Windstar Cruise Deals

More Reasons to Say Yes

There are even 'More Reasons to Say Yes' with Windstar's latest cruise offer including a complimentary 'Beyond Inclusive Package' gives you more ways to explore with all-inclusive perks (unlimited select beer, cocktails & wine by the glass, Wi-Fi and gratuities) PLUS reduced deposits of just £300 per room on selected voyages sailing through December 2027 booked by 17 November 2026.

Europe 2028 Early Booking Bonus

There's more to look forward to as Windstar's Brand NEW Europe 2028 collection is here wiith the return of 5 small yacht-style luxury ships, offering over 45 itineraries across the Mediterranean & Northern Europe.

Secure your chosen holiday today & enjoy an 'Early Booking Bonus' including a complimentary all-inclusive perks (unlimited select beer, cocktails & wine by the glass, Wi-Fi and gratuities) PLUS up to $100pp onboard credit on selected voyages booked by 31 October 2026.

Simply use the search filter below to browse through all the Windstar sailing up to 2029. All prices shown are based on cruise only with no pre/post elements & may not be applicable with some offers shown

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558 cruises found matching your search criteria.

First 51 holiday results are shown by your chosen sort filter. To view more cruises use "Filter your Holiday options" for a more detailed search

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Caribbean Explorations

Wind Surf | Windstar

Departure Date: 02 January 2027
Departure Port: Philipsburg
Duration: 14 Nights
Holiday ID: SU20270102-14D

Prices from £4,713 pp*

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A Remote Caribbean Getaway

Wind Surf | Windstar

Departure Date: 02 January 2027
Departure Port: Philipsburg
Duration: 7 Nights
Holiday ID: SU20270102-7D

Prices from £2,487 pp*

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Costa Rica & Panama Canal

Wind Star | Windstar

Departure Date: 02 January 2027
Departure Port: Colon (tours to Panama Canal)
Duration: 7 Nights
Holiday ID: ST20270102-7D

Prices from £2,553 pp*

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Lovely Leewards

Star Pride | Windstar

Departure Date: 03 January 2027
Departure Port: San Juan
Duration: 14 Nights
Holiday ID: PR20270103-14D

Prices from £6,102 pp*

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Windward Islands Surf & Sunsets

Star Pride | Windstar

Departure Date: 03 January 2027
Departure Port: San Juan
Duration: 7 Nights
Holiday ID: PR20270103-7D

Prices from £2,284 pp*

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Costa Rica & Panama Canal

Star Legend | Windstar

Departure Date: 05 January 2027
Departure Port: Colon (tours to Panama Canal)
Duration: 7 Nights
Holiday ID: LE20270105-7D

Prices from £2,419 pp*

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Hidden Gems of the Canary Islands & Madeira

Wind Spirit | Windstar

Departure Date: 06 January 2027
Departure Port: Tenerife
Duration: 10 Nights
Holiday ID: SP20270106-10D

Prices from £2,959 pp*

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Tahiti & Tuamotu Adventures

Star Breeze | Windstar

Departure Date: 07 January 2027
Departure Port: Tahiti (Papeete)
Duration: 14 Nights
Holiday ID: BR20270107-14D

Prices from £4,499 pp*

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Dreams of Tahiti

Star Breeze | Windstar

Departure Date: 07 January 2027
Departure Port: Tahiti (Papeete)
Duration: 7 Nights
Holiday ID: BR20270107-7D

Prices from £2,500 pp*

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Caribbean Explorations

Wind Surf | Windstar

Departure Date: 09 January 2027
Departure Port: Philipsburg
Duration: 14 Nights
Holiday ID: SU20270109-14D

Prices from £4,461 pp*

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Classic Caribbean

Wind Surf | Windstar

Departure Date: 09 January 2027
Departure Port: Philipsburg
Duration: 7 Nights
Holiday ID: SU20270109-7D

Prices from £2,677 pp*

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San Juan & the Virgin Islands

Star Pride | Windstar

Departure Date: 10 January 2027
Departure Port: San Juan
Duration: 7 Nights
Holiday ID: PR20270110-7D

Prices from £4,118 pp*

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Costa Rica & Panama Canal

Star Legend | Windstar

Departure Date: 12 January 2027
Departure Port: Puerto Caldera
Duration: 7 Nights
Holiday ID: LE20270112-7D

Prices from £2,067 pp*

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Tahiti & Tuamotu Adventures

Star Breeze | Windstar

Departure Date: 14 January 2027
Departure Port: Tahiti (Papeete)
Duration: 14 Nights
Holiday ID: BR20270114-14D

Prices from £4,297 pp*

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Tuamotu Islands & Bora Bora

Star Breeze | Windstar

Departure Date: 14 January 2027
Departure Port: Tahiti (Papeete)
Duration: 7 Nights
Holiday ID: BR20270114-7D

Prices from £2,425 pp*

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Hidden Gems of the Canary Islands & Madeira

Wind Spirit | Windstar

Departure Date: 16 January 2027
Departure Port: Tenerife
Duration: 10 Nights
Holiday ID: SP20270116-10D

Prices from £3,031 pp*

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Caribbean Explorations

Wind Surf | Windstar

Departure Date: 16 January 2027
Departure Port: Philipsburg
Duration: 14 Nights
Holiday ID: SU20270116-14D

Prices from £5,367 pp*

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A Remote Caribbean Getaway

Wind Surf | Windstar

Departure Date: 16 January 2027
Departure Port: Philipsburg
Duration: 7 Nights
Holiday ID: SU20270116-7D

Prices from £2,211 pp*

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Costa Rica & Panama Canal

Star Legend | Windstar

Departure Date: 19 January 2027
Departure Port: Colon (tours to Panama Canal)
Duration: 7 Nights
Holiday ID: LE20270119-7D

Prices from £2,192 pp*

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Comprehensive Tahiti & Marquesas Adventure

Star Breeze | Windstar

Departure Date: 21 January 2027
Departure Port: Tahiti (Papeete)
Duration: 21 Nights
Holiday ID: BR20270121-21D

Prices from £5,834 pp*

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Dreams of Tahiti

Star Breeze | Windstar

Departure Date: 21 January 2027
Departure Port: Tahiti (Papeete)
Duration: 7 Nights
Holiday ID: BR20270121-7D

Prices from £2,274 pp*

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Caribbean Explorations

Wind Surf | Windstar

Departure Date: 23 January 2027
Departure Port: Philipsburg
Duration: 14 Nights
Holiday ID: SU20270123-14D

Prices from £5,819 pp*

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Classic Caribbean

Wind Surf | Windstar

Departure Date: 23 January 2027
Departure Port: Philipsburg
Duration: 7 Nights
Holiday ID: SU20270123-7D

Prices from £3,406 pp*

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Costa Rica & Panama Canal

Wind Star | Windstar

Departure Date: 24 January 2027
Departure Port: Puerto Caldera
Duration: 7 Nights
Holiday ID: ST20270124-7D

Prices from £3,383 pp*

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Costa Rica & Panama Canal

Star Legend | Windstar

Departure Date: 26 January 2027
Departure Port: Puerto Caldera
Duration: 7 Nights
Holiday ID: LE20270126-7D

Prices from £3,501 pp*

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The Colorful Canary Islands

Wind Spirit | Windstar

Departure Date: 26 January 2027
Departure Port: Tenerife
Duration: 10 Nights
Holiday ID: SP20270126-10D

Prices from £2,276 pp*

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Tahitian Treasures & Magnificent Marquesas

Star Breeze | Windstar

Departure Date: 28 January 2027
Departure Port: Tahiti (Papeete)
Duration: 14 Nights
Holiday ID: BR20270128-14D

Prices from £4,136 pp*

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Comprehensive Tahiti & Marquesas Adventure

Star Breeze | Windstar

Departure Date: 28 January 2027
Departure Port: Tahiti (Papeete)
Duration: 21 Nights
Holiday ID: BR20270128-21D

Prices from £5,984 pp*

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Caribbean Explorations

Wind Surf | Windstar

Departure Date: 30 January 2027
Departure Port: Philipsburg
Duration: 14 Nights
Holiday ID: SU20270130-14D

Prices from £5,568 pp*

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A Remote Caribbean Getaway

Wind Surf | Windstar

Departure Date: 30 January 2027
Departure Port: Philipsburg
Duration: 7 Nights
Holiday ID: SU20270130-7D

Prices from £2,713 pp*

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Costa Rica & Panama Canal

Wind Star | Windstar

Departure Date: 31 January 2027
Departure Port: Colon (tours to Panama Canal)
Duration: 8 Nights
Holiday ID: ST20270131-8D

Prices from £3,685 pp*

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Costa Rica & Panama Canal

Star Legend | Windstar

Departure Date: 02 February 2027
Departure Port: Colon (tours to Panama Canal)
Duration: 7 Nights
Holiday ID: LE20270202-7D

Prices from £2,797 pp*

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Caribbean Explorations

Wind Surf | Windstar

Departure Date: 06 February 2027
Departure Port: Philipsburg
Duration: 14 Nights
Holiday ID: SU20270206-14D

Prices from £4,863 pp*

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Classic Caribbean

Wind Surf | Windstar

Departure Date: 06 February 2027
Departure Port: Philipsburg
Duration: 7 Nights
Holiday ID: SU20270206-7D

Prices from £3,130 pp*

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Naturally Costa Rica

Star Legend | Windstar

Departure Date: 09 February 2027
Departure Port: Puerto Caldera
Duration: 7 Nights
Holiday ID: LE20270209-7D

Prices from £3,262 pp*

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Star Collector: Twice the Tahiti

Star Breeze | Windstar

Departure Date: 11 February 2027
Departure Port: Tahiti (Papeete)
Duration: 18 Nights
Holiday ID: BR20270211-18D

Prices from £5,714 pp*

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Dreams of Tahiti

Star Breeze | Windstar

Departure Date: 11 February 2027
Departure Port: Tahiti (Papeete)
Duration: 7 Nights
Holiday ID: BR20270211-7D

Prices from £2,400 pp*

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Caribbean Explorations

Wind Surf | Windstar

Departure Date: 13 February 2027
Departure Port: Philipsburg
Duration: 14 Nights
Holiday ID: SU20270213-14D

Prices from £4,009 pp*

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A Remote Caribbean Getaway

Wind Surf | Windstar

Departure Date: 13 February 2027
Departure Port: Philipsburg
Duration: 7 Nights
Holiday ID: SU20270213-7D

Prices from £2,236 pp*

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Windward Islands & Spanish New World

Star Legend | Windstar

Departure Date: 16 February 2027
Departure Port: Fuerte Amador (for Panama City)
Duration: 14 Nights
Holiday ID: LE20270216-14D

Prices from £7,267 pp*

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Tahiti & the Tuamotu Islands

Star Breeze | Windstar

Departure Date: 18 February 2027
Departure Port: Tahiti (Papeete)
Duration: 11 Nights
Holiday ID: BR20270218-11D

Prices from £3,845 pp*

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Caribbean Explorations

Wind Surf | Windstar

Departure Date: 20 February 2027
Departure Port: Philipsburg
Duration: 14 Nights
Holiday ID: SU20270220-14D

Prices from £3,958 pp*

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Classic Caribbean

Wind Surf | Windstar

Departure Date: 20 February 2027
Departure Port: Philipsburg
Duration: 7 Nights
Holiday ID: SU20270220-7D

Prices from £2,148 pp*

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Windward Ways & Tobago Cays

Star of the Seas | Windstar

Departure Date: 22 February 2027
Departure Port: Oranjestad
Duration: 8 Nights
Holiday ID: LE20270222-8D

Prices from £4,181 pp*

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Caribbean Explorations

Wind Surf | Windstar

Departure Date: 27 February 2027
Departure Port: Philipsburg
Duration: 14 Nights
Holiday ID: SU20270227-14D

Prices from £4,009 pp*

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A Remote Caribbean Getaway

Wind Surf | Windstar

Departure Date: 27 February 2027
Departure Port: Philipsburg
Duration: 7 Nights
Holiday ID: SU20270227-7D

Prices from £2,211 pp*

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Tahiti & the Tuamotu Islands

Star Breeze | Windstar

Departure Date: 01 March 2027
Departure Port: Tahiti (Papeete)
Duration: 10 Nights
Holiday ID: BR20270301-10D

Prices from £3,819 pp*

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Star Collector: Twice the Tahiti

Star Breeze | Windstar

Departure Date: 01 March 2027
Departure Port: Tahiti (Papeete)
Duration: 17 Nights
Holiday ID: BR20270301-17D

Prices from £6,008 pp*

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Dreams of Tahiti

Wind Star | Windstar

Departure Date: 01 March 2027
Departure Port: Tahiti (Papeete)
Duration: 7 Nights
Holiday ID: ST20270301-7D

Prices from £3,694 pp*

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Caribbean Explorations

Wind Surf | Windstar

Departure Date: 06 March 2027
Departure Port: Philipsburg
Duration: 14 Nights
Holiday ID: SU20270306-14D

Prices from £4,009 pp*

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Classic Caribbean

Wind Surf | Windstar

Departure Date: 06 March 2027
Departure Port: Philipsburg
Duration: 7 Nights
Holiday ID: SU20270306-7D

Prices from £2,173 pp*

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