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Windstar's Flagship Sailing Ship
On any day, our 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. During their cruise, you will find the perfect setting for ‘making an entrance’ in the beautiful reception area – and, appropriately, that’s only the beginning.
When you return to your stateroom, the luxury gets personal. Windstar’s signature bowl of fresh fruit will still be waiting for you, along with rich tufted headboards, soft seascape colors, beautiful new upholstery, and fine count Egyptian cotton linens welcome you to an oasis of relaxing indulgence.
Wind Surf underwent a significant renovation of public spaces and suites, including an expanded lounge with new lights and sound for upcoming stage performances. Relax into the destinations you’re visiting at the new World Spa by Windstar, which will offer regional spa treatments, including massage styles like Swedish, Japanese Shiatsu and Hawaiian Lomi Lomi. An Officer’s Suite, which might be the only one of its kind, provides you with the chance to stay in the heart of the officer quarters tucked right behind the Bridge.
Everything about Wind Surf speaks of welcome. Come aboard and see it for yourself.
Windstar has always been known for our iconic sailing ships, and now we are embarking on a multi-year refresh of the Wind Class ships. The initiative, Setting Sails: A Wind Class Refresh, brings the tight-knit connection of the Windstar community to the forefront through the redesign of public spaces and staterooms. From a revamped lobby to a new pool and larger pool bar, new World Spa by Windstar to a redesigned lounge, this initiative also includes intricate details like new teak decks and décor for a timeless and welcoming experience. Wind Surf will complete her redesign in 2026.
| 17th February 2026 for 11 nights | |
Cozumel ~ Grand Cayman ~ Cayman Brac ~ Ocho Rios ~ Santo Domingo ~ La Romana ~ Great Harbour, Jost Van Dyke ~ Philipsburg | |
Cruise Only from Oceanview £2,446pp Suite £4,045pp Please Call for Flights |
| 17th February 2026 for 18 nights | |
Cozumel ~ Grand Cayman ~ Cayman Brac ~ Ocho Rios ~ Santo Domingo ~ La Romana ~ Great Harbour, Jost Van Dyke ~ Philipsburg ~ Roseau ~ Mayreau Island ~ Deshaies ~ Basseterre, Saint Kitts ~ Gustavia ~ Philipsburg | |
Please call for availability |
| 28th February 2026 for 7 nights | |
Philipsburg ~ Roseau ~ Mayreau Island ~ Deshaies ~ Basseterre, Saint Kitts ~ Gustavia ~ Philipsburg | |
Cruise Only from Oceanview £2,637pp Suite Please Call for Flights |
| 28th February 2026 for 14 nights | |
Philipsburg ~ Roseau ~ Mayreau Island ~ Deshaies ~ Basseterre, Saint Kitts ~ Gustavia ~ Philipsburg ~ Falmouth ~ Road Bay ~ Sopers Hole, Tortola ~ Great Harbour, Jost Van Dyke ~ Gustavia ~ Philipsburg | |
Cruise Only from Oceanview £4,338pp Suite Please Call for Flights |
| 7th March 2026 for 7 nights | |
Philipsburg ~ Falmouth ~ Road Bay ~ Sopers Hole, Tortola ~ Great Harbour, Jost Van Dyke ~ Gustavia ~ Philipsburg | |
Cruise Only from Oceanview £1,949pp Suite £3,399pp Please Call for Flights |
| 14th March 2026 for 7 nights | |
Philipsburg ~ Falmouth ~ Road Bay ~ Sopers Hole, Tortola ~ Great Harbour, Jost Van Dyke ~ Gustavia ~ Philipsburg | |
Cruise Only from Oceanview £1,899pp Suite £3,349pp Please Call for Flights |
| 14th March 2026 for 14 nights | |
Philipsburg ~ Falmouth ~ Road Bay ~ Sopers Hole, Tortola ~ Great Harbour, Jost Van Dyke ~ Gustavia ~ Philipsburg ~ Roseau ~ Mayreau Island ~ Terre-de-Haut ~ Basseterre, Saint Kitts ~ Gustavia ~ Philipsburg | |
Cruise Only from Oceanview £3,288pp Suite Please Call for Flights |
| 21st March 2026 for 14 nights | |
Philipsburg ~ Roseau ~ Mayreau Island ~ Terre-de-Haut ~ Basseterre, Saint Kitts ~ Gustavia ~ Philipsburg ~ Road Bay ~ Sopers Hole, Tortola ~ Great Harbour, Jost Van Dyke ~ Gustavia ~ Philipsburg | |
Cruise Only from Oceanview £4,238pp Suite Please Call for Flights |
| 21st March 2026 for 7 nights | |
Philipsburg ~ Roseau ~ Mayreau Island ~ Terre-de-Haut ~ Basseterre, Saint Kitts ~ Gustavia ~ Philipsburg | |
Cruise Only from Oceanview £1,936pp Suite £3,386pp Please Call for Flights |
| 28th March 2026 for 21 nights | |
Philipsburg ~ Road Bay ~ Sopers Hole, Tortola ~ Great Harbour, Jost Van Dyke ~ Gustavia ~ Philipsburg ~ Ponta Delgada, Azores ~ Lisbon | |
Cruise Only from Oceanview £3,194pp Suite £5,319pp Please Call for Flights |
| 28th March 2026 for 7 nights | |
Philipsburg ~ Road Bay ~ Sopers Hole, Tortola ~ Great Harbour, Jost Van Dyke ~ Gustavia ~ Philipsburg | |
Cruise Only from Oceanview £2,149pp Suite £3,499pp Please Call for Flights |
| 4th April 2026 for 22 nights | |
Philipsburg ~ Ponta Delgada, Azores ~ Lisbon ~ Cádiz ~ Gibraltar ~ Málaga ~ Cartagena ~ Palma de Mallorca ~ Barcelona | |
Cruise Only from Oceanview £3,265pp Suite Please Call for Flights |
| 4th April 2026 for 14 nights | |
Philipsburg ~ Ponta Delgada, Azores ~ Lisbon | |
Cruise Only from Oceanview £1,619pp Suite £2,469pp Please Call for Flights |
| 14th April 2026 for 8 nights | |
Lisbon ~ Cádiz ~ Gibraltar ~ Málaga ~ Cartagena ~ Palma de Mallorca ~ Barcelona | |
Cruise Only from Oceanview £3,960pp Suite Please Call for Flights |
| 18th April 2026 for 16 nights | |
Lisbon ~ Cádiz ~ Gibraltar ~ Málaga ~ Cartagena ~ Palma de Mallorca ~ Barcelona ~ Palamós ~ Port-Vendres ~ Sanary-sur-Mer ~ Monte-Carlo ~ Cannes ~ Portofino ~ Portoferraio ~ Rome | |
Cruise Only from Oceanview £3,381pp Suite Please Call for Flights |
| 18th April 2026 for 8 nights | |
Lisbon ~ Cádiz ~ Gibraltar ~ Málaga ~ Cartagena ~ Palma de Mallorca ~ Barcelona ~ Madrid | |
Cruise Only from Oceanview £5,453pp Suite Please Call for Flights |
| 18th April 2026 for 8 nights | |
Lisbon ~ Cádiz ~ Gibraltar ~ Málaga ~ Cartagena ~ Palma de Mallorca ~ Barcelona | |
Cruise Only from Oceanview £2,244pp Suite Please Call for Flights |
| 18th April 2026 for 25 nights | |
Lisbon ~ Cádiz ~ Gibraltar ~ Málaga ~ Cartagena ~ Palma de Mallorca ~ Barcelona ~ Palamós ~ Port-Vendres ~ Sanary-sur-Mer ~ Monte-Carlo ~ Cannes ~ Portofino ~ Portoferraio ~ Rome ~ Sorrento ~ Giardini Naxos ~ Kotor ~ Dubrovnik ~ Split ~ Rovinj ~ Venice | |
Please call for availability |
| 22nd April 2026 for 8 nights | |
Madrid ~ Barcelona ~ Palamós ~ Port-Vendres ~ Sanary-sur-Mer ~ Monte-Carlo ~ Cannes ~ Portofino ~ Portoferraio ~ Rome | |
Cruise Only from Oceanview £4,743pp Suite Please Call for Flights |
| 26th April 2026 for 8 nights | |
Barcelona ~ Palamós ~ Port-Vendres ~ Sanary-sur-Mer ~ Monte-Carlo ~ Cannes ~ Portofino ~ Portoferraio ~ Rome | |
Cruise Only from Oceanview £2,952pp Suite Please Call for Flights |
| 26th April 2026 for 8 nights | |
Barcelona ~ Palamós ~ Port-Vendres ~ Sanary-sur-Mer ~ Monte-Carlo ~ Cannes ~ Portofino ~ Portoferraio ~ Rome | |
Cruise Only from Oceanview £1,534pp Suite Please Call for Flights |
| 4th May 2026 for 9 nights | |
Rome ~ Sorrento ~ Giardini Naxos ~ Kotor ~ Dubrovnik ~ Split ~ Rovinj ~ Venice | |
Please call for availability |
| 4th May 2026 for 9 nights | |
Rome ~ Sorrento ~ Giardini Naxos ~ Kotor ~ Dubrovnik ~ Split ~ Rovinj ~ Venice ~ Cernobbio | |
Please call for availability |
| 10th May 2026 for 8 nights | |
Cernobbio ~ Venice ~ Rovinj ~ Split ~ Dubrovnik ~ Kotor ~ Giardini Naxos ~ Sorrento ~ Rome | |
Please call for availability |
| 13th May 2026 for 8 nights | |
Venice ~ Rovinj ~ Split ~ Dubrovnik ~ Kotor ~ Giardini Naxos ~ Sorrento ~ Rome | |
Please call for availability |