Embark on a 14-night round-trip journey from San Juan aboard Windstar’s Star Pride, exploring the best of the Leeward Islands in true small-ship luxury. Discover Old San Juan’s historic charm before sailing to postcard-perfect destinations including St. John, St. Barts, St. Kitts, St. Maarten, Jost Van Dyke, Virgin Gorda, Bequia, Mayreau, Les Saintes, and Marigot.
Enjoy pristine beaches, vibrant marine life, boutique shopping, and cultural gems at every stop. Onboard, savor attentive service, open-bridge access, local culinary inspirations, water sports right from the yacht, and the ease of complimentary daily laundry. This immersive Caribbean voyage blends relaxation, adventure, and Windstar’s signature intimate sailing experience.
- Sunday, December 20 - San Juan (Embark: 7pm)
- Monday, December 21 - At Sea
- Tuesday, December 22 - St. George's (9am-10pm)
- Wednesday, December 23 - Bequia (8am-10pm)
- Thursday, December 24 - Mayreau (8am-5pm)
- Friday, December 25 - Les Saintes (10am-5pm)
- Saturday, December 26 - Marigot, St. Martin (8am-3pm)
- Sunday, December 27 - San Juan (7am-7pm)
- Monday, December 28 - CRUZ BAY, ST. JOHN, Virgin Islands (8am-6pm)
- Tuesday, December 29, Gustavia (8am-10pm)
- Wednesday, December 30 - Basseterre (8am-5pm)
- Thursday, December 31 - Philipsburg, St. Maarten (8am-10pm)
- Friday, January 1 - Jost Van Dyke, Great Harbour (9am-10pm)
- Saturday, January 2 - Virgin Gorda / Prickly Pear, British Virgin Islands (8am-5pm)
- Sunday, January 3 - San Juan (Disembark 7am)
Starting at $4,412 per person Based on Double Occupancy
These rooms represent a nod to the sailing tradition of porthole windows. And while sailors might have had cramped quarters, your 277 square foot stateroom is wonderfully spacious and furnished with all the modern amenities and comforts of home.
Amenities
- Queen Size Bed with Luxurious Linens
- Interactive Television
- Safe
- L'Occitane Bath Amenities
- Fresh Fruit
- Wi-Fi Internet Access (various plans available for purchase)
- Waffle Weave Robe and Slippers
- Fully Stocked Mini Bar/Refrigerator
- Direct Dial Phone
- Hair Dryers and 110/220 Outlets
- Mirrored Closet with Ample Drawer Space
- Granite Vanity with Magnifying Mirror and Chair
Starting at $4,682 per person Based on Double Occupancy
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, and savor a treat from the fresh fruit bowl.
Amenities
- Queen Size Bed with Luxurious Linens
- Interactive Television
- Safe
- L'Occitane Bath Amenities
- Fresh Fruit
- Wi-Fi Internet Access (various plans available for purchase)
- Waffle Weave Robe and Slippers
- Fully Stocked Mini Bar/Refrigerator
- Direct Dial Phone
- Hair Dryers and 110/220 Outlets
- Mirrored Closet with Ample Drawer Space
- Granite Vanity with Magnifying Mirror and Chair
Starting at $6,590 per person Based on Double Occupancy
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
Amenities
- Queen Size Bed with Luxurious Linens
- Interactive Television
- Safe
- L'Occitane Bath Amenities
- Fresh Fruit
- Wi-Fi Internet Access (various plans available for purchase)
- Waffle Weave Robe and Slippers
- Fully Stocked Mini Bar/Refrigerator
- Direct Dial Phone
- Hair Dryers and 110/220 Outlets
- Mirrored Closet with Ample Drawer Space
- Granite Vanity with Magnifying Mirror and Chair