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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.
| 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 £6,924pp Suite £12,716pp 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 £4,229pp Suite £8,118pp Please Call for Flights |
| 15th October 2026 for 10 nights | |
Venice ~ Rovinj ~ Split ~ Dubrovnik ~ Kotor ~ Giardini Naxos ~ Sorrento ~ Civitavecchia | |
Cruise Only from Oceanview £2,925pp Suite £5,666pp Please Call for Flights |
| 25th October 2026 for 5 nights | |
Civitavecchia ~ Portofino ~ Monte-Carlo ~ Sanary-sur-Mer ~ Palamós ~ Barcelona | |
Cruise Only from Oceanview £1,508pp 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 £4,164pp Suite £7,342pp Please Call for Flights |
| 30th October 2026 for 8 nights | |
Barcelona ~ Palma de Mallorca ~ Cartagena ~ Málaga ~ Gibraltar ~ Cádiz ~ Lisbon | |
Cruise Only from Oceanview £2,830pp Suite £4,815pp 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 £5,688pp Suite £9,318pp Please Call for Flights |
| 19th December 2026 for 7 nights | |
Philipsburg ~ Gustavia ~ Falmouth ~ Road Bay ~ Sopers Hole, Tortola ~ Great Harbour, Jost Van Dyke ~ Philipsburg | |
Cruise Only from Oceanview £2,694pp Suite £4,612pp 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 £3,253pp Suite £5,172pp 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 £5,014pp Suite £8,695pp 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 £2,019pp Suite £3,938pp 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 £3,614pp Suite £7,088pp Please Call for Flights |
| 9th January 2027 for 7 nights | |
Philipsburg ~ Terre-de-Haut ~ Mayreau Island ~ Roseau ~ Basseterre, Saint Kitts ~ Gustavia ~ Philipsburg | |
Cruise Only from Oceanview £1,956pp Suite £3,875pp Please Call for Flights |
| 9th January 2027 for 14 nights | |
Philipsburg ~ Terre-de-Haut ~ Mayreau Island ~ Roseau ~ Basseterre, Saint Kitts ~ Gustavia ~ Philipsburg ~ Road Bay ~ Sopers Hole, Tortola ~ Great Harbour, Jost Van Dyke ~ Gustavia ~ Falmouth ~ Philipsburg | |
Cruise Only from Oceanview £4,185pp Suite £8,022pp Please Call for Flights |
| 16th January 2027 for 7 nights | |
Philipsburg ~ Road Bay ~ Sopers Hole, Tortola ~ Great Harbour, Jost Van Dyke ~ Gustavia ~ Falmouth ~ Philipsburg | |
Cruise Only from Oceanview £2,408pp Suite £4,534pp Please Call for Flights |
| 16th January 2027 for 14 nights | |
Philipsburg ~ Road Bay ~ Sopers Hole, Tortola ~ Great Harbour, Jost Van Dyke ~ Gustavia ~ Falmouth ~ Philipsburg ~ Roseau ~ Mayreau Island ~ Terre-de-Haut ~ Basseterre, Saint Kitts ~ Gustavia ~ Philipsburg | |
Cruise Only from Oceanview £5,585pp Suite £9,422pp Please Call for Flights |
| 23rd January 2027 for 7 nights | |
Philipsburg ~ Roseau ~ Mayreau Island ~ Terre-de-Haut ~ Basseterre, Saint Kitts ~ Gustavia ~ Philipsburg | |
Cruise Only from Oceanview £3,460pp Suite £5,378pp Please Call for Flights |
| 23rd January 2027 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 ~ Falmouth ~ Philipsburg | |
Cruise Only from Oceanview £5,585pp Suite £9,370pp Please Call for Flights |
| 30th January 2027 for 7 nights | |
Philipsburg ~ Road Bay ~ Sopers Hole, Tortola ~ Great Harbour, Jost Van Dyke ~ Gustavia ~ Falmouth ~ Philipsburg | |
Cruise Only from Oceanview £2,408pp Suite £4,457pp Please Call for Flights |
| 30th January 2027 for 14 nights | |
Philipsburg ~ Road Bay ~ Sopers Hole, Tortola ~ Great Harbour, Jost Van Dyke ~ Gustavia ~ Falmouth ~ Philipsburg ~ Roseau ~ Mayreau Island ~ Terre-de-Haut ~ Basseterre, Saint Kitts ~ Gustavia ~ Philipsburg | |
Cruise Only from Oceanview £4,288pp Suite £8,281pp Please Call for Flights |
| 6th February 2027 for 7 nights | |
Philipsburg ~ Roseau ~ Mayreau Island ~ Terre-de-Haut ~ Basseterre, Saint Kitts ~ Gustavia ~ Philipsburg | |
Cruise Only from Oceanview £2,060pp Suite £4,212pp Please Call for Flights |
| 6th February 2027 for 14 nights | |
Philipsburg ~ Roseau ~ Mayreau Island ~ Terre-de-Haut ~ Basseterre, Saint Kitts ~ Gustavia ~ Philipsburg ~ Falmouth ~ Road Bay ~ Sopers Hole, Tortola ~ Great Harbour, Jost Van Dyke ~ Gustavia ~ Philipsburg | |
Cruise Only from Oceanview £4,029pp Suite £7,918pp Please Call for Flights |
| 13th February 2027 for 7 nights | |
Philipsburg ~ Falmouth ~ Road Bay ~ Sopers Hole, Tortola ~ Great Harbour, Jost Van Dyke ~ Gustavia ~ Philipsburg | |
Cruise Only from Oceanview £2,357pp Suite £4,508pp Please Call for Flights |
| 13th February 2027 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 £4,807pp Suite £8,488pp Please Call for Flights |
| 20th February 2027 for 7 nights | |
Philipsburg ~ Roseau ~ Mayreau Island ~ Terre-de-Haut ~ Basseterre, Saint Kitts ~ Gustavia ~ Philipsburg | |
Cruise Only from Oceanview £2,941pp Suite £4,860pp Please Call for Flights |