SMALL SHIP CARIBBEAN CRUISES
Experience the Caribbean in Windstar Style
Anguilla has some of the most beautiful sunsets and delicious rum punch to be found in the Caribbean. It is also home to Cuban tree frogs, red-footed tortoise, green iguanas, and five species of bats.
With its protected shoreline, calm surf, spectacular coral reefs, and sugar-soft beaches, Road Bay has become a destination for boaters, eager to visit its delightful restaurants, bars, and shops.
Visit ports reserved for small ships and private yachts like Mayreau, Bequia, Jost Van Dyke, and Virgin Gorda.
Kayak, paddleboard or swim directly off the complimentary Marina Platform located at the back of the yacht, and enjoy your own set of personalized snorkel gear to use throughout your cruise.
Enjoy Windstar’s Signature Beach Party and a Signature Onboard Barbecue on every itinerary — events that are always a highlight for our guests.
Get Closer to the Caribbean
The perfect island itinerary would look a lot like these. Ports of call would include tiny towns and hidden harbors known only to small ships and private yachts like ours. Schedules would allow for dropping the Marina Platform in cerulean seas and raising sails on the way to your next island rendezvous. And the laid-back island vibe continues on board with a mouthwatering Signature Onboard Barbecue. Best of all, every sailing includes a landing on a secluded beach for Windstar’s Signature Beach Party, elaborate buffet and watersports included.
Yachtsman's Secrets
Shh. There are still secret places here that the big ships pass by. Places where there’s only one beach bar in sight, closed if the proprietor decides to go spear fishing. Your Windstar yacht has an uncanny ability to find places like this. Places where your day’s activities are timed by the rumble of your stomach, the drowsiness following a good swim, an iridescent sunset that heralds “sailor’s delight” on the morrow. But then, one glance at your itinerary already told you that.
Windstar Voyages to Caribbean
Sample body copy to show what it looks like.
7 Nights in Star Pride Yacht
From $4,852 USD/Suite
7 Nights in Star Pride Yacht
From $5,324 USD/Suite
14 Nights in Star Pride Yacht
From $9,386 USD/Suite
13 Nights in Star Pride Yacht
From $8,196 USD/Suite
Star Collector: Central America & the Caribbean - Cloud Forest, Canal Locks & Calypso Concerts
20 Nights in Star Pride Yacht
From $12,912 USD/Suite
Barefoot Break in the British Virgin Islands
5 Nights in Wind Surf Yacht
From $4,300 USD/Suite
Star Collector: Ivory Beaches & Sapphire Seas of the Caribbean
12 Nights in Wind Surf Yacht
From $7,004 USD/Suite
7 Nights in Wind Surf Yacht
From $4,702 USD/Suite
14 Nights in Wind Surf Yacht
From $7,638 USD/Suite
Beach Fun & Sun: A Remote Caribbean Getaway
7 Nights in Wind Surf Yacht
From $4,934 USD/Suite
15 Nights in Wind Spirit Yacht
From $9,686 USD/Suite
8 Nights in Wind Spirit Yacht
From $5,852 USD/Suite
*NEW Star Collector: Bridgetown to Philipsburg
17 Nights in Wind Spirit Yacht
From $10,474 USD/Suite
7 Nights in Wind Spirit Yacht
From $6,232 USD/Suite
21 Nights in Wind Surf Yacht
From $12,740 USD/Suite
Star Collector: Grand Caribbean Adventure
55 Nights in Wind Surf Yacht
From $39,092 USD/Suite
Star Collector: Leeward & Windward Caribbean Havens
14 Nights in Wind Surf Yacht
From $8,494 USD/Suite
Star Collector: The Best of the Windward & Leeward Isles
28 Nights in Wind Surf Yacht
From $18,390 USD/Suite
10 Nights in Wind Spirit Yacht
From $6,840 USD/Suite
Lush & Lovely Islands of the Lesser Antilles
7 Nights in Wind Surf Yacht
From $5,472 USD/Suite
14 Nights in Wind Surf Yacht
From $8,718 USD/Suite
10 Nights in Wind Spirit Yacht
From $9,266 USD/Suite
Star Collector: Hidden Gems of the Caribbean
17 Nights in Wind Spirit Yacht
From $13,588 USD/Suite
8 Nights in Star Seeker Yacht
From $11,792 USD/Suite
14 Nights in Wind Surf Yacht
From $9,894 USD/Suite
7 Nights in Wind Surf Yacht
From $5,444 USD/Suite
15 Nights in Wind Surf Yacht
From $10,732 USD/Suite
7 Nights in Wind Surf Yacht
From $6,048 USD/Suite
7 Nights in Star Seeker Yacht
From $7,054 USD/Suite
Star Collector: Deep Dive into the Blue - Underwater Worlds of the Caribbean
18 Nights in Wind Surf Yacht
From $11,430 USD/Suite
11 Nights in Wind Surf Yacht
From $8,126 USD/Suite
Star Collector: Grand Caribbean & Panamanian Adventure
28 Nights in Wind Spirit Yacht
From $16,830 USD/Suite
Star Collector: Blue Seas of the Windward Islands
14 Nights in Wind Spirit Yacht
From $8,266 USD/Suite
7 Nights in Star Pride Yacht
From $5,238 USD/Suite
10 Nights in Star Seeker Yacht
From $8,314 USD/Suite
49 Nights in Star Seeker Yacht
From $37,086 USD/Suite
Star Collector: Historic Caribbean - Legendary Islands, Colombia and Panama
24 Nights in Star Seeker Yacht
From $18,676 USD/Suite
17 Nights in Star Seeker Yacht
From $11,768 USD/Suite
Star Collector: Spectacular Transatlantic Journey - Caribbean to the Azores
21 Nights in Wind Surf Yacht
From $8,188 USD/Suite
7 Nights in Star Seeker Yacht
From $6,452 USD/Suite
Star Collector: Central American Explorations via the Panama Canal
22 Nights in Star Seeker Yacht
From $17,810 USD/Suite
Star Collector: Rainforest Refuges of Panama & Costa Rica via the Panama Canal
14 Nights in Star Seeker Yacht
From $12,160 USD/Suite
8 Nights in Star Pride Yacht
From $4,852 USD/Suite
11 Nights in Star Pride Yacht
From $7,314 USD/Suite
11 Nights in Wind Star Yacht
From $8,060 USD/Suite
Star Collector: The Caribbean, Colombia, Panama & Costa Rica via the Panama Canal
18 Nights in Wind Star Yacht