14 nights onboard Wind Spirit

Star Collector: Caribbean Explorations

Skip the usual Caribbean cruise stops and discover the small harbors, overlooked havens and most remote secrets among the Leeward Islands. Whether you're looking for hidden shops, sampling new cuisine or seeking a local place to sip rum cocktails over the melodic beat of steel drums, this highly personalized adventure is an intimate opportunity to familiarize yourself with the lesser-known charms of Les Saintes, Anse Mitan, Pigeon Island and much more.
Leaving from: Philipsburg
Cruise ship: Wind Spirit
Visiting: Philipsburg Sopers Hole, Tortola Great Harbour, Jost Van Dyke Great Harbour, Jost Van Dyke
Windstar Cruises Logo
Windstar Cruises

Windstar Cruises operates a fleet of small luxury cruise ships. The cruise line has six yachts - three of which are masted sailing ships - and offers laid-back luxury with a tinge of historic seafaring adventure.

Wind Star and Wind Spirit each carry 148 guests, whereas Wind Surf carries 342. 'Power yachts' Star Pride, Star Breeze and Star Legend all carry 312 passengers. It's a unique experience, by all means!

148
Passengers
101
Crew
1998
Launched
2012
Last refit
5307t
Tonnage
110m
Length
15m
Width
10kts
Speed
4
Decks
USD
Currency
Cruise Itinerary
Day 1
Philipsburg, Sint Maarten (Dutch part)
Day 2
Sopers Hole, Tortola, British Virgin Islands
Days 2 - 3
Great Harbour, Jost Van Dyke, British Virgin Islands
Day 5
Gustavia, Saint Barthélemy
Day 6
Road Bay, Anguilla
Day 7
Falmouth, Antigua and Barbuda
Day 8
Philipsburg, Sint Maarten (Dutch part)
Day 10
Roseau, Dominica
Day 11
Pigeon Island, Saint Lucia
Day 12
Terre-de-Haut, Guadeloupe
Day 13
Gustavia, Saint Barthélemy
Day 14
Basseterre, Saint Kitts, Saint Kitts and Nevis
Day 15
Philipsburg, Sint Maarten (Dutch part)
Philipsburg, Sint Maarten (Dutch part) image
Day 1
Philipsburg, Sint Maarten (Dutch part)
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.
Sopers Hole, Tortola, British Virgin Islands image
Day 2
Sopers Hole, Tortola, British Virgin Islands
Great Harbour, Jost Van Dyke, British Virgin Islands image
Days 2 - 3
Great Harbour, Jost Van Dyke, British Virgin Islands
Jost Van Dyke, four miles long, is truly known as the 'barefoot island'. The smallest of the British Virgin Islands, it is known as a popular destination for yachts and is celebrated for its casual lifestyle, protected anchorages, fine beaches and beachfront restaurants and bars. The island has fewer than 200 inhabitants and they are widely known as a welcoming people. The island's name conjures up its rich, colorful past. Jost Van Dyke is said to have been named for an early Dutch settler, a former pirate. At Great Harbour, Little Harbour, and White Bay there are safe, protected bays and pristine beaches shaded with coconut palms and seagrape trees. Discover inviting shops selling local treasures, restaurants, and bars. 'The Painkiller', one of the Caribbean’s most popular drinks, originated at the Soggy Dollar Bar. Foxy’s and Gertrude's in White Bay are renowned for drinks made with the island's famous rum, frosty beers, and tales of pirates and sunken treasure. Explore Jost Van Dyke's history in the vegetation-covered ruins of centuries-old sugar mills, or on the old trails that crisscross the island. Revel in the natural beauty of the pristine, untouched beaches. Hike up to the highest spot on the island, Majohnny Point, and take in a stunning 360 degree view of the Caribbean. Relax in the natural 'bubble pool', a popular tourist attraction. Jost Van Dyke conjures up images of what the British Virgin Islands may have looked like many years ago.
Gustavia, Saint Barthélemy image
Day 5
Gustavia, Saint Barthélemy
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.
Road Bay, Anguilla image
Day 6
Road Bay, Anguilla
Falmouth, Antigua and Barbuda image
Day 7
Falmouth, Antigua and Barbuda
Falmouth oozes with Jamaica's Caribbean cool, serving as the vibrant center of local culture and entertainment. Dive into the bustling streets and discover local establishments like the Glistening Waters Luminous Lagoon, where bioluminescent organisms light up the night. For history buffs, the Falmouth Historic District offers a glimpse into the island's colonial past, with beautifully preserved Georgian architecture and the historic Water Square.
Philipsburg, Sint Maarten (Dutch part) image
Day 8
Philipsburg, Sint Maarten (Dutch part)
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.
Roseau, Dominica image
Day 10
Roseau, Dominica
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.
Pigeon Island, Saint Lucia image
Day 11
Pigeon Island, Saint Lucia
Terre-de-Haut, Guadeloupe image
Day 12
Terre-de-Haut, Guadeloupe
Gustavia, Saint Barthélemy image
Day 13
Gustavia, Saint Barthélemy
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.
Basseterre, Saint Kitts, Saint Kitts and Nevis image
Day 14
Basseterre, Saint Kitts, Saint Kitts and Nevis
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.
Philipsburg, Sint Maarten (Dutch part) image
Day 15
Philipsburg, Sint Maarten (Dutch part)
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.
Ship Details
Windstar Cruises
Wind Spirit

The Wind Spirit is a sleek, 4-masted sailing ship accommodating 148 guests. With four decks and a gross tonnage of 5,736, Wind Spirit feels like your own private small ship.

Find your perfect cruise!
Cabins
All Prices