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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.
| 27th September 2026 for 18 nights | |
Civitavecchia ~ Siracuse, Sicily ~ Valletta ~ Porto Empedocle ~ Trapani, Sicily ~ Lipari ~ Sorrento ~ Amalfi ~ Civitavecchia ~ Sorrento ~ Giardini Naxos ~ Kotor ~ Dubrovnik ~ Trogir ~ Rovinj ~ Venice | |
Cruise Only from Oceanview £7,130pp Suite £10,930pp Please Call for Flights |
| 27th September 2026 for 10 nights | |
Civitavecchia ~ Siracuse, Sicily ~ Valletta ~ Porto Empedocle ~ Trapani, Sicily ~ Lipari ~ Sorrento ~ Amalfi ~ Civitavecchia | |
Cruise Only from Oceanview £4,694pp Suite £6,435pp Please Call for Flights |
| 5th October 2026 for 10 nights | |
Rome ~ Civitavecchia ~ Sorrento ~ Giardini Naxos ~ Kotor ~ Dubrovnik ~ Trogir ~ Rovinj ~ Venice | |
Please call for availability |
| 7th October 2026 for 8 nights | |
Civitavecchia ~ Sorrento ~ Giardini Naxos ~ Kotor ~ Dubrovnik ~ Trogir ~ Rovinj ~ Venice | |
Cruise Only from Oceanview £2,761pp Suite £5,043pp Please Call for Flights |
| 7th October 2026 for 12 nights | |
Civitavecchia ~ Sorrento ~ Giardini Naxos ~ Kotor ~ Dubrovnik ~ Trogir ~ Rovinj ~ Venice ~ Cernobbio | |
Please call for availability |
| 12th October 2026 for 13 nights | |
Cernobbio ~ Venice ~ Rovinj ~ Split ~ Dubrovnik ~ Kotor ~ Giardini Naxos ~ Sorrento ~ Civitavecchia | |
Please call for availability |
| 15th October 2026 for 10 nights | |
Venice ~ Rovinj ~ Split ~ Dubrovnik ~ Kotor ~ Giardini Naxos ~ Sorrento ~ Civitavecchia | |
Cruise Only from Oceanview £3,332pp Suite £5,666pp Please Call for Flights |
| 15th October 2026 for 15 nights | |
Venice ~ Rovinj ~ Split ~ Dubrovnik ~ Kotor ~ Giardini Naxos ~ Sorrento ~ Civitavecchia ~ Portofino ~ Monte-Carlo ~ Sanary-sur-Mer ~ Palamós ~ Barcelona | |
Cruise Only from Oceanview £4,618pp Suite £8,118pp Please Call for Flights |
| 15th October 2026 for 23 nights | |
Venice ~ Rovinj ~ Split ~ Dubrovnik ~ Kotor ~ Giardini Naxos ~ Sorrento ~ Civitavecchia ~ Portofino ~ Monte-Carlo ~ Sanary-sur-Mer ~ Palamós ~ Barcelona ~ Palma de Mallorca ~ Cartagena ~ Málaga ~ Gibraltar ~ Cádiz ~ Lisbon | |
Cruise Only from Oceanview £9,394pp Suite £14,931pp Please Call for Flights |
| 15th October 2026 for 12 nights | |
Venice ~ Rovinj ~ Split ~ Dubrovnik ~ Kotor ~ Giardini Naxos ~ Sorrento ~ Civitavecchia ~ Rome ~ Vatican City | |
Please call for availability |
| 23rd October 2026 for 7 nights | |
Venice ~ Rome ~ Civitavecchia ~ Portofino ~ Monte-Carlo ~ Sanary-sur-Mer ~ Palamós ~ Barcelona | |
Please call for availability |
| 25th October 2026 for 5 nights | |
Civitavecchia ~ Portofino ~ Monte-Carlo ~ Sanary-sur-Mer ~ Palamós ~ Barcelona | |
Cruise Only from Oceanview £1,489pp Suite £2,860pp Please Call for Flights |
| 25th October 2026 for 13 nights | |
Civitavecchia ~ Portofino ~ Monte-Carlo ~ Sanary-sur-Mer ~ Palamós ~ Barcelona ~ Palma de Mallorca ~ Cartagena ~ Málaga ~ Gibraltar ~ Cádiz ~ Lisbon | |
Cruise Only from Oceanview £6,235pp Suite £9,509pp Please Call for Flights |
| 25th October 2026 for 9 nights | |
Civitavecchia ~ Portofino ~ Monte-Carlo ~ Sanary-sur-Mer ~ Palamós ~ Barcelona ~ Madrid | |
Please call for availability |
| 26th October 2026 for 12 nights | |
Madrid ~ Barcelona ~ Palma de Mallorca ~ Cartagena ~ Málaga ~ Gibraltar ~ Cádiz ~ Lisbon | |
Please call for availability |
| 30th October 2026 for 8 nights | |
Barcelona ~ Palma de Mallorca ~ Cartagena ~ Málaga ~ Gibraltar ~ Cádiz ~ Lisbon | |
Cruise Only from Oceanview £5,023pp Suite £7,097pp Please Call for Flights |
| 30th October 2026 for 12 nights | |
Barcelona ~ Palma de Mallorca ~ Cartagena ~ Málaga ~ Gibraltar ~ Cádiz ~ Lisbon | |
Please call for availability |
| 5th December 2026 for 21 nights | |
Lisbon ~ Philipsburg ~ Gustavia ~ Falmouth ~ Road Bay ~ Sopers Hole, Tortola ~ Great Harbour, Jost Van Dyke ~ Philipsburg | |
Please call for availability |
| 5th December 2026 for 14 nights | |
Lisbon ~ Philipsburg | |
Please call for availability |
| 19th December 2026 for 7 nights | |
Philipsburg ~ Gustavia ~ Falmouth ~ Road Bay ~ Sopers Hole, Tortola ~ Great Harbour, Jost Van Dyke ~ Philipsburg | |
Cruise Only from Oceanview £2,979pp Suite £4,560pp Please Call for Flights |
| 19th December 2026 for 14 nights | |
Philipsburg ~ Gustavia ~ Falmouth ~ Road Bay ~ Sopers Hole, Tortola ~ Great Harbour, Jost Van Dyke ~ Philipsburg ~ Gustavia ~ Roseau ~ Mayreau Island ~ Terre-de-Haut ~ Basseterre, Saint Kitts ~ Philipsburg | |
Cruise Only from Oceanview £6,570pp Suite £9,888pp Please Call for Flights |
| 26th December 2026 for 7 nights | |
Philipsburg ~ Gustavia ~ Roseau ~ Mayreau Island ~ Terre-de-Haut ~ Basseterre, Saint Kitts ~ Philipsburg | |
Cruise Only from Oceanview £3,927pp Suite £5,846pp Please Call for Flights |
| 26th December 2026 for 14 nights | |
Philipsburg ~ Gustavia ~ Roseau ~ Mayreau Island ~ Terre-de-Haut ~ Basseterre, Saint Kitts ~ Philipsburg ~ Falmouth ~ Road Bay ~ Sopers Hole, Tortola ~ Great Harbour, Jost Van Dyke ~ Gustavia ~ Philipsburg | |
Cruise Only from Oceanview £6,207pp Suite £9,836pp Please Call for Flights |
| 2nd January 2027 for 7 nights | |
Philipsburg ~ Falmouth ~ Road Bay ~ Sopers Hole, Tortola ~ Great Harbour, Jost Van Dyke ~ Gustavia ~ Philipsburg | |
Cruise Only from Oceanview £2,564pp Suite £4,482pp Please Call for Flights |
| 2nd January 2027 for 14 nights | |
Philipsburg ~ Falmouth ~ Road Bay ~ Sopers Hole, Tortola ~ Great Harbour, Jost Van Dyke ~ Gustavia ~ Philipsburg ~ Terre-de-Haut ~ Mayreau Island ~ Roseau ~ Basseterre, Saint Kitts ~ Gustavia ~ Philipsburg | |
Cruise Only from Oceanview £4,859pp Suite £8,281pp Please Call for Flights |