Windstar Cruises January 2026
Save up to 75% on Windstar cruises
As a large-scale seller of Windstar Cruises January 2026, we are able to offer you unbeatable prices and unparalleled value. With cruise line volume buys plus our low everyday prices you can save up to 75% versus the brochure price! Once you have found the discounted Windstar cruise of your choice, please call our cruise consultants to book your vacation and save money with our first-rate personalized service! Book your Windstar cruise today with AffordableTours.com, your discounted cruise headquarters.
![Windstar Image](https://img.affordabletours.com/AffordableCruisesWeb/Cruises/192__201701300936__.png.webp)
Sail Date | Cruise Line | Ship | Destination | Departs | Length | Price | You Save | Discounts | |
---|---|---|---|---|---|---|---|---|---|
24 reviews ![]() | Jan 04, 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 | $2,599 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
24 reviews ![]() | Jan 04, 2026 | Windstar | Wind Surf | Philipsburg | Bridgetown | 14 Nights | Basseterre | Bridgetown | Deshaies | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Little Bay | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $4,099 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
24 reviews ![]() | Jan 04, 2026 | Windstar | Wind Surf | Philipsburg | Bridgetown | 21 Nights | Anse Mitan | Basseterre | Bequia | Bridgetown | Castries | Deshaies | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Little Bay | Mayreau | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. George's | St. Maarten | Virgin Gorda / Prickly Pear | $6,299 Up To $750 Onboard Credit | |
24 reviews ![]() | Jan 04, 2026 | Windstar | Wind Surf | Philipsburg | Oranjestad | 28 Nights | Anse Mitan | Basseterre | Bequia | Bridgetown | Castries | Deshaies | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Kralendijk | Little Bay | Man-O-War Bay | Mayreau | Oranjestad | Pigeon Island | Road Bay | Roseau | Soper's Hole | Soufriere | St. George's | St. Maarten | Virgin Gorda / Prickly Pear | Willemstad | $8,399 Up To $1000 Onboard Credit | Onboard Credit! |
24 reviews ![]() | Jan 04, 2026 | Windstar | Wind Surf | Philipsburg | Philipsburg | 55 Nights | Anse Mitan | Basseterre | Belize City | Bequia | Bocas del Toro | Bridgetown | Cartagena | Castries | Cayman Brac | Colón | Costa Maya | Cozumel | Deshaies | Falmouth Harbour | Grand Cayman | Gustavia | Isla San Andres | Jost Van Dyke, Great Harbour | Kralendijk | La Romana | Little Bay | Man-O-War Bay | Mayreau | Oranjestad | Pigeon Island | Port Antonio | Road Bay | Roatan | Roseau | Santa Marta | Santo Domingo | Soper's Hole | Soufriere | St. George's | St. Maarten | Virgin Gorda / Prickly Pear | Willemstad | $16,699 Up To $1000 Onboard Credit | Onboard Credit! |
24 reviews ![]() | Jan 11, 2026 | Windstar | Wind Surf | Philipsburg | Bridgetown | 7 Nights | Basseterre | Bridgetown | Deshaies | Gustavia | Little Bay | Pigeon Island | Roseau | St. Maarten | $2,599 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
24 reviews ![]() | Jan 11, 2026 | Windstar | Wind Surf | Philipsburg | Bridgetown | 14 Nights | Anse Mitan | Basseterre | Bequia | Bridgetown | Castries | Deshaies | Gustavia | Little Bay | Mayreau | Pigeon Island | Roseau | St. George's | St. Maarten | $4,199 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
5 reviews ![]() | Jan 12, 2026 | Windstar | Star Legend | Rome | Barcelona | 16 Nights | Barcelona | Cartagena | Genoa, Italy | Gibraltar | Livorno | Málaga | Nice | Palma de Mallorca | Rome | Valencia | $5,299 Up To $750 Onboard Credit | |
11 reviews ![]() | Jan 14, 2026 | Windstar | Wind Spirit | Philipsburg | Philipsburg | 17 Nights | Anse Mitan | Bequia | Castries | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Mayreau | Road Bay | Roseau | Soper's Hole | St. George's | St. Maarten | Virgin Gorda / Prickly Pear | $4,799 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
11 reviews ![]() | Jan 14, 2026 | Windstar | Wind Spirit | Philipsburg | Philipsburg | 10 Nights | Anse Mitan | Bequia | Castries | Gustavia | Les Saintes | Little Bay | Mayreau | Roseau | St. George's | St. Maarten | $3,499 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
24 reviews ![]() | Jan 18, 2026 | Windstar | Wind Surf | Bridgetown | Bridgetown | 7 Nights | Anse Mitan | Bequia | Bridgetown | Castries | Mayreau | Pigeon Island | St. George's | $2,699 Up To $300 Onboard Credit | Onboard Credit! |
24 reviews ![]() | Jan 18, 2026 | Windstar | Wind Surf | Bridgetown | Oranjestad | 14 Nights | Anse Mitan | Bequia | Bridgetown | Castries | Kralendijk | Man-O-War Bay | Mayreau | Oranjestad | Pigeon Island | Soufriere | St. George's | Willemstad | $4,299 Up To $500 Onboard Credit | |
5 reviews ![]() | Jan 19, 2026 | Windstar | Star Legend | Barcelona | Rome | 16 Nights | Barcelona | Cartagena | Genoa, Italy | Gibraltar | Livorno | Málaga | Nice | Palma de Mallorca | Rome | Valencia | $5,299 Up To $750 Onboard Credit | Suite! |
11 reviews ![]() | Jan 24, 2026 | Windstar | Wind Spirit | Philipsburg | Philipsburg | 7 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $2,499 Up To $250 Onboard Credit | |
24 reviews ![]() | Jan 25, 2026 | Windstar | Wind Surf | Bridgetown | Oranjestad | 7 Nights | Bridgetown | Kralendijk | Man-O-War Bay | Mayreau | Oranjestad | Soufriere | Willemstad | $2,699 Up To $300 Onboard Credit | Onboard Credit! |
11 reviews ![]() | Jan 31, 2026 | Windstar | Wind Spirit | Philipsburg | Philipsburg | 7 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $2,499 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
11 reviews ![]() | Jan 31, 2026 | Windstar | Wind Spirit | Philipsburg | Philipsburg | 14 Nights | Basseterre | Charlestown | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $4,099 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
15 reviews ![]() | Jan 03, 2026 | Windstar | Star Pride | Lima | Colon | 11 Nights | Colón | Guayaquil, Ecuador | Lima, Peru | Manta, Equador | Panama Canal | Trujillo, Peru | $7,999 Up To $1000 Onboard Credit | |
5 reviews ![]() | Jan 04, 2026 | Windstar | Star Legend | Venice | Barcelona | 15 Nights | Barcelona | Dubrovnik | Genoa, Italy | Livorno | Messina (Taormina) | Naples | Nice | Rome | Venice | Zadar | $5,099 Up To $750 Onboard Credit | |
5 reviews ![]() | Jan 12, 2026 | Windstar | Star Legend | Rome | Barcelona | 7 Nights | Barcelona | Genoa, Italy | Livorno | Nice | Rome | $3,099 Up To $500 Onboard Credit | Suite! |
Departure Ports
- Papeete, French Polynesia Cruises (187)
- Athens (Piraeus), Greece Cruises (136)
- Rome, Italy Cruises (71)
- Philipsburg, St. Maarten Cruises (63)
- Barcelona, Spain Cruises (58)
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- Colon, Panama Cruises (18)
- Puerto Caldera, Costa Rica Cruises (16)
Destinations
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- Europe - Northern Cruises (63)
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