Wind Surf | The Best Of The Windward Leeward Isles 28D Ph1-Orj (Jan 4 2026) from Philipsburg, St. Maarten | The Cruise Web
 
Windstar Cruises

The Best Of The Windward & Leeward Isles 28d Ph1-Orj (Jan 4 2026)

Highlights

  • Get away from the crowd and journey to unique destinations aboard Windstar’s intimate small ships.

  • Dining in elegance on a James Beard Foundation Culinary cruise, attending VIP events at the Monaco Grand Prix, or skipping the lines to the Sistine Chapel are all possible on a themed cruise or cruise tour with Windstar Cruises.

  • Offering both French and Dutch experiences, St. Maarten is a leading destination in the Caribbean. You can always find exciting and interesting activities for everyone on this friendly island.

  • Wind Surf - Passenger Capacity: 342 (double occupancy) Year Built: 1990 Last Refurbished: 2019
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Special Promotions*

Free Gratuities for Balcony and above on NCL*

Royal Caribbean: 60% OFF 2nd Guest and Kids Free*

Norwegian Cruise Line: 70% OFF Guest 2 and FREE...

Celebrity Cruises: 75% OFF 2nd Guest*

Cunard: FREE Upgrade plus up to $2,000 OBC*

Oceania Cruises: FREE Air, Drinks, WiFi, Excurs...

Atlas Ocean Voyages: 2nd Guest Sails FREE*

Princess Cruises: up to 35% OFF and Kids Sail FREE

Holland America: Included Drinks, Tours, Specia...

Exclusive: Free Excursion Credits for NCL*

Silversea: Choose from THREE All-Inclusive Fares!

NEW! Choose from 3 Cruise Packages for Princess

Regent: FREE Air, Excursions, Drinks, WiFi, Tips

Princess MedallionClass Vacation

Celebrity Cruises: Choose ALL INCLUDED or NO PERK*

RSSC Ambassador Program: $250 Future Cruise Credit

Up to $500 FREE Onboard Credit* - TCW Exclusive

Norwegian Cruise Line: up to $50 Onboard Credit*

Atlas: ALL-INCLUSIVE Luxury Expedition Cruises

MSC Cruises: Kids Sail FREE on select sailings*

Princess: up to $250 Onboard Credit for Military

Seabourn: FREE Tips, Drinks, Gourmet Dining...

Uniworld: Free Gratuities, Unlimited Drinks...

Silversea: FREE Gratuities, FREE Drinks, Butler...

Cunard: up to $250 Onboard Credit for Military

Windstar: Exclusive Private Event and MORE

MSC Cruises Military Discount: up to 10% OFF*

Celebrity Alaska Cruisetour Packages

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Celebrity Cruises Europe Cruisetours

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The Best Of The Windward & Leeward Isles 28d Ph1-Orj (Jan 4 2026) sailing on the Wind Surf

Departure Dates: Jan 2026 - Jan 2026

Stateroom prices for Jan. 4, 2026

Oceanview

Wind Surf Oceanview Stateroom

Published prices from

$7,899

Based on Oceanview cabin prices



Special Promotions*

Free Gratuities for Balcony and above on NCL*

Royal Caribbean: 60% OFF 2nd Guest and Kids Free*

Norwegian Cruise Line: 70% OFF Guest 2 and FREE...

Celebrity Cruises: 75% OFF 2nd Guest*

Cunard: FREE Upgrade plus up to $2,000 OBC*

Oceania Cruises: FREE Air, Drinks, WiFi, Excurs...

Atlas Ocean Voyages: 2nd Guest Sails FREE*

Princess Cruises: up to 35% OFF and Kids Sail FREE

Holland America: Included Drinks, Tours, Specia...

Exclusive: Free Excursion Credits for NCL*

Silversea: Choose from THREE All-Inclusive Fares!

NEW! Choose from 3 Cruise Packages for Princess

Regent: FREE Air, Excursions, Drinks, WiFi, Tips

Princess MedallionClass Vacation

Celebrity Cruises: Choose ALL INCLUDED or NO PERK*

RSSC Ambassador Program: $250 Future Cruise Credit

Up to $500 FREE Onboard Credit* - TCW Exclusive

Norwegian Cruise Line: up to $50 Onboard Credit*

Atlas: ALL-INCLUSIVE Luxury Expedition Cruises

MSC Cruises: Kids Sail FREE on select sailings*

Princess: up to $250 Onboard Credit for Military

Seabourn: FREE Tips, Drinks, Gourmet Dining...

Uniworld: Free Gratuities, Unlimited Drinks...

Silversea: FREE Gratuities, FREE Drinks, Butler...

Cunard: up to $250 Onboard Credit for Military

Windstar: Exclusive Private Event and MORE

MSC Cruises Military Discount: up to 10% OFF*

Celebrity Alaska Cruisetour Packages

Celebrity Asia Cruisetour Packages

Celebrity Australia Cruisetour Packages

Celebrity Europe Cruisetour Packages

Celebrity South America Cruisetour Packages

Celebrity Cruises Europe Cruisetours

Holland America Alaska Cruisetour Packages

Norwegian Europe Cruisetour Packages

Norwegian Hawaii Cruisetour Packages

Norwegian Europe Cruisetours

Princess Alaska Cruisetour Packages

Princess Asia Cruisetour Packages

Princess Australia Cruisetour Packages

Princess Canada and New England Cruisetours

Princess Europe Cruisetour Packages

Princess South America Cruisetours

Princess Europe Cruisetours

Royal Caribbean Alaska Cruisetour Packages

Get Deal
Daily Itinerary
Date Port Arrival Time Departure Time

Philipsburg, St. Maarten

-- 7:00 PM

Falmouth Harbour, Antigua

8:00 AM 6:00 PM

Cruising

8:00 AM 6:00 PM

Jost Van Dyke, British Virgin Islands

7:00 PM 11:59 PM

Sopers Hole, British Virgin Islands

8:00 AM 6:00 PM

Jost Van Dyke, British Virgin Islands

12:00 AM 10:00 PM

Virgin Gorda, British Virgin Islands

8:00 AM 5:00 PM

Gustavia, St. Barts

8:00 AM 10:00 PM

Philipsburg, St. Maarten

6:00 AM 7:00 PM

Port of Basseterre, St. Kitts, St. Kitts and Nevis

7:00 AM 10:00 PM

Little Bay, Montserrat, Leeward Islands

8:00 AM 6:00 PM

Gustavia, St. Barts

8:00 AM 11:00 PM

Deshaies, Guadeloupe

12:30 PM 10:00 PM

Roseau, Dominica

8:00 AM 5:00 PM

Pigeon Island, St. Lucia

7:00 AM 4:00 PM

Bridgetown, Barbados

5:00 AM 6:00 PM

Cruising

9:00 AM 11:00 PM

Pigeon Island, St. Lucia

6:00 PM 11:59 PM

Casablanca, Morocco

8:00 AM 4:00 PM

Pigeon Island, St. Lucia

12:00 AM 6:00 PM

Bequia, Grenadines

8:00 AM 10:00 PM

Mayreau, Grenadines

8:00 AM 6:00 PM

St. Georges, Grenada, West Indies

7:00 AM 2:00 PM

Bridgetown, Barbados

6:00 AM 6:00 PM

Cruising

8:00 AM 5:00 PM

Mayreau, Grenadines

8:00 AM 6:00 PM

Cruising

8:00 AM 4:00 PM

Cruising

-- --

KRALENDIJK, BONAIRE

1:00 PM 10:00 PM

Cruising

8:00 AM 6:00 PM

Port of Oranjestad, Aruba, Caribbean

6:00 AM --

Rates & offers are subject to select dates & categories, cruise only, per person, based on double occupancy, in US Dollars, & include NCCF. Government taxes & fees are additional. All rates & offers are capacity controlled, are subject to availability & confirmation, & may change without notice. Additional restrictions may apply. Information deemed reliable but not guaranteed -- please confirm details at time of booking. Stateroom photos are for sample purposes only -- actual design and layout may vary.

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