Jewels of The Windward Islands - Bridgetown to Bridgetown

7 nights Nov 27, 2026

The Jewels of The Windward Islands - Bridgetown to Bridgetown is a 7-night Caribbean cruise aboard Star Legend, operated by Windstar Cruises. Departing Bridgetown, Barbados on November 27, 2026, the voyage visits 7 ports. Fares start from $2,380 per person.

from $2,380

$340 / night per person, incl. taxes & fees

See prices

You'll continue on Windstar Cruises's official site. Affiliate disclosure

from $2,380 pp

Continues on Windstar Cruises's site

See prices

Itinerary

Day 1 Nov 27, 2026 Bridgetown, Barbados Departs 18:00 When you arrive in Barbados on an MSC Caribbean and Antilles cruise, begin your exploration with the capital, Bridgetown. There are many attractions in this small Caribbean city, but by all means pause to admire its many colonial buildings, the Parliament Building and the statue of Lord Nelson standing in what is currently called the National Heroes Square. Barbados has retained somewhat of a British feel, with its place names, cricket, horse-racing and polo, Anglican parish churches and even a hilly district known as Scotland. But the Britishness can be exaggerated, for this is a distinctly West Indian country, covered by a patch-work of sugarcane fields and dotted with tiny rum shops. The Garrison Historic Area, a UNESCO World Heritage Site with magnificent 18th- and 19th-century buildings, is a must-see stop, featuring one of the world's finest collection of cannons. It also includes the George Washington House, where the American patriot spent six weeks of his life. The current St. John's Church, in the eastern parish of the same name, is the fifth reconstruction of the oldest local church, in Barbadian Gothic style. Perched on a cliff 800 feet above the sea, it dates back to 1836. Its interior hosts a sculpture by 18th-century British artist Richard Westmacott, while its churchyard contains the tomb of Ferdinando Paleologus, a direct descendant of the brother of Constantine XI, the last Byzantine emperor. Book an MSC excursion to discover the island’s history at the Barbados Museum and Historical Society in the St. Michael neighbourhood. And tour Sunbury Plantation House, located in the tranquil St. Philip countryside. Dating back to 1650, it’s a living monument to plantation life and a bygone era. Harrison’s Cave, in St. Thomas district, is a wonder of nature with its stalactites, stalagmites, streams, lakes and waterfalls. In one of the caverns, the play of light on the rocks is so in-tense that it has been nicknamed “The Crystal Room”. For some fun at the beach, head to Pirates Cove, one of the best beaches on Barbados. Featuring palm trees and chickee huts, white sand and crystal-clear water, it’s the perfect place to relax, just a stone’s throw from Bridgetown. If you’re brave enough to dive into the deep, set out on an MSC excursion inside a real submarine, the Atlantis, to explore the coral reef and discover the beauty that the depths reveal. Go to Bridgetown, Barbados Cruises visiting Bridgetown, Barbados

Bridgetown, Barbados photo — Day 1 Nov 27, 2026 Bridgetown, Barbados Departs 18:00 When you arrive in Barbados on an MSC Caribbean and Antilles cruise, begin your exploration with the capital, Bridgetown. There are many attractions in this small Caribbean city, but by all means pause to admire its many colonial buildings, the Parliament Building and the statue of Lord Nelson standing in what is currently called the National Heroes Square. Barbados has retained somewhat of a British feel, with its place names, cricket, horse-racing and polo, Anglican parish churches and even a hilly district known as Scotland. But the Britishness can be exaggerated, for this is a distinctly West Indian country, covered by a patch-work of sugarcane fields and dotted with tiny rum shops. The Garrison Historic Area, a UNESCO World Heritage Site with magnificent 18th- and 19th-century buildings, is a must-see stop, featuring one of the world's finest collection of cannons. It also includes the George Washington House, where the American patriot spent six weeks of his life. The current St. John's Church, in the eastern parish of the same name, is the fifth reconstruction of the oldest local church, in Barbadian Gothic style. Perched on a cliff 800 feet above the sea, it dates back to 1836. Its interior hosts a sculpture by 18th-century British artist Richard Westmacott, while its churchyard contains the tomb of Ferdinando Paleologus, a direct descendant of the brother of Constantine XI, the last Byzantine emperor. Book an MSC excursion to discover the island’s history at the Barbados Museum and Historical Society in the St. Michael neighbourhood. And tour Sunbury Plantation House, located in the tranquil St. Philip countryside. Dating back to 1650, it’s a living monument to plantation life and a bygone era. Harrison’s Cave, in St. Thomas district, is a wonder of nature with its stalactites, stalagmites, streams, lakes and waterfalls. In one of the caverns, the play of light on the rocks is so in-tense that it has been nicknamed “The Crystal Room”. For some fun at the beach, head to Pirates Cove, one of the best beaches on Barbados. Featuring palm trees and chickee huts, white sand and crystal-clear water, it’s the perfect place to relax, just a stone’s throw from Bridgetown. If you’re brave enough to dive into the deep, set out on an MSC excursion inside a real submarine, the Atlantis, to explore the coral reef and discover the beauty that the depths reveal. Go to Bridgetown, Barbados Cruises visiting Bridgetown, Barbados

Day 4 Nov 30, 2026 Castries, St. Lucia 08:00 – 15:00 7.0 hrs ashore Travel on an MSC Caribbean and Antilles cruise to St. Lucia in the Lesser Antilles to see magnificent white-sand beaches, lush rainforests and the prized Pitons. These are spectacular twin volcanic peaks that are protected as UNESCO World Heritage Sites and appear as symbols on the nation’s flag. Initially founded by the French in the 1664, St. Lucia changed hands between French and British rule so many times over the years that it was called the “Helen of the West Indies,” until the British took definite control in 1814. From architecture to cuisine, you’ll still find hints of French and British inspired heritage throughout the island, which declared its independence in 1979. This is particularly evident in Castries, its capital. MSC excursions in St. Lucia offer something for everyone. Take a trolley through the busy streets of the city of Castries. Cruise by catamaran to the Pitons for scenic views of Petit Piton and Gros Piton, at an altitude of around 2,500 feet. Or breeze past banana plantations and visit picturesque Marigot Bay, named the most beautiful bay of the Caribbean by the late American novelist James Michener. For something truly special, explore the world of batik prints at Caribelle Batik, then see the Pitons from land during a beautiful drive to the 18th-century Soufriere Estate for a lesson on coconuts and cocoa. When you get there, find out how coconuts are opened, roasted in a traditional oven and turned into copra (dry coconut) before being processed into everyday items such as soap, sun tan lotion and cooking oil. And learn how cocoa is fermented, dried on racks in the sun and crushed into powder to make cocoa sticks before being turned into chocolate. Thirsting for adventure? Then get your adrenaline running and enjoy a bird's eye view while you zip from tree to tree. Drive past pools of bubbling lava and into the world's only drive-in volcano at the Sulphur Springs or snorkel within the marine reserve to discover a plethora of vibrant wildlife featuring a variety of corals, urchins and more. Go to Castries, St. Lucia Cruises visiting Castries, St. Lucia

Castries, St. Lucia photo — Day 4 Nov 30, 2026 Castries, St. Lucia 08:00 – 15:00 7.0 hrs ashore Travel on an MSC Caribbean and Antilles cruise to St. Lucia in the Lesser Antilles to see magnificent white-sand beaches, lush rainforests and the prized Pitons. These are spectacular twin volcanic peaks that are protected as UNESCO World Heritage Sites and appear as symbols on the nation’s flag. Initially founded by the French in the 1664, St. Lucia changed hands between French and British rule so many times over the years that it was called the “Helen of the West Indies,” until the British took definite control in 1814. From architecture to cuisine, you’ll still find hints of French and British inspired heritage throughout the island, which declared its independence in 1979. This is particularly evident in Castries, its capital. MSC excursions in St. Lucia offer something for everyone. Take a trolley through the busy streets of the city of Castries. Cruise by catamaran to the Pitons for scenic views of Petit Piton and Gros Piton, at an altitude of around 2,500 feet. Or breeze past banana plantations and visit picturesque Marigot Bay, named the most beautiful bay of the Caribbean by the late American novelist James Michener. For something truly special, explore the world of batik prints at Caribelle Batik, then see the Pitons from land during a beautiful drive to the 18th-century Soufriere Estate for a lesson on coconuts and cocoa. When you get there, find out how coconuts are opened, roasted in a traditional oven and turned into copra (dry coconut) before being processed into everyday items such as soap, sun tan lotion and cooking oil. And learn how cocoa is fermented, dried on racks in the sun and crushed into powder to make cocoa sticks before being turned into chocolate. Thirsting for adventure? Then get your adrenaline running and enjoy a bird's eye view while you zip from tree to tree. Drive past pools of bubbling lava and into the world's only drive-in volcano at the Sulphur Springs or snorkel within the marine reserve to discover a plethora of vibrant wildlife featuring a variety of corals, urchins and more. Go to Castries, St. Lucia Cruises visiting Castries, St. Lucia

Day 5 Dec 1, 2026 Mayreau 08:00 – 18:00 10.0 hrs ashore Sip a tangy rum cocktail and leave your phone behind, as you sink into unbridled, undeveloped Caribbean bliss. An island gem of the Grenadines, Mayreau is the smallest island to house permanent residents, and a tiny gathering of just 200 are lucky enough to call it home. With limited infrastructure, and less than two square miles to explore, this is a place to enjoy the simple beauty of the here and now, as waves gently splash and the sun bronzes your skin. View less Dive spots invite you below the surface to a world of coral and tropical fish. Or you can stay put on Mayreau, to sprawl out across beautiful beaches like Saline Bay's - perhaps the island’s most enticing wedge of sand and tranquil blue waters. If that sounds too indulgent, earn your beachside bliss with a short hike up the small, densely-forested hill. You'll be rewarded with a great lookout across the other emerald islands, emerging from the azure seas. Jump aboard and hold on tight as your speedboat rips across the waves, or take a leisurely sailing tour of the surrounding islands of paradise. The glorious Tobago Cays are close by, and these uninhabited lands sparkle with a world of colour and sensory indulgence, immersing you in vistas lifted straight from the pages of a travel guide. Swim, snorkel, and let it all go.

Day 6 Dec 2, 2026 St Georges, Grenada 08:00 – 22:00 14.0 hrs ashore Scents of spices such as cloves, cinnamon and nutmeg waft through the air as you arrive on MSC Caribbean and Antilles cruise to St. George’s, the capital of the island of Grenada. Nicknamed the “Spice Island” for its agriculture, Grenada’s symbol is the nutmeg, the island’s most famous product, which also appears on the nation’s flag. Originally colonized by the French in the 1600s, who wiped out the native Carib peoples during conflicts, Grenada was captured by the British in 1762 and remained under British rule until its independence in 1974. St. George’s offers many attractions starting with its beautiful views, botanical gardens, parks and heavenly beaches, most notably the Grand Anse Beach nearby. Start your journey with a guided walk on an MSC excursion through the capital’s winding maze of streets from the Carenage, the horseshoe-shaped harbour, with its lively waterfront promenade. Gaze at picturesque 19th-century pastel-coloured Creole houses made of brick and stone with red-tile roofs made from ship ballasts. Get a first-hand look at the wonderful palette of spices and scents of the island on an MSC excursion that stops at Dougaldston Estate. At this rustic, 300-year-old cocoa plantation in Gouyave, discover what drying trays for spices and cacao look like and learn how these spices are processed from seed pods, or how cinnamon is harvested from the bark of a tree. From there, proceed to an old-fashioned nutmeg cooperative plant where the work is done by hand. Grenada features a host of beautiful waterfalls, the most spectacular of which are Annandale Falls, about 7 miles from St. George’s. Hidden by a grotto of dense vegetation in the mountains, the waterfall cascades 30 feet down into the midst of leaves and branches, creating a natural pool where you can swim. For a throw-back to Grenada’s past, hop on a Creole bus on a guided MSC excursion along a labyrinth of steep roads to higher elevations. Enjoy sumptuous panoramas from the 18th-century forts of Fort George and Fort Frederick, nicknamed “The Backward Facing Fort,” for the cannons facing the land and not the sea.

Day 7 Dec 3, 2026 Bequia 08:00 – 17:00 9.0 hrs ashore An almost mythical utopia of virgin beaches, rustic rum shacks and bays so scenic you feel like you’re intruding - Bequia Island is an island mirage of Caribbean perfection. This is the real, unspoiled experience - and with just 6,000 locals living here, you quickly start to recognise the same smiling faces, welcoming you with outstretched arms. Offering glorious - often deserted - beaches of pure golden sand, and hillside sweeps of forest and almond trees, Bequia Island is an extraordinary feast for the senses. Unlike some of the flashier Caribbean islands, Bequia - a part of the Grenadines - is a rustic, unassuming and off-the-beaten-path choice. The staggeringly picturesque natural harbour, Admiralty Bay, greets you on arrival, and is peppered with day-tripping yachts bobbing on the gentle waves. The island’s tiny capital, Port Elizabeth, sits behind, with its bustling fruit and vegetable market, turtle sanctuary, and stalls selling hand-crafted model ships. This tiny, pretty island is ridged along the centre, and you can earn your beachside bliss with a gentle hike to the top of Mount Peggy, looking out over views of Grenada and St Vincent. At just seven miles long, you can discover the whole island in a few hours – but that would be to miss the point somewhat. Bequia Island coaxes you in to slow the pace and soothe your soul on blissful beaches, where you can revel in the uncomplicated joys of sitting, reading and swimming in heavenly shallow waters. The royally approved Princess Margaret Beach is one of the finest - an arching band of soft sand and cobalt-blue waters. As evening sets in, you may find you’re beckoned to share with communal barbecues of the day’s fresh catch with the locals, or to indulge in rum-heavy cocktails at beachside bars, lashed together from sea-blanched wooden limbs. Go to Bequia Cruises visiting Bequia

Bequia photo — Day 7 Dec 3, 2026 Bequia 08:00 – 17:00 9.0 hrs ashore An almost mythical utopia of virgin beaches, rustic rum shacks and bays so scenic you feel like you’re intruding - Bequia Island is an island mirage of Caribbean perfection. This is the real, unspoiled experience - and with just 6,000 locals living here, you quickly start to recognise the same smiling faces, welcoming you with outstretched arms. Offering glorious - often deserted - beaches of pure golden sand, and hillside sweeps of forest and almond trees, Bequia Island is an extraordinary feast for the senses. Unlike some of the flashier Caribbean islands, Bequia - a part of the Grenadines - is a rustic, unassuming and off-the-beaten-path choice. The staggeringly picturesque natural harbour, Admiralty Bay, greets you on arrival, and is peppered with day-tripping yachts bobbing on the gentle waves. The island’s tiny capital, Port Elizabeth, sits behind, with its bustling fruit and vegetable market, turtle sanctuary, and stalls selling hand-crafted model ships. This tiny, pretty island is ridged along the centre, and you can earn your beachside bliss with a gentle hike to the top of Mount Peggy, looking out over views of Grenada and St Vincent. At just seven miles long, you can discover the whole island in a few hours – but that would be to miss the point somewhat. Bequia Island coaxes you in to slow the pace and soothe your soul on blissful beaches, where you can revel in the uncomplicated joys of sitting, reading and swimming in heavenly shallow waters. The royally approved Princess Margaret Beach is one of the finest - an arching band of soft sand and cobalt-blue waters. As evening sets in, you may find you’re beckoned to share with communal barbecues of the day’s fresh catch with the locals, or to indulge in rum-heavy cocktails at beachside bars, lashed together from sea-blanched wooden limbs. Go to Bequia Cruises visiting Bequia

Pricing

Lowest fare we've tracked over the observed 83-day span: $2,238 · range $2,238–$3,099

Lower than 85% of peers This week-long sailing's from-price per night is lower than 85% of comparable sailings.

same cruise line, destination, and duration · from-price per night · as of Jun 22, 2026 · Broader cohort: same cruise line and duration, compared by from-price per night.

Current prices

Per person · 2 guests · incl. taxes & fees

Inside

Not available

Oceanview

from $2,380

$340 / night

Fare rows

Star Porthole Suite

Cabin grade

Available

from $2,380

$340 / night

per person · incl. taxes

Ocean View Suite

Cabin grade

Available

from $2,485

$355 / night

per person · incl. taxes

Ocean View Suite

Cabin grade

Available

from $2,555

$365 / night

per person · incl. taxes

Star Ocean View Suite

Cabin grade

Available

from $2,695

$385 / night

per person · incl. taxes

Ocean View Suite

Cabin grade

Available

from $2,765

$395 / night

per person · incl. taxes

Ocean View Suite

Cabin grade

Available

from $2,905

$415 / night

per person · incl. taxes

Balcony

from $3,535

$505 / night

Fare rows

Balcony Suite

Cabin grade

Available

from $3,535

$505 / night

per person · incl. taxes

Star Balcony Suite

Cabin grade

Available

from $3,605

$515 / night

per person · incl. taxes

Balcony Suite

Cabin grade

Available

from $3,745

$535 / night

per person · incl. taxes

Star Balcony Suite

Cabin grade

Available

from $3,885

$555 / night

per person · incl. taxes

Suite

from $5,635

$805 / night

Fare rows

Deluxe Suite

Cabin grade

Available

from $5,635

$805 / night

per person · incl. taxes

Classic Suite

Cabin grade

Available

from $6,510

$930 / night

per person · incl. taxes

Owner's Suite

Cabin grade

Available

from $7,105

$1,015 / night

per person · incl. taxes

Prices verified Jun 22, 2026

Prices come from third-party data feeds via Windstar Cruises and may differ from the cruise line's current fare. Confirm the final price before booking. How our pricing works

Show all 13 cabin grades

Name	Supplier code	Type
Balcony Suite	BS	Balcony
Balcony Suite	BS1	Balcony
Star Balcony Suite	SBS	Balcony
Star Balcony Suite	SBS1	Balcony
Ocean View Suite	S	Oceanview
Ocean View Suite	S1	Oceanview
Ocean View Suite	S2	Oceanview
Ocean View Suite	S3	Oceanview
Star Porthole Suite	SP	Oceanview
Star Ocean View Suite	SS1	Oceanview
Classic Suite	CS	Suite
Deluxe Suite	DS	Suite
Owner's Suite	OW	Suite