Island-Hopping in Windstar Style

Hidden Harbors. Private Beaches. Let Your Soul Dance in the Caribbean.


Earn an additional $200 Shipboard credit to spend in the World Spa by Windstar, the Signature Shop, or to simply enjoy mojitos on deck.


Candy-colored cocktails sipped in seaside watering holes. Carefree days followed by calypso-flavored nights. These are the siren songs that lure anyone with a yacht and a yearning to escape to the incomparable Caribbean Islands. Whether you’re cruising through turquoise waters or lazing on powdery white beaches, the glamorous harbors and unknown coves of the Caribbean remain a hidden treasure.

Not Too Big and Not Too Small

Banish cliché, toss aside regimen, steer clear of the ordinary. Windstar’s perfectly sized ships make it possible to flip the script on cruising. Free yourself from crowds and indulge all your senses, especially your sense of wonder. Experience cultures in ways that are personal and authentic, with the power to change your perspective. With 148–342 guests, a Windstar ship is large enough to pamper, yet small enough to explore secluded coves and remote islands, and dock in the heart of charming villages and sparkling cities.


* Per person, double occupancy, Ocean View. Price subject to change and availability; please contact us for details.

Star Collector: Antilles Adventures

From $2,299 USD* + $200 USD taxes
Sailing aboard Wind Surf
Select dates from Jan 2, Jan 23, and Mar 13, 2021, 14 days
St. Maarten → Bridgetown (or reverse)

Discover less-traveled roads and concealed refuges throughout the Caribbean on this 14-day cruise that blends iconic destinations and little-known shorelines like a favorite beachside cocktail.


Philipsburg, St. Maarten; Basseterre, St. Kitts; Gustavia, St. Barthélemy; Little Bay, Montserrat, BWI; Les Saintes, Guadeloupe; Roseau, Dominica; Pigeon Island, St. Lucia; Bridgetown, Barbados; Pigeon Island, St. Lucia; Castries, St. Lucia; Scenic Cruising The Pitons; Anse Mitan, Martinique; Mayreau, St. Vincent & The Grenadines; St. George's, Grenada; Bequia, St. Vincent & The Grenadines; Bridgetown, Barbados

• All meals in all venues
• All non-alcoholic drinks
• Complimentary laundry

* Per person, double occupancy, Ocean View. Price subject to change and availability; please contact us for details.

Star Collector: Caribbean Explorations

From $2,599 USD* + $350 USD taxes
Sailing aboard Wind Surf
Select dates from Feb 6, 2021, 13 days
Roundtrip → St. Maarten

Whether you’re looking for hidden shops, sampling new cuisine or seeking a local place to sip rum cocktails over the melodic beat of steel drums, this highly personalized adventure is an intimate opportunity to familiarize yourself with the lesser-known charms of the Leeward Islands.


Philipsburg, St. Maarten; Road Bay, Anguilla; Soper's Hole, Tortola, B.V.I.; Jost Van Dyke, Great Harbour, B.V.I.; Jost Van Dyke, Great Harbour, B.V.I.; Virgin Gorda, B.V.I.; Gustavia, St. Barthélemy; Falmouth Harbour, Antigua; Philipsburg, St. Maarten; Charlestown, Nevis; Roseau, Dominica; Pigeon Island, St. Lucia; Les Saintes, Guadeloupe; Basseterre, St. Kitts; Gustavia, St. Barthélemy; Philipsburg, St. Maarten

• All meals in all venues
• All non-alcoholic drinks
• Complimentary laundry

* Per person, double occupancy, Ocean View Suite. Price subject to change and availability; please contact us for details.

Star Collector: Lovely Leewards

From $2,499 USD* + $350 USD taxes
Sailing aboard Star Breeze
Select dates from Jan 9, 2021, 14 days
Roundtrip → San Juan

Whether you’re passionate about swimming among rarely seen undersea wildlife or the intricate cultures and intertwined European histories of the Windward Islands, this 2-week cruise offers the best combinations of charm, island heritage and natural beauty.


San Juan, Puerto Rico; St. Thomas; Gustavia, St. Barthélemy; Little Bay, Montserrat, BWI; Philipsburg, St. Maarten; Jost Van Dyke, Great Harbour, B.V.I.; Virgin Gorda, B.V.I.; San Juan, Puerto Rico; St. George's, Grenada; Bequia, St. Vincent & The Grenadines; Pigeon Island, St. Lucia; Les Saintes, Guadeloupe; Philipsburg, St. Maarten; San Juan, Puerto Rico

• All meals in all venues
• All non-alcoholic drinks
• Complimentary laundry

Terms & Conditions

All fares mentioned are per person, in US dollars; cruise only, based on double occupancy in lowest category, and include non-discountable amounts. Suggested onboard gratuities are extra. Taxes, Fees & Port Expenses are additional. Unless otherwise specified, Windstar is offering on select cruises a shipboard credit (SBC) in the amount of $100 per person, subject to a maximum of $200 per stateroom or suite. Single fares will earn a $100 SBC. Consult your Windstar representative for promotional offer or discount combinability. Bookings are non-transferable; no name changes can be made nor can this offer be applied retroactively. Cancellation fees may apply, please see website for details. Certain restrictions apply. Fuel surcharges may be imposed or increased over time. Information contained herein is accurate at the time of publication and subject to change without notice. All terms and conditions apply. Cruise is provided subject to the terms and conditions of the Passage Contract. Offer expires on August 31, 2020. Ships' registry: Bahamas.