Your Caribbean - Southern Results
Your Caribbean - Southern Results
Sail Date | Cruise Line | Ship | Destination | Departs | Length | Price | You Save | Discounts | |
---|---|---|---|---|---|---|---|---|---|
15 reviews | Mar 29, 2025 | Windstar | Star Pride | Bridgetown | Bridgetown | 7 Nights | Anse Mitan | Bequia | Bridgetown | Castries | Mayreau | Pigeon Island | St. George's | The Pitons | $2,299 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
24 reviews | Dec 07, 2025 | Windstar | Wind Surf | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,299 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
24 reviews | Feb 28, 2026 | Windstar | Wind Surf | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,299 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
24 reviews | Mar 21, 2026 | Windstar | Wind Surf | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,299 Up To $250 Onboard Credit | Onboard Credit! |
11 reviews | Dec 28, 2024 | Windstar | Wind Spirit | Bridgetown | Bridgetown | 7 Nights | Anse Mitan | Bridgetown | Les Saintes | Little Bay | Pigeon Island | Roseau | $2,399 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
11 reviews | Jan 04, 2025 | Windstar | Wind Spirit | Bridgetown | Bridgetown | 7 Nights | Bequia | Bridgetown | Castries | Kingstown | Mayreau | Pigeon Island | St. George's | The Pitons | $2,399 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
11 reviews | Jan 25, 2025 | Windstar | Wind Spirit | Bridgetown | Bridgetown | 7 Nights | Anse Mitan | Bridgetown | Les Saintes | Little Bay | Pigeon Island | Roseau | $2,399 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
11 reviews | Feb 08, 2025 | Windstar | Wind Spirit | Bridgetown | Bridgetown | 7 Nights | Anse Mitan | Bridgetown | Les Saintes | Little Bay | Pigeon Island | Roseau | $2,399 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
24 reviews | Dec 14, 2025 | Windstar | Wind Surf | Philipsburg | Philipsburg | 7 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $2,399 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
11 reviews | Feb 28, 2026 | Windstar | Wind Spirit | Philipsburg | Bridgetown | 7 Nights | Basseterre | Bridgetown | Gustavia | Les Saintes | Little Bay | Pigeon Island | Roseau | St. Maarten | $2,399 Up To $250 Onboard Credit | Onboard Credit! |
24 reviews | Mar 07, 2026 | Windstar | Wind Surf | Philipsburg | Philipsburg | 7 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $2,399 Up To $250 Onboard Credit | Onboard Credit! |
24 reviews | Mar 14, 2026 | Windstar | Wind Surf | Philipsburg | Philipsburg | 7 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $2,399 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
24 reviews | Mar 28, 2026 | Windstar | Wind Surf | Philipsburg | Philipsburg | 7 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $2,399 Up To $250 Onboard Credit | |
10 reviews | Nov 05, 2024 | Windstar | Wind Star | Lisbon | Bridgetown | 14 Nights | Bridgetown | Lisbon | $2,499 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
11 reviews | Nov 13, 2024 | Windstar | Wind Spirit | Lisbon | Bridgetown | 14 Nights | Bridgetown | Lisbon | $2,499 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
11 reviews | Dec 07, 2024 | Windstar | Wind Spirit | Bridgetown | Bridgetown | 7 Nights | Bequia | Bridgetown | Castries | Kingstown | Mayreau | Pigeon Island | St. George's | The Pitons | $2,499 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
11 reviews | Dec 14, 2024 | Windstar | Wind Spirit | Bridgetown | Bridgetown | 7 Nights | Anse Mitan | Bridgetown | Les Saintes | Little Bay | Pigeon Island | Roseau | $2,499 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
15 reviews | Jan 04, 2025 | Windstar | Star Pride | Oranjestad | Bridgetown | 7 Nights | Bridgetown | Kralendijk | Man-O-War Bay | Mayreau | Oranjestad | Soufriere | Willemstad | $2,499 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
11 reviews | Feb 15, 2025 | Windstar | Wind Spirit | Bridgetown | Bridgetown | 7 Nights | Bequia | Bridgetown | Castries | Kingstown | Mayreau | Pigeon Island | St. George's | The Pitons | $2,499 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
11 reviews | Nov 04, 2025 | Windstar | Wind Spirit | Lisbon | Bridgetown | 14 Nights | Bridgetown | Lisbon | $2,499 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
How It Works
Vacationing has never been easier or cheaper with the help of a dedicated travel consultant from AffordableTours.com
1. Free Quote
Find your perfect trip on our website and simply request a free quote. Need to speak to a live person? Call us 7 days a week at 1-800-627-3753. No robots here!
2. Dedicated Travel Consultant
Your personal travel consultant will reach out and be your point of contact for your entire travel experience from start to finish. Did we mention you'll be working with an award winning team? Sweet!
3. Lowest Price Guaranteed
Because we're one of the largest sellers of travel, we're able to give you a discount on your vacation package. No one beats our prices!
4. Stress Free Travel
Knowing you got the best deal, all that's left is for you to pack your bags and enjoy your vacation!