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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.
| 19th December 2026 for 7 nights | |
Philipsburg ~ Gustavia ~ Falmouth ~ Road Bay ~ Sopers Hole, Tortola ~ Great Harbour, Jost Van Dyke ~ Philipsburg | |
Cruise Only from Oceanview £2,796pp Suite £4,585pp 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 £6,036pp Suite £9,562pp 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 £3,551pp Suite £5,469pp 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 £5,984pp Suite £9,614pp 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 £2,693pp Suite £4,611pp 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 £4,844pp Suite £8,318pp 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 £2,616pp Suite £4,535pp 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 £5,051pp Suite £8,888pp 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 £2,667pp Suite £4,793pp 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 £6,244pp Suite £10,081pp 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 £3,861pp Suite £5,779pp 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 £6,192pp Suite £9,977pp 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 £2,641pp Suite £4,689pp 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 £5,518pp Suite £9,511pp 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 £3,135pp Suite £5,287pp 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 £5,259pp Suite £9,096pp 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 £2,615pp Suite £4,767pp 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 £4,533pp Suite £8,163pp 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 £2,331pp Suite £4,250pp Please Call for Flights |
| 20th February 2027 for 14 nights | |
Philipsburg ~ Roseau ~ Mayreau Island ~ Terre-de-Haut ~ Basseterre, Saint Kitts ~ Gustavia ~ Philipsburg ~ Sopers Hole, Tortola ~ Great Harbour, Jost Van Dyke ~ Gustavia ~ Road Bay ~ Falmouth ~ Philipsburg | |
Cruise Only from Oceanview £4,222pp Suite £7,644pp Please Call for Flights |
| 27th February 2027 for 7 nights | |
Philipsburg ~ Sopers Hole, Tortola ~ Great Harbour, Jost Van Dyke ~ Gustavia ~ Road Bay ~ Falmouth ~ Philipsburg | |
Cruise Only from Oceanview £2,278pp Suite £4,196pp Please Call for Flights |
| 27th February 2027 for 14 nights | |
Philipsburg ~ Sopers Hole, Tortola ~ Great Harbour, Jost Van Dyke ~ Gustavia ~ Road Bay ~ Falmouth ~ Philipsburg ~ Roseau ~ Mayreau Island ~ Terre-de-Haut ~ Basseterre, Saint Kitts ~ Gustavia ~ Philipsburg | |
Cruise Only from Oceanview £4,170pp Suite £7,800pp Please Call for Flights |
| 6th March 2027 for 7 nights | |
Philipsburg ~ Roseau ~ Mayreau Island ~ Terre-de-Haut ~ Basseterre, Saint Kitts ~ Gustavia ~ Philipsburg | |
Cruise Only from Oceanview £2,305pp Suite £4,379pp Please Call for Flights |
| 6th March 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 £4,429pp Suite £8,163pp Please Call for Flights |
| 13th March 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 £5,051pp Suite £8,681pp Please Call for Flights |