Windstar Cruises

STAR COLLECTOR: GRAND CARIBBEAN & PANAMANIAN ADVENTURE

Get acquainted with the Caribbean’s most iconic and little-known vacation destinations during this comprehensive and romantic 28-port, 20-country voyage to the Windward and Leeward Islands, Colombia, and a guided daylight transit of the Panama Canal. Zipline through the shady Antigua Rainforest near Falmouth Harbour. Savor deep-fried pastries filled with warm and tasty seafood on Bonaire. Board a semi-submersible bound for underwater marine parks and sunken ships off the shores of St. Barts. Master delicious Creole cuisine during a beachside cooking class with a local Martinique chef. Swim and snorkel prior to an overnight stay in Jost Van Dyke. Cook up decadent chocolate confections from locally grown cocoa nibs near Castries. See Cartagena’s colonial architecture from a classic horse-drawn carriage perspective. Relax during a narrated daylight transit of the Panama Canal as you uncover how early engineers overcame formidable and deadly challenges.  Linger on deck on warm, moonlight nights with the gentle lapping of the water below and the sparkling plethora of stars above.

05/16/2025 through 02/15/2026
05/16/2025 through 03/21/2026

Day 1 The capital of Saint Maarten, the Dutch side of this two nation island, Philipsburg is located on the isthmus between Groot Baai (Great Bay) and the Salt Pond. Founded in 1733 as a free port, the city is now the home to outstanding shopping, casinos, and a variety of hotels and resorts, including nearby Mullet Bay Resort and Golf Club.
Day 2

Saint John's, the vibrant capital of Antigua and Barbuda, is a captivating destination known for its colorful colonial architecture. The city offers visitors a charming mix of history, culture, and natural beauty. A must-see landmark is the stunning St. John's Cathedral, an iconic structure built in the 19th century, which offers visitors a glimpse into the island’s religious heritage. The city is also home to the bustling Heritage Quay, a popular shopping district where tourists can find everything from luxury items to local handicrafts. There visitors can bask in the lively atmosphere, peruse local markets offering fresh produce and seafood, and enjoy waterfront dining with views of the harbor.

One of the most enticing aspects of Saint John is its proximity to some of the island’s most stunning beaches. With 365 beaches to choose from, there’s a perfect spot for every type of beachgoer. Dickenson Bay, known for its white sandy shores and crystal-clear waters, is a favorite among visitors. The city’s vibrant atmosphere, combined with its natural beauty and historical charm, makes it a must-visit destination in the Caribbean.



Arrive Time: 8:00 AM – Depart Time: 6:00 PM
Day 3

Anguilla, a serene island in the eastern Caribbean, offers a slice of paradise with its pristine beaches and crystal-clear waters. Known for its luxurious resorts and laid-back atmosphere, Anguilla invites visitors to unwind on its 33 stunning beaches, such as Shoal Bay East and Rendezvous Bay, which are consistently ranked among the best in the world. Whether you're looking to lounge on soft white sands, snorkel in vibrant coral reefs, or simply enjoy a tranquil sunset, Anguilla delivers an idyllic escape from the everyday.

The island's charm extends beyond its beaches. Anguilla boasts a rich cultural heritage, with influences from African, Caribbean, and European traditions. The island's culinary scene is a testament to this diverse background, featuring everything from gourmet dining at establishments to local eateries serving up fresh seafood and Caribbean specialties. Visitors can also explore Anguilla's history and culture at the Heritage Museum in The Valley, which provides insights into the island's past and its path to independence.

For nature enthusiasts, Anguilla offers more than just beautiful beaches. The island's landscape includes mangrove swamps, salt ponds, and the unique Limestone Hill, which provides panoramic views of the surrounding waters. One of the island's most intriguing natural features is its network of underground caves, which can be explored with guided tours.

A fun fact about Anguilla is that it is known for its impressive collection of over 100 traditional Caribbean rum shops, where visitors can experience local culture and taste homemade rums. This charming aspect of island life adds an authentic touch to any visit. For the best experience, plan your visit between December and April when the weather is pleasant and ideal for enjoying all that Anguilla has to offer.



Arrive Time: 9:00 AM – Depart Time: 6:00 PM
Day 4 Tortola, the largest island in the British Virgin Islands, beckons travelers with its idyllic beaches and vibrant culture. Known for its stunning natural beauty, Tortola offers crystal-clear waters, lush landscapes, and a range of outdoor activities. Cane Garden Bay, one of the island’s most famous beaches, is renowned for its powdery white sand and turquoise waters. Whether you’re lounging under a palm tree or snorkeling among vibrant coral reefs, this beach provides a quintessential Caribbean experience. For more information on activities, visit the British Virgin Islands Tourism website.

The island’s capital city, Road Town, is a lively hub of local culture and commerce. Here, visitors can explore the colorful markets and historical sites such as the Old Government House Museum. This museum offers insights into the island's colonial past and its transformation into a modern destination. The town also features charming shops and restaurants where you can savor local cuisine, including fresh seafood and Caribbean specialties.

For nature enthusiasts, Tortola is a paradise. Hike the trails of Mount Sage National Park, the highest point on the island, to enjoy panoramic views of the surrounding archipelago. The park’s diverse flora and fauna make it a rewarding destination for eco-tourists. Additionally, Tortola is a gateway to the nearby Virgin Gorda and Anegada islands, each offering unique attractions such as the famous Baths on Virgin Gorda and the stunning coral reefs of Anegada.

Fun Fact: Tortola is named after the Spanish word "tortola," which means "turtledove." The island’s lush environment and tranquil waters provide an ideal habitat for these birds, adding a touch of local charm to your visit.
Day 5 Part of the British Virgin Islands, Virgin Gorda is an island in the Caribbean famous for The Baths National Park, whose natural geologic granite formations dot the island's beaches and create stunning tidal pools and grottoes.

Arrive Time: 8:00 AM – Depart Time: 5:00 PM
Day 6 Tortola, the largest island in the British Virgin Islands, beckons travelers with its idyllic beaches and vibrant culture. Known for its stunning natural beauty, Tortola offers crystal-clear waters, lush landscapes, and a range of outdoor activities. Cane Garden Bay, one of the island’s most famous beaches, is renowned for its powdery white sand and turquoise waters. Whether you’re lounging under a palm tree or snorkeling among vibrant coral reefs, this beach provides a quintessential Caribbean experience. For more information on activities, visit the British Virgin Islands Tourism website.

The island’s capital city, Road Town, is a lively hub of local culture and commerce. Here, visitors can explore the colorful markets and historical sites such as the Old Government House Museum. This museum offers insights into the island's colonial past and its transformation into a modern destination. The town also features charming shops and restaurants where you can savor local cuisine, including fresh seafood and Caribbean specialties.

For nature enthusiasts, Tortola is a paradise. Hike the trails of Mount Sage National Park, the highest point on the island, to enjoy panoramic views of the surrounding archipelago. The park’s diverse flora and fauna make it a rewarding destination for eco-tourists. Additionally, Tortola is a gateway to the nearby Virgin Gorda and Anegada islands, each offering unique attractions such as the famous Baths on Virgin Gorda and the stunning coral reefs of Anegada.

Fun Fact: Tortola is named after the Spanish word "tortola," which means "turtledove." The island’s lush environment and tranquil waters provide an ideal habitat for these birds, adding a touch of local charm to your visit.
Day 7 One of the four islands that make up the British Virgin Islands, Jost van Dyke is a Caribbean paradise known for its white sand beaches, turquoise sea pools, and marinas filled with yachts.

Arrive Time: 8:00 AM – Depart Time: 5:00 PM
Day 8

The capital of picturesque St. Barthélemy, Gustavia is a veritable island paradise in the Caribbean. A former French colony, this small city on St. Barths’s west coast offers a variety of fine dining, designer shopping, and spectacular beachside activities to ensure a relaxing tropical getaway. Be sure to visit the historic site of Fort Karl for a panoramic view of Gustavia’s glittering harbor, then walk to Shell Beach to take a dip in warm, turquoise waters.



Arrive Time: 8:00 AM – Depart Time: 10:00 PM
Day 9 The capital of Saint Maarten, the Dutch side of this two nation island, Philipsburg is located on the isthmus between Groot Baai (Great Bay) and the Salt Pond. Founded in 1733 as a free port, the city is now the home to outstanding shopping, casinos, and a variety of hotels and resorts, including nearby Mullet Bay Resort and Golf Club.

Arrive Time: 6:00 AM – Depart Time: 7:00 PM
Day 10

Nestled under the imposing view of volcanic Mount Liamuiga, charming Basseterre is the best place to begin your next Caribbean adventure to St. Kitts. From the island’s untouched natural beauty, best seen by boarding the famous St. Kitts Scenic Railway, to the glittering beaches of Frigate Bay, perfect for snorkeling and jet skiing, there are plenty of excursions guaranteed to thrill you in Basseterre. Be sure to stop by the city center to visit Independence Square or venture thirty minutes outside of Basseterre to scenic Brimstone Hill Fortress; both sites will give you a glimpse into the area’s French colonial past. Set sail for this Caribbean capital and soak up the tropical sun!



Arrive Time: 8:00 AM – Depart Time: 9:00 PM
Day 11

The capital of picturesque St. Barthélemy, Gustavia is a veritable island paradise in the Caribbean. A former French colony, this small city on St. Barths’s west coast offers a variety of fine dining, designer shopping, and spectacular beachside activities to ensure a relaxing tropical getaway. Be sure to visit the historic site of Fort Karl for a panoramic view of Gustavia’s glittering harbor, then walk to Shell Beach to take a dip in warm, turquoise waters.



Arrive Time: 8:00 AM – Depart Time: 10:00 PM
Day 12

Saint John's, the vibrant capital of Antigua and Barbuda, is a captivating destination known for its colorful colonial architecture. The city offers visitors a charming mix of history, culture, and natural beauty. A must-see landmark is the stunning St. John's Cathedral, an iconic structure built in the 19th century, which offers visitors a glimpse into the island’s religious heritage. The city is also home to the bustling Heritage Quay, a popular shopping district where tourists can find everything from luxury items to local handicrafts. There visitors can bask in the lively atmosphere, peruse local markets offering fresh produce and seafood, and enjoy waterfront dining with views of the harbor.

One of the most enticing aspects of Saint John is its proximity to some of the island’s most stunning beaches. With 365 beaches to choose from, there’s a perfect spot for every type of beachgoer. Dickenson Bay, known for its white sandy shores and crystal-clear waters, is a favorite among visitors. The city’s vibrant atmosphere, combined with its natural beauty and historical charm, makes it a must-visit destination in the Caribbean.



Arrive Time: 8:00 AM – Depart Time: 9:00 PM
Day 13 Terre-de-Haut is an island off the coast of Guadeloupe and replete with a variety of stunning viewpoints to gaze out at the sparkling waters of the Caribbean Sea. Highlights include Plage de Pompierre, Fort Napoléon des Saintes, and Le Chameau, Terre-de-Haut's highest point.

Arrive Time: 8:00 AM – Depart Time: 5:00 PM
Day 14 Roseau is the capital and largest city on Dominica, a small Caribbean island off the coast of Venezuela. This island getaway is renowned for its verdant rainforest landscape and natural wonders, including gorges, waterfalls, and geysers.

Arrive Time: 8:00 AM – Depart Time: 1:00 PM
Day 15 No airport, a single unnamed village, clear waters and white-sand beaches make Mayreau a quiet, rustic getaway. About 200 people live on this 1.5 mile (2.5km) long island just west of the Tobago Cays. Most visitors arrive via small cruise ships that dock at Saline Bay on the southwestern shore - making the island's other beaches best for seclusion. Salt Whistle Bay, at the northern end of the island, is protected from rough Atlantic breakers by a long narrow arm. This gorgeous bay has clear waters, beautiful white sands, calm swimming conditions and a protected anchorage for visiting yachts. The 20 minute walk from the village (near the middle of the western coast) to Salt Whistle Bay follows a path lined by cacti and scored by birdsong. There's a good view from the hilltop stone church at the northern side of the village.

Take a time machine to another century. One road, one pick up truck and more farm animals than citizens. Hunt for sea shells, sunbathe and surrender to the peace and quiet that make this a most serene island.

Arrive Time: 8:00 AM – Depart Time: 4:00 PM
Day 16

A former English colonial stronghold, Bridgetown, the capital of Barbados, will entice you with its unique Bajan flair and centuries-old English style architecture. This Caribbean haven, a favorite for Caribbean cruise-goers, offers plenty of adventurous and tropical excursions that will surely entertain you! Beachside attractions are a must – hop on a catamaran to go snorkeling offshore, plunge the ocean depths in a local submarine, or unwind on the sands of Carlisle Bay. Explore the historical remnants of Bridgetown’s English occupation, including St. Michael’s Cathedral, the Morgan Lewis Sugar Mill, Arlington House Museum, and Chamberlain Bridge. Better yet, sample the island’s best rums made from local sugarcane at St. Nicholas Abbey or Mount Gay Rum. Delight in Barbados’s natural wonders at Harrison’s Cave, the cavernous limestone grotto concealing striking calcite deposits and warm waters. Stroll the verdant walkways replete with hundreds of blooming flowers at Hunte’s Gardens or the Andromeda Botanic Gardens.

Travel to Bridgetown and immerse yourself in this Bajan paradise!



Arrive Time: 7:00 AM – Depart Time: 5:00 PM
Day 17 Enjoy this day at sea as you travel to your next port of call. This is an opportunity to swim, catch some sun on deck or take advantage of the many activities that are onboard your ship. Eat heartily, take a nap and get ready for the next port of call ! This is what makes cruising so great.
Day 18

Nestled under the imposing view of volcanic Mount Liamuiga, charming Basseterre is the best place to begin your next Caribbean adventure to St. Kitts. From the island’s untouched natural beauty, best seen by boarding the famous St. Kitts Scenic Railway, to the glittering beaches of Frigate Bay, perfect for snorkeling and jet skiing, there are plenty of excursions guaranteed to thrill you in Basseterre. Be sure to stop by the city center to visit Independence Square or venture thirty minutes outside of Basseterre to scenic Brimstone Hill Fortress; both sites will give you a glimpse into the area’s French colonial past. Set sail for this Caribbean capital and soak up the tropical sun!



Arrive Time: 9:00 AM – Depart Time: 5:00 PM
Day 19

Saint John's, the vibrant capital of Antigua and Barbuda, is a captivating destination known for its colorful colonial architecture. The city offers visitors a charming mix of history, culture, and natural beauty. A must-see landmark is the stunning St. John's Cathedral, an iconic structure built in the 19th century, which offers visitors a glimpse into the island’s religious heritage. The city is also home to the bustling Heritage Quay, a popular shopping district where tourists can find everything from luxury items to local handicrafts. There visitors can bask in the lively atmosphere, peruse local markets offering fresh produce and seafood, and enjoy waterfront dining with views of the harbor.

One of the most enticing aspects of Saint John is its proximity to some of the island’s most stunning beaches. With 365 beaches to choose from, there’s a perfect spot for every type of beachgoer. Dickenson Bay, known for its white sandy shores and crystal-clear waters, is a favorite among visitors. The city’s vibrant atmosphere, combined with its natural beauty and historical charm, makes it a must-visit destination in the Caribbean.



Arrive Time: 8:00 AM – Depart Time: 6:00 PM
Day 20 Terre-de-Haut is an island off the coast of Guadeloupe and replete with a variety of stunning viewpoints to gaze out at the sparkling waters of the Caribbean Sea. Highlights include Plage de Pompierre, Fort Napoléon des Saintes, and Le Chameau, Terre-de-Haut's highest point.

Arrive Time: 9:00 AM – Depart Time: 10:00 PM
Day 21 Roseau is the capital and largest city on Dominica, a small Caribbean island off the coast of Venezuela. This island getaway is renowned for its verdant rainforest landscape and natural wonders, including gorges, waterfalls, and geysers.

Arrive Time: 8:00 AM – Depart Time: 1:00 PM
Day 22 No airport, a single unnamed village, clear waters and white-sand beaches make Mayreau a quiet, rustic getaway. About 200 people live on this 1.5 mile (2.5km) long island just west of the Tobago Cays. Most visitors arrive via small cruise ships that dock at Saline Bay on the southwestern shore - making the island's other beaches best for seclusion. Salt Whistle Bay, at the northern end of the island, is protected from rough Atlantic breakers by a long narrow arm. This gorgeous bay has clear waters, beautiful white sands, calm swimming conditions and a protected anchorage for visiting yachts. The 20 minute walk from the village (near the middle of the western coast) to Salt Whistle Bay follows a path lined by cacti and scored by birdsong. There's a good view from the hilltop stone church at the northern side of the village.

Take a time machine to another century. One road, one pick up truck and more farm animals than citizens. Hunt for sea shells, sunbathe and surrender to the peace and quiet that make this a most serene island.

Arrive Time: 8:00 AM – Depart Time: 5:00 PM
Day 23

Arrive Time: 7:30 AM – Depart Time: 2:00 PM
Day 24

A former English colonial stronghold, Bridgetown, the capital of Barbados, will entice you with its unique Bajan flair and centuries-old English style architecture. This Caribbean haven, a favorite for Caribbean cruise-goers, offers plenty of adventurous and tropical excursions that will surely entertain you! Beachside attractions are a must – hop on a catamaran to go snorkeling offshore, plunge the ocean depths in a local submarine, or unwind on the sands of Carlisle Bay. Explore the historical remnants of Bridgetown’s English occupation, including St. Michael’s Cathedral, the Morgan Lewis Sugar Mill, Arlington House Museum, and Chamberlain Bridge. Better yet, sample the island’s best rums made from local sugarcane at St. Nicholas Abbey or Mount Gay Rum. Delight in Barbados’s natural wonders at Harrison’s Cave, the cavernous limestone grotto concealing striking calcite deposits and warm waters. Stroll the verdant walkways replete with hundreds of blooming flowers at Hunte’s Gardens or the Andromeda Botanic Gardens.

Travel to Bridgetown and immerse yourself in this Bajan paradise!



Arrive Time: 7:00 AM – Depart Time: 6:00 PM
Day 25 This cluster of five tiny islets, remain uninhabited, and are protected as a national park. Unspoiled beaches and sheltered anchorages are a favorite amongst yachtsmen and snorkelers alike!

Arrive Time: 8:00 AM – Depart Time: 6:00 PM
Day 26
Day 27
Day 28 St. Lucia is an island of verdant landscapes in every direction: A dense rain forest rises up and covers The Pitons' twin peaks, and in the valleys, the sun's rays dance upon the large yellow-green leaves of banana plants. Beyond all the greenery, you'll find isolated coves, stunning beaches, colonial towns, quiet fishing villages and first-class yachting facilities.

Sports-enthusiasts needn't worry about feeling idle on a St. Lucia vacation. The island has plenty of activities to partake in, from water sports such as diving and snorkeling to land options like hiking through the rain forest and exploring a volcano.

Lucia's beaches are awe-inspiring, with strands of black volcanic sand, mile-long stretches of white beach and gorgeous palm-fringed bays bordered by towering mountains. Nature's impact on St. Lucia's beaches has made each one more breathtaking than the last.

Arrive Time: 5:30 PM – Depart Time: 6:30 PM
Day 29 Castries, St. Lucia's capital and a busy port city, is an idyllic Caribbean wonderland. Tourists will find craft and fruit markets, photo-ready murals and a general cozy charm here. One must-do activity is getting to the top Morne Fortune (Hill of Good Luck) to drink in the lovely panoramic views. Be sure to visit the museum at Derek Walcott Square, and soak up the sun on Vigie Beach!

Arrive Time: 8:00 AM – Depart Time: 3:00 PM
Day 30 No airport, a single unnamed village, clear waters and white-sand beaches make Mayreau a quiet, rustic getaway. About 200 people live on this 1.5 mile (2.5km) long island just west of the Tobago Cays. Most visitors arrive via small cruise ships that dock at Saline Bay on the southwestern shore - making the island's other beaches best for seclusion. Salt Whistle Bay, at the northern end of the island, is protected from rough Atlantic breakers by a long narrow arm. This gorgeous bay has clear waters, beautiful white sands, calm swimming conditions and a protected anchorage for visiting yachts. The 20 minute walk from the village (near the middle of the western coast) to Salt Whistle Bay follows a path lined by cacti and scored by birdsong. There's a good view from the hilltop stone church at the northern side of the village.

Take a time machine to another century. One road, one pick up truck and more farm animals than citizens. Hunt for sea shells, sunbathe and surrender to the peace and quiet that make this a most serene island.

Arrive Time: 8:00 AM – Depart Time: 6:00 PM
Day 31 Bequia, the largest of the Grenadines, is a hidden gem in the Caribbean Sea that captivates visitors with its unspoiled beauty and warm, welcoming atmosphere. Often described as the "island in the clouds," Bequia (pronounced "Bek-way") offers a tranquil escape where turquoise waters meet lush green hills. The island's charm lies in its simplicity—no sprawling resorts or crowded beaches, just a peaceful haven where time seems to stand still.

Port Elizabeth, the island's main town, is a delightful blend of vibrant colors and laid-back vibes. Stroll along the Belmont Walkway, where you can browse local crafts, enjoy fresh seafood at waterfront restaurants, or simply take in the stunning views of Admiralty Bay. Bequia's maritime heritage is celebrated at the Bequia Maritime Museum, where you can learn about the island's rich history of boat building and whaling. For a taste of local culture, visit the Bequia Easter Regatta, a beloved annual event that draws sailing enthusiasts from around the world.

For nature lovers, Bequia is a paradise waiting to be explored. The island is home to several beautiful beaches, each with its own unique charm. Princess Margaret Beach, named after the British royal who once swam there, is a crescent of golden sand lapped by clear, calm waters, perfect for swimming and snorkeling. If you're looking for a more secluded spot, Lower Bay offers a tranquil retreat where you can relax under the shade of palm trees. Bequia is also a gateway to the stunning Tobago Cays, a group of uninhabited islands surrounded by coral reefs, where you can dive with sea turtles and explore vibrant underwater worlds.

Fun Fac: Bequia is one of the few places in the world where traditional whaling is still practiced, albeit on a small and sustainable scale, permitted by international agreements.

Bequia’s blend of natural beauty, rich culture, and relaxed pace makes it an irresistible destination for those seeking a true Caribbean experience. Whether you're exploring its vibrant marine life, soaking up the sun on its pristine beaches, or immersing yourself in its rich history, Bequia promises a vacation that you'll never forget.

Arrive Time: 8:00 AM – Depart Time: 2:00 PM
Day 32

A former English colonial stronghold, Bridgetown, the capital of Barbados, will entice you with its unique Bajan flair and centuries-old English style architecture. This Caribbean haven, a favorite for Caribbean cruise-goers, offers plenty of adventurous and tropical excursions that will surely entertain you! Beachside attractions are a must – hop on a catamaran to go snorkeling offshore, plunge the ocean depths in a local submarine, or unwind on the sands of Carlisle Bay. Explore the historical remnants of Bridgetown’s English occupation, including St. Michael’s Cathedral, the Morgan Lewis Sugar Mill, Arlington House Museum, and Chamberlain Bridge. Better yet, sample the island’s best rums made from local sugarcane at St. Nicholas Abbey or Mount Gay Rum. Delight in Barbados’s natural wonders at Harrison’s Cave, the cavernous limestone grotto concealing striking calcite deposits and warm waters. Stroll the verdant walkways replete with hundreds of blooming flowers at Hunte’s Gardens or the Andromeda Botanic Gardens.

Travel to Bridgetown and immerse yourself in this Bajan paradise!


Anguilla

Anguilla is a level coral atoll with abundant breath-taking beaches. The name comes from the Spanish word for eel, named apparently because of the island’s long, narrow profile. The most northerly of the Leeward Islands in the eastern Caribbean, Anguilla is 16 miles (25km) long and three miles (5km) wide. The highest point on the island is only 213 feet (65m) above sea level. The main town, The Valley, is found almost in the middle of the island. Most hotels and restaurants
are found on the western point of the island.

02/21/26 - 03/21/26

Starting At $8,299

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