Avoya Travel will match or beat any competitor’s best deal! We combine our exclusive offers with Windstar Cruises’ top offers to ensure you get the best possible deal on your desired sail date.
Exclusive Avoya Offers: These exclusive deals can be combined with many of Windstar Cruises’ offers.
Saint Maarten (Phillipsburg) → Saint Kitts And Nevis (Basse Terre) → Saint Barthelemy (Gustavia) → San Jose → Isle De Saintes → Saint Vincent And Grenadines (Mayreau) → Saint Vincent And Grenadines (Kingstown) → Bridgetown
Saint Maarten (Phillipsburg) → Saint Kitts And Nevis (Basse Terre) → Saint Barthelemy (Gustavia) → San Jose → Isle De Saintes → Saint Vincent And Grenadines (Mayreau) → Saint Vincent And Grenadines (Kingstown) → Bridgetown
Departs
Jan 11, 2026
from
Saint Maarten (Phillipsburg), Netherlands Antilles
Saint Maarten (Phillipsburg) → Saint Kitts And Nevis (Basse Terre) → Saint Barthelemy (Gustavia) → San Jose → Isle De Saintes → Saint Vincent And Grenadines (Mayreau) → Saint Vincent And Grenadines (Kingstown) → Bridgetown → Anse Mitan → Casablanca → Saint Lucia (Pigeon) → Saint Vincent And Grenadines (Bequia) → Saint George's
Saint Maarten (Phillipsburg) → Saint Kitts And Nevis (Basse Terre) → Saint Barthelemy (Gustavia) → San Jose → Isle De Saintes → Saint Vincent And Grenadines (Mayreau) → Saint Vincent And Grenadines (Kingstown) → Bridgetown → Anse Mitan → Casablanca → Saint Lucia (Pigeon) → Saint Vincent And Grenadines (Bequia) → Saint George's
Departs
Jan 11, 2026
from
Saint Maarten (Phillipsburg), Netherlands Antilles
Saint Maarten (Phillipsburg) → Saint Kitts And Nevis (Basse Terre) → Roseau → Casablanca → Anse Mitan → Isle De Saintes → Saint Kitts And Nevis (Charlestown) → Virgin Gorda → Jost Van Dyke → Saint Barthelemy (Gustavia) → Saint Maarten (Phillipsburg)
Saint Maarten (Phillipsburg) → Saint Kitts And Nevis (Basse Terre) → Roseau → Casablanca → Anse Mitan → Isle De Saintes → Saint Kitts And Nevis (Charlestown) → Virgin Gorda → Jost Van Dyke → Saint Barthelemy (Gustavia) → Saint Maarten (Phillipsburg)
Departs
Jan 14, 2026
from
Saint Maarten (Phillipsburg), Netherlands Antilles
Saint Maarten (Phillipsburg) → Saint Kitts And Nevis (Basse Terre) → Roseau → Casablanca → Anse Mitan → Isle De Saintes → Saint Kitts And Nevis (Charlestown) → Virgin Gorda → Jost Van Dyke → Saint Barthelemy (Gustavia) → San Jose → Road Bay → Soper's Hole → Saint Maarten (Phillipsburg)
Saint Maarten (Phillipsburg) → Saint Kitts And Nevis (Basse Terre) → Roseau → Casablanca → Anse Mitan → Isle De Saintes → Saint Kitts And Nevis (Charlestown) → Virgin Gorda → Jost Van Dyke → Saint Barthelemy (Gustavia) → San Jose → Road Bay → Soper's Hole → Saint Maarten (Phillipsburg)
Departs
Jan 14, 2026
from
Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals
including an Avoya Exclusive
Oceanview From
$6,699
Top Picks Rank:
8
8-night caribbean cruise
$5,849
Windstar Cruises –
Star Seeker
Date:
Jan 15, 2026
Ports:
Miami → Puerto Plata → Samana → Jost Van Dyke → Virgin Gorda → Soper's Hole → San Juan
Bridgetown → Anse Mitan → Casablanca → Saint Lucia (Pigeon) → Saint Vincent And Grenadines (Bequia) → Saint Vincent And Grenadines (Mayreau) → Saint George's → Bridgetown
Bridgetown → Anse Mitan → Casablanca → Saint Lucia (Pigeon) → Saint Vincent And Grenadines (Bequia) → Saint Vincent And Grenadines (Mayreau) → Saint George's → Bridgetown
Bridgetown → Anse Mitan → Casablanca → Saint Lucia (Pigeon) → Saint Vincent And Grenadines (Bequia) → Saint Vincent And Grenadines (Mayreau) → Saint George's → Saint Lucia (Soufriere) → Kralendijk → Willemstad → Oranjestad
Bridgetown → Anse Mitan → Casablanca → Saint Lucia (Pigeon) → Saint Vincent And Grenadines (Bequia) → Saint Vincent And Grenadines (Mayreau) → Saint George's → Saint Lucia (Soufriere) → Kralendijk → Willemstad → Oranjestad
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) → 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
Jan 24, 2026
from
Saint Maarten (Phillipsburg), Netherlands Antilles
Bridgetown → Saint Vincent And Grenadines (Bequia) → Saint Vincent And Grenadines (Mayreau) → Saint Lucia (Soufriere) → Kralendijk → Willemstad → Oranjestad
Bridgetown → Saint Vincent And Grenadines (Bequia) → Saint Vincent And Grenadines (Mayreau) → Saint Lucia (Soufriere) → Kralendijk → Willemstad → Oranjestad
Bridgetown → Saint Vincent And Grenadines (Bequia) → Saint Vincent And Grenadines (Mayreau) → Saint Lucia (Soufriere) → Kralendijk → Willemstad → Oranjestad → Cartagena → Bocas Del Toro → Colon
Bridgetown → Saint Vincent And Grenadines (Bequia) → Saint Vincent And Grenadines (Mayreau) → Saint Lucia (Soufriere) → Kralendijk → Willemstad → Oranjestad → Cartagena → Bocas Del Toro → Colon
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
Terms and Conditions vary by offer. To view the Terms and Conditions of the promotions listed, please refer to the individual links above.
Offers apply to new bookings only.
Offers vary in combinability and applicable sailings; not all offers listed may be combinable with each other. Please contact an Avoya Travel Windstar Cruises Specialist for more information.
Offers are capacity controlled and subject to change or removal at any time without prior notice.
Deposit may be required within an offer’s booking window to qualify.
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 Travel Windstar Cruises Specialist for more information.
Prior to booking, we strongly recommend reviewing both the U.S. State Department and U.S. Centers For Disease Control travel advisories. The State Department and Centers for Disease Control provide valuable, up-to-date information on safety and health conditions, visa requirements, and other important factors that may affect your trip.