Duration
55 Nights
Journey Type
Cruise only (Please call for flight options)
Ports
46 Ports
4 January
Setting sail from Philipsburg
Philipsburg is the gateway to an intriguing little Caribbean island with a dual personality: the Dutch side, St. Maarten, is the livelier of the two, with shopping malls, casinos and more of a nightlife scene, while French-speaking St. Martin is a more refined (and more expensive) affair, with a laid-back, continental air and a host of exclusive resorts and restaurants. Travelling between the two halves of the island is hassle-free, and both sides boast beautiful beaches, friendly locals and pleasant little towns and villages.
There are some amazing hikes on the island, so if you feel up to it, hire a guide to take you on one of the trails.
5 January
Antigua and Barbuda: Falmouth Harbour
Antigua is famously home to 365 beaches - one for every day of the year - and there is an undeniable allure to the many white sand coves dotted along the coast. Falmouth Harbour lies on the south of the island, close to historic Nelson’s Dockyard and the lookout at Shirley Heights.
6 January
Anguilla: Road Bay
Tiny Anguilla is home to no less than 33 beaches, blessed with some of the most gloriously white sands in the Caribbean. A clutch of high end hotels and gourmet restaurants attract a well-to-do crowd, but the island has a more low key, laid back vibe than its glitzy neighbours, St Martin and St Barths.
7 January
British Virgin Islands: Soper’s Hole (Tortola)
7-8 January
British Virgin Islands: Jost Van Dyke
The idyllic island of Jost Van Dyke, named after an early Dutch settler, is known for its laid back vibe and friendly beach bars, including the famous Foxy’s, which counts Keith Richards amongst its past customers. It’s a place to kick back and relax, and the clear blue waters are also perfect for snorkelling.
9 January
British Virgin Islands: Virgin Gorda
Languid, laid-back Virgin Gorda is blessed with beautiful beaches and wonderfully friendly people. Life proceeds at a slower pace here, and highlights include The Baths, an unusual collection of granite boulders, grottoes and pools on the island’s southwest shore.
10 January
Saint Barthélemy: Gustavia
Gustavia is the chic and petite capital of Saint Barths, a tiny French Caribbean island that’s renowned as a haunt of the rich and the famous. You can certainly live well here if you’ve got the means, with an array of gourmet restaurants and luxury boutiques aimed squarely at the A-list. The beautiful beaches, on the other hand, are free and open to all.
11 January
Sint Maarten: Philipsburg
Philipsburg is the gateway to an intriguing little Caribbean island with a dual personality: the Dutch side, St. Maarten, is the livelier of the two, with shopping malls, casinos and more of a nightlife scene, while French-speaking St. Martin is a more refined (and more expensive) affair, with a laid-back, continental air and a host of exclusive resorts and restaurants.
12 January
Saint Kitts and Nevis: Basseterre (Saint Kitts)
Laid back and low key, Saint Kitts is an island typified by rolling green hills, characterful beach bars and the lingering remnants of the sugar cane trade that once dominated here. Attractions include the UNESCO-listed Brimstone Hill fortress, the 18-mile Scenic Railway and the faded Georgian elegance of the capital, Basseterre.
13 January
Montserrat: Little Bay
Montserrat garnered global attention in 1995 when the Soufrière Hills volcano erupted, burying the island’s capital, Plymouth. Although an exclusion zone is still in place in the south, visitors are often surprised by how lush and unspoilt the rest of the island is, home to a colourful variety of birdlife.
14 January
Saint Barthélemy: Gustavia
Gustavia is the chic and petite capital of Saint Barths, a tiny French Caribbean island that’s renowned as a haunt of the rich and the famous. You can certainly live well here if you’ve got the means, with an array of gourmet restaurants and luxury boutiques aimed squarely at the A-list. The beautiful beaches, on the other hand, are free and open to all.
15 January
Guadeloupe: Deshaies
16 January
Dominica: Roseau
The island of Dominica stands out from the rest of the Caribbean, a rugged natural paradise that remains blissfully free of mass market tourism. The capital, Roseau, is pleasant enough, but the island interior offers so much more, including thick jungle, bubbling hot springs, cascading waterfalls and abundant birdlife.
17 January
Saint Lucia: Pigeon Island
Connected to the mainland by a man-made causeway, Pigeon Island is one of Saint Lucia’s most important historical sites. The British admiral George Rodney gave his name to the fort built here in the 18th century to spy on the French in Martinique, as well as the beautiful bay that the fort overlooks.
18 January
Barbados: Bridgetown
There’s more to Barbados than just beaches; the delightful architecture of the old garrison in Bridgetown, the capital, is fully deserving of its UNESCO World Heritage status, and the island interior is littered with old sugar plantations and natural wonders such as Harrison’s Cave.
19 January
Martinique: Trois-Îlets
Trois-Îlets is perhaps best known for the plantation La Pagerie, the birthplace and childhood home of Joséphine Bonaparte. The main beach, Anse Mitan, is a picturesque spot with a few shops and restaurants close by, and you can catch a ferry across the bay to Martinique’s bustling capital, Fort-de-France.
20 January
Saint Lucia: Castries
Castries, Saint Lucia’s diminutive capital, is home to some interesting markets and colonial buildings. The island’s highlights are situated elsewhere, however, and we’d recommend either heading south towards Soufrière, where the iconic Piton mountains guard a beautiful bay, or north to the bars, restaurants and beaches of Rodney Bay.
20-21 January
Saint Lucia: Pigeon Island
Connected to the mainland by a man-made causeway, Pigeon Island is one of Saint Lucia’s most important historical sites. The British admiral George Rodney gave his name to the fort built here in the 18th century to spy on the French in Martinique, as well as the beautiful bay that the fort overlooks.
22 January
St. Vincent & Grenadines: Bequia
Bequia is an incredibly friendly, laid-back island blessed with pristine golden sand beaches and some excellent restaurants. It’s also a popular sailing destination; the yachts tend to congregate around Admiralty Bay, where you’ll find the little waterfront town of Port Elizabeth.
23 January
St. Vincent & Grenadines: Mayreau
Situated just to the west of the Tobago Cays, Mayreau is a tiny, barely inhabited island that can only be reached by boat. There is very little to do, which is the main attraction for those lucky few who wash up here; the palm-fringed beaches and gently lapping waters are the Caribbean island idyll par excellence.
24 January
Grenada: St George's
Browse the markets of charming St George’s, fragrant with the scent of cinnamon and nutmeg, and you’ll soon understand why Grenada is known as the ‘isle of spice’. This is one of the Caribbean’s most enchanting islands, fringed by gorgeous beaches and largely unsullied by mass market tourism.
25 January
Barbados: Bridgetown
There’s more to Barbados than just beaches; the delightful architecture of the old garrison in Bridgetown, the capital, is fully deserving of its UNESCO World Heritage status, and the island interior is littered with old sugar plantations and natural wonders such as Harrison’s Cave.
26 January
Trinidad and Tobago: Man O War Bay
27 January
St. Vincent & Grenadines: Mayreau
Situated just to the west of the Tobago Cays, Mayreau is a tiny, barely inhabited island that can only be reached by boat. There is very little to do, which is the main attraction for those lucky few who wash up here; the palm-fringed beaches and gently lapping waters are the Caribbean island idyll par excellence.
28 January
Saint Lucia: Soufrière
Soufrière is Saint Lucia’s oldest city, founded by the French in 1746 in the stunning south of the island. Nearby natural wonders include the iconic Piton mountains, the Diamond Botanical Gardens and the world’s only drive-in volcano, where you can soak in the restorative sulphur springs.
29 January
At sea
30 January
Bonaire, Sint Eustatius and Saba: Kralendijk
The quiet, cactus-covered Dutch Caribbean island of Bonaire is internationally renowned for its diving, ringed by spectacular coral reefs that teem with life. The capital, Kralendijk, is home to some pretty colonial architecture, and the island is also known for its flamingos and pink sand beaches.
31 January
Curaçao: Willemstad
The gabled houses of Willemstad lend an undeniably Dutch feel to the capital of little Curaçao, with a splash of Caribbean colour thrown in. The island itself is not your typical lush tropical paradise - the landscape is characterised instead by thorny shrubs and cacti - but there are some fantastic beaches and quaint little villages.
1 February
Aruba: Oranjestad
The tiny Dutch Caribbean island of Aruba, located just off the coast of Venezuela, lies outside of the hurricane belt, meaning it enjoys a largely dry climate, and boasts some of the best beaches in the region, if not the world.
2 February
At sea
3 February
Colombia: Santa Marta
Situated on Colombia’s Caribbean coast, Santa Marta is the oldest surviving Spanish colonial city in South America. The modern city lacks some of the charm of nearby Cartagena, but tourism has come on leaps and bounds in recent years, with a number of ambitious regeneration projects and a host of new restaurants and bars.
4 February
Colombia: Cartagena
Cartagena was founded by Spanish conquistadors in 1533, and the beautifully preserved centre is a real highlight of Colombia’s Caribbean coast. The walled old town, the Ciudad Amurallada, is a camera-friendly collection of cobbled streets and colourful, colonial-era buildings.
5 February
At sea
6 February
Panama: Bocas del Toro
The Bocas del Toro archipelago is one of Panama’s most appealing tourist destinations, a collection of idyllic Caribbean islands blessed with beautiful beaches, lush mangroves and wildlife including sloths, iguanas and turtles.
7 February
At sea
8-9 February
Panama: Colón
Situated at the Atlantic entrance to the Panama Canal, Colón is not somewhere you will want to hang around for long, and serves merely as a gateway to the Canal, which will carry you to much nicer places.
10 February
Panama: Bocas del Toro
The Bocas del Toro archipelago is one of Panama’s most appealing tourist destinations, a collection of idyllic Caribbean islands blessed with beautiful beaches, lush mangroves and wildlife including sloths, iguanas and turtles.
11 February
Colombia: Rada El Cove (Isla San Andres)
12-13 February
At sea
14 February
Honduras: Roatán
Roatán is the largest and busiest of the Bay Islands, which sit off the coast of Honduras in the crystal clear waters of the Caribbean Sea. It’s a fantastic destination for divers and snorkellers, with a stunning reef just offshore, and also boasts some lovely beaches.
15 February
Belize: Belize City
Belize’s capital does not enjoy the best reputation, and we wouldn’t recommend spending too much time here; use it instead as a jumping-off point to explore the fascinating Mayan ruins of Xunantunich, Lamanai and Altun Ha, or take a snorkelling trip to the beautiful Barrier Reef, including the famous Blue Hole.
16 February
Mexico: Costa Maya
The port at Costa Maya is a purpose-built facility for cruise passengers, with amenities including swimming pools, restaurants and bars. The neighbouring village of Mahahual will give you a slightly more authentic taste of the Yucatán, and the ruined Mayan city of Chacchoben is an hour’s drive away.
17 February
Mexico: Cozumel
Cozumel first made its name as an off the beaten track destination for divers, thanks to the crystalline waters and low key beach vibe. These days the cat is very much out of the bag, but get away from the craft shops and jewellery stores of the busy port and you’ll find a welcoming island community that is still authentically Mexican.
18 February
At sea
19 February
Cayman Islands: Grand Cayman
Far more than just an offshore tax haven, Grand Cayman boasts the staggeringly beautiful white sands of Seven Mile Beach and some fantastic snorkelling in crystal clear waters. The capital, George Town, is a compact and friendly place, home to some interesting architecture and a suspiciously large number of registered companies.
20 February
Bermuda: West End
21 February
Jamaica: Port Antonio
Situated on Jamaica’s north east coast, Port Antonio has a quieter, more authentic feel than the big resorts on the west of the island, and was once a haunt of Hollywood stars such as Errol Flynn. This part of Jamaica is rich in natural beauty, with pristine rainforest, secluded beaches, cascading waterfalls and misty mountains.
22 February
At sea
23 February
Dominican Republic: Santo Domingo
Santo Domingo is the oldest continuously inhabited European settlement in the Americas, founded in 1496 by Bartholomew Columbus (Christopher’s brother). The city’s history is most keenly felt amongst the streets of the Zona Colonial, home to beautiful old churches and colonial era houses.
24 February
Dominican Republic: La Romana
La Romana is situated on the south east coast of the Dominican Republic, with several nearby attractions worth your time. Next to the sprawling Casa de Campo resort you’ll find the pretty tourist village of Altos de Chavón, while the beaches of Isla Saona and Isla Catalina are a short boat ride away.
25 February
At sea
26 February
British Virgin Islands: Jost Van Dyke
The idyllic island of Jost Van Dyke, named after an early Dutch settler, is known for its laid back vibe and friendly beach bars, including the famous Foxy’s, which counts Keith Richards amongst its past customers. It’s a place to kick back and relax, and the clear blue waters are also perfect for snorkelling.
27 February
British Virgin Islands: Virgin Gorda
Languid, laid-back Virgin Gorda is blessed with beautiful beaches and wonderfully friendly people. Life proceeds at a slower pace here, and highlights include The Baths, an unusual collection of granite boulders, grottoes and pools on the island’s southwest shore.
28 February
Arriving in Philipsburg
Our tip
For a change of pace, go to Loterie Farm at the foot of Pic Paradis, the highest point on Saint Martin, where you can cool off, see the wildlife and rent a cabana for a day of swimming in the cascades.
Your home from home
Windstar’s flagship sailing yacht is a stunning sail assisted cruise ship, which combines the refinement of a modern vessel with the romance of a tall ship.
What we love
Gracious staterooms provide a compact yet comfortable retreat. Facilities include several dining options and a variety of bars and lounges, a small swimming pool with two whirlpools and even a watersports platform. The décor is fresh and modern throughout.
Capacity | 342 Guests |
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Crew | 210 International Staff |
Style | This is laid-back luxury at its best with relaxed informal days, refined yet comfortable evenings and a friendly and welcoming crew. |
Inclusions |
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Tailor-make your trip
Where to stay in Saint Martin
Le Petit Hotel in Grand Case is such a fantastic choice – right on the beach, and great value.