Windstar Cruises
Up to $300 to Spend on Board
Save 5% on a tropical escape to Tahiti
Here's Why You Should Always Book With Freer & Associates - Dream Vacations
  • You May Qualify for One or More Windstar Cruises Offers
Plus, We Make You Our Priority.
As your full-service Travel Advisors, we're committed to offering you the best deals and experience when you book with us. Learn more.
Recommended Windstar Cruises

Our Featured Deals

  • Star Legend
    4.4 rating out of 5  (25 reviews)

    7 Night Europes Winter Riviera

    Star Legend

    Departing from: Barcelona, Spain
    Ports of Call:
    • Marseille (Provence), France
    • Nice, France
    • Genoa (Portofino), Italy
    • Livorno (Florence & Pisa), Italy
    • Civitavecchia (Rome), Italy
    Sailing Dates:
    • January 2025
    • February 2025
    • March 2025
    interior from
    Not Available
    oceanview from
    Not Available
    balcony from
    Not Available
    suite from
    $2,366
    $338pernight
    All the Cruise Line Offers & More:
    • Pick Your Perk: Up to $1,000 to Spend and More
    • Exclusive: Up to $300 to Spend on Board
    • Call for rates too low to show!
     
    Suite from $2,366
    ($338pernight)
    4.4 rating out of 5  (25 reviews)
  • Wind Surf
    4.4 rating out of 5  (78 reviews)

    7 Night Classic Caribbean

    Wind Surf

    Departing from: Philipsburg, St. Maarten
    Ports of Call:
    • Charlestown, Nevis
    • Roseau, Dominica
    • Pigeon Island, St. Lucia
    • Iles Des Saintes, Guadeloupe
    • Gustavia, St. Barts
    • Basseterre, St. Kitts
    Sailing Dates:
    • January 2025
    • December 2025
    • February 2026
    • March 2026
    interior from
    Not Available
    oceanview from
    $2,419
    $346pernight
    balcony from
    Not Available
    suite from
    $5,319
    $760pernight
    All the Cruise Line Offers & More:
    • Pick Your Perk: Up to $1,000 to Spend and More
    • Exclusive: Up to $300 to Spend on Board
    • Call for rates too low to show!
     
    Oceanview from $2,419
    ($346pernight)
    4.4 rating out of 5  (78 reviews)
  • Star Breeze
    4.4 rating out of 5  (40 reviews)

    10 Night Tahiti & the Tuamotu Islands

    Star Breeze

    Departing from: Papeete, Tahiti
    Ports of Call:
    • Fakarava, Tuamotu Archipelago
    • Rangiroa, French Polynesia
    • Taha'a, Society Islands
    • Bora Bora, French Polynesia
    • Huahine, French Polynesia
    • Moorea, French Polynesia
    Sailing Dates:
    • May 2025
    • August 2025
    • November 2025
    • December 2025
    • May 2026
    interior from
    Not Available
    oceanview from
    Not Available
    balcony from
    Not Available
    suite from
    $4,715
    $472pernight
    All the Cruise Line Offers & More:
    • Limited-Time: Up to 5% Bonus Savings
    • Pick Your Perk: Up to $1,000 to Spend and More
    • Exclusive: Up to $300 to Spend on Board
     
    Suite from $4,715
    ($472pernight)
    4.4 rating out of 5  (40 reviews)

New Ship: Star Seeker

  • Star Seeker

    8 Night Creatures & Cultures of Costa Rica & Mexico

    Star Seeker - New Ship!

    Departing from: Puerto Caldera (Puntarenas), Costa Rica
    Ports of Call:
    • Curu (Reserve), Costa Rica
    • Playas Del Coco, Costa Rica
    • Puerto Chiapas (Tapachula), Mexico
    • Huatulco, Mexico
    • Manzanillo, Mexico
    • Puerto Vallarta, Mexico
    Sailing Dates:
    • April 2026
    interior from
    Not Available
    oceanview from
    Not Available
    balcony from
    Not Available
    suite from
    $3,704
    $463pernight
    All the Cruise Line Offers & More:
    • Pick Your Perk: Up to $1,000 to Spend and More
    • Exclusive: Up to $300 to Spend on Board
     
    Suite from $3,704
    ($463pernight)
  • Star Seeker

    7 Night Scenic Alaska

    Star Seeker - New Ship!

    Departing from: Vancouver (Canada Place), British Columbia
    Ports of Call:
    • Cruise Misty Fjords, Alaska
    • Ketchikan, Alaska
    • Sitka, Alaska
    • Haines, Alaska
    • Juneau, Alaska
    Sailing Dates:
    • July 2026
    interior from
    Not Available
    oceanview from
    Not Available
    balcony from
    Not Available
    suite from
    $5,441
    $777pernight
    All the Cruise Line Offers & More:
     
    Suite from $5,441
    ($777pernight)

South Pacific Windstar Cruises

Experience breathtaking beaches and unbeatable cuisine on a Windstar South Pacific cruise. Explore new islands each day and receive complimentary onboard perks on Windstar South Pacific cruises, including these Windstar cruises:
  • Star Breeze
    4.4 rating out of 5  (40 reviews)

    11 Night Tahiti & the Tuamotu Islands

    Star Breeze

    Departing from: Papeete, Tahiti
    Ports of Call:
    • Fakarava, Tuamotu Archipelago
    • Rangiroa, French Polynesia
    • Taha'a, Society Islands
    • Raiatea, French Polynesia
    • Bora Bora, French Polynesia
    • Huahine, French Polynesia
    • Moorea, French Polynesia
    Sailing Dates:
    • July 2025
    interior from
    Not Available
    oceanview from
    Not Available
    balcony from
    Not Available
    suite from
    $5,417
    $492pernight
    All the Cruise Line Offers & More:
    • Limited-Time: Up to 5% Bonus Savings
    • Pick Your Perk: Up to $1,000 to Spend and More
     
    Suite from $5,417
    ($492pernight)
    4.4 rating out of 5  (40 reviews)
  • Star Breeze
    4.4 rating out of 5  (40 reviews)

    14 Night Tahitian Treasures & Magnificent Marquesas

    Star Breeze

    Departing from: Papeete, Tahiti
    Ports of Call:
    • Fakarava, Tuamotu Archipelago
    • Fatu Hiva, Marquesas
    • Atuona, Hiva Oa, Marquesas
    • Taiohae, Nuku Hiva, Marquesas
    • Rangiroa, French Polynesia
    • Taha'a, Society Islands
    • Bora Bora, French Polynesia
    • Moorea, French Polynesia
    Sailing Dates:
    • March 2025
    • June 2025
    • September 2025
    interior from
    Not Available
    oceanview from
    Not Available
    balcony from
    Not Available
    suite from
    $7,518
    $537pernight
    All the Cruise Line Offers & More:
    • Limited-Time: Up to 5% Bonus Savings
    • Pick Your Perk: Up to $1,000 to Spend and More
     
    Suite from $7,518
    ($537pernight)
    4.4 rating out of 5  (40 reviews)

Caribbean Windstar Cruises

Set sail for a destination that's far from ordinary aboard a luxury cruise line that will let you indulge in paradise the right way. When you sail with Windstar to the Caribbean, not only are you guaranteed some of the... finest sun, surf and sand – you're also sure to have the ultimate of luxury cruising experiences. If your Windstar Caribbean cruise takes you through St. George's, be sure to browse the colorful open-air markets. Explore the lush forests and vegetation that make St. Lucia such a popular, yet pristine, tropical destination. Don't forget your camera, and be sure to take pictures of "The Baths" in Virgin Gorda. Most Windstar Caribbean cruises range between 7 and 14 nights, so be sure to take the time to explore all the wonders that paradise has to offer.

  • Wind Surf
    4.4 rating out of 5  (78 reviews)

    7 Night Beach Fun & Sun: A Remote Caribbean Getaway

    Wind Surf

    Departing from: Philipsburg, St. Maarten
    Ports of Call:
    • Falmouth, Antigua
    • Road Bay, Anguilla
    • Soper's Hole, Tortola, B.V.I.
    • Great Harbour, Jost Van Dyke, B.V.I.
    • Virgin Gorda, B.V.I.
    • Gustavia, St. Barts
    Sailing Dates:
    • December 2024
    • January 2025
    • March 2025
    • December 2025
    • March 2026
    interior from
    Not Available
    oceanview from
    $2,447
    $350pernight
    balcony from
    Not Available
    suite from
    $5,394
    $771pernight
    All the Cruise Line Offers & More:
    • Pick Your Perk: Up to $1,000 to Spend and More
    • Exclusive: Up to $300 to Spend on Board
    • Call for rates too low to show!
     
    Oceanview from $2,447
    ($350pernight)
    4.4 rating out of 5  (78 reviews)
  • Star Pride
    4.4 rating out of 5  (39 reviews)

    7 Night Windward Ways & Tobago Cays

    Star Pride

    Departing from: Oranjestad, Aruba
    Ports of Call:
    • Willemstad, Curacao
    • Kralendijk, Bonaire
    • Soufriere, St. Lucia
    • Mayreau, Grenadines
    • Man-O-War Bay, Charlotteville, Trinidad & Tobago
    • Bridgetown, Barbados
    Sailing Dates:
    • January 2025
    • March 2025
    interior from
    Not Available
    oceanview from
    Not Available
    balcony from
    Not Available
    suite from
    $3,219
    $460pernight
    All the Cruise Line Offers & More:
    • Pick Your Perk: Up to $1,000 to Spend and More
    • Exclusive: Up to $300 to Spend on Board
    • Call for rates too low to show!
     
    Suite from $3,219
    ($460pernight)
    4.4 rating out of 5  (39 reviews)

Departure Ports for Caribbean Windstar Cruises:

Canada/New England Windstar Cruises

  • Star Pride
    4.4 rating out of 5  (39 reviews)

    11 Night Southeast Canadian Explorations

    Star Pride

    Departing from: Boston, Massachusetts
    Ports of Call:
    • Portland, Maine
    • Bar Harbor, Maine
    • Lunenburg, Nova Scotia
    • Halifax, Nova Scotia
    • Louisbourg, Nova Scotia
    • Cap-Aux-Meules, Quebec
    • Gaspe, Quebec
    • Quebec City, Quebec
    • Montreal, Quebec, Canada
    Sailing Dates:
    • September 2025
    interior from
    Not Available
    oceanview from
    Not Available
    balcony from
    Not Available
    suite from
    $5,995
    $545pernight
    All the Cruise Line Offers & More:
    • Pick Your Perk: Up to $1,000 to Spend and More
    • Exclusive: Up to $300 to Spend on Board
     
    Suite from $5,995
    ($545pernight)
    4.4 rating out of 5  (39 reviews)
  • Star Pride
    4.4 rating out of 5  (39 reviews)

    11 Night Southeast Canadian Explorations

    Star Pride

    Departing from: Montreal, Quebec, Canada
    Ports of Call:
    • Quebec City, Quebec
    • Gaspe, Quebec
    • Cap-Aux-Meules, Quebec
    • Louisbourg, Nova Scotia
    • Halifax, Nova Scotia
    • Lunenburg, Nova Scotia
    • Bar Harbor, Maine
    • Portland, Maine
    • Boston, Massachusetts
    Sailing Dates:
    • September 2025
    interior from
    Not Available
    oceanview from
    Not Available
    balcony from
    Not Available
    suite from
    $6,195
    $563pernight
    All the Cruise Line Offers & More:
    • Pick Your Perk: Up to $1,000 to Spend and More
    • Exclusive: Up to $300 to Spend on Board
     
    Suite from $6,195
    ($563pernight)
    4.4 rating out of 5  (39 reviews)

Europe Windstar Cruises

If you've been looking for the perfect way to explore Europe, look no further than a Windstar luxury cruise. Known for providing one-of-a-kind resort-type experiences at sea, you're guaranteed personalized service, pampering and the utmost of comfort and style onboard... every Windstar cruise. Perhaps you'll have the opportunity to see the vast Acropolis of Athens. Maybe your cruise will take you to the breathtaking palaces of Istanbul. Enjoy a decadent cup of some of the finest coffee in the world in Bodrum. Wherever your Windstar European cruise takes you, you're sure to have adventures and memories that will last a lifetime.

  • Star Legend
    4.4 rating out of 5  (25 reviews)

    7 Night Southern Spain Winter Escapes

    Star Legend

    Departing from: Barcelona, Spain
    Ports of Call:
    • Palma De Mallorca, Balearic Islands
    • Valencia, Spain
    • Cartagena, Spain
    • Gibraltar (U.K.)
    • Malaga (Granada), Spain
    Sailing Dates:
    • November 2025
    interior from
    Not Available
    oceanview from
    Not Available
    balcony from
    Not Available
    suite from
    $2,442
    $349pernight
    All the Cruise Line Offers & More:
    • Pick Your Perk: Up to $1,000 to Spend and More
     
    Suite from $2,442
    ($349pernight)
    4.4 rating out of 5  (25 reviews)
  • Wind Spirit
    4.5 rating out of 5  (20 reviews)

    9 Night Adriatic Icons & Venetian Treasures

    Wind Spirit

    Departing from: Venice, Italy
    Ports of Call:
    • Rovinj, Croatia
    • Zadar, Croatia
    • Hvar, Croatia
    • Dubrovnik, Croatia
    • Kotor, Montenegro
    • Piran, Slovenia
    Sailing Dates:
    • July 2025
    • August 2025
    interior from
    Not Available
    oceanview from
    $3,507
    $390pernight
    balcony from
    Not Available
    suite from
    $8,007
    $890pernight
    All the Cruise Line Offers & More:
    • Pick Your Perk: Up to $1,000 to Spend and More
    • Exclusive: Up to $300 to Spend on Board
     
    Oceanview from $3,507
    ($390pernight)
    4.5 rating out of 5  (20 reviews)
  • Wind Spirit
    4.5 rating out of 5  (20 reviews)

    7 Night Mediterranean Island Mosaic

    Wind Spirit

    Departing from: Civitavecchia (Rome), Italy
    Ports of Call:
    • Portoferraio, Elba
    • Bastia, Corsica, France
    • Calvi, Corsica
    • Mahon (Mao), Menorca, Balearic Islands
    • Palma De Mallorca, Balearic Islands
    • Barcelona, Spain
    Sailing Dates:
    • October 2025
    interior from
    Not Available
    oceanview from
    $3,198
    $457pernight
    balcony from
    Not Available
    suite from
    Call for availability
    All the Cruise Line Offers & More:
    • Pick Your Perk: Up to $1,000 to Spend and More
    • Exclusive: Up to $300 to Spend on Board
     
    Oceanview from $3,198
    ($457pernight)
    4.5 rating out of 5  (20 reviews)
  • Wind Surf
    4.4 rating out of 5  (78 reviews)

    8 Night Classic Italy & Dalmatian Coast

    Wind Surf

    Departing from: Venice, Italy
    Ports of Call:
    • Rovinj, Croatia
    • Split, Croatia
    • Dubrovnik, Croatia
    • Kotor, Montenegro
    • Giardini Di Naxos (Taormina), Sicily, Italy
    • Sorrento/Capri, Italy
    • Civitavecchia (Rome), Italy
    Sailing Dates:
    • May 2025
    • September 2025
    • October 2025
    • May 2026
    • July 2026
    • August 2026
    interior from
    Not Available
    oceanview from
    $4,047
    $506pernight
    balcony from
    Not Available
    suite from
    $5,567
    $696pernight
    All the Cruise Line Offers & More:
    • Pick Your Perk: Up to $1,000 to Spend and More
    • Exclusive: Up to $300 to Spend on Board
     
    Oceanview from $4,047
    ($506pernight)
    4.4 rating out of 5  (78 reviews)
  • Wind Star
    4.5 rating out of 5  (17 reviews)

    7 Night Treasures of the Greek Isles

    Wind Star

    Departing from: Piraeus (Athens), Greece
    Ports of Call:
    • Mykonos, Greece
    • Kusadasi (Ephesus), Turkey
    • Patmos, Greece
    • Santorini (Thira), Greece
    • Monemvasia, Greece
    • Nafplion (Nauplion), Greece
    Sailing Dates:
    • May 2025
    • June 2025
    • July 2025
    • August 2025
    • September 2025
    interior from
    Not Available
    oceanview from
    $4,931
    $704pernight
    balcony from
    Not Available
    suite from
    $8,431
    $1,204pernight
    All the Cruise Line Offers & More:
    • Pick Your Perk: Up to $1,000 to Spend and More
    • Exclusive: Up to $300 to Spend on Board
     
    Oceanview from $4,931
    ($704pernight)
    4.5 rating out of 5  (17 reviews)

Windstar Cruises...Five-Star Vacations at Sea

Book Your Luxury Cruise with Windstar Cruises & Freer & Associates - Dream Vacations

Relax, unwind and sail away aboard the ultimate in luxury accommodations with Windstar Cruises. Each Windstar cruise ship is designed to provide an intimate cruising experience with an average of just 148 guests per ship, all the while providing the luxury and services you’d expect from a larger cruise line. These elegant, streamlined ships afford you the opportunity to wine, dine and dance your days away at exotic destinations such as Santorini, Barbados and Portofino. All staterooms are elegantly and tastefully decorated to provide the comforts of home, as well as the benefits of lavish resorts including queen-sized beds, granite vanities and Bose speakers, plus picturesque oceanview windows in every room.

Mealtimes aboard Windstar Cruises are nothing short of spectacular. Choose open-seating for dinner under the stars at Candles, or indulge in a delicious meal at The Restaurant, both of which offer five-star dining and hand-selected wines to complement your meal. After dinner, treat yourself to a nightcap at the piano bar and a game of luck at the onboard casino. Or, simply relax on deck and enjoy live music and the gorgeous night skies of paradise.

Begin your day with a refreshing dip in the sparkling waters of the cooling saltwater pool, or simply soak in the warm sun on one of the many comfortable chaise lounges. With the ocean as your backyard, there’s never been a better time to try kayaking, windsurfing or even waterskiing from the onboard Watersports platform. After a long day of ocean adventures, let your cares melt away with a soothing and indulgent aromatherapy massage at the WindSpa.

Choose your own adventures with Windstar Cruises. With voyages averaging between 7 and 13 days, it’s easy to build your own dream vacation. Take a stunning holiday in the Greek Isles, and visit breathtaking cities like Mykonos, Athens and Istanbul. If the tropics are more your flavor, take advantage of a dazzling weeklong sailing through the Windward Islands and visit the exotic Tobago Cays, open-air markets of St. George’s and more. Make memories that will last a lifetime with Windstar Cruises. Let Freer & Associates - Dream Vacations help you plan the perfect cruise today!