INTERNATIONAL NUMBERS
HEALTH & SAFETY
YACHT CLUB
WISHLIST
MY WINDSTAR
Call Your Travel Advisor or
800.258.7245
Find a Cruise
Destinations
Why Windstar
Booked Guests
Beyond Ordinary
Romance
Shore Excursions
Watersports Platform
Services & Enrichment
James Beard Foundation
Culinary Excellence
Local Immersion
Onboard Dining
Yachts
Specials
Request Info & Plan
Search for:
DESTINATIONS AROUND THE GLOBE
MOST POPULAR CRUISES
Our Select Sailings
A curated list of our best of the best.
Tahiti
Mediterranean
Northern Europe & Iceland
Greece
BY DESTINATION
Alaska
Asia
Canada & New England
Canary Islands
Caribbean
Costa Rica & Panama Canal
Culinary & Wine Cruises
Europe
Grand Adventures
Iceland
Italy
Latin America
Mexico
Ocean Crossings
South America
South Pacific
Themed Cruises
U.S. Coastals
BEYOND ORDINARY
Cruise Tours - Best of the Land & Sea Together
Star Collectors - Back to Back Cruises of 13+ Days
STAR PLUS CLASS ~ All-Suite Motor Yachts
Star Breeze
Star Legend
Star Pride
WIND CLASS ~ Classic Sailing Yachts
Wind Star
Wind Surf
Wind Spirit
NEW! Star Seeker
Featuring Voyages in Alaska & Japan
Be one of the first to experience Windstar's newest yacht. Inaugural season begins in 2026!
REQUEST INFO
SIGN UP FOR EMAIL
Receive news and specials
REQUEST A BROCHURE
Or browse our e-brochure
REQUEST A CALL
We want to help you plan
PLANNING RESOURCES
Booked Guests Log In
General Info / FAQ
Cruise Documents
Pre & Post Hotels
Shore Excursions
Travel Protection
Health & Safety
Terms & Conditions
Accessibility
Find a Cruise
Destinations
Alaska
Asia
Canada & New England
Canary Islands
Caribbean
Costa Rica & Panama Canal
Cruise Tours
Culinary & Wine Cruises
Europe
Grand Adventures
Greece
Iceland
Italy
Latin America
Mediterranean
Mexico
Northern Europe & Iceland
Ocean Crossings
Select Sailings
South America
South Pacific
Star Collector Voyages
Tahiti
Themed Cruises
U.S. Coastals
Why Windstar
Booked Guests
Beyond Ordinary
Romance
Shore Excursions
Watersports Platform
Culinary Excellence
Services & Enrichment
Local Immersion
Onboard Dining
James Beard Foundation
Yachts
Wind Surf
Wind Star
Wind Spirit
Star Pride
Star Breeze
Star Legend
Star Seeker
Specials
Request Info & Plan
Request a Brochure
Sign Up for Email Specials
Request a Call
Booked Guests Log In
General Info / FAQ
Cruise Documents
Pre & Post Hotels
Shore Excursions
Travel Protection
Health & Safety
Terms & Conditions
Accessibility
INTERNATIONAL NUMBERS
HEALTH & SAFETY
YACHT CLUB
WISHLIST
MY WINDSTAR
Call Your Travel Advisor or
800.258.7245
Star Collector: Leeward & Windward Caribbean Havens
Philipsburg, St. Maarten to Bridgetown
Sat Feb 21, 2026 - Sat Mar 7, 2026,
14 days
on Wind Spirit
VIEW ALL DATES
Call For Availability
OVERVIEW & ITINERARY
OVERVIEW
ITINERARY & EXCURSIONS
ACCOMMODATIONS & PRICES
HOTELS
LIFE ONBOARD
SHARE
COPIED TO CLIPBOARD
CLOSE
ADD TO
WISH LIST
REMOVE
FROM
WISH LIST
REQUEST A CALL
Accommodations & Pricing
Star Collector: Leeward & Windward Caribbean Havens
Port to port
Philipsburg, St. Maarten to Bridgetown
Duration
14 days
Close
Day
Port
Day 1
Philipsburg, St. Maarten
Day 2
St. John's
Day 3
Road Bay
Day 4
Virgin Gorda / Prickly Pear, British Virgin Islands
Day 4
Soper's Hole
Day 5
Soper's Hole
Day 6
Jost Van Dyke, Great Harbour
Day 7
Gustavia
Day 8
Philipsburg, St. Maarten
Day 9
Basseterre
Day 10
Gustavia
Day 11
St. John's
Day 12
Les Saintes
Day 13
Roseau
Day 14
Mayreau
Day 15
Bridgetown
ALL DATES &
FARES
Pick Your Perk
Great cruise-only fares or make it an all-inclusive voyage with unlimited beer, wine, and cocktails, Wi-Fi, and gratuities. From $99 per guest per day.
Windstar’s Pick Your Perk offer is back for another season of savings. With options that match your travel style, you get to make the most of your vacation, your way. Reserve a cruise departing through June 2026 and you'll get to choose between an onboard credit, a hotel stay or — for Premium Suite guests — an All-Inclusive package.
Date
Ship
All-Inclusive
From
Cruise Only
From
Sun
Jan 4
2026
WIND SURF
$5,485
$4,099
VIEW
SAILING
Sat
Feb 21
2026
WIND SPIRIT
Call For Availability
VIEW
SAILING
Click on the date to view the map and itinerary by date
SELECT THE NUMBER OF GUESTS
2
ADULTS
GO BACK
CONTINUE