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14-Day Windward & Leeward Islands

Summary

Cruise line Seabourn

Duration 14 nights

Type Ocean Cruise

Regions Caribbean,
Americas,
South America

Itinerary & Map

Miami, Florida → Miami, Florida 15 days · 11 ports · 0 sea days
Day 1 Miami, Florida Embark

Miami is one of the world’s most popular holiday spots. It has so much to offer; from its countless beach areas, to culture and museums, from spa and shopping d...

Full description
Day 4 Cruz Bay, Saint John
Day 5 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 6 South Friars Bay
Day 7 Fort-de-France

The largest of the Windward Islands, Martinique is 4,261 mi (6,817 km) from Paris, but its spirit and language are decidedly French, with more than a soupçon of...

Full description
Day 8 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 9 Montserrat
Day 10 Antigua
Day 11 Road Bay
Day 12 Great Harbour, Jost Van Dyke

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 ya...

Full description
Day 15 Miami, Florida Disembark

Miami is one of the world’s most popular holiday spots. It has so much to offer; from its countless beach areas, to culture and museums, from spa and shopping d...

Full description
Scroll for all 15 days
Route overview map
Day 1 Miami, Florida Embark

Miami is one of the world’s most popular holiday spots. It has so much to offer; from its countless beach areas, to culture and museums, from spa and shopping d...

Full description
Day 4 Cruz Bay, Saint John
Day 5 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 6 South Friars Bay
Day 7 Fort-de-France

The largest of the Windward Islands, Martinique is 4,261 mi (6,817 km) from Paris, but its spirit and language are decidedly French, with more than a soupçon of...

Full description
Day 8 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 9 Montserrat
Day 10 Antigua
Day 11 Road Bay
Day 12 Great Harbour, Jost Van Dyke

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 ya...

Full description
Day 15 Miami, Florida Disembark

Miami is one of the world’s most popular holiday spots. It has so much to offer; from its countless beach areas, to culture and museums, from spa and shopping d...

Full description

Miami, Florida

Miami is one of the world’s most popular holiday spots. It has so much to offer; from its countless beach areas, to culture and museums, from spa and shopping days out, to endless cuban restaurants and cafes. Miami is a multicultural city that has something to offer to everyone.

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.

Fort-de-France

The largest of the Windward Islands, Martinique is 4,261 mi (6,817 km) from Paris, but its spirit and language are decidedly French, with more than a soupçon of West Indian spice. Tangible, edible evidence of the fact is the island's cuisine, a superb blend of French and creole. Martinique is lushly landscaped with tropical flowers. Trees bend under the weight of fruits such as mangoes, papayas, lemons, limes, and bright-red West Indian cherries. Acres of banana plantations, pineapple fields, and waving sugarcane stretch to the horizon. The towering mountains and verdant rain forest in the north lure hikers, while underwater sights and sunken treasures attract snorkelers and scuba divers. Martinique is also wonderful if your idea of exercise is turning over every 10 minutes to get an even tan and your taste in adventure runs to duty-free shopping. A popular cruise-ship excursion goes to St-Pierre, which was buried by ash when Mont Pelée erupted in 1902.

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.

Great Harbour, Jost Van Dyke

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.

Date & price

Departs

Sat 4 Dec 2027

from £5,598 pp

Enquire now Call 020 7590 0610

Per person, based on two sharing, cruise only. Updated daily and confirmed when you book.

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Sat 4 Dec 2027
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