Windward Ways & Tobago Cays - Bridgetown to Oranjestad

The Windward Ways & Tobago Cays - Bridgetown to Oranjestad is a 8-night Caribbean cruise aboard Star Legend, operated by Windstar Cruises. Departing Bridgetown, Barbados on December 4, 2026, the voyage visits 8 ports. Fares start from $2,680 per person.

Length: 8 nights
Departs: Dec 4, 2026
Returns: Dec 12, 2026
Ports of call: 8
Days at sea: 2

from $2,680

$335 / night per person, incl. taxes & fees

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Itinerary

Day 1 Dec 4, 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. Bridgetown, Barbados port guide Search cruises visiting Bridgetown, Barbados

Bridgetown, Barbados photo — Day 1 Dec 4, 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. Bridgetown, Barbados port guide Search cruises visiting Bridgetown, Barbados

Day 3 Dec 6, 2026 Scarborough, Trinidad 08:00 – 17:00 9.0 hrs ashore A bustling city seeped in history, Tobago’s capital offers up a snapshot of days gone by. Sprawled over the hillside, it’s overlooked by the Fort King George, a 17th-century hideout that sits proudly at the summit. Wander through the town to Upper Scarborough and take a look at the House of Assembly – it’s one of the best examples of Georgian architecture in the Caribbean. Head down by the port, and you’ll find colourful houses lining the harbour and lively markets dominating the streets. Here, you can pick up island favourites like fresh coconut milk and syrup-coated ice-cream, as well as arts and crafts.

Day 4 Dec 7, 2026 Bequia 08:00 – 22:00 14.0 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. Bequia port guide Search cruises visiting Bequia

Bequia photo — Day 4 Dec 7, 2026 Bequia 08:00 – 22:00 14.0 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. Bequia port guide Search cruises visiting Bequia

Day 5 Dec 8, 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 9, 2026 St Georges, Grenada 08:00 – 21:00 13.0 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 8 Dec 11, 2026 Willemstad, Curacao 08:00 – 18:00 10.0 hrs ashore A beauty to behold, Curaçao, a Dutch Caribbean island just off the coast of Venezuela, offers dramatic coastlines, hidden beaches tucked into coves, expansive coral reefs, wondrous caves and two different climates: one wet and tropical, the other dry. Abuzz with European flair, Willemstad, the capital, boasts a thriving art and culinary scene, pretty pastel-coloured colonial architecture, museums and a go-go attitude, thanks in part to its booming economy. As you arrive on an MSC Caribbean and Antilles cruise in Willemstad, you’ll have options for MSC excursions at your fingertips as diverse as its climate: Cultural tours or nature tours? Beach or hiking? A blend of both? The choice is yours. Start by exploring the narrow alleys and gaze at the curious houses in bright colours in the picturesque old town of Willemstad, a UNESCO World Heritage Site. Dutch colonial-style houses with sloping roofs, and alternating pink, light green, blue and yellow colours contrast with the monochrome blue of the sky and sea, a panorama worthy of Instagram. MSC excursions let you hop on a trolley tour or join a guided walking tour to marvel at the city’s best known sites. At the mouth of the bay of Sint Annabaai, between the two districts of Willemstad, lies Fort Amsterdam, one of the most important forts on the island. Built in 1635, the fort is now the seat of the governor, and houses a Protestant church and a museum. The church, built in 1769, was fired upon by a British warship in 1804, and you can still find a cannonball embedded in the southwestern wall of the church. Another fort worth seeing is Fort Beekenburg, overlooking Caracas Bay. Constructed in 1703, it was actively used in the 19th century to defend against the French, British and pirates, and is one of the best-preserved fortifications in the Caribbean. A Curaçao cruise lets you tour the factory where the world-famous Curaçao liqueur is made. At the sunshine yellow Chobolo Mansion, visit the old distillery to learn how the distillation process works and, of course, you get to sample the Blue Curaçao liqueur. For an otherworldly experience, opt for a short drive to the north of Willemstad, passing salt flats and flamingos, to explore the Hato Caves on a guided tour. At this natural wonder, you’ll learn about stalagmites, stalactites, limestone formations and, if you're lucky, you’ll spot long-nosed fruit bats. Or to observe the stunning coastline, another MSC excursion takes you on a country drive, past old plantation homes, to Boka Tabla, part of Shete Boka National Park, on the north coast. Admire the phenomenon of how the pounding surf has over time formed beautiful coves and interesting rock shapes stretching over seven miles of unspoiled shoreline. Willemstad, Curacao port guide Search cruises visiting Willemstad, Curacao

Willemstad, Curacao photo — Day 8 Dec 11, 2026 Willemstad, Curacao 08:00 – 18:00 10.0 hrs ashore A beauty to behold, Curaçao, a Dutch Caribbean island just off the coast of Venezuela, offers dramatic coastlines, hidden beaches tucked into coves, expansive coral reefs, wondrous caves and two different climates: one wet and tropical, the other dry. Abuzz with European flair, Willemstad, the capital, boasts a thriving art and culinary scene, pretty pastel-coloured colonial architecture, museums and a go-go attitude, thanks in part to its booming economy. As you arrive on an MSC Caribbean and Antilles cruise in Willemstad, you’ll have options for MSC excursions at your fingertips as diverse as its climate: Cultural tours or nature tours? Beach or hiking? A blend of both? The choice is yours. Start by exploring the narrow alleys and gaze at the curious houses in bright colours in the picturesque old town of Willemstad, a UNESCO World Heritage Site. Dutch colonial-style houses with sloping roofs, and alternating pink, light green, blue and yellow colours contrast with the monochrome blue of the sky and sea, a panorama worthy of Instagram. MSC excursions let you hop on a trolley tour or join a guided walking tour to marvel at the city’s best known sites. At the mouth of the bay of Sint Annabaai, between the two districts of Willemstad, lies Fort Amsterdam, one of the most important forts on the island. Built in 1635, the fort is now the seat of the governor, and houses a Protestant church and a museum. The church, built in 1769, was fired upon by a British warship in 1804, and you can still find a cannonball embedded in the southwestern wall of the church. Another fort worth seeing is Fort Beekenburg, overlooking Caracas Bay. Constructed in 1703, it was actively used in the 19th century to defend against the French, British and pirates, and is one of the best-preserved fortifications in the Caribbean. A Curaçao cruise lets you tour the factory where the world-famous Curaçao liqueur is made. At the sunshine yellow Chobolo Mansion, visit the old distillery to learn how the distillation process works and, of course, you get to sample the Blue Curaçao liqueur. For an otherworldly experience, opt for a short drive to the north of Willemstad, passing salt flats and flamingos, to explore the Hato Caves on a guided tour. At this natural wonder, you’ll learn about stalagmites, stalactites, limestone formations and, if you're lucky, you’ll spot long-nosed fruit bats. Or to observe the stunning coastline, another MSC excursion takes you on a country drive, past old plantation homes, to Boka Tabla, part of Shete Boka National Park, on the north coast. Admire the phenomenon of how the pounding surf has over time formed beautiful coves and interesting rock shapes stretching over seven miles of unspoiled shoreline. Willemstad, Curacao port guide Search cruises visiting Willemstad, Curacao

Day 9 Dec 12, 2026 Oranjestad, Aruba Arrives 06:00 Located in the southern Caribbean, Aruba stands out with its desert-like vistas, wind-shaped trees, natural rock formations and breath-taking beaches. Its terrain offers plenty of opportunity for exploration and off-road trekking. As you arrive on an MSC Caribbean and Antilles cruise in Oranjestad, the tax-free capital named after William I (the Prince of Orange and the first King of the Netherlands), admire the city’s charming Dutch Colonial architecture with its antique buildings and houses that blend in with today’s modern architecture. Not much grows on Aruba. However, its hot dry climate is ideal for aloe farming. Book an MSC excursion to the Aruba Aloe Museum & Factory, and learn about the 160-year history of aloe farming on the island. If adventure is on your agenda, get on a UTV on an MSC excursion that will take you through Aruba's outback, skirting along the coastline with visits to the Alto Vista Chapel, the Bushiribana Gold Mill ruins that remind us of Aruba's 19th-century gold rush, and to the early 20th-century California Lighthouse, which bears the name of an unfortunate ship that sank nearby in 1891. An on-road driving MSC excursion will visit those sites as well, along with the amazing Casibari Rock Formation, or huge diorite boulders found in the centre of the island. Take a “Natural Aruba” MSC excursion to tour the Butterfly Farm, then pass countless divi divi trees and cacti before arriving at Aruba’s Natural Bridge, a wonder carved out of solid coral by the relentlessly pounding surf. Or relax in the calm waters lapping Arashi Beach and Palm Beach, while snorkelers will enjoy our catamaran sailing excursion that explores Boca Cathalina and the “Antilla” World War II shipwreck, considered to be one of the top dive and snorkel sites of the Caribbean. Oranjestad, Aruba port guide Search cruises visiting Oranjestad, Aruba

Pricing

Lowest fare we've tracked over the observed 85-day span: $2,680 · range $2,680–$3,499

Lower than 97% of peers This week-long sailing's from-price per night is lower than 97% of comparable sailings.

same cruise line and duration · from-price per night · as of Jun 27, 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 $2,680

$335 / night

Fare rows

Star Porthole Suite

Cabin grade

Available

from $2,680

$335 / night

per person · incl. taxes

Ocean View Suite

Cabin grade

Available

from $2,880

$360 / night

per person · incl. taxes

Ocean View Suite

Cabin grade

Available

from $3,000

$375 / night

per person · incl. taxes

Star Ocean View Suite

Cabin grade

Available

from $3,120

$390 / night

per person · incl. taxes

Ocean View Suite

Cabin grade

Available

from $3,200

$400 / night

per person · incl. taxes

Ocean View Suite

Cabin grade

Available

from $3,360

$420 / night

per person · incl. taxes

Balcony

from $4,240

$530 / night

Fare rows

Balcony Suite

Cabin grade

Available

from $4,240

$530 / night

per person · incl. taxes

Star Balcony Suite

Cabin grade

Available

from $4,320

$540 / night

per person · incl. taxes

Balcony Suite

Cabin grade

Available

from $4,480

$560 / night

per person · incl. taxes

Star Balcony Suite

Cabin grade

Available

from $4,600

$575 / night

per person · incl. taxes

Suite

from $6,600

$825 / night

Fare rows

Deluxe Suite

Cabin grade

Available

from $6,600

$825 / night

per person · incl. taxes

Classic Suite

Cabin grade

Available

from $8,600

$1,075 / night

per person · incl. taxes

Owner's Suite

Cabin grade

Available

from $10,600

$1,325 / night

per person · incl. taxes

Prices verified Jun 24, 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

Cabin grades and pricing
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