Windward Ways & Tobago Cays

 
Bridgetown to Oranjestad
Fri Dec 4, 2026 - Sat Dec 12, 2026,
 8 days
 on Star Legend
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Starting from $3,499 USD
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When you book your hotel through Windstar, you get the peace of mind to enjoy and relax your vacation. Not only does Windstar hand-select and curate premium hotels, we offer only preferred category rooms for your comfort. If you’re looking to explore during your stay, all you need to do is stop by Windstar-hosted on-property service desk for insider tips, day trip itineraries, restaurant recommendations, and where to find the best place for viewing the sunset

Hilton Barbados Resort

Hilton Barbados Resort

Hilton Barbados Resort is a stunning beachfront retreat located on the lush Needham’s Point peninsula in Bridgetown. Nestled between two pristine white-sand beaches and crystal-clear waters, the resort offers spacious ocean-view rooms, a luxurious full-service spa, and an inviting infinity pool. Guests enjoy direct access to the historic Charles Fort, making it ideal for both relaxation and discovery in the heart of the Caribbean. The resort’s diverse dining options serve delicious local and international dishes, complemented by tropical cocktails with breathtaking sea views. Featuring a modern fitness center and close proximity to vibrant downtown Bridgetown, Hilton Barbados Resort promises an unforgettable island getaway for travelers of all ages.