images of the Windward Islands—St Lucia, St Vincent, the Tobago Cays, and Grenada—in many Caribbean guides. They’re stunning, but they’re hundreds of miles south and suit separate trips (or deliveries). For a one-week itinerary starting in Koolbaai, the northern islands of the Leewards are the practical, time-efficient choice.

Catamaran Charter Caribbean vs Monohull vs Power

Catamaran charter Caribbean: space, stability, shallow draft

A catamaran spreads living areas across twin hulls and a wide deck, keeping the boat level under sail and comfortable at anchor—perfect for mixed-ability crews and families. The shallow draft helps you edge closer to sand in secluded anchorages and step straight into turquoise waters for snorkeling or paddle sessions. Most cats feature large fridges, shade on the deck, and easy swim platforms.

Sailing boats Caribbean: classic feel and lively passages

If you enjoy heel, trim, and upwind performance, a monohull offers that classic sail-by-feel yachting experience. They’re often more economical for the same cabin count and make quick work of reaching legs between St Martin, St Barts, and Anguilla.

Power catamarans Caribbean: quick hops and simple schedules

Power cats and motorboats fit crews with limited time who want to “see it all.” You’ll cover more water in a day, slotting in a snorkel stop at Creole Rock, a lunch swim off Tintamarre, and an evening cruise to a harbor without waiting on breeze. Fuel planning and reserve days for weather are key.

Snorkeling, Diving and Shore Time: Reefs and Calm Cays

Coral reefs and easy snorkels

• Creole Rock (Grand Case): Calm water, lots of small fish, great for first-timers.

• Tintamarre: A low, sandy islet with turtle sightings on the grass flats.

• Pinel Island: Sheltered shallows and beach cafés; kayak or dinghy from the boat.

If you’re building a bigger charter bucket list for future trips, mark the Tobago Cays in the Grenadines for rays and turtles, and Virgin Gorda in the Virgin Islands for reef gardens—both better reached on dedicated itineraries.

Practical Notes for a Smooth Koolbaai Yacht Charter

Formalities and protected areas

The island has both French (St Martin) and Dutch (St Maarten) administrations. Moving between them is straightforward; clearing to Anguilla or St Barts involves standard paperwork and fees. In marine parks, use moorings where provided and avoid anchoring on reefs or seagrass.

Provisioning, fuel and moorings

Koolbaai/Simpson Bay Lagoon is ringed by chandleries, supermarkets, fuel docks and repair services. Many bays use mooring fields; arrive early in high season or have a nearby plan B.

Bareboat, skippered, and what an “experienced sailor” needs

For bareboat bookings, your résumé should reflect recent, relevant experience in similar wind and boat size. If you prefer to focus on the holiday, add a captain (skipper) at checkout; you still enjoy a private trip with local insight on weather windows, remote anchorages, and dinner spots ashore.

Sample 7-Night Koolbaai Yacht Charters Route (Adapt as Weather Dictates)

• Night 1 – Anse Marcel or Grand Case (St Martin): Protected start, sunset swim.

• Night 2 – Gustavia (St Barts): Moor in the harbor; stroll the waterfront and dine ashore.

• Night 3 – Colombier (St Barts): Quiet bay, hike the ridge trail in the morning.

• Night 4 – Road Bay (Anguilla): Long beach, clear water; check local rules for marine parks.

• Night 5 – Crocus Bay (Anguilla): Kayak to limestone cliffs, relaxed evening.

• Night 6 – Tintamarre (St Martin): Sand, turtles, and stargazing from the foredeck.

• Night 7 – Marigot or Simpson Bay (St Martin/St Maarten): Easy return for fuel and checkout.

This rhythm keeps sails short, maximizes water time, and balances nights in secluded anchorages with marina comforts.

What to Pack and Expect On Board

Soft luggage stores easily; bring reef-safe sunscreen, polarized sunglasses for reading water color over sand vs grass, deck shoes, and light spray gear for trades. Many boats include a dinghy, snorkeling sets, and cockpit shade; confirm watermaker, generator, and air-conditioning if those amenities matter to your family or guests.

Book Your Koolbaai Yacht Charters with Boataround

Ready to explore St Martin/St Maarten from Koolbaai? Boataround lets you compare yacht charters, check real-time availability, and reserve securely—whether you want a catamaran, a classic sailing yacht, or a quick power cat. Filter by cabins, gear (AC, watermaker), skipper options, and departure location. Start here: Yacht Charter and Boat Rental – Anse Marcel & St Martin, pick the yacht that fits your crew, and map an itinerary of calm bays, snorkeling stops, and easy island hops. A simple plan, reliable service, and the right boat turn a good Caribbean week into a relaxed, memorable adventure.

Catamaran rental in Koolbaai

Charter a catamaran and explore Koolbaai! Prices start from 459 AU$ per day. Experience the authentic charm of Koolbaai by renting one of our 9 available catamarans. Multihulls in Koolbaai offer you ultimate comfort and space and are ideal for a relaxing family vacation. With great stability, catamarans are easy to sail and a pleasure to live a vacation afloat.

It’s ideal for a family with children as it can anchor in a bay just a few meters from the shore at a depth of only 2 meters.

Our fleet of catamarans in Koolbaai includes popular brands such as Bali, Leopard and Lagoon.

Catamarans in Koolbaai range from 36.1 to 78.7 feet (11 to 24 m) in length. Whether you’re an experienced sailor seeking a bareboat catamaran charter, or a novice desiring a skippered catamaran, we ensure a seamless and memorable sailing experience.

These are some of the best places to charter a catamaran in Koolbaai:

• Catamaran rental Yacht Club Port De Plaisance