CARIBBEAN CRUISES...The Ultimate Tropical Vacation

Score an Unbeatable Deal on Your Caribbean Cruise

Leave all your stress onshore, and hop on board a Caribbean cruise. No matter where you sail in the Caribbean, you'll find year-round gorgeous weather, pristine beaches, and an array of water sports: diving, snorkeling, boating, surfing, and more. From natural wonders to delicious cuisine and duty-free shopping, you'll experience it all from the comfort of your floating resort.

Spend a long weekend in the Eastern Caribbean on a convenient, fun-filled cruise to St. Thomas or St. John, or take a more leisurely getaway to Western Caribbean hotspots like Costa Maya, Mexico or Ocho Rios, Jamaica. For a more exotic vacation experience, head to the more remote Southern Caribbean islands, where you'll find incredibly pristine beaches in Aruba and Antigua, charming pastel-colored houses in Curacao, and Green Vervet Monkeys in St. Kitts and Nevis.

Comfortable accommodations, world-class entertainment, and fine dining await you no matter which cruise line you choose. With so many fascinating islands to visit, there's no better way to see them all than a convenient, carefree Caribbean cruise. cruises.inspirato.com brings you exclusive offers and savings, so you can sail away with the knowledge that you scored the very best deal on your tropical vacation.

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Sail in Paradise with a Caribbean Cruise
Enjoy year-round sunshine, white sandy beaches, turquoise blue ocean water & more

Caribbean Cruises

Caribbean Cruises

  • SeaDream II
    Brochure price $6,400 – Save up to 69%

    5 Night Caribbean

    5 rating out of 5  (3 reviews)

    SeaDream II

    Departing from: Charlotte Amalie, St. Thomas, U.S.V.I.
    Ports of Call:
    • Cruz Bay, St. John, U.S.V.I.
    • Leverick Bay, Virgin Gorda, B.V.I
    • Spanish Town, Virgin Gorda, B.V.I.
    • Gustavia, St. Barts
    • Jost Van Dyke, B.V.I.
    • San Juan, Puerto Rico
    Sailing Dates:
    • December 2018
    interior from
    N/A
    oceanview from
    $1,999
    $400pernight
    balcony from
    N/A
    suite from
    $3,599
    $720pernight
    Bonus Offers Available:
    • Luxury Sailngs: Up to $1,000 in Travel Credit!
    See Details
  • Riviera
    Brochure price $8,298 – Save up to 76%

    10 Night Sunny Charms

    4.2 rating out of 5  (150 reviews)

    Riviera

    Departing from: Miami, Florida
    Ports of Call:
    • Great Stirrup Cay (Cruiseline Private Island), Bahamas
    • San Juan, Puerto Rico
    • Gustavia, St. Barts
    • Castries, St. Lucia
    • St. John's, Antigua
    • Philipsburg, St. Maarten
    Sailing Dates:
    • February 2019
    • March 2019
    interior from
    $1,999
    $200pernight
    oceanview from
    $2,499
    $250pernight
    balcony from
    $2,899
    $290pernight
    suite from
    $4,099
    $410pernight
    Bonus Offers Available:
    • Luxury Sailngs: Up to $1,000 in Travel Credit!
    • OLife Choice: Choose one of 3 Amenities
    See Details
  • Silver Wind

    7 Night Southern Caribbean

    4 rating out of 5  (7 reviews)

    Silver Wind

    Departing from: Bridgetown, Barbados
    Ports of Call:
    • Bequia, Grenadines
    • Castries, St. Lucia
    • Iles Des Saintes, Guadeloupe
    • St. John's, Antigua
    • Gustavia, St. Barts
    • Road Town, Tortola, B.V.I.
    • San Juan, Puerto Rico
    Sailing Dates:
    • March 2019
    interior from
    N/A
    oceanview from
    N/A
    balcony from
    N/A
    suite from
    $3,400
    $486pernight
    Bonus Offers Available:
    • Luxury Sailngs: Up to $1,000 in Travel Credit!
    See Details
  • Azamara Journey

    10 Night Cuba Intensive

    4.3 rating out of 5  (92 reviews)

    Azamara Journey

    Departing from: Miami, Florida
    Ports of Call:
    • Havana, Cuba
    • Cienfuegos, Cuba
    • Santiago De Cuba, Cuba
    • Labadee (Cruiseline Private Island)
    Sailing Dates:
    • January 2019
    interior from
    $3,099
    $310pernight
    oceanview from
    $3,499
    $350pernight
    balcony from
    $4,199
    $420pernight
    suite from
    $9,439
    $944pernight
    Bonus Offers Available:
    • Luxury Sailngs: Up to $1,000 in Travel Credit!
    • Special requirements for travel to Cuba!
    See Details
  • Riviera
    Brochure price $15,398 – Save up to 75%

    14 Night Caribbean Pearls

    4.2 rating out of 5  (150 reviews)

    Riviera

    Departing from: Miami, Florida
    Ports of Call:
    • Great Stirrup Cay (Cruiseline Private Island), Bahamas
    • San Juan, Puerto Rico
    • Gustavia, St. Barts
    • Fort-De-France, Martinique
    • Bridgetown, Barbados
    • Kingstown, St. Vincent
    • Roseau, Dominica
    • Castries, St. Lucia
    • St. John's, Antigua
    • Philipsburg, St. Maarten
    Sailing Dates:
    • December 2018
    interior from
    $3,799
    $271pernight
    oceanview from
    Call
    balcony from
    Call
    suite from
    $14,699
    $1,050pernight
    Bonus Offers Available:
    • Luxury Sailngs: Up to $1,000 in Travel Credit!
    • OLife Choice: Choose one of 3 Amenities
    See Details
  • Insignia
    Brochure price $19,798 – Save up to 74%

    15 Night Caribbean New Year

    3.9 rating out of 5  (47 reviews)

    Insignia

    Departing from: Miami, Florida
    Ports of Call:
    • Santa Marta, Colombia
    • Oranjestad, Aruba
    • Willemstad, Curacao
    • Kralendijk, Bonaire
    • St. George's, Grenada
    • Castries, St. Lucia
    • Pointe-A-Pitre, Guadeloupe
    • Gustavia, St. Barts
    • San Juan, Puerto Rico
    • New York, New York
    Sailing Dates:
    • December 2018
    interior from
    Call
    oceanview from
    Call
    balcony from
    $5,099
    $340pernight
    suite from
    Call
    Bonus Offers Available:
    • Luxury Sailngs: Up to $1,000 in Travel Credit!
    • OLife Choice: Choose one of 3 Amenities
    • CALL: Free pre-paid gratuities!
    • Call for rates too low to show!
    See Details
  • Seven Seas Voyager
    Brochure price $17,598 – Save up to 57%

    12 Night Holidays and Havana

    4 rating out of 5  (72 reviews)

    Seven Seas Voyager

    Departing from: Miami, Florida
    Ports of Call:
    • San Juan, Puerto Rico
    • St. John's, Antigua
    • Fort-De-France, Martinique
    • Bridgetown, Barbados
    • Castries, St. Lucia
    • Philipsburg, St. Maarten
    • Havana, Cuba
    Sailing Dates:
    • December 2018
    interior from
    N/A
    oceanview from
    N/A
    balcony from
    N/A
    suite from
    $7,499
    $625pernight
    Bonus Offers Available:
    • Luxury Sailngs: Up to $1,000 in Travel Credit!
    • Special requirements for travel to Cuba!
    See Details
Caribbean Cruises
Departure Ports for Caribbean Cruises:
Baltimore, MD
Bayonne, NJ
Boston, MA
Charleston, SC
Fort Lauderdale, FL
Galveston, TX
Houston, TX
About Caribbean

Search Cruise Lines Traveling to Caribbean:

Azamara Club Cruises from $1,099
Crystal Cruises from $4,340
Cunard from $1,299
Oceania Cruises from $1,499
Regent Seven Seas Cruises from $3,599
Seabourn from $3,299
Silversea Cruises from $2,900

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Terms & Conditions

Price is in U.S. dollars per person based on two people staying in the same stateroom. Price does not include airport and/or government taxes and fees, nor does pricing include fuel supplements. Prices do not include government taxes and fees, airfare, or a non-refundable $24.99 processing fee per booking. All offers are for selected dates only, are subject to availability, are limited and apply to new bookings only. Your exact price depends on the time of the actual booking. Additional restrictions may apply. All prices and dates may not be available at the time of booking. Passengers receiving special rates based on residency or age will be required to show a government-issued form of identification (passport, or birth certificate and driver's license) at the pier to validate state of residency or age prior to boarding the cruise ship.

Special requirements
If you or a guest is pregnant or traveling with an infant child, or if there is a need to communicate a request for special meals, medical conditions or physical challenges, we ask that you please call 800-895-3771. Cruise Specialists are available 24 hours a day, 7 days a week. We will do everything we can to meet your needs and answer all of your questions.

Minimum age requirements may apply.
Free upgrade!

Book an eligible stateroom on any qualifying sailing and receive a free upgrade! In some cases, you'll be upgraded to a more desirable location aboard your ship. In other instances, you'll be upgraded to a stateroom with extra space and/or a better view. It's also possible that you might receive all of these benefits. Select your sailing date to see which upgrades are available.