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Star Collector: Bermuda & Caribbean Island Explorer

Oct 22, 2027 — Nov 8, 2027

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Complimentary All-In Package

Free Laundry for Collectors:

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BOSTON, MA → SAN JUAN

17 Nights on Star Pride

Sail from the North Atlantic into the heart of the Caribbean on an extended journey shaped by island character and days unrushed at sea. Take advantage of rare overnights in Bermuda’s historic towns before continuing toward San Juan’s timeless fortresses and colorful shoreline. You’ll also have two full days to experience Gustavia and Virgin Gorda, giving you more time to enjoy their beaches, cafés, and sheltered bays. From there, explore quiet anchorages in the Virgin Islands, snorkel pristine bays, and wander small-ship harbors like Jost Van Dyke and Virgin Gorda.

Map routes may vary by sailing. Actual itineraries are listed below.
1
OCT 22, 2027
Boston
EMBARK
1:00 PM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
2

Founded in 1630 by Puritan settlers, Boston is one of the oldest cities in the U.S. It was a pivotal place during the American Revolution for the Boston Massacre, the Boston Tea Party, the Battle of Bunker Hill and the Siege of Boston. Tourists to Boston see the Faneuil Hall Marketplace, the JFK Library and Museum, the Museum of Fine Arts, the New England Aquarium, and the USS Constitution.

Available Excursions

Boston

Discover Boston’s colonial gems, from Back Bay and Beacon Hill to the Freedom Trail and USS Constitution.

Time
10:01 AM
Duration
2.5 Hours
Activity Level
Easy

Add during booking

$149

Boston

Explore Boston’s Back Bay, Beacon Hill, Freedom Trail landmarks and a glimpse of the historic USS Constitution!

Time
10:01 AM
Duration
2.5 Hours
Activity Level
Easy

Add during booking

$149

2
OCT 23, 2027
AT SEA
3
OCT 24, 2027
AT SEA
4
OCT 25, 2027
Hamilton
ARRIVE
8:45 AM
DEPART
11:59 PM
MARINA
NO
SHORE EXCURSIONS
0

The capital of Bermuda is the energetic heart of Bermuda. A walk along Front Street on the harbor features interesting pastel-colored colonial buildings and boutiques. Sites to see here include the Cathedral of the Most Holy Trinity, built in 1869 with a tower that displays panoramic views of the city. Find the Bermuda National Gallery and the Bermuda Aquarium, Museum and Zoo.

5
OCT 26, 2027
Hamilton
ARRIVE
12:00 AM
DEPART
7:00 AM
MARINA
NO
SHORE EXCURSIONS
0

The capital of Bermuda is the energetic heart of Bermuda. A walk along Front Street on the harbor features interesting pastel-colored colonial buildings and boutiques. Sites to see here include the Cathedral of the Most Holy Trinity, built in 1869 with a tower that displays panoramic views of the city. Find the Bermuda National Gallery and the Bermuda Aquarium, Museum and Zoo.

St. George's
ARRIVE
10:00 AM
DEPART
11:59 PM
MARINA
NO
SHORE EXCURSIONS
3

In 2000 St. George's was named a UNESCO World Heritage Site, founded in 1609 by an English ship that got blown off course, Strolling the streets of St George's will feel like a step back in time. The well-preserved buildings and fortress have made it a haven of British colonial architecture including St. Peter's Church. Natural sites to see here in addition include Tobacco Bay Beach, Tom Moore's Jungle, Cooper's Island Nature Reserve, Ferry Reach National Park, and the Crystal Caves of Bermuda.

Available Excursions

St. George's

Time
10:30 AM
Duration
1.5 Hours
Activity Level
Moderate

Add during booking

$59

St. George's

Time
10:30 AM
Duration
1.5 Hours
Activity Level
Moderate

Add during booking

$59

St. George's

Time
10:30 AM
Duration
2.5 Hours
Activity Level
Moderate

Add during booking

$119

6
OCT 27, 2027
St. George's
ARRIVE
12:00 AM
DEPART
12:00 PM
MARINA
NO
SHORE EXCURSIONS
0

In 2000 St. George's was named a UNESCO World Heritage Site, founded in 1609 by an English ship that got blown off course, Strolling the streets of St George's will feel like a step back in time. The well-preserved buildings and fortress have made it a haven of British colonial architecture including St. Peter's Church. Natural sites to see here in addition include Tobacco Bay Beach, Tom Moore's Jungle, Cooper's Island Nature Reserve, Ferry Reach National Park, and the Crystal Caves of Bermuda.

7
OCT 28, 2027
AT SEA
8
OCT 29, 2027
AT SEA
9
OCT 30, 2027
Gustavia
ARRIVE
10:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
0

Affectionately known as St. Barts, the Caribbean's most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island's signature ti punch as kite surfers fly by.

10
OCT 31, 2027
Virgin Gorda / Prickly Pear, British Virgin Islands
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
NO
SHORE EXCURSIONS
2

The  beautiful Bank Barrier coral reef wavers just beneath you as your ship makes the break to the bird sanctuary of Prickly Pear Island, so named because it is dotted with prickly pear cacti. Althought uninhabited, it does have a beach bar and water sports facilities. Not far away lies the curious assembly of house-sized boulders called "The Baths," which form huge underground pools and caverns

Available Excursions

Virgin Gorda / Prickly Pear, British Virgin Islands

Time
8:30 AM
Duration
2.75 Hours
Activity Level
Moderate-Strenuous

Add during booking

$299

Virgin Gorda / Prickly Pear, British Virgin Islands

Time
8:30 AM
Duration
4 Hours
Activity Level
Strenuous

Add during booking

$99

11
NOV 01, 2027
San Juan
ARRIVE
7:00 AM
DEPART
7:00 PM
MARINA
NO
SHORE EXCURSIONS
0

The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan.

12
NOV 02, 2027
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
NO
SHORE EXCURSIONS
4

CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)

Available Excursions

CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate

Add during booking

$149

CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)

Time
8:30 AM
Duration
2.5 Hours
Activity Level
Easy

Add during booking

$99

CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)

Time
8:30 AM
Duration
3.5 Hours
Activity Level
Moderate

Add during booking

$139

CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate

Add during booking

$139

13
NOV 03, 2027
Basseterre
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
5

With Georgian architecture situated against an irresistible backdrop of emerald green hills, Basseterre is one of the loveliest of the Caribbean's small capitals. Beyond town, more than a quarter of St. Kitts has been set aside as Brimstone Hill Fortress national Park, a UNESCO World Heritage Site.

Available Excursions

Basseterre

Time
8:30 AM
Duration
3 Hours
Activity Level
Strenuous

Add during booking

$139

Basseterre

Time
8:30 AM
Duration
4 Hours
Activity Level
Strenuous

Add during booking

$129

Basseterre

Time
8:30 AM
Duration
3.25 Hours
Activity Level
Easy-Moderate

Add during booking

$89

Basseterre

Time
9:00 AM
Duration
3.5 Hours
Activity Level
Easy

Add during booking

$99

Basseterre

Time
10:30 AM
Duration
2.5 Hours
Activity Level
Moderate

Add during booking

$69

14
NOV 04, 2027
Gustavia
ARRIVE
7:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
0

Affectionately known as St. Barts, the Caribbean's most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island's signature ti punch as kite surfers fly by.

15
NOV 05, 2027
Philipsburg, St. Maarten
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
NO
SHORE EXCURSIONS
0

Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience.

16
NOV 06, 2027
Jost Van Dyke, Great Harbour
ARRIVE
9:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
0

For an island comprised of a mere eight square miles, it's amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis  Drake Waterway. After all that, you'll be ready for an evening drink on the beach - where you can admire your Windstar ship aglow in the harbor.

17
NOV 07, 2027
Virgin Gorda / Prickly Pear, British Virgin Islands
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
2

The  beautiful Bank Barrier coral reef wavers just beneath you as your ship makes the break to the bird sanctuary of Prickly Pear Island, so named because it is dotted with prickly pear cacti. Althought uninhabited, it does have a beach bar and water sports facilities. Not far away lies the curious assembly of house-sized boulders called "The Baths," which form huge underground pools and caverns

Available Excursions

Virgin Gorda / Prickly Pear, British Virgin Islands

Time
8:30 AM
Duration
2.75 Hours
Activity Level
Moderate-Strenuous

Add during booking

$299

Virgin Gorda / Prickly Pear, British Virgin Islands

Time
8:30 AM
Duration
4 Hours
Activity Level
Strenuous

Add during booking

$99

18
NOV 08, 2027
San Juan
ARRIVE
7:00 AM
DISEMBARK
8:00 AM
MARINA
NO
SHORE EXCURSIONS
0

The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan.

Star Pride

number of decks
6 Decks
yacht length
522 ft (159 meters)
yacht crew size
200 Crew Members
yacht guest capacity
312 Guests
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Staterooms

Room Size 575 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 400 sq ft
Max. Occupancy 2 Passengers
Amenities

Starting from

Room Size 468 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 2 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 2 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 2 Passengers
Amenities

Room Size 277 sq ft
Max. Occupancy 2 Passengers
Amenities
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Available Dates

No other dates are available.

Star Collector: Bermuda & Caribbean Island Explorer

BOSTON, MA → SAN JUAN

17 Nights on Star Pride

Oct 22, 2027 — Nov 8, 2027

Sail from the North Atlantic into the heart of the Caribbean on an extended journey shaped by island character and days unrushed at sea. Take advantage of rare overnights in Bermuda’s historic towns before continuing toward San Juan’s timeless fortresses and colorful shoreline. You’ll also have two full days to experience Gustavia and Virgin Gorda, giving you more time to enjoy their beaches, cafés, and sheltered bays. From there, explore quiet anchorages in the Virgin Islands, snorkel pristine bays, and wander small-ship harbors like Jost Van Dyke and Virgin Gorda.

1
OCT 22, 2027
Boston
EMBARK
1:00 PM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
2

Founded in 1630 by Puritan settlers, Boston is one of the oldest cities in the U.S. It was a pivotal place during the American Revolution for the Boston Massacre, the Boston Tea Party, the Battle of Bunker Hill and the Siege of Boston. Tourists to Boston see the Faneuil Hall Marketplace, the JFK Library and Museum, the Museum of Fine Arts, the New England Aquarium, and the USS Constitution.

Boston, City Tour With Transfer To Airport

See some of Boston's most famous colonial sites on this comprehensive sightseeing tour. You'll pass the Back Bay, the Hancock Tower, and Henry Hobson Richardson's beautiful Trinity Church. Then, pass by the upscale 19th century neighborhood of Beacon Hill and see other historic sites along the Freedom Trail. Before heading to the airport, you might catch a glimpse of the USS Constitution, the oldest actively commissioned warship in the Navy. Please note: This tour can be wheelchair accessible upon request. Tour is not recommend for guests with flights before 1:00PM

Port
Boston
Time
10:01 AM
Duration
2.5 Hours
Activity Level
Easy

Add during booking

$149 USD

Boston, City Tour With Transfer To Windstar Hotel

See some of Boston's most famous colonial sites on this comprehensive sightseeing tour. You'll pass the Back Bay, the Hancock Tower, and Henry Hobson Richardson's beautiful Trinity Church. Then, pass by the upscale 19th century neighborhood of Beacon Hill and see other historic sites along the Freedom Trail. Before heading to the hotel, you might catch a glimpse of the USS Constitution, the oldest actively commissioned warship in the Navy. You will be transferred to your Windstar hotel. Please note : This tour can be wheelchair accessible upon request.

Port
Boston
Time
10:01 AM
Duration
2.5 Hours
Activity Level
Easy

Add during booking

$149 USD

2
OCT 23, 2027
AT SEA
3
OCT 24, 2027
AT SEA
4
OCT 25, 2027
Hamilton
ARRIVE
8:45 AM
DEPART
11:59 PM
MARINA
NO
SHORE EXCURSIONS
0

The capital of Bermuda is the energetic heart of Bermuda. A walk along Front Street on the harbor features interesting pastel-colored colonial buildings and boutiques. Sites to see here include the Cathedral of the Most Holy Trinity, built in 1869 with a tower that displays panoramic views of the city. Find the Bermuda National Gallery and the Bermuda Aquarium, Museum and Zoo.

5
OCT 26, 2027
Hamilton
ARRIVE
12:00 AM
DEPART
7:00 AM
MARINA
NO
SHORE EXCURSIONS
0

The capital of Bermuda is the energetic heart of Bermuda. A walk along Front Street on the harbor features interesting pastel-colored colonial buildings and boutiques. Sites to see here include the Cathedral of the Most Holy Trinity, built in 1869 with a tower that displays panoramic views of the city. Find the Bermuda National Gallery and the Bermuda Aquarium, Museum and Zoo.

St. George's
ARRIVE
10:00 AM
DEPART
11:59 PM
MARINA
NO
SHORE EXCURSIONS
3

In 2000 St. George's was named a UNESCO World Heritage Site, founded in 1609 by an English ship that got blown off course, Strolling the streets of St George's will feel like a step back in time. The well-preserved buildings and fortress have made it a haven of British colonial architecture including St. Peter's Church. Natural sites to see here in addition include Tobacco Bay Beach, Tom Moore's Jungle, Cooper's Island Nature Reserve, Ferry Reach National Park, and the Crystal Caves of Bermuda.

St. Georges, St Georges Heritage Walking Tour *

Learn about the history of Bermuda's UNESCO World Heritage Site, the Town of St. George, with an award-winning local tour guide. During her 60-minute walking tour, you'll see some incredible centuries-old properties, including Tucker House, St. Peter's Church and The Globe Hotel, and one of the oldest stone buildings in the New World, State House, built in 1620. Join your local guide as she accounts important events while exploring the charm of our 400 year old town. Please note: Wear comfortable walking shoes.

Port
St. George's
Time
10:30 AM
Duration
1.5 Hours
Activity Level
Moderate

Add during booking

$59 USD

St. Georges, St Georges Heritage Walking Tour *

Learn about the history of Bermuda's UNESCO World Heritage Site, the Town of St. George, with an award-winning local tour guide. During her 60-minute walking tour, you'll see some incredible centuries-old properties, including Tucker House, St. Peter's Church and The Globe Hotel, and one of the oldest stone buildings in the New World, State House, built in 1620. Join your local guide as she accounts important events while exploring the charm of our 400 year old town. Please note: Wear comfortable walking shoes.

Port
St. George's
Time
10:30 AM
Duration
1.5 Hours
Activity Level
Moderate

Add during booking

$59 USD

St. Georges, Crystal Caves Discovery Tour

Departing the pier take a short drive through the Old Town of St. George to the Crystal Caves, an amazing natural grotto of stalactites and stalagmites floodlit for your viewing pleasure. So named the Crystal Caves for the clear flowing deep lake and azure blue water, so clear that you can actually see the cave's floor, found 55 feet below the surface. This intriguing and fascinating attraction was discovered by accident by boys searching for a lost ball stumbled across the cave in 1907. Descending 81 steps to the floor of the cave, you'll cross floating pontoons constructed over the waters of the lake as your guide leads, you'll get to see the original entrance the boys lowered themselves from, which appears as a small skylight in the cave's roof. Following your adventure, your guide will drive you through the exclusive residential area of Tuckers Town which culminates in "Billionaires Row," where you'll view the waterfront estates of Ross Perot and Michael Bloomberg. Please note : To enter the cave you must descend down 81 steps and then proceed over pontoon bridges. The tour is not available to guests who utilize a wheelchair and not recommended for those guests with mobility concerns. Comfortable, flat walking shoes are suggested. Minimum 6/maximum 6 per minivan Max 42 guests

Port
St. George's
Time
10:30 AM
Duration
2.5 Hours
Activity Level
Moderate

Add during booking

$119 USD

6
OCT 27, 2027
St. George's
ARRIVE
12:00 AM
DEPART
12:00 PM
MARINA
NO
SHORE EXCURSIONS
0

In 2000 St. George's was named a UNESCO World Heritage Site, founded in 1609 by an English ship that got blown off course, Strolling the streets of St George's will feel like a step back in time. The well-preserved buildings and fortress have made it a haven of British colonial architecture including St. Peter's Church. Natural sites to see here in addition include Tobacco Bay Beach, Tom Moore's Jungle, Cooper's Island Nature Reserve, Ferry Reach National Park, and the Crystal Caves of Bermuda.

7
OCT 28, 2027
AT SEA
8
OCT 29, 2027
AT SEA
9
OCT 30, 2027
Gustavia
ARRIVE
10:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
0

Affectionately known as St. Barts, the Caribbean's most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island's signature ti punch as kite surfers fly by.

10
OCT 31, 2027
Virgin Gorda / Prickly Pear, British Virgin Islands
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
NO
SHORE EXCURSIONS
2

The  beautiful Bank Barrier coral reef wavers just beneath you as your ship makes the break to the bird sanctuary of Prickly Pear Island, so named because it is dotted with prickly pear cacti. Althought uninhabited, it does have a beach bar and water sports facilities. Not far away lies the curious assembly of house-sized boulders called "The Baths," which form huge underground pools and caverns

Virgin Gorda: Snorkel Adventure

Board a 36-foot Newton Dive Special vessel for a fun and relaxing cruise through the islands surrounding Virgin Gorda. Motor across the stunning Virgin Gorda waters with views of neighboring islands. The boat will moor at your first snorkel spot, chosen by the Captain as the best location for the day. The crew will assist with getting your snorkel gear ready, give a safety briefing and guide you in the water while pointing out interesting sea life. Once back on board, the Captain will pick out a second snorkel spot for you to enjoy. The tour will end with refreshments on board and a cruise back to shore in time for your beach barbecue. Please note: wear your swimsuit under your clothes, bring a towel, a dry t-shirt or sweatshirt, reef friendly sunscreen, waterproof camera (if you want to record the boulders ashore), and a hat. Participants must sign a waiver before departing the dock. Depending on weather and sea state the snorkel locations might have to be adjusted. Minimum age is 7 years. The only way to experience this natural wonder is with our pre- arranged shore excursion being offered onboard.

Port
Virgin Gorda / Prickly Pear, British Virgin Islands
Time
8:30 AM
Duration
2.75 Hours
Activity Level
Moderate-Strenuous

Add during booking

$299 USD

Virgin Gorda: Highlights & Bath Tour

Enjoy the best that Virgin Gorda has to offer when you take this Island Tour to the world famous Baths. Board your open air safari bus at Gun Creek and wind up the hills to Gorda Peak where you will have the opportunity to photograph the impressive archipelago of the B.V.I. Your route will take you on down the spine of this beautiful island. From here you will drive to The Baths. These massive granite boulders stand out against powdery white sand and crystal-clear waters, so seize this chance to scramble through narrow gaps, intricate pools and passages which comprise this adventurous footpath before it opens out to the spectacular white sands of Devil's Bay. The beach at The Baths boasts an appealing bar, souvenir stand and restrooms. For those not physically inclined, you can still be witness to these dramatic batholiths should you take a drink at the Top of The Baths, or the less strenuous path direct down to Devils Bay. Before boarding the safari busses, sample a complimentary rum punch, punch or water at the gazebo above the Baths, and then enjoy the remainder of your circular island tour via Nail Bay with homes of the rich and famous and Hog's Heaven for some stunning shots of the ship anchored in North Sound. Please note : Wear your swimsuit under your clothes, bring reef-friendly sun screen, towel, camera, reef or aqua shoes to explore the Baths, flip-flops are not recommended. This tour is not recommended for those with mobility issues. Use caution while walking down the trail and through the boulders in the caves. Path is uneven and slippery. On some days expect crowds. Please be aware of the National Flag Warning System and adhere to it at all times. Red Flag: Danger - No Swimming. Yellow Flag: Caution - Weak swimmers are discouraged from entering the water. Purple Flag: Jellyfish Warning. The only way to experience this natural wonder is with our pre- arranged shore excursion being offered onboard.

Port
Virgin Gorda / Prickly Pear, British Virgin Islands
Time
8:30 AM
Duration
4 Hours
Activity Level
Strenuous

Add during booking

$99 USD

11
NOV 01, 2027
San Juan
ARRIVE
7:00 AM
DEPART
7:00 PM
MARINA
NO
SHORE EXCURSIONS
0

The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan.

12
NOV 02, 2027
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
NO
SHORE EXCURSIONS
4

CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)

St. John, Trunk Bay Snorkeling Experience

St. John is a breathtaking island known for its pristine white-sand beaches and lush tropical landscapes. Enjoy scenic views of Cruz Bay, Hawksnest Bay, and the historic Caneel Bay Plantation as you make your way to the highlight of the tour—iconic Trunk Bay. Here, a unique underwater snorkeling trail awaits. Spend more than 90 minutes swimming and snorkeling along the marked route, where vibrant corals and tropical fish are easy to spot, or simply unwind beneath the shade of a palm tree. Snorkel gear, instruction, and a lounge chair are all included.

Please note: Wear a swimsuit and bring a towel, sunscreen, and a hat.

Port
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate

Add during booking

$149 USD

St. John, Island tour Featuring Annaberg Ruins

Port
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Time
8:30 AM
Duration
2.5 Hours
Activity Level
Easy

Add during booking

$99 USD

St. John, Cinnamon Beach Getaway

Spend a relaxing self-guided day at Cinnamon Bay Beach, with at least three hours to swim, explore historic ruins, or unwind beneath the palms in complimentary lounge chairs. Enjoy a casual snack lunch and drinks from the beachside snack shack whenever you’re feeling thirsty or hungry.

Port
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Time
8:30 AM
Duration
3.5 Hours
Activity Level
Moderate

Add during booking

$139 USD

St. John, Lind Point Trail Eco Hike

Set out from Cruz Bay with an ecologist guide for a scenic hike through lush tropical forest, learning about local wildlife, native history, and island culture. Take in sweeping views of St. Thomas and the British Virgin Islands before reaching tranquil Honeymoon Beach, where you can swim or relax beneath coconut trees. Continue along the Lind Point trail back to Cruz Bay.

Port
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate

Add during booking

$139 USD

13
NOV 03, 2027
Basseterre
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
5

With Georgian architecture situated against an irresistible backdrop of emerald green hills, Basseterre is one of the loveliest of the Caribbean's small capitals. Beyond town, more than a quarter of St. Kitts has been set aside as Brimstone Hill Fortress national Park, a UNESCO World Heritage Site.

Basseterre: St Kitts Quad ATV Adventure

Here is a unique way to experience the Caribbean! This exciting exploration will begin with a transfer from the dock to the Quad Bike (ATV) base. After an introduction and full orientation on the use of the bikes and safety precautions, you will be ready to mount the four-wheel ATV bikes for a wildly exhilarating adventure. Your experienced guide will lead you on a thrilling ride through cane fields and down country dirt tracks and up scenic slopes with views of neighboring islands. On the way you may also be able to taste local fruits in season. Then it will be time once more to get back on the bikes and return to the tour base. Enjoy a cool drink before you will be transferred back to the pier. Please note : You will be provided with a helmet. This tour is not recommended for those with mobility issues or back problems as you will be traveling off road over hilly and bumpy terrain. You will be required to sign a waiver to participate on this tour. Maximum weight is 250 lbs.

Port
Basseterre
Time
8:30 AM
Duration
3 Hours
Activity Level
Strenuous

Add during booking

$139 USD

Basseterre: Sky Safari Zipline Adventure

Fly along zip lines up to 1,400 feet in length, 25 stories above the ground! This is a spectacular 5-line zip line journey based at the Historic Wingfield Estate . After a short orientation, training session, and riding the first (trainer) line, you will hop into vehicles for a trek up the famous Valley of the Giants . You will see fantastic panoramic views of Brimstone Hill Fortress, Old Road Village , former sugar estates, the Caribbean Sea, and Mount Liamuiga. With a mile of zip lines you will soar at speeds up to 50 miles per hour . Thanks to the cutting edge technology of this system you will fly hands and feet free, just like a bird. All you have to do is sit back, and enjoy the experience! You will also be given an opportunity to walk around the Wingfield Estate Ruins. View the first British masonry in the entire New World as well as the remnants of the different methods of processing sugar which are all on site.

Please note : This tour is not available for guests who are pregnant, have a heart condition or serious medical condition, previous neck or back injuries. To participate on this tour guests must wear closed-toe shoes, weigh at least 60 pounds but no more than 275 pounds and sign a waiver. Any guests wishing to bring along personal items will have the option to leave items at the base and rent a locker to store them in. Price per locker is $5 US and payable directly to the Sky Safari facility.

Port
Basseterre
Time
8:30 AM
Duration
4 Hours
Activity Level
Strenuous

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$129 USD

Basseterre, Brimstone Hill Fortress & Fairview Great House

On this tour, you will enjoy an overview of the capital of St. Kitts & Nevis and get an up-close look at the island's colonial splendor. Board your motor coach for the 30-minute drive with your guide into Basseterre, one of the oldest towns in the Eastern Caribbean. Admire impressive Victorian and Georgian architecture and view important landmarks such as the Berkeley Memorial Clock Tower and Independence Square, once a slave market and today host to a picturesque fountain and a centuries-old church. You will stop at the Fairview Great House and Tropical Garden. At this 300-year-old colonial property, you will explore perfectly preserved rooms, including the original kitchen with its volcanic stone and brick oven and the bathing room with its sun-warmed bath. Follow the stone bridge to the lush tropical botanical garden, where many of the plants such as palms and fruit trees date back as far as the 1700s. Then explore the 300-year-old Brimstone Fortress, perched 780 feet above sea level. This magnificent structure is the second largest of its type in the entire Western Hemisphere and is one of the best preserved. This Gibraltar of the West Indies is a UNESCO World Heritage Site and more battles were fought here than at any other single site in British and French naval history. Its spectacular panoramic views include part of the Kittitian coastline, countryside and five neighboring islands. Please note : This tour is not wheelchair accessible.

Port
Basseterre
Time
8:30 AM
Duration
3.25 Hours
Activity Level
Easy-Moderate

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$89 USD

Basseterre, Concierge Collection: Caribbean Cooking, History & Folklore in St. Kitts

A unique culinary experience! You may have previously enjoyed the exotic flavors of West Indian cooking, but do you know the actual ingredients of the dishes or their history? Regardless of whether you are a seasoned cook or just a lover of tasty cuisine, this demonstration will appeal to you. After a short drive you will arrive at Fairview Great House & Tropical Garden. Enjoy regional dishes prepared before your eyes . As ingredients are added, the historian cook will recount tales about the history of the regional foods, and talk about the development of dishes that use African, European, and Indian cooking methods. Then you will sample the dishes along with homemade refreshments. Explore the Fairview Great House & Botanical Garden. You may also choose to meander through the different areas of the beautifully landscaped 2.5-acre botanical garden at your leisure. Complimentary copies of the recipes of the dishes prepared during your tour will be yours to take home as a souvenir of your unique experience in St. Kitts. Please note : Due to the limited space available on this tour, it will sell out quickly.

Port
Basseterre
Time
9:00 AM
Duration
3.5 Hours
Activity Level
Easy

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$99 USD

Basseterre, Island History & Rum Tasting

Your tour will begin with a narrated drive around historic Basseterre, one the oldest towns in the Eastern Caribbean. You will view Victorian and Georgian style architecture, important monuments such as the Berkeley Memorial Clock Tower, Independence Square (once a former slave market) with its prominent fountain and impressive centuries-old Catholic Co-Cathedral across the street. See the newly restored Fairview Great House & Botanical Garden. Here you will enjoy a guided tour around the Great House, which is believed to have been originally built in 1701 by the French. The inhabitants who have been recorded to reside here include American legal luminary John Gardiner and Lawyer James Stephen -advocate of the enslaved. The rich history of the site and the island is well displayed with its superbly furnished historical information room that brings to life the 1700s - 1800 with true impressions of what life was like on an Estate in St. Kitts during that era. From the cobblestone courtyard view the original kitchen building with its volcanic stone and brick oven; the original bathing room with its large sun warmed volcanic stone bath; the stone bridge leading from the rear veranda of the Great House to the rear area of the tropical botanical garden. While in the courtyard don't forget to wander into the old stone cellar where you will find a slavery exhibit. This self guided exhibit provides a glimpse of the African-Caribbean slavery story which began in Africa. The experience includes details of the journey through the Middle Passage to the Caribbean. Learn about the life of the slaves on the plantation during the pre and post emancipation period. You will be given the opportunity to taste several flavors of rum, hear the history of where rum came from in the Caribbean and how Caribbean people made their own rum. Hear stories of when the Irish settled on St. Kitts and the rum legacies they left and how and where rum drinking has evolved on the island. After your rum tasting experience, take time to wander in the 2 1/2 acre Botanical Garden. Don't forget to peek inside the gift shop and pick up some keepsakes that will remind you of this unique experience for years to come. Please note: Bring your camera, cash, credit card, sunscreen, sunglasses, and hat.

Port
Basseterre
Time
10:30 AM
Duration
2.5 Hours
Activity Level
Moderate

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$69 USD

14
NOV 04, 2027
Gustavia
ARRIVE
7:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
0

Affectionately known as St. Barts, the Caribbean's most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island's signature ti punch as kite surfers fly by.

15
NOV 05, 2027
Philipsburg, St. Maarten
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
NO
SHORE EXCURSIONS
0

Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience.

16
NOV 06, 2027
Jost Van Dyke, Great Harbour
ARRIVE
9:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
0

For an island comprised of a mere eight square miles, it's amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis  Drake Waterway. After all that, you'll be ready for an evening drink on the beach - where you can admire your Windstar ship aglow in the harbor.

17
NOV 07, 2027
Virgin Gorda / Prickly Pear, British Virgin Islands
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
2

The  beautiful Bank Barrier coral reef wavers just beneath you as your ship makes the break to the bird sanctuary of Prickly Pear Island, so named because it is dotted with prickly pear cacti. Althought uninhabited, it does have a beach bar and water sports facilities. Not far away lies the curious assembly of house-sized boulders called "The Baths," which form huge underground pools and caverns

Virgin Gorda: Snorkel Adventure

Board a 36-foot Newton Dive Special vessel for a fun and relaxing cruise through the islands surrounding Virgin Gorda. Motor across the stunning Virgin Gorda waters with views of neighboring islands. The boat will moor at your first snorkel spot, chosen by the Captain as the best location for the day. The crew will assist with getting your snorkel gear ready, give a safety briefing and guide you in the water while pointing out interesting sea life. Once back on board, the Captain will pick out a second snorkel spot for you to enjoy. The tour will end with refreshments on board and a cruise back to shore in time for your beach barbecue. Please note: wear your swimsuit under your clothes, bring a towel, a dry t-shirt or sweatshirt, reef friendly sunscreen, waterproof camera (if you want to record the boulders ashore), and a hat. Participants must sign a waiver before departing the dock. Depending on weather and sea state the snorkel locations might have to be adjusted. Minimum age is 7 years. The only way to experience this natural wonder is with our pre- arranged shore excursion being offered onboard.

Port
Virgin Gorda / Prickly Pear, British Virgin Islands
Time
8:30 AM
Duration
2.75 Hours
Activity Level
Moderate-Strenuous

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$299 USD

Virgin Gorda: Highlights & Bath Tour

Enjoy the best that Virgin Gorda has to offer when you take this Island Tour to the world famous Baths. Board your open air safari bus at Gun Creek and wind up the hills to Gorda Peak where you will have the opportunity to photograph the impressive archipelago of the B.V.I. Your route will take you on down the spine of this beautiful island. From here you will drive to The Baths. These massive granite boulders stand out against powdery white sand and crystal-clear waters, so seize this chance to scramble through narrow gaps, intricate pools and passages which comprise this adventurous footpath before it opens out to the spectacular white sands of Devil's Bay. The beach at The Baths boasts an appealing bar, souvenir stand and restrooms. For those not physically inclined, you can still be witness to these dramatic batholiths should you take a drink at the Top of The Baths, or the less strenuous path direct down to Devils Bay. Before boarding the safari busses, sample a complimentary rum punch, punch or water at the gazebo above the Baths, and then enjoy the remainder of your circular island tour via Nail Bay with homes of the rich and famous and Hog's Heaven for some stunning shots of the ship anchored in North Sound. Please note : Wear your swimsuit under your clothes, bring reef-friendly sun screen, towel, camera, reef or aqua shoes to explore the Baths, flip-flops are not recommended. This tour is not recommended for those with mobility issues. Use caution while walking down the trail and through the boulders in the caves. Path is uneven and slippery. On some days expect crowds. Please be aware of the National Flag Warning System and adhere to it at all times. Red Flag: Danger - No Swimming. Yellow Flag: Caution - Weak swimmers are discouraged from entering the water. Purple Flag: Jellyfish Warning. The only way to experience this natural wonder is with our pre- arranged shore excursion being offered onboard.

Port
Virgin Gorda / Prickly Pear, British Virgin Islands
Time
8:30 AM
Duration
4 Hours
Activity Level
Strenuous

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$99 USD

18
NOV 08, 2027
San Juan
ARRIVE
7:00 AM
DISEMBARK
8:00 AM
MARINA
NO
SHORE EXCURSIONS
0

The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan.