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Bermuda Bliss

Oct 22, 2027 — Nov 1, 2027

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BOSTON, MA → SAN JUAN

10 Nights on Star Pride

Embark on a voyage from the East Coast to San Juan with an overnight in St. George’s, Bermuda. Indulge in the luxury of multiple sea days, where you’ll have uninterrupted relaxation. Explore the UNESCO World Heritage Site of St. George’s, Bermuda. Take in the charming streets lined with colonial buildings, visit the iconic St. Peter's Church, one of the oldest Anglican churches in the Western Hemisphere, and discover the fascinating history at the Bermuda National Trust Museum. For nature enthusiasts, St. George's offers stunning coastal views, and Tobacco Bay provides an opportunity for snorkeling in crystal-clear waters teeming with marine life. Arrive in the historic and vibrant city of San Juan, Puerto Rico. Traverse the cobblestone streets of Old San Juan, visit ancient forts, and immerse yourself in the rich local culture. From colonial charm to lively markets, San Juan welcomes you with a blend of history and Caribbean flair.

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
2.5 Hours
Activity Level
Moderate

Add during booking

$119

St. George's

Time
10:30 AM
Duration
1.5 Hours
Activity Level
Moderate

Add during booking

$59

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
4 Hours
Activity Level
Strenuous

Add during booking

$99

Virgin Gorda / Prickly Pear, British Virgin Islands

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

Add during booking

$299

11
NOV 01, 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

Starting from

Room Size 277 sq ft
Max. Occupancy 2 Passengers
Amenities
Expand all

Available Dates

Date Yacht
Starting from
Actions
Oct 20 (Tue) – Oct 28 (Wed), 2026October 20 (Tue) – October 28 (Wed), 2026Star Pride

Bermuda Bliss

BOSTON, MA → SAN JUAN

10 Nights on Star Pride

Oct 22, 2027 — Nov 1, 2027

Embark on a voyage from the East Coast to San Juan with an overnight in St. George’s, Bermuda. Indulge in the luxury of multiple sea days, where you’ll have uninterrupted relaxation. Explore the UNESCO World Heritage Site of St. George’s, Bermuda. Take in the charming streets lined with colonial buildings, visit the iconic St. Peter's Church, one of the oldest Anglican churches in the Western Hemisphere, and discover the fascinating history at the Bermuda National Trust Museum. For nature enthusiasts, St. George's offers stunning coastal views, and Tobacco Bay provides an opportunity for snorkeling in crystal-clear waters teeming with marine life. Arrive in the historic and vibrant city of San Juan, Puerto Rico. Traverse the cobblestone streets of Old San Juan, visit ancient forts, and immerse yourself in the rich local culture. From colonial charm to lively markets, San Juan welcomes you with a blend of history and Caribbean flair.

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, 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

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

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: 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

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

11
NOV 01, 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.