VINCENT VACATIONS
17 NIGHTS | WINDSTAR | STAR PRIDE

17-Night Star Collector: Bermuda & Caribbean Island Explorer Cruise

Aboard Star Pride (Windstar) | Departing Boston to San Juan | 1 Available Departures from $5,615

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17 NightsDuration
WindstarCruise LineStar PrideCruise ShipBostonEmbarkation PortCaribbeanRegion$5,615Starting Fare
PORTS OF CALL ON THIS VOYAGEBoston, Hamilton, St George's, Gustavia, Virgin Gorda, San Juan, Cruz Bay, Basseterre
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Upcoming Sailings & Stateroom Fares (1)

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Departure DateReturn DateInsideOceanviewBalconySuiteAdvisor Quote & Perks
Oct 22, 2027
Voyage #PR20271022-17D
Nov 08, 2027Call for Exclusive Rate$5,615$10,120$6,859
PORT-BY-PORT TIMELINE

Day-by-Day Cruise Itinerary

Star Collector: Bermuda & Caribbean Island Explorer Route Map
Day 1

BOSTON, MA (USBOS)

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 Lib

Day 2

At Sea (SEAD)

Day 3

At Sea (SEAD)

Day 4

HAMILTON (BMHMT)

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 ci

Day 5

HAMILTON (BMHMT)

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 ci

Day 5

ST GEORGES BERMUDA (BMSGB)

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 includin

Day 6

ST GEORGES BERMUDA (BMSGB)

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 includin

Day 7

At Sea (SEAD)

Day 8

At Sea (SEAD)

Day 9

GUSTAVIA, ST BARTHELEMY (BLGUS)

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 10

VIRGIN GORDA/PRICKLY PEAR, BVI (VGVIJ)

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 a

Day 11

SAN JUAN (PRSJU)

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 12

CRUZ BAY, ST JOHN (VICZB)

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

Day 13

BASSETERRE, ST KITTS (KNBAS)

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, ST BARTHELEMY (BLGUS)

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, ST MAARTEN (SXPHI)

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

Day 16

GREAT HARBOUR, JOST VAN DYKE (VGJVD)

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 r

Day 17

VIRGIN GORDA/PRICKLY PEAR, BVI (VGVIJ)

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 a

Day 18

SAN JUAN (PRSJU)

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.

COMPLIMENTARY EXTRAS

Available Promotions & Onboard Credits

Reduced Deposit

One or more fares on this sailing includes a reduced deposit promotion.

THE SIGNATURE TRAVEL NETWORK ADVANTAGE

Why Book 17-Night Star Collector: Bermuda & Caribbean Island Explorer (Star Pride) with Vincent Vacations Instead of Direct?

You pay the exact same promotional cruise line rate with $0 agency booking fees, while unlocking exclusive consortium perks unavailable on retail websites:

✓ $100–$600+ Shipboard Credits✓ Private Car & Driver Shore Excursions✓ Hosted Voyages & VIP Receptions✓ 100% Loyalty Points + Promo Stacking✓ Price-Drop Monitoring Before Final Payment
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EXPERT CRUISE GUIDANCE

Frequently Asked Questions About 17-Night Star Collector: Bermuda & Caribbean Island Explorer (Star Pride)

What is included in the 17-Night Star Collector: Bermuda & Caribbean Island Explorer cruise aboard Star Pride?

This 17-night Windstar voyage aboard Star Pride embarks in Boston and concludes in San Juan, visiting Boston, Hamilton, St George's, Gustavia, Virgin Gorda, San Juan, Cruz Bay, Basseterre. Fares start at $5,615 per person based on double occupancy, plus eligible Vincent Vacations onboard credits.

How do I claim complimentary onboard credit on Star Pride?

Click any stateroom fare or 'Get Quote & Perks' button in the departure table above, or call 1-888-883-0460. Our certified advisors lock in the lowest promotional rate on Star Pride and attach all eligible Signature Travel Network shipboard credits and VIP amenities.

Signature Travel Network Perks: Up to $600 Shipboard Credit + Price-Match Guarantee + $0 Booking Fees
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