Yacht Club Past Guest Rewards – Save up to 10%, up to $100 Free Onboard Credit, Private Cocktail Reception PLUS More!
Book with Avoya Travel as a member of Windstar’s Yacht Club to receive Past Guest Rewards that may include Savings up to 10% per person, up to $100 Free Onboard Credit, a Private Cocktail Reception PLUS More!Check out our cruise only prices below and contact an Avoya Travel Windstar Cruises Specialist to see how much Savings and FREE Perks your desired sail date qualifies for!
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Book NOW to receive $75-$4,500 Instant Avoya Cash on sailings departing through December 2026!
This Exclusive is Combinable With All Deals - Call
1-888-447-8459
to book before June 30th
San Juan → Saint Vincent And Grenadines (Bequia) → Saint Vincent And Grenadines (Mayreau) → Saint Lucia (Soufriere) → Isle De Saintes → Saint Martin (Marigot) → San Juan
San Juan → Saint Vincent And Grenadines (Bequia) → Saint Vincent And Grenadines (Mayreau) → Saint Lucia (Soufriere) → Isle De Saintes → Saint Martin (Marigot) → San Juan
Departs
Jan 30, 2026
from
San Juan, Puerto Rico
Up to 2 deals
including an Avoya Exclusive
Oceanview From
$3,499
Top Picks Rank:
8
14-night caribbean cruise
$6,799
Windstar Cruises –
Star Seeker
Date:
Jan 30, 2026
Ports:
San Juan → Saint Vincent And Grenadines (Bequia) → Saint Vincent And Grenadines (Mayreau) → Saint Lucia (Soufriere) → Isle De Saintes → Saint Martin (Marigot) → Saint John → Saint Kitts And Nevis (Basse Terre) → Saint Barthelemy (Gustavia) → Saint Maarten (Phillipsburg) → Jost Van Dyke → Virgin Gorda → San Juan
San Juan → Saint Vincent And Grenadines (Bequia) → Saint Vincent And Grenadines (Mayreau) → Saint Lucia (Soufriere) → Isle De Saintes → Saint Martin (Marigot) → Saint John → Saint Kitts And Nevis (Basse Terre) → Saint Barthelemy (Gustavia) → Saint Maarten (Phillipsburg) → Jost Van Dyke → Virgin Gorda → San Juan
Saint Maarten (Phillipsburg) → San Jose → Road Bay → Jost Van Dyke → Soper's Hole → Virgin Gorda → Saint Barthelemy (Gustavia) → Saint Maarten (Phillipsburg)
Saint Maarten (Phillipsburg) → San Jose → Road Bay → Jost Van Dyke → Soper's Hole → Virgin Gorda → Saint Barthelemy (Gustavia) → Saint Maarten (Phillipsburg)
Departs
Jan 31, 2026
from
Saint Maarten (Phillipsburg), Netherlands Antilles
Saint Maarten (Phillipsburg) → San Jose → Road Bay → Jost Van Dyke → Soper's Hole → Virgin Gorda → Saint Barthelemy (Gustavia) → Saint Kitts And Nevis (Charlestown) → Roseau → Saint Vincent And Grenadines (Mayreau) → Anse Mitan → Saint Kitts And Nevis (Basse Terre) → Saint Maarten (Phillipsburg)
Saint Maarten (Phillipsburg) → San Jose → Road Bay → Jost Van Dyke → Soper's Hole → Virgin Gorda → Saint Barthelemy (Gustavia) → Saint Kitts And Nevis (Charlestown) → Roseau → Saint Vincent And Grenadines (Mayreau) → Anse Mitan → Saint Kitts And Nevis (Basse Terre) → Saint Maarten (Phillipsburg)
Departs
Jan 31, 2026
from
Saint Maarten (Phillipsburg), Netherlands Antilles
San Juan → Saint John → Saint Kitts And Nevis (Basse Terre) → Saint Barthelemy (Gustavia) → Saint Maarten (Phillipsburg) → Jost Van Dyke → Virgin Gorda → San Juan
San Juan → Saint John → Saint Kitts And Nevis (Basse Terre) → Saint Barthelemy (Gustavia) → Saint Maarten (Phillipsburg) → Jost Van Dyke → Virgin Gorda → San Juan
San Juan → Saint John → Saint Kitts And Nevis (Basse Terre) → Saint Barthelemy (Gustavia) → Saint Maarten (Phillipsburg) → Jost Van Dyke → Virgin Gorda → Saint Vincent And Grenadines (Bequia) → Saint Vincent And Grenadines (Mayreau) → Saint Lucia (Soufriere) → Isle De Saintes → Saint Martin (Marigot) → San Juan
San Juan → Saint John → Saint Kitts And Nevis (Basse Terre) → Saint Barthelemy (Gustavia) → Saint Maarten (Phillipsburg) → Jost Van Dyke → Virgin Gorda → Saint Vincent And Grenadines (Bequia) → Saint Vincent And Grenadines (Mayreau) → Saint Lucia (Soufriere) → Isle De Saintes → Saint Martin (Marigot) → San Juan
Saint Maarten (Phillipsburg) → Saint Kitts And Nevis (Charlestown) → Roseau → Saint Vincent And Grenadines (Mayreau) → Anse Mitan → Saint Kitts And Nevis (Basse Terre) → Saint Barthelemy (Gustavia) → Saint Maarten (Phillipsburg)
Saint Maarten (Phillipsburg) → Saint Kitts And Nevis (Charlestown) → Roseau → Saint Vincent And Grenadines (Mayreau) → Anse Mitan → Saint Kitts And Nevis (Basse Terre) → Saint Barthelemy (Gustavia) → Saint Maarten (Phillipsburg)
Departs
Feb 07, 2026
from
Saint Maarten (Phillipsburg), Netherlands Antilles
Saint Maarten (Phillipsburg) → Saint Kitts And Nevis (Charlestown) → Roseau → Saint Vincent And Grenadines (Mayreau) → Anse Mitan → Saint Kitts And Nevis (Basse Terre) → Saint Barthelemy (Gustavia) → San Jose → Road Bay → Jost Van Dyke → Soper's Hole → Virgin Gorda → Saint Maarten (Phillipsburg)
Saint Maarten (Phillipsburg) → Saint Kitts And Nevis (Charlestown) → Roseau → Saint Vincent And Grenadines (Mayreau) → Anse Mitan → Saint Kitts And Nevis (Basse Terre) → Saint Barthelemy (Gustavia) → San Jose → Road Bay → Jost Van Dyke → Soper's Hole → Virgin Gorda → Saint Maarten (Phillipsburg)
Departs
Feb 07, 2026
from
Saint Maarten (Phillipsburg), Netherlands Antilles
Colon → Bocas Del Toro → San Andres Island → Roatan → Belize City → Costa Maya → Cozumel → Grand Cayman → Cayman Brac → Ocho Rios → Santo Domingo → La Romana → Jost Van Dyke → Virgin Gorda → Saint Maarten (Phillipsburg)
Colon → Bocas Del Toro → San Andres Island → Roatan → Belize City → Costa Maya → Cozumel → Grand Cayman → Cayman Brac → Ocho Rios → Santo Domingo → La Romana → Jost Van Dyke → Virgin Gorda → Saint Maarten (Phillipsburg)
Papeete (Tahiti) → Fakarava → Rangiroa → Raiatea → Tahaa → Bora Bora → Huahine → Moorea → Papeete (Tahiti)
Departs
Feb 12, 2026
from
Papeete (Tahiti), French Polynesia
Up to 2 deals
including an Avoya Exclusive
Suite From
$4,899
Top Picks Rank:
8
14-night caribbean cruise
$5,799
Windstar Cruises –
Star Seeker
Date:
Feb 13, 2026
Ports:
San Juan → Saint Vincent And Grenadines (Bequia) → Saint Vincent And Grenadines (Mayreau) → Saint Lucia (Soufriere) → Isle De Saintes → Saint Martin (Marigot) → Saint John → Saint Kitts And Nevis (Basse Terre) → Saint Maarten (Phillipsburg) → Saint Barthelemy (Gustavia) → Jost Van Dyke → Virgin Gorda → San Juan
San Juan → Saint Vincent And Grenadines (Bequia) → Saint Vincent And Grenadines (Mayreau) → Saint Lucia (Soufriere) → Isle De Saintes → Saint Martin (Marigot) → Saint John → Saint Kitts And Nevis (Basse Terre) → Saint Maarten (Phillipsburg) → Saint Barthelemy (Gustavia) → Jost Van Dyke → Virgin Gorda → San Juan
Saint Maarten (Phillipsburg) → San Jose → Road Bay → Jost Van Dyke → Soper's Hole → Virgin Gorda → Saint Barthelemy (Gustavia) → Saint Maarten (Phillipsburg)
Saint Maarten (Phillipsburg) → San Jose → Road Bay → Jost Van Dyke → Soper's Hole → Virgin Gorda → Saint Barthelemy (Gustavia) → Saint Maarten (Phillipsburg)
Departs
Feb 14, 2026
from
Saint Maarten (Phillipsburg), Netherlands Antilles
Cozumel → Grand Cayman → Cayman Brac → Ocho Rios → Santo Domingo → La Romana → Jost Van Dyke → Virgin Gorda → Saint Maarten (Phillipsburg) → Saint Kitts And Nevis (Charlestown) → Roseau → Saint Vincent And Grenadines (Mayreau) → Deshaies → Saint Kitts And Nevis (Basse Terre) → Saint Barthelemy (Gustavia)
Cozumel → Grand Cayman → Cayman Brac → Ocho Rios → Santo Domingo → La Romana → Jost Van Dyke → Virgin Gorda → Saint Maarten (Phillipsburg) → Saint Kitts And Nevis (Charlestown) → Roseau → Saint Vincent And Grenadines (Mayreau) → Deshaies → Saint Kitts And Nevis (Basse Terre) → Saint Barthelemy (Gustavia)
Departs
Feb 17, 2026
from
Cozumel, Mexico
Up to 2 deals
including an Avoya Exclusive
Oceanview From
$5,599
Top Picks Rank:
8
7-night caribbean cruise
$3,399
Windstar Cruises –
Star Seeker
Date:
Feb 20, 2026
Ports:
San Juan → Saint John → Saint Kitts And Nevis (Basse Terre) → Saint Maarten (Phillipsburg) → Saint Barthelemy (Gustavia) → Jost Van Dyke → Virgin Gorda → San Juan
San Juan → Saint John → Saint Kitts And Nevis (Basse Terre) → Saint Maarten (Phillipsburg) → Saint Barthelemy (Gustavia) → Jost Van Dyke → Virgin Gorda → San Juan
Departs
Feb 20, 2026
from
San Juan, Puerto Rico
Up to 2 deals
including an Avoya Exclusive
Oceanview From
$3,399
Top Picks Rank:
8
14-night caribbean cruise
$5,699
Windstar Cruises –
Star Seeker
Date:
Feb 20, 2026
Ports:
San Juan → Saint John → Saint Kitts And Nevis (Basse Terre) → Saint Maarten (Phillipsburg) → Saint Barthelemy (Gustavia) → Jost Van Dyke → Virgin Gorda → Isle De Saintes → Saint Vincent And Grenadines (Mayreau) → Saint Vincent And Grenadines (Bequia) → Saint Lucia (Soufriere) → San Juan
San Juan → Saint John → Saint Kitts And Nevis (Basse Terre) → Saint Maarten (Phillipsburg) → Saint Barthelemy (Gustavia) → Jost Van Dyke → Virgin Gorda → Isle De Saintes → Saint Vincent And Grenadines (Mayreau) → Saint Vincent And Grenadines (Bequia) → Saint Lucia (Soufriere) → San Juan
Saint Maarten (Phillipsburg) → San Jose → Road Bay → Soper's Hole → Virgin Gorda → Jost Van Dyke → Saint Barthelemy (Gustavia) → Saint Maarten (Phillipsburg)
Saint Maarten (Phillipsburg) → San Jose → Road Bay → Soper's Hole → Virgin Gorda → Jost Van Dyke → Saint Barthelemy (Gustavia) → Saint Maarten (Phillipsburg)
Departs
Feb 21, 2026
from
Saint Maarten (Phillipsburg), Netherlands Antilles
Saint Maarten (Phillipsburg) → San Jose → Road Bay → Soper's Hole → Virgin Gorda → Jost Van Dyke → Saint Barthelemy (Gustavia) → Saint Kitts And Nevis (Basse Terre) → Isle De Saintes → Roseau → Saint Vincent And Grenadines (Mayreau) → Bridgetown
Saint Maarten (Phillipsburg) → San Jose → Road Bay → Soper's Hole → Virgin Gorda → Jost Van Dyke → Saint Barthelemy (Gustavia) → Saint Kitts And Nevis (Basse Terre) → Isle De Saintes → Roseau → Saint Vincent And Grenadines (Mayreau) → Bridgetown
Departs
Feb 21, 2026
from
Saint Maarten (Phillipsburg), Netherlands Antilles
Book with Avoya Travel as a member of Windstar’s Yacht Club to receive Past Guest Rewards that may include Savings up to 10% per person, up to $100 Free Onboard Credit, a Private Cocktail Reception PLUS More!
Offer applicable to new bookings only and is combinable with select offers. Please contact an Avoya Travel Windstar Cruises Specialist to see what other offers may be combined with your desired sail date.
Guests are enrolled in the Yacht Club after completion of their first voyage with Windstar Cruises and provided a Yacht Club Number.
Savings up to 10% are per person, in U.S. dollars, apply to select sailings only, are not reflected in the pricing above, and vary by member level and date of booking.
Free Onboard Credit is up to $100 per eligible past guest, in U.S. dollars, applies to select sailings only, applies to qualifying Yacht Club member guests only, and varies by member level.
Additional Past Guest Benefits may vary by membership level and include, but are not limited to, a private onboard member cocktail reception, onboard savings, invitation to dine with the Captain or Ship’s Officers, Refer-a-Friend Rewards, and onboard gifts.
Offer is capacity controlled and subject to change or removal at any time without notice.
Deposit must be made within the booking window for offer to apply.
Select pricing may not be combinable with this promotion.
Prices listed are in U.S. dollars and are cruise only, per person, based on double occupancy, and subject to availability at time of booking.
Additional restrictions may apply, please call an Avoya Windstar Cruises Specialist for more information.
Hurry, this is a limited time offer!
NOTICE: Prior to booking, please consult all applicable U.S. Centers for Disease Control travel advisories, warnings, or recommendations, at cdc.gov/travel/notices. For cruises, if a certain threshold level of COVID-19 is detected onboard the ship during your voyage, the voyage will end immediately, the ship will return to the port of embarkation, and your subsequent travel, including your return home, may be restricted or delayed. Health and safety protocols, guest conduct rules, and regional travel restrictions vary by ship and destination, and are subject to change without notice. Due to evolving health protocols, imagery and messaging may not accurately reflect onboard and destination experiences, offerings, features, or itineraries. These may not be available during your voyage, may vary by ship and destination, and may be subject to change without notice. For other travel, travel suppliers and governments may impose requirements from time to time, such as health affidavit forms, health screenings prior to departure or upon arrival, face coverings, entry restrictions, or quarantines. For the latest COVID-19 government travel regulations, we recommend going to IATA’s website at https://www.iatatravelcentre.com/inter...226297.htm. For the latest travel supplier requirements, check the supplier’s home page. https://www.avoyatravel.com/about/reso...termsofuse