menu
Home Cruise Lines Windstar Cruises Wind Surf Wind Surf Photo Gallery
Cruise Itinerary Details

7 Night Yachtman's Caribbean

Wind Surf

Departing from: Philipsburg, St. Maarten
Ports of Call: View more
4.0 / 5  (21 reviews)
oceanview from
$1,999
$286/night
Oceanview
Suite
Casino
Compass Rose
Yacht Club
Gift Shop
Pool
Stella Bistro
The Veranda
The Veranda
Candles
AmphorA Restaurant
Fitness Center
Click Image to Enlarge
Select Your Sailing Date
Interior
Oceanview
from $1,999
Balcony
Suite
from $3,399
December 19, 2015
December 26, 2015
SaturdaySaturday
N/A
$2,599
$371/night
N/A
$3,999
$571/night
Bonus Offers Available:
Call to book Limited Time All-Inclusive Offer
Call to book Limited Time All-Inclusive Offer
Heres your ticket to paradise in luxury. For a limited time only, call to book select tropical Windstar cruises to destinations like Costa Rica, the Caribbean and more, and you can enjoy all-inclusive cruising. Sail away with a beverage package, unlimited WiFi, three shore excursions and pre-paid gratuities - in addition to Windstars signature complimentary savings of specialty dining, Private Event land excursion and use of the Water Sports Platform. Inclusive offer is based on double occupancy, valid on new reservations and may have additional restrictions. Not all fares displaying online qualify for this offer. Call for more details - hurry offer ends 11:59 pm EST on September 18th!
Up to $1,000 Cash back
Up to $1,000 Cash back
Up to $1,000 Cashback when you book your luxury cruise today!
Use Your Orbitz Rewards Visa: Earn 5% in Orbucks
Use Your Orbitz Rewards Visa: Earn 5% in Orbucks
Book your next cruise with the Orbitz Rewards Visa Card and earn 5% in Orbucks! By land or by sea, this card comes with no fees - its the most rewarding travel card around. All qualifying Orbitz bookings earn 5% back in Orbucks on the total booking cost. All other purchases earn 2% back in Orbucks per dollar spent. Orbucks will be automatically deposited within two billing cycles.
December 26, 2015
January 02, 2016
SaturdaySaturday
N/A
$2,599
$371/night
N/A
$3,999
$571/night
Bonus Offers Available:
Call to book Limited Time All-Inclusive Offer
Call to book Limited Time All-Inclusive Offer
Heres your ticket to paradise in luxury. For a limited time only, call to book select tropical Windstar cruises to destinations like Costa Rica, the Caribbean and more, and you can enjoy all-inclusive cruising. Sail away with a beverage package, unlimited WiFi, three shore excursions and pre-paid gratuities - in addition to Windstars signature complimentary savings of specialty dining, Private Event land excursion and use of the Water Sports Platform. Inclusive offer is based on double occupancy, valid on new reservations and may have additional restrictions. Not all fares displaying online qualify for this offer. Call for more details - hurry offer ends 11:59 pm EST on September 18th!
Up to $1,000 Cash back
Up to $1,000 Cash back
Up to $1,000 Cashback when you book your luxury cruise today!
Use Your Orbitz Rewards Visa: Earn 5% in Orbucks
Use Your Orbitz Rewards Visa: Earn 5% in Orbucks
Book your next cruise with the Orbitz Rewards Visa Card and earn 5% in Orbucks! By land or by sea, this card comes with no fees - its the most rewarding travel card around. All qualifying Orbitz bookings earn 5% back in Orbucks on the total booking cost. All other purchases earn 2% back in Orbucks per dollar spent. Orbucks will be automatically deposited within two billing cycles.
January 02, 2016
January 09, 2016
SaturdaySaturday
N/A
$1,999
$286/night
N/A
$3,399
$486/night
Bonus Offers Available:
Call to book Limited Time All-Inclusive Offer
Call to book Limited Time All-Inclusive Offer
Heres your ticket to paradise in luxury. For a limited time only, call to book select tropical Windstar cruises to destinations like Costa Rica, the Caribbean and more, and you can enjoy all-inclusive cruising. Sail away with a beverage package, unlimited WiFi, three shore excursions and pre-paid gratuities - in addition to Windstars signature complimentary savings of specialty dining, Private Event land excursion and use of the Water Sports Platform. Inclusive offer is based on double occupancy, valid on new reservations and may have additional restrictions. Not all fares displaying online qualify for this offer. Call for more details - hurry offer ends 11:59 pm EST on September 18th!
Up to $1,000 Cash back
Up to $1,000 Cash back
Up to $1,000 Cashback when you book your luxury cruise today!
Use Your Orbitz Rewards Visa: Earn 5% in Orbucks
Use Your Orbitz Rewards Visa: Earn 5% in Orbucks
Book your next cruise with the Orbitz Rewards Visa Card and earn 5% in Orbucks! By land or by sea, this card comes with no fees - its the most rewarding travel card around. All qualifying Orbitz bookings earn 5% back in Orbucks on the total booking cost. All other purchases earn 2% back in Orbucks per dollar spent. Orbucks will be automatically deposited within two billing cycles.
January 16, 2016
January 23, 2016
SaturdaySaturday
N/A
$2,099
$300/night
N/A
$3,499
$500/night
Bonus Offers Available:
Call to book Limited Time All-Inclusive Offer
Call to book Limited Time All-Inclusive Offer
Heres your ticket to paradise in luxury. For a limited time only, call to book select tropical Windstar cruises to destinations like Costa Rica, the Caribbean and more, and you can enjoy all-inclusive cruising. Sail away with a beverage package, unlimited WiFi, three shore excursions and pre-paid gratuities - in addition to Windstars signature complimentary savings of specialty dining, Private Event land excursion and use of the Water Sports Platform. Inclusive offer is based on double occupancy, valid on new reservations and may have additional restrictions. Not all fares displaying online qualify for this offer. Call for more details - hurry offer ends 11:59 pm EST on September 18th!
Up to $1,000 Cash back
Up to $1,000 Cash back
Up to $1,000 Cashback when you book your luxury cruise today!
Use Your Orbitz Rewards Visa: Earn 5% in Orbucks
Use Your Orbitz Rewards Visa: Earn 5% in Orbucks
Book your next cruise with the Orbitz Rewards Visa Card and earn 5% in Orbucks! By land or by sea, this card comes with no fees - its the most rewarding travel card around. All qualifying Orbitz bookings earn 5% back in Orbucks on the total booking cost. All other purchases earn 2% back in Orbucks per dollar spent. Orbucks will be automatically deposited within two billing cycles.
January 23, 2016
January 30, 2016
SaturdaySaturday
N/A
$2,299
$328/night
N/A
$3,699
$528/night
Bonus Offers Available:
Call to book Limited Time All-Inclusive Offer
Call to book Limited Time All-Inclusive Offer
Heres your ticket to paradise in luxury. For a limited time only, call to book select tropical Windstar cruises to destinations like Costa Rica, the Caribbean and more, and you can enjoy all-inclusive cruising. Sail away with a beverage package, unlimited WiFi, three shore excursions and pre-paid gratuities - in addition to Windstars signature complimentary savings of specialty dining, Private Event land excursion and use of the Water Sports Platform. Inclusive offer is based on double occupancy, valid on new reservations and may have additional restrictions. Not all fares displaying online qualify for this offer. Call for more details - hurry offer ends 11:59 pm EST on September 18th!
Up to $1,000 Cash back
Up to $1,000 Cash back
Up to $1,000 Cashback when you book your luxury cruise today!
Use Your Orbitz Rewards Visa: Earn 5% in Orbucks
Use Your Orbitz Rewards Visa: Earn 5% in Orbucks
Book your next cruise with the Orbitz Rewards Visa Card and earn 5% in Orbucks! By land or by sea, this card comes with no fees - its the most rewarding travel card around. All qualifying Orbitz bookings earn 5% back in Orbucks on the total booking cost. All other purchases earn 2% back in Orbucks per dollar spent. Orbucks will be automatically deposited within two billing cycles.
February 06, 2016
February 13, 2016
SaturdaySaturday
N/A
$2,299
$328/night
N/A
$3,699
$528/night
Bonus Offers Available:
Call to book Limited Time All-Inclusive Offer
Call to book Limited Time All-Inclusive Offer
Heres your ticket to paradise in luxury. For a limited time only, call to book select tropical Windstar cruises to destinations like Costa Rica, the Caribbean and more, and you can enjoy all-inclusive cruising. Sail away with a beverage package, unlimited WiFi, three shore excursions and pre-paid gratuities - in addition to Windstars signature complimentary savings of specialty dining, Private Event land excursion and use of the Water Sports Platform. Inclusive offer is based on double occupancy, valid on new reservations and may have additional restrictions. Not all fares displaying online qualify for this offer. Call for more details - hurry offer ends 11:59 pm EST on September 18th!
Up to $1,000 Cash back
Up to $1,000 Cash back
Up to $1,000 Cashback when you book your luxury cruise today!
Use Your Orbitz Rewards Visa: Earn 5% in Orbucks
Use Your Orbitz Rewards Visa: Earn 5% in Orbucks
Book your next cruise with the Orbitz Rewards Visa Card and earn 5% in Orbucks! By land or by sea, this card comes with no fees - its the most rewarding travel card around. All qualifying Orbitz bookings earn 5% back in Orbucks on the total booking cost. All other purchases earn 2% back in Orbucks per dollar spent. Orbucks will be automatically deposited within two billing cycles.
February 20, 2016
February 27, 2016
SaturdaySaturday
N/A
$2,299
$328/night
N/A
$3,699
$528/night
Bonus Offers Available:
Call to book Limited Time All-Inclusive Offer
Call to book Limited Time All-Inclusive Offer
Heres your ticket to paradise in luxury. For a limited time only, call to book select tropical Windstar cruises to destinations like Costa Rica, the Caribbean and more, and you can enjoy all-inclusive cruising. Sail away with a beverage package, unlimited WiFi, three shore excursions and pre-paid gratuities - in addition to Windstars signature complimentary savings of specialty dining, Private Event land excursion and use of the Water Sports Platform. Inclusive offer is based on double occupancy, valid on new reservations and may have additional restrictions. Not all fares displaying online qualify for this offer. Call for more details - hurry offer ends 11:59 pm EST on September 18th!
Up to $1,000 Cash back
Up to $1,000 Cash back
Up to $1,000 Cashback when you book your luxury cruise today!
Use Your Orbitz Rewards Visa: Earn 5% in Orbucks
Use Your Orbitz Rewards Visa: Earn 5% in Orbucks
Book your next cruise with the Orbitz Rewards Visa Card and earn 5% in Orbucks! By land or by sea, this card comes with no fees - its the most rewarding travel card around. All qualifying Orbitz bookings earn 5% back in Orbucks on the total booking cost. All other purchases earn 2% back in Orbucks per dollar spent. Orbucks will be automatically deposited within two billing cycles.
February 27, 2016
March 05, 2016
SaturdaySaturday
N/A
$2,299
$328/night
N/A
$3,699
$528/night
Bonus Offers Available:
Call to book Limited Time All-Inclusive Offer
Call to book Limited Time All-Inclusive Offer
Heres your ticket to paradise in luxury. For a limited time only, call to book select tropical Windstar cruises to destinations like Costa Rica, the Caribbean and more, and you can enjoy all-inclusive cruising. Sail away with a beverage package, unlimited WiFi, three shore excursions and pre-paid gratuities - in addition to Windstars signature complimentary savings of specialty dining, Private Event land excursion and use of the Water Sports Platform. Inclusive offer is based on double occupancy, valid on new reservations and may have additional restrictions. Not all fares displaying online qualify for this offer. Call for more details - hurry offer ends 11:59 pm EST on September 18th!
Up to $1,000 Cash back
Up to $1,000 Cash back
Up to $1,000 Cashback when you book your luxury cruise today!
Use Your Orbitz Rewards Visa: Earn 5% in Orbucks
Use Your Orbitz Rewards Visa: Earn 5% in Orbucks
Book your next cruise with the Orbitz Rewards Visa Card and earn 5% in Orbucks! By land or by sea, this card comes with no fees - its the most rewarding travel card around. All qualifying Orbitz bookings earn 5% back in Orbucks on the total booking cost. All other purchases earn 2% back in Orbucks per dollar spent. Orbucks will be automatically deposited within two billing cycles.
March 12, 2016
March 19, 2016
SaturdaySaturday
N/A
$2,299
$328/night
N/A
$3,699
$528/night
Bonus Offers Available:
Call to book Limited Time All-Inclusive Offer
Call to book Limited Time All-Inclusive Offer
Heres your ticket to paradise in luxury. For a limited time only, call to book select tropical Windstar cruises to destinations like Costa Rica, the Caribbean and more, and you can enjoy all-inclusive cruising. Sail away with a beverage package, unlimited WiFi, three shore excursions and pre-paid gratuities - in addition to Windstars signature complimentary savings of specialty dining, Private Event land excursion and use of the Water Sports Platform. Inclusive offer is based on double occupancy, valid on new reservations and may have additional restrictions. Not all fares displaying online qualify for this offer. Call for more details - hurry offer ends 11:59 pm EST on September 18th!
Up to $1,000 Cash back
Up to $1,000 Cash back
Up to $1,000 Cashback when you book your luxury cruise today!
Use Your Orbitz Rewards Visa: Earn 5% in Orbucks
Use Your Orbitz Rewards Visa: Earn 5% in Orbucks
Book your next cruise with the Orbitz Rewards Visa Card and earn 5% in Orbucks! By land or by sea, this card comes with no fees - its the most rewarding travel card around. All qualifying Orbitz bookings earn 5% back in Orbucks on the total booking cost. All other purchases earn 2% back in Orbucks per dollar spent. Orbucks will be automatically deposited within two billing cycles.
March 26, 2016
April 02, 2016
SaturdaySaturday
N/A
$2,299
$328/night
N/A
$3,699
$528/night
Bonus Offers Available:
Call to book Limited Time All-Inclusive Offer
Call to book Limited Time All-Inclusive Offer
Heres your ticket to paradise in luxury. For a limited time only, call to book select tropical Windstar cruises to destinations like Costa Rica, the Caribbean and more, and you can enjoy all-inclusive cruising. Sail away with a beverage package, unlimited WiFi, three shore excursions and pre-paid gratuities - in addition to Windstars signature complimentary savings of specialty dining, Private Event land excursion and use of the Water Sports Platform. Inclusive offer is based on double occupancy, valid on new reservations and may have additional restrictions. Not all fares displaying online qualify for this offer. Call for more details - hurry offer ends 11:59 pm EST on September 18th!
Up to $1,000 Cash back
Up to $1,000 Cash back
Up to $1,000 Cashback when you book your luxury cruise today!
Use Your Orbitz Rewards Visa: Earn 5% in Orbucks
Use Your Orbitz Rewards Visa: Earn 5% in Orbucks
Book your next cruise with the Orbitz Rewards Visa Card and earn 5% in Orbucks! By land or by sea, this card comes with no fees - its the most rewarding travel card around. All qualifying Orbitz bookings earn 5% back in Orbucks on the total booking cost. All other purchases earn 2% back in Orbucks per dollar spent. Orbucks will be automatically deposited within two billing cycles.
Prices listed are per person, cruise only, based on double occupancy.
Accessibility: Wind Surf
Your personal concierge will be in touch today to discuss your luxury cruise.*

*Consultation requests submitted after 6 PM (EST) or on Sundays/holidays may receive a call on the following business day.
From booking to boarding and beyond, a personal concierge's expert knowledge can help guide you in arranging the luxury cruise of your dreams.
Please fill out the form to the right and a concierge will call you shortly.
1-800-441-3659 | 9am-9pm EST M-F, 9am-6pm EST Sat
Top
Cruise Deals by Email

Receive exclusive offers and discounts to your inbox. Don't worry - we hate spam and we won't sell your email address to a third party.