Beach Fun & Sun: A Remote Caribbean Getaway from St. Maarten - Fly Cruise, 19 November 2027 (10 nights)

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Ship Wind Surf  -  Windstar

Cruise + Flight + Hotel

date 19 November 2027 · 10 nights

Alternative packages

  • Cruise + Flight + Hotel 17 November 2027 · 12 nights
Ocean View Stateroom from £4,079 per person
  • Overview of a Ocean View Stateroom Ocean View Stateroom from - £4,079 per person
  • Overview of a Owner's Suite Owner's Suite from - £7,879 per person
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ID: 467527 Icon for 467527
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Bespoke Handcrafted Cruise & Stay Package! Book any sailing departing before 31st December 2027 and Enjoy a Complimentary All-Inclusive Package including gratuities, unlimited Wi-Fi and select beers, cocktails and wine by the glass + a reduced deposit - Offer ends 17th November

Luxury
Free all inclusive
Transfers included
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Your itinerary

  • Excursion information
    Day 1 Pre-cruise
    • Day 1
      • Day at Flight Flight departs
        19 Nov 2027
        • Departure time Departs TBC TBC
        • Arrival time Arrives TBC TBC
        Flight details for this itinerary are not yet available. We will provide full information, including departure times and airlines, as soon as they are confirmed.
      • Day at hotel St Maarten Hotel Stay
        19 Nov 2027
        Transfers to Hotel Included
        Hotel information will be confirmed closer to departure

        While your specific hotel isn't confirmed just yet, you can book with confidence knowing it will be carefully selected from our trusted partners. Closer to your cruise departure, we'll confirm the details.

  • Day at Cruise
    Day 2-10 Cruise from Philipsburg, St. Maarten and back
    • Day 2
      • Day at Port Cruise departs from Philipsburg, St. Maarten
        20 Nov 2027
        Departs at: 7 pm
        Transfers to Port Included
        Bask in the Beauty of Philipsburg
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        Fort Amsterdam
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        Great Bay Beach
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        The Rusty Parrot

        Relax on white-sand beaches, shop duty-free on Front Street, and watch planes soar over Maho Beach in this lively Caribbean gem.

    • Day 3
      • Day at Port Gustavia, St. Barts
        21 Nov 2027
        Arrives at: 8 am, Departs at: 10 pm (14 hours in port)
        Gustavia, St. Barts
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        Fort Karl
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        Gustavia Lighthouse
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        Shell Beach

        The capital of Saint Bart's, Gustavia boasts a relaxed vibe, lots of historic sites and picturesque scenery. Top highlights in the capital include the 17th century fort, Fort Karl, the Gustavia Lighthouse and the breathtaking Shell Beach.

    • Day 4
      • Day at Port St. John's, Antigua
        22 Nov 2027
        Arrives at: 8 am, Departs at: 10 pm (14 hours in port)
        Unwind in Vibrant St. John’s
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        Fort James
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        Art Gallery
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        Museum

        Explore colourful markets, relax on sun-drenched beaches, and discover Antigua’s rich history at Nelson’s Dockyard.

    • Day 5
      • Day at Port Deshaies
        23 Nov 2027
        Arrives at: 7 am, Departs at: 5 pm (10 hours in port)
        Deshaies
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        Deshaies Botanical Garden
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        Take a Death in Paradise Tour
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        Hike to Pointe de Gros Morne

        Deshaies is a charming fishing village located on the northwest coast of Basse-Terre in Guadeloupe. Known for its authentic Caribbean atmosphere, it features colourful wooden houses, waterfront seafood restaurants, and a picturesque bay filled with sailboats. The town gained international fame as the primary filming location for the BBC series Death in Paradise (serving as the fictional town of Honoré). Beyond its TV stardom, Deshaies is surrounded by some of the island's most beautiful landscapes, including the lush Deshaies Botanical Garden.

    • Day 6
      • Day at Port Road Bay, Anguilla
        24 Nov 2027
        Arrives at: 8 am, Departs at: 6 pm (10 hours in port)
        Road Bay (Anguilla)
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        Sandy Ground Beach
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        Boat Trip to Sandy Island
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        Dining and Nightlife

        Road Bay is Anguilla's main, bustling coastal hub, with breathtaking, tranquil blue waters and a relaxing, rustic appeal. A bustling, real Caribbean village atmosphere with a mix of fishing boats, sailboats, and small, relaxed beach bars. It is famed for its pristine white beaches, lively nightlife, and role as the island's major port and harbour.

    • Day 7
      • Day at Port Soper's Hole
        25 Nov 2027
        Arrives at: 8 am, Departs at: 6 pm (10 hours in port)
        Soper's Hole (Tortola)
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        Rhone National Marine Park
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        Shopping
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        Marina

        Soper's Hole, located on a secluded peninsula along Tortola's southwestern coast, is regarded as one of the most appealing marinas in the British Virgin Islands, with access to stunning beaches that range from lively to tranquil. Known for its charming Caribbean atmosphere and bustling harbour. It includes pastel-colored buildings, shops, and restaurants, all situated in a serene and scenic bay perfect for boat watching.

      • Day at Port Great Harbour, Jost Van Dyke - Overnight onboard
        25 Nov 2027
        Arrives at: 7 pm, Departs at: 10 pm (27 hours in port)
        Great Harbour, Jost van Dyke
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        White Bay
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        The Bubbly Pool
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        Sandy Spit & Sandy Cay

        A picturesque destination, you can spend your time in the harbour relaxing on the beautiful beach, exploring the nearby shops and cafes or snorkelling in the crystal-clear lagoon. A fantastic stop-off in the British Virgin Islands, you're guaranteed an unforgettable day ashore.

    • Day 9
      • Day at Port Prickly Pear
        27 Nov 2027
        Arrives at: 8 am, Departs at: 5 pm (9 hours in port)
        Prickly Pear Cays (Anguilla)
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        Coral Reef
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        Beach Amenities

        Prickly Pear Cays in Anguilla is a magnificent, isolated set of islands famed for its pure white sand beaches, crystal-clear turquoise waters, and excellent snorkelling. It's a calm, laid-back paradise perfect for relaxing, sunning, and avoiding crowds. Primarily a day-trip destination, it has a 'deserted island' vibe with rustic restaurants on the beach like Prickly Pear Bar & Restaurant, which serves fresh grilled lobster, ribs and cocktails.

    • Day 10
      • Day at Port Philipsburg, St. Maarten
        28 Nov 2027
        Arrives at: 6 am
        Bask in the Beauty of Philipsburg
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        Fort Amsterdam
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        Great Bay Beach
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        The Rusty Parrot

        Relax on white-sand beaches, shop duty-free on Front Street, and watch planes soar over Maho Beach in this lively Caribbean gem.

  • Day at Flight
    DAY 10-11 Flight 28-29 Nov 2027
    Flight details for this itinerary are not yet available. We will provide full information, including departure times and airlines, as soon as they are confirmed.
    • Departure time Departs TBC TBC
    • Arrival time Arrives TBC TBC
    Transfer Transfers to Airport Included
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0203 848 3639
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What's included

Included

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Choose to fly from a variety of airports included within the price.

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Choose from a variety of things to entertain yourself including restaurants, bars, theatre, pools and much more.

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Image related to Meals Meals

Breakfast, lunch, dinner and snacks from the buffet and main dining restaurants are all included. Meals from the specialty dining restaurants are additional.

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Your cabin is included in the price of the cruise.

Image related to Port Fees & Taxes Port Fees & Taxes

No surprises. All port fees and taxes are included in the price.

Extras

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Wi-Fi

Wi-Fi isn't included within the base price but is included in the All-Inclusive Fare. Alternatively you can purchase Wi-Fi packages which start at $60 USD for 200MB data.

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Drinks

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Tips

Tips/gratuities are not included in the base cruise fare but are included along with Wi-Fi and alcoholic drinks when upgrading to the All-Inclusive Fare. If you're not on the All-Inclusive Fare, gratuities are typically added to your bill. The recommended gratuity for dining and housekeeping staff is around $14 to $18 per guest, per day, depending on the cruise.

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Car parking

Car parking at the port or airport is not included in the cost of your cruise, and this cannot currently be booked through Iglu Cruise. However, please contact us after you have made your booking if you would like to add this to your package, so we can discuss options. An approximate cost for parking during a cruise is around £12 to £20 per car per day. Alternatively, transfers can be arranged.

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Excursions

If you would like to do any excursions/tours while docked these will be an additional charge. Excursions/tours can’t currently be booked with us online but please contact us after you have made the booking if you would like to add these to your package. Alternatively these can be bought while on the ship but may be more expensive than pre-booking.

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Transfers (home to port)

Transfers from your home to the port or airport aren't included but we can help organise coach transfers, taxis etc to make your life easier. Please contact us after you have made the booking if you would like to add these to your package.

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Travel insurance

Travel insurance is not included in your cruise package. However, Iglu Cruise has partnered with Holiday Extras to provide this service. With flexible policies and cruise-specific cover, you can rest assured that you’re completely covered when you go away. Get a Holiday Extras travel insurance quote right here.

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Visa

Visas are not included with your cruise fare and are not provided by Iglu Cruise. Important visas and travel documents must be obtained by the individual guest prior to embarkation. To help, Iglu Cruise has partnered with The Travel Visa Company for professional assistance with all your travel documentation and visa needs.

Ship Facilities

Image related to Wind Surf
Wind Surf - By Windstar
Good for couples Exploration Informal Luxury Ship Small Ship Yacht style Luxury
Year: 1990 · Refurbished: 2019 · 6 Decks · Max capacity: 342 people
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Cruises on Wind Surf

Cabins on Wind Surf

Select cabin
  • Outside from £4,079
  • Ocean View £4,079 pp
  • Deluxe Ocean View £4,279 pp
  • Suite from £7,879
  • Owner's Suite £7,879 pp
Select cabin
  • Outside from £4,079
  • Ocean View £4,079 pp
  • Deluxe Ocean View £4,279 pp
  • Suite from £7,879
  • Owner's Suite £7,879 pp
Select cabin
  • Outside from £4,079
  • Ocean View £4,079 pp
  • Deluxe Ocean View £4,279 pp
  • Suite from £7,879
  • Owner's Suite £7,879 pp
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Ocean View

from £4,079 per person

Comfortable cabins with premium amenities and portholes to enjoy, an affordable option for sailing with Windstar Cruises.

Cabin Size 188 square feet

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Deluxe Ocean View

from £4,279 per person

With a little more room to relax, relish in these stylish staterooms complete with premium amenities and porthole windows.

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Owner's Suite

from £7,879 per person

Sitting near the Bridge and Owners’ quarters onboard, these elegant suites come complete with enhanced premium amenities.

Cabin Size 242 square feet

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To book an accessible cabin, please give us a call 020 3991 1166

Iglu Cruise customer reviews for Wind Surf

5.0
star star star star star
Based on 3 reviews
Cabin
5
Service
5
Excursions
5
Dining
5
Activities
5
Value for money
5
Entertainment
5
star star star star star

From boarding which was smooth to disembarking it was great. Food, service excellent. Plenty of choice and have to mention the freshly caught tuna on the deck bbq, wow! Crew talent show was special, some great dancers and singers and the syncronised swimming was hilarious! Sail away when they put the sails up for the first time was a special moment. Having the marina off the back of the ship was an experience, great fun too. Ports of call all beautiful but very hot. All in all would definitely recommend this yacht/cruise. So nice to have no crowds on board too, very chilled and relaxed. Only thing my husband and I missed were some more brits, think we were the only 2 on this cruise. Must just mention that our cabin was great apart from being at the rear if the yacht we had horrendous noise when going into port, general engine noise all the time which was ok but super noisy going into port. Worth noting when booking.

couple
couple
2-5 cruises
6 Jul 2025
star star star star star

Lovely ship, excellent facilities and the staff were superb. Departing early February 2020, The itinerary was two ports in Columbia, one in Costa Rica, one in Panama ( in addition to Colon), and a canal transit. Our one disappointment was that a "Transit" of the Panama canal was intimated and confirmed by a telephone call, when in fact a full transit was never intended. The "Panama Canal Transit" was detailed in published daily schedules, and only referred to as a partial transit in the last few days, when I suspect other passengers realised the status. The vessel was never designed to enter the Panama Canal. The lifeboats had to be removed, and a new Panama Fairlead installed aft requiring us to spend a day in the Port of Colon to accommodate this. This accommodation was only possible by cancelling The Panama port visit (Boco del Toro), therefore we only visited three of the planned four ports, and a planned "Day at Sea" was in fact a day at anchor outside the Canal. Without requiring to pass under the "Bridge of the Americas" and enter the Pacific, the vessel could have completed a full transit of the Canal, disembarking passengers in Panama City, rather than Colon, and embarking new passengers there to complete a second transit northwards. We were compensated for the missed port, $50 and $15 fees, (less than a dinner bottle of wine.) A very disappointing end to a potentially wonderful experience. The Ship was wonderful, the holiday was not.

user
user
1 cruise
27 Feb 2020
star star star star star

great cabins, and wonderful experience

user
user
1 cruise
4 Jun 2017
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Terms and Conditions

Book select sailings between 1 July – 17 November 2026 for voyages departing by 31 December 2027 and enjoy exclusive benefits as outlined in the specific offer details. Amenities, credits, and services may vary by promotion and are subject to availability. Certain sailings, packages, and destinations may be excluded. Complimentary services or credits are non-transferable, have no cash value, and may be subject to restrictions on use. Fares are per person, cruise-only, based on double occupancy; taxes and fees are additional. Offers are valid on new bookings only, non-transferable, and not combinable with other offers except where specifically stated. Cancellation fees may apply. Offers are capacity-controlled and may be withdrawn or modified at any time without notice. Fuel surcharges may apply. All Windstar website terms and the Passage Contract apply.

All offers and prices are subject to change and availability at time of enquiry. Prices are based on two passengers sharing unless otherwise stated and are subject to the Tour Operator's terms and conditions. Cabin and Flight supplements may apply. Other supplements may apply in addition to the price shown above. Flight details, timings and routing may be subject to alteration. Other tour operator charges may also apply. Any Onboard Spending money or drinks package value shown will be per cabin, again based on two sharing.

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