All cruises › Windstar Caribbean cruises from San Juan
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Windstar · Star Pride
- 6 ports
- Round trip
- Sails Nov 15, 2026
- From $6,153 pp
- Luxury
- Cruz Bay Trunk Bay Underwater Snorkel Trail & VI National Park
- Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
- Gustavia Private Open-Top Mini Moke Island Tour of St. Barts
Windstar · Star Pride
- 6 ports
- Round trip
- Sails Nov 29, 2026
- From $3,913 pp
- Luxury
- Cruz Bay Trunk Bay Underwater Snorkel Trail & VI National Park
- Gustavia Private Open-Top Mini Moke Island Tour of St. Barts
- Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Windstar · Star Pride
- 6 ports
- Round trip
- Sails Dec 13, 2026
- From $3,983 pp
- Luxury
- Cruz Bay Trunk Bay Underwater Snorkel Trail & VI National Park
- Gustavia Private Open-Top Mini Moke Island Tour of St. Barts
- Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Windstar · Star Pride
- 6 ports
- Round trip
- Sails Dec 27, 2026
- From $3,563 pp
- Luxury
- Cruz Bay Trunk Bay Underwater Snorkel Trail & VI National Park
- Gustavia Private Open-Top Mini Moke Island Tour of St. Barts
- Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Windstar · Star Pride
- 6 ports
- Round trip
- Sails Jan 10, 2027
- From $4,928 pp
- Luxury
- Cruz Bay Trunk Bay Underwater Snorkel Trail & VI National Park
- Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
- Gustavia Private Open-Top Mini Moke Island Tour of St. Barts
Windstar · Star Pride
- 6 ports
- Round trip
- Sails Nov 15, 2027
- From $2,443 pp
- Luxury
- Cruz Bay Trunk Bay Underwater Snorkel Trail & VI National Park
- Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
- Gustavia Private Open-Top Mini Moke Island Tour of St. Barts
Windstar · Star Pride
- 6 ports
- Round trip
- 2 departures Dec 2026 – Jan 2027
- From $3,636 pp
- Luxury
- St. Georges Grenada Private Taxi Tour: Your Island, Your Way
- Mayreau Salt Whistle Bay: Dawn Swim Before the Boats Arrive
- Deshaies Jardin Botanique de Deshaies at Opening Hour
Windstar · Star Pride
- 9 ports
- Round trip
- Sails Oct 28, 2026
- From $3,930 pp
- Luxury
- Cruz Bay Trunk Bay Underwater Snorkel Trail & VI National Park
- Gustavia Private Open-Top Mini Moke Island Tour of St. Barts
- Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Windstar · Star Pride
- 6 ports
- Round trip
- Sails Nov 8, 2026
- From $2,411 pp
- Luxury
- St. Georges Grenada Private Taxi Tour: Your Island, Your Way
- Mayreau Salt Whistle Bay: Dawn Swim Before the Boats Arrive
- Les Saintes Sail Into the Bay of Les Saintes at Dawn
Windstar · Star Pride
- 6 ports
- Round trip
- Sails Mar 13, 2028
- From $2,656 pp
- Luxury
- St. Georges Grenada Private Taxi Tour: Your Island, Your Way
- Mayreau Salt Whistle Bay: Dawn Swim Before the Boats Arrive
- Les Saintes Sail Into the Bay of Les Saintes at Dawn