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.

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

Caribbean Cruises

Caribbean Cruises

  • Queen Mary 2

    13 Night Eastern Caribbean

    4.1 rating out of 5  (268 reviews)

    Queen Mary 2

    Departing from: New York, New York
    Ports of Call:
    • Charlotte Amalie, St. Thomas, U.S.V.I.
    • English Harbour, Antigua
    • Bridgetown, Barbados
    • Castries, St. Lucia
    • Philipsburg, St. Maarten
    • Tortola, British Virgin Islands
    Sailing Dates:
    • November 2018
    interior from
    $1,199
    $92pernight
    oceanview from
    $1,399
    $108pernight
    balcony from
    $1,399
    $108pernight
    suite from
    $6,399
    $492pernight
  • SeaDream II
    Brochure price $6,400 – Save up to 69%

    5 Night Caribbean

    5 rating out of 5  (2 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
  • Riviera
    Brochure price $6,698 – Save up to 72%

    10 Night Sunny Charms

    4.2 rating out of 5  (142 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:
    • December 2018
    • January 2019
    • February 2019
    • March 2019
    interior from
    $1,899
    $190pernight
    oceanview from
    $2,299
    $230pernight
    balcony from
    $2,499
    $250pernight
    suite from
    $3,699
    $370pernight
    Bonus Offers Available:
    • OLife Choice: Choose one of 3 Amenities
    • CALL: Free pre-paid gratuities!
  • Azamara Journey

    4 Night Havana Intensive

    4.3 rating out of 5  (86 reviews)

    Azamara Journey

    Departing from: Miami, Florida
    Ports of Call:
    • Havana, Cuba
    Sailing Dates:
    • November 2018
    interior from
    $2,699
    $675pernight
    oceanview from
    $3,199
    $800pernight
    balcony from
    $3,899
    $975pernight
    suite from
    Call
    Bonus Offers Available:
    • Special requirements for travel to Cuba!
  • Riviera
    Brochure price $9,498 – Save up to 71%

    12 Night Balmy Breezes

    4.2 rating out of 5  (142 reviews)

    Riviera

    Departing from: Miami, Florida
    Ports of Call:
    • Oranjestad, Aruba
    • Kralendijk, Bonaire
    • St. George's, Grenada
    • Bridgetown, Barbados
    • Castries, St. Lucia
    • Basseterre, St. Kitts
    • Philipsburg, St. Maarten
    Sailing Dates:
    • November 2018
    interior from
    Call
    oceanview from
    $2,799
    $233pernight
    balcony from
    $2,999
    $250pernight
    suite from
    $4,699
    $392pernight
    Bonus Offers Available:
    • OLife Choice: Choose one of 3 Amenities
    • CALL: Free pre-paid gratuities!
  • Azamara Journey

    10 Night Cuba Intensive

    4.3 rating out of 5  (86 reviews)

    Azamara Journey

    Departing from: Miami, Florida
    Ports of Call:
    • Key West, Florida
    • Havana, Cuba
    • George Town, Grand Cayman
    • Cienfuegos, Cuba
    • Santiago De Cuba, Cuba
    Sailing Dates:
    • December 2018
    interior from
    Call
    oceanview from
    $2,799
    $280pernight
    balcony from
    Call
    suite from
    Call
    Bonus Offers Available:
    • Special requirements for travel to Cuba!
  • Silver Wind

    7 Night Southern Caribbean

    4 rating out of 5  (5 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
    $3,510
    $501pernight
    Bonus Offers Available:
    • Book Early and Save 10% Per Person: CALL!
    • BONUS: Up to $200 FREE Onboard Credit - CALL
  • Azamara Journey

    10 Night Circle Cuba

    4.3 rating out of 5  (86 reviews)

    Azamara Journey

    Departing from: Miami, Florida
    Ports of Call:
    • Santiago De Cuba, Cuba
    • George Town, Grand Cayman
    • Cienfuegos, Cuba
    • Havana, Cuba
    Sailing Dates:
    • November 2018
    interior from
    $2,599
    $260pernight
    oceanview from
    $2,399
    $240pernight
    balcony from
    $3,999
    $400pernight
    suite from
    Call
    Bonus Offers Available:
    • Special requirements for travel to Cuba!
  • Azamara Journey

    10 Night Cuba Intensive

    4.3 rating out of 5  (86 reviews)

    Azamara Journey

    Departing from: Miami, Florida
    Ports of Call:
    • Havana, Cuba
    • Cienfuegos, Cuba
    • Santiago De Cuba, Cuba
    • Labadee (Cruiseline Private Island)
    Sailing Dates:
    • November 2018
    • January 2019
    interior from
    $3,099
    $310pernight
    oceanview from
    $2,199
    $220pernight
    balcony from
    Call
    suite from
    $7,149
    $715pernight
    Bonus Offers Available:
    • EXCLUSIVE: Limited Time Reduced Rates!
    • Special requirements for travel to Cuba!
  • Riviera
    Brochure price $14,798 – Save up to 76%

    14 Night Caribbean Pearls

    4.2 rating out of 5  (142 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
    $3,499
    $250pernight
    oceanview from
    $4,499
    $321pernight
    balcony from
    $5,149
    $368pernight
    suite from
    Call
    Bonus Offers Available:
    • OLife Choice: Choose one of 3 Amenities
  • Insignia
    Brochure price $19,798 – Save up to 74%

    15 Night Caribbean New Year

    3.8 rating out of 5  (45 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:
    • OLife Choice: Choose one of 3 Amenities
    • CALL: Free pre-paid gratuities!
    • Call for rates too low to show!
  • Seven Seas Voyager
    Brochure price $11,098 – Save up to 61%

    10 Night Sage Mountain to Grand Pitons

    4 rating out of 5  (69 reviews)

    Seven Seas Voyager

    Departing from: Miami, Florida
    Ports of Call:
    • Tortola, British Virgin Islands
    • St. John's, Antigua
    • Bridgetown, Barbados
    • Castries, St. Lucia
    • Gustavia, St. Barts
    Sailing Dates:
    • November 2018
    interior from
    N/A
    oceanview from
    N/A
    balcony from
    N/A
    suite from
    $4,299
    $430pernight
    Bonus Offers Available:
    • Up to $200 FREE Onboard Spending - CALL
  • Crystal Esprit

    7 Night West Indies Yachting Explorer

    Crystal Esprit

    Departing from: Marigot, Saint Martin
    Ports of Call:
    • Sandy Ground, Anguilla
    • Saba, Netherlands Special Municipality
    • Falmouth, Antigua
    • Coconut Grove, Nevis
    • Gustavia, St. Barts
    • Orient Bay, Saint Martin
    Sailing Dates:
    • November 2018
    • December 2018
    interior from
    N/A
    oceanview from
    N/A
    balcony from
    N/A
    suite from
    $4,455
    $636pernight
  • Seven Seas Voyager
    Brochure price $17,198 – Save up to 58%

    12 Night Holidays and Havana

    4 rating out of 5  (69 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
    $7,299
    $608pernight
    Bonus Offers Available:
    • Up to $200 FREE Onboard Spending - CALL
    • Special requirements for travel to Cuba!
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

More Ways to Find Cruise Deals
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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.