Star Collector: Bermuda & Caribbean Island Explorer

FREE ALL-INCLUSIVE OFFER
Dining
£3,249pp
sparks

Free All-Inclusive Offer

Drinks, gratuities, and WiFi included plus up to exclusive savings on selected sailings - only with The Cruise Line. Secure your suite or stateroom with a £150pp deposit (applies to voyages departing more than 90 days after the date of booking).

Voyage Code: WIND1050238
moon 17 nights
anchorStar Pride
calendar 22 Oct '27

Cruise overview

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.

Boston, Massachusetts
Hamilton
Hamilton
Saint George
Gustavia
San Juan (Puerto Rico)
Basseterre, Saint Kitts
Gustavia
Philipsburg
Great Harbour, Jost Van Dyke
San Juan (Puerto Rico)

Itinerary

Day 1

Boston, Massachusetts


There’s history and culture around every bend in Boston—skyscrapers nestle next to historic hotels while modern marketplaces line the antique cobblestone streets. But to Bostonians, living in a city that blends yesterday and today is just another day in beloved Beantown.

Day 2

at-sea At sea

Day 3

at-sea At sea

Day 4

Hamilton

Day 5

Hamilton

Day 6

Saint George

Day 7

at-sea At sea

Day 8

at-sea At sea

Day 9

Gustavia

Day 10

at-sea At sea

Day 11

San Juan (Puerto Rico)

Day 12

at-sea At sea

Day 13

Basseterre, Saint Kitts

Day 14

Gustavia

Day 15

Philipsburg

Day 16

Great Harbour, Jost Van Dyke

Day 17

at-sea At sea

Day 18

San Juan (Puerto Rico)

Star Porthole Suitefrom£3,249pp
Ocean View Suitefrom£3,369pp
Ocean View Suitefrom£3,519pp
Star Ocean View Suitefrom£3,769pp
Gracious Balcony from£5,719pp
Star Balcony Suitefrom£5,819pp
Deluxe Suitefrom£8,519pp
Classic Suitesfrom£10,289pp
Grand Owner's Suite Midshipfrom£11,479pp
Owner's Suite Midshipfrom£11,479pp
Sea Island SuiteCall for price
Broadmoor SuiteCall for price

Star Porthole Suite

from£3,249pp
Enquire now

The Star Porthole Suite offers cosy sophistication with charming porthole windows providing a classic maritime feel. Well-appointed and thoughtfully designed, these suites feature comfortable sleeping and sitting areas, ideal for guests seeking intimate, elegant accommodation without compromising on Windstar’s renowned luxury and service.

Amenities

  • Queen or Twin Configuration
  • Shower
  • Room Service Available
  • TV
  • Safe
  • Hair Dryer
  • Telephone
  • Desk
  • Lounge Area
  • Mini Bar (Additional Cost)
  • Wi-Fi (Additional Cost)

Ship features

Star Pride offers suite-only luxury, refreshed venues and modern amenities tailored for boutique cruising.

Overview
Accommodation
Dining
Amenities
Spa
Families
  • Completely all-suite ship after Star Plus refit
  • New dining options: Cuadro 44, Star Grill
  • Infiniti pool with ocean views
  • Watersports platform with complimentary use of kayaks and paddleboards
  • Open-bridge access for guests
  • Refreshed lounges, spa, fitness facilities and library
  • Beauty salon, boutique, destination office and screening room
  • Low-key evening entertainment and local music