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Classic Caribbean

Summary

From the lush volcanic landscapes of Nevis Peak to the captivating charm of Les Saintes; hidden coves and secret beaches to exotic markets and lively cafés, you’ll discover the best of this region on a single Caribbean voyage. Sandy beaches, turquoise waters, verdant hills, and beautiful waterfalls blend seamlessly with the music, flavors, and joie de vivre that define Caribbean life.

Cruise line Windstar Cruises

Ship Wind Surf

Duration 7 nights

Type Ocean Cruise

Regions Caribbean,
Americas,
South America

Itinerary & Map

Philipsburg → Philipsburg 8 days · 7 ports · 1 sea day
Day 1 Philipsburg Embark

The capital of Dutch St. Maarten stretches about a mile (1½ km) along an isthmus between Great Bay and the Salt Pond and has five parallel streets. Most of the...

Full description
Day 2 At Sea
Day 3 Terre-de-Haut
Day 4 Mayreau Island

The small island of Mayreau, just one and 1/2 square miles in area (3.9 square kilometres) is the smallest inhabited island of The Grenadines, and is part of th...

Full description
Day 5 Roseau

Although it's one of the smallest capitals in the Caribbean, Roseau has the highest concentration of inhabitants of any town in the eastern Caribbean. Caribbean...

Full description
Day 6 Basseterre, Saint Kitts

Mountainous St. Kitts, the first English settlement in the Leeward Islands, crams some stunning scenery into its 65 square miles (168 square km). Vast, brillian...

Full description
Day 7 Gustavia

You can easily explore all of Gustavia during a two-hour stroll. Some shops close from noon to 3 or 4, so plan lunch accordingly, but stores stay open past 7 in...

Full description
Day 8 Philipsburg Disembark

The capital of Dutch St. Maarten stretches about a mile (1½ km) along an isthmus between Great Bay and the Salt Pond and has five parallel streets. Most of the...

Full description
Scroll for all 8 days
Route overview map
Day 1 Philipsburg Embark

The capital of Dutch St. Maarten stretches about a mile (1½ km) along an isthmus between Great Bay and the Salt Pond and has five parallel streets. Most of the...

Full description
Day 2 At Sea
Day 3 Terre-de-Haut
Day 4 Mayreau Island

The small island of Mayreau, just one and 1/2 square miles in area (3.9 square kilometres) is the smallest inhabited island of The Grenadines, and is part of th...

Full description
Day 5 Roseau

Although it's one of the smallest capitals in the Caribbean, Roseau has the highest concentration of inhabitants of any town in the eastern Caribbean. Caribbean...

Full description
Day 6 Basseterre, Saint Kitts

Mountainous St. Kitts, the first English settlement in the Leeward Islands, crams some stunning scenery into its 65 square miles (168 square km). Vast, brillian...

Full description
Day 7 Gustavia

You can easily explore all of Gustavia during a two-hour stroll. Some shops close from noon to 3 or 4, so plan lunch accordingly, but stores stay open past 7 in...

Full description
Day 8 Philipsburg Disembark

The capital of Dutch St. Maarten stretches about a mile (1½ km) along an isthmus between Great Bay and the Salt Pond and has five parallel streets. Most of the...

Full description

Philipsburg

The capital of Dutch St. Maarten stretches about a mile (1½ km) along an isthmus between Great Bay and the Salt Pond and has five parallel streets. Most of the village's dozens of shops and restaurants are on Front Street, narrow and cobblestone, closest to Great Bay. It's generally congested when cruise ships are in port, because of its many duty-free shops and several casinos. Little lanes called steegjes connect Front Street with Back Street, which has fewer shops and considerably less congestion. Along the beach is a ½-mile-long (1-km-long) boardwalk with restaurants and several Wi-Fi hot spots.Wathey Square (pronounced watty) is in the heart of the village. Directly across from the square are the town hall and the courthouse, in a striking white building with cupola. The structure was built in 1793 and has served as the commander's home, a fire station, a jail, and a post office. The streets surrounding the square are lined with hotels, duty-free shops, restaurants, and cafés. The Captain Hodge Pier, just off the square, is a good spot to view Great Bay and the beach that stretches alongside.

Mayreau Island

The small island of Mayreau, just one and 1/2 square miles in area (3.9 square kilometres) is the smallest inhabited island of The Grenadines, and is part of the independent state of St.Vincent in the eastern Caribbean Sea. Two of the best known islands in The Grenadines are Mustique and Bequia, the second largest island in this group. The Grenadine Islands are strung out in a gentle sweep between St.Vincent and Grenada. Most visitors to Mayreau arrive from cruise ships, on the regular ferry, or by yacht. There are no proper roads on the island, only a few vehicles, no airport and only a single unnamed village. Mayreau and the neighboring Tobago Cays are very popular for divers and snorkellers. Saline Bay, on the west coast of the island, has a wonderful broad beach and a few local vendors selling T-shirts and local craft. A climb up the road to the hilltop village on the island provides breathtaking views across Mayreau, Canouan, the Tobago Cays and Carriacou.

Roseau

Although it's one of the smallest capitals in the Caribbean, Roseau has the highest concentration of inhabitants of any town in the eastern Caribbean. Caribbean vernacular architecture and a bustling marketplace transport visitors back in time. Although you can walk the entire town in about an hour, you'll get a much better feel for the place on a leisurely stroll. For some years now, the Society for Historical Architectural Preservation and Enhancement (SHAPE) has organized programs and projects to preserve the city's architectural heritage. Several interesting buildings have already been restored. Lilac House, on Kennedy Avenue, has three types of gingerbread fretwork, latticed verandah railings, and heavy hurricane shutters. The J.W. Edwards Building, at the corner of Old and King George V sreets, has a stone base and a wooden second-floor gallery. The Old Market Plaza is the center of Roseau's historic district, which was laid out by the French on a radial plan rather than a grid, so streets such as Hanover, King George V, and Old radiate from this area. South of the marketplace is the Fort Young Hotel, built as a British fort in the 18th century; the nearby statehouse, public library, and Anglican cathedral are also worth a visit. New developments at the bay front on Dame M.E. Charles Boulevard have brightened up the waterfront.

Basseterre, Saint Kitts

Mountainous St. Kitts, the first English settlement in the Leeward Islands, crams some stunning scenery into its 65 square miles (168 square km). Vast, brilliant green fields of sugarcane (the former cash crop, now slowly being replanted) run to the shore. The fertile, lush island has some fascinating natural and historical attractions: a rain forest replete with waterfalls, thick vines, and secret trails; a central mountain range dominated by the 3,792-foot Mt. Liamuiga, whose crater has long been dormant; and Brimstone Hill, known in the 18th century as the Gibraltar of the West Indies. St. Kitts and Nevis, along with Anguilla, achieved self-government as an associated state of Great Britain in 1967. In 1983 St. Kitts and Nevis became an independent nation. English with a strong West Indian lilt is spoken here. People are friendly but shy; always ask before you take photographs. Also, be sure to wear wraps or shorts over beach attire when you're in public places.

Gustavia

You can easily explore all of Gustavia during a two-hour stroll. Some shops close from noon to 3 or 4, so plan lunch accordingly, but stores stay open past 7 in the evening. Parking in Gustavia is a challenge, especially during vacation times. A good spot to park is rue de la République, alongside the catamarans, yachts, and sailboats.

Dates & prices

Why book with Wexas Travel?

At Wexas, we specialise in bespoke travel experiences. Our itineraries are just samples of what we can arrange, and can be changed depending on your precise needs, finances and ideas by our experienced destination specialists.

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Sat 9 Jan 2027
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