Star Collector: Bermuda & Caribbean Island Explorer
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 Bermud...
Cruise only — prices from Solo cruise only — from
Ports of Call & Itinerary
17-night voyage departing Boston, Massachusetts, arriving San Juan (Puerto Rico).
Printable Itinerary (PDF)Route Map
Star Collector: Bermuda & Caribbean Island Explorer
12 ports plotted · click a marker for details
Day 1
Boston, Massachusetts , United States
Friday, 22/10/2027
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.
Day 4
Hamilton , Bermuda
Monday, 25/10/2027
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.
Day 5
Hamilton , Bermuda
Tuesday, 26/10/2027
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.
Day 5
Saint George , Bermuda
Tuesday, 26/10/2027
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.
Day 6
Saint George , Bermuda
Wednesday, 27/10/2027
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.
Day 9
Gustavia , Saint Barthélemy
Saturday, 30/10/2027
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.
Day 11
San Juan (Puerto Rico) , Puerto Rico
Monday, 01/11/2027
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.
Day 13
Basseterre, Saint Kitts , Saint Kitts and Nevis
Wednesday, 03/11/2027
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.
Day 14
Gustavia , Saint Barthélemy
Thursday, 04/11/2027
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.
Day 15
Philipsburg , Sint Maarten (Dutch part)
Friday, 05/11/2027
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.
Day 16
Great Harbour, Jost Van Dyke , British Virgin Islands
Saturday, 06/11/2027
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.
Day 18
San Juan (Puerto Rico) , Puerto Rico
Monday, 08/11/2027
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.
Room Type & Prices
All prices per person based on double occupancy. Solo traveller prices — single occupancy. Contact our cruise experts for the latest availability and best fares.
Star Ocean View Suite
277 sqft · Up to 2 guests
Balcony Suite
277 sqft · Up to 2 guests
Star Porthole Suite
277 sqft · Up to 2 guests
Ocean View Suite
277 sqft · Up to 2 guests
Star Balcony Suite
277 sqft · Up to 2 guests
Deluxe Suite
468 sqft · Up to 2 guests
Broadmoor Suite/Sea Island Suite
400 sqft · Up to 2 guests
Owner's Suite
575 sqft · Up to 2 guests
Oceanview
| Cabin | Grade | Per Person | Avail. | |
|---|---|---|---|---|
| Star Ocean View Suite · 277 sqft | SS1 | Enquire → |
Star Ocean View Suite · 277 sqft
SS1
Balcony
Suite
| Cabin | Grade | Per Person | Avail. | |
|---|---|---|---|---|
| Star Porthole Suite · 277 sqft | SP | Enquire → | ||
| Ocean View Suite · 277 sqft | S Ocean View Suite (Deck 4, forward) | Enquire → | ||
| S1 Ocean View Suite 1 (Deck 4) | Enquire → | |||
| S2 Ocean View Suite 2 (Deck 5) | Enquire → | |||
| S3 Ocean View Suite 3 (Deck 6) | Enquire → | |||
| Star Balcony Suite (Deck 5) | SBS | Enquire → | ||
| Star Balcony Suite · 277 sqft | SBS1 Star Balcony Suite 1 (Deck 6) | Enquire → | ||
| Deluxe Suite · 468 sqft | DS | Enquire → | ||
| Broadmoor Suite/Sea Island Suite · 400 sqft | CS Classic Suite | Enquire → | ||
| Owner's Suite · 575 sqft | OW Owner's Suite | Enquire → |
Star Porthole Suite · 277 sqft
SP
Ocean View Suite · 277 sqft
S Ocean View Suite (Deck 4, forward)
Ocean View Suite · 277 sqft
S1 Ocean View Suite 1 (Deck 4)
Ocean View Suite · 277 sqft
S2 Ocean View Suite 2 (Deck 5)
Ocean View Suite · 277 sqft
S3 Ocean View Suite 3 (Deck 6)
Star Balcony Suite (Deck 5)
SBS
Star Balcony Suite · 277 sqft
SBS1 Star Balcony Suite 1 (Deck 6)
Deluxe Suite · 468 sqft
DS
Broadmoor Suite/Sea Island Suite · 400 sqft
CS Classic Suite
Owner's Suite · 575 sqft
OW Owner's Suite
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Your Ship
Star Pride
Serving just 312 guests, Star Pride is the perfect size — small enough to offer unique experiences that set Windstar apart from other cruise lines (like our complimentary Signature Beach Party), yet large enough for you to make plenty of new connections on board — all without ever feeling crowded.
