The Most Beautiful Towns to Visit While Sailing in Saint Martin

Philipsburg, The capital of Dutch Sint Maarten, is many visitors' first stop on the island
Philipsburg, The capital of Dutch Sint Maarten, is many visitors' first stop on the island | © Jeremy Graham / Alamy Stock Photo
Photo of Lexi Fisher
27 October 2021

Saint Martin is an island of two nations – the northern part is French, whilst the southern part, Sint Maarten, is Dutch. With rolling Caribbean hills and palm-lined beaches backed by European cafes and boulangeries, this Leeward Island brings together the best of both worlds for yachting visitors – and don’t forget about the duty-free shopping. Here’s our rundown of the top spots to explore.

Discover Saint Martin in style by renting a yacht for the day from SamBoat. Alternatively, hire a boat for a multi-day sailing adventure with Dream Yacht Charter – no experience necessary.

Grand Case

Natural Feature
Beach and houses at Grand Case on St. Martin or St. Maarten in the Caribbean
© Brian Atkinson / Alamy Stock Photo / Alamy Stock Photo
A single main road traces the arc of a long sandy crescent beach. Brightly coloured shutters and roofs trimmed with lace-like fascia cap verandahs overhanging the water. Street-side, sandwich boards with daily specials line the sidewalk; this is the island’s culinary mecca. Stroll down the main street, taking your time to read about the night’s specials between stops at boutiques, selling breezy linen and delicate jewellery. Return in the evening for a gourmet meal.


Architectural Landmark
The Boardwalk, Philipsburg, St Maarten, Saint Martin, Lesser Antilles, Caribbean
© Greg Balfour Evans / Alamy Stock Photo
The capital of Dutch Sint Maarten, Philipsburg is a cross-hatch of cobblestone streets, backed by seemingly endless rows of duty-free shopping. The closer to the waterfront you get, the higher the polished glass and price tags become. Get lost in the alleyways between streets, and when your feet get tired, hop aboard the bright red tour train. Be sure to pop into the Guavaberry Emporium for a taste of the island’s fruity, one-of-a-kind liquor.


Architectural Landmark
Colonial architecture in Marigot, St. Martin, French territory, West Indies, Caribbean, Central America
© Michael Runkel / robertharding / Alamy Stock Photo
Cafe windows filled with flaky croissants and decadent macarons tempt you on almost every corner of the capital of French Saint Martin. Find a quiet table to read a novel with a fresh latte, or browse the lively market where colourful pareos and fine French linens billow in the tropical tradewinds. The short hike up to Fort St Louis provides a commanding view of the bay and vibrant valley below.

Anse Marcel

Natural Feature
Glorious beach at Anse Marcel on St Martin, Caribbean
© Zoonar GmbH / Alamy Stock Photo
A small marina and resort village on the outskirts of the National Nature Reserve of Saint Martin, Anse Marcel is the place to go to get away from the noise of the city. More popular with local holidaymakers than tourists, the airy beachside restaurant comes highly recommended. Rent a cabana or beach chair and umbrella for attentive cocktail service, or wander along the lagoon behind the restaurant to spot the green and orange iguanas living in the mangroves.

Orient Bay

Architectural Landmark
Orient Bay with kite surfers on St. Maarten or St. Martin, Caribbean
© Brian Atkinson / Alamy Stock Photo / Alamy Stock Photo
For a more lively beach town, visit Orient Bay on the windswept eastern coast, where rows of red, orange and yellow beach umbrellas contrast against the turquoise waters. Windsurfers cruise along the horizon between the reefs, while parasailers glide above. Get lost among the tropical palms and winding paths between upscale resorts and barefoot-chic restaurants. Feeling brave? Flaunt your birthday suit at the south end of the beach, where clothing is optional.


Architectural Landmark
Cul-de-Sac with boats and beach on St. Martin, Caribbean
© Michelle Jirsensky / Alamy Stock Photo
A short walk up the hillside from the waterfront, Cul-de-Sac is a sleepy little local town that is beautiful in its simplicity. You won’t have trouble finding an unpretentious eatery or boulangerie for your morning coffee. Put on your walking shoes and trek up one of the winding hillside roads for a towering view of the town and coastline below. If you’re in town on a Friday night, make a beeline for Hercule Resto Créole – they serve great barbecue chicken, plus its karaoke night.

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