Wind Surf - 15 Nights - 19 December 2027
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Cruise Ship: Wind Surf -
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Holiday Summary
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Departure Date19 December 2027 |
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Cruise Duration: 15 NightsWind Surf | Windstar Embark: Philipsburg, St Maarten | 19 December 2027 |
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Return Date03 January 2028 |
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Pricing Availability
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Cruise Itinerary
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| Day 1 | Philipsburg, St Maarten | |
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| Day 2 | Gustavia, St Barts | |
| Day 3 | St Johns, Antigua | |
| Day 4 | Guadeloupe, Guadeloupe | |
| Day 5 | Road Bay, Anguilla | |
| Day 6 | Tortola, British Virgin Islands | |
| Day 7 | Jost Van Dyke, British Virgin Islands - Tender Port | |
| Day 8 | Virgin Gorda, British Virgin Islands - Tender Port | |
| Day 9 | Philipsburg, St Maarten | |
| Day 10 | Nevis, St Kitts & Nevis | |
| Day 11 | Roseau, Dominica | |
| Day 12 | Mayreau, St Vincent & Grenadines | |
| Day 13 | Guadeloupe (Iles Des Saintes) | |
| Day 14 | Basseterre, St Kitts | |
| Day 15 | Gustavia, St Barts | |
| Day 16 | Philipsburg, St Maarten |
Please Note: We endeavour to have the most up to date itinerary shown, however on occassions these can be subject to change by Windstar due factors including unavailable ports, port congestion, weather etc. Once booked, we will email any itinerary change notifications to guests & will try to update all itineraries on the website as quickly as possible. However, we may not always recieved notification & these itineraries may remain incorrect
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All prices shown below are based on 2 guests sharing. For 3rd/4th, single guest prices or to add regional flights & transfers please contact us via enquire now in availability section above
More Reasons to Say Yes
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What facilities & features can I find onboard Wind Surf during my Caribbean Explorations Cruise departing 19 December 2027
On any day, the 342-guest flagship, Wind Surf, the world's largest sailing ship, 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 colours, 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 are 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.
Alternative Wind Surf Cruises
Scroll through the below table to see all alternative cruises available on Wind Surf, click on each one to see details
Booking Terms and Conditions:
1).Price per person based on two adults sharing (on a cruise only basis) and includes applicable taxes unless stated otherwise. 2) Current deals shown may not be applicable, please ask for details of see promotional t&c's below. 3) Fly-Cruise Booking: Flights & overseas transfers are booked through Windstar & are subject to their t&c's. 4) Cruise & Stay Holidays: All packages are subject to availability. Overseas transfers may not be for full duration of holiday (unless stated otherwise). Flights, hotels & transfers are booked through our preferred partners, once booked you will be subject their booking terms & conditions in addition any cruise line promotional t&c's. 5) We will endeavour to have the most accurate pricing/availability & itineraries, on occasions these maybe incorrect & we reserve the right update/amend/remove where accordingly. All prices & available rooms shown are subject to live availability in Celebrity Cruises reservation system. 6) Windstar & Pure Holidays full booking terms & conditions apply.
Promotion Terms and Conditions:
- More Reasons to Say Yes Windstar is offering a complimentary All-Inclusive package (valued at USD$99 per guest per day) for voyages through December 31, 2027. A reduced deposit of $£300 per stateroom/suite (£150 per person) applies to all new bookings made during the promotional period. Solo travelers will pay a reduced deposit of £150 and triples will pay £150 per guest. All fares mentioned are per person, in US dollars, cruise only, based on double occupancy in lowest category.
Certain sailings and their Star Collectors are excluded from this offer including Grand Prix voyages, Eclipse voyages, Mystery Cruises, or other specialty cruises. These exclusions include Explorer: 12/28/26, Legend: 11/4/26, 6/1/27, Pride: 8/10/26, 4/15/27, Seeker: 9/14/27, Spirit: 8/6/26, 6/2/27, Star: 3/1/27, Surf: 7/27/27. Also excluded are any Star Collector sailings that overlap with the above dates. Government Taxes & Fees are additional and are published at www.windstarcruises.com. Offer is valid on new bookings only and subject to availability. Bookings are non-transferable; no name changes can be made.
This offer is not combinable with any other offers and cannot be applied retroactively. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer expires on November 17, 2026.
Windstar reserves the right to correct any errors, inaccuracies, or omissions and to change or update fares, fees, and surcharges at any time without prior notice. ©2026 Windstar Cruises Marshall Islands, LLC. Ships’ registry: Bahamas. Available for UK residents only - 7-for-7 & Late Booking Offer: Terms & Conditions 7-for-7 & Late Booking Offers: All fares mentioned are per person, in Pound Sterling (GBP); cruise only, based on double occupancy in lowest category, and include non-discountable amounts, Taxes, Fees and Port Expenses. Taxes, Fees and Port Expenses are subject to change and final amounts will be advised at time of booking. Suggested onboard gratuities are extra. Offer is valid on new bookings only for select departures and subject to availability.
Consult your Windstar representative for promotional offer or discount combinability. Bookings are non-transferable; no name changes can be made nor can this offer be applied retroactively. Cancellation fees may apply, please see website for details. Certain restrictions apply. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar's discretion at any time. Information contained herein is accurate at the time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruise is provided subject to the terms and conditions of the Passage Contract. 7-for-7Offers are valid for 7 days after launch, or until sold out or withdrawn. Late Booking Offers are valid subject to availability & inventory.