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Relax in the Caribbean with 50% Off Cruise Upgrades & More

In 2026–2027, escape the winter chill in favor of sun-soaked Caribbean beaches on a Holland America cruise. The cruise line’s onboard Signature Pool Experience offers ambient live music, curated drink service, and serene vibes at the adults-only outdoor Sea View Pool, creating the perfect setting in which to unwind and connect. Experience effortless relaxation on the white-sand shores of RelaxAway, Half Moon Cay™ — Holland America’s private island deep in the heart of the Bahamas, included on nearly all Caribbean itineraries and boasting exciting new upgrades including pickleball courts and more. Book during Holland America’s Travel by Sea Sale and receive free prepaid Crew Appreciation, up to $300 Onboard Credit per stateroom, and more!

Expedia® Extras*

Reserve a 2026–2027 Holland America Caribbean cruise by July 23, 2026, and enjoy the following:

* Travel by Sea Sale*
        o CARIBBEAN BONUS Up to $300 Onboard Credit when you book a Verandah stateroom or Suite with code CBBONUS26.
        o FREE Prepaid Crew Appreciation
        o FREE Kids’ Fares
        o 50% Reduced Deposit
        o Have It All Package
                  *  Up to $300 Shore Excursion Credit
                  *  Up to Three Nights of Specialty Dining
                  *  Signature Beverage Package
                  *  Surf Wi-Fi Package

From live steel drum performances and fresh island flavors to exclusive shore excursions curated with the HISTORY® Channel, Holland America’s Caribbean cruises offer a more authentic, unhurried experience designed for discovery and destination immersion. Plus, with convenient weekend departures and more 9+ day sailings than any other cruise line, Holland America makes it easy to discover the unique history, culture, and character of the islands. In 2026–2027, explore beyond the beach and experience the Caribbean refreshingly free of amusement parks, overcrowded beaches, and boring buffets. Contact us today so we can help you save big and plan the ultimate Caribbean cruise vacation with Holland America.

*Fares are based on Promo(s) VH/OL*. Ships’ Registry: The Netherlands.

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Featured Deals

  • 7 night Caribbean Cruise

    7 night Caribbean Cruise
    Depart: Sat, Dec 5, 2026
    Returns: Sat, Dec 12, 2026
    Depart – Miami, United States
    Miami, Florida, US | Grand Turk, Turks and Caicos | San Juan, Puerto Rico | St Thomas, USVI | RelaxAway Half Moon Cay, Bahamas | Miami, Florida, US
    Returns – Miami, United States
    Miami, Florida, US | Grand Turk, Turks and Caicos | San Juan, Puerto Rico | St Thomas, USVI | RelaxAway Half Moon Cay, Bahamas | Miami, Florida, US
    Expedia® Extras* (Extras vary and apply to select staterooms and prices)
    • Have It All - Includes Drinks, Shore Excursions, Dining, and Wi-Fi
    • Up to 50% Off
    • Up to $200 Onboard Credit per stateroom
    • show more 
    from
    $728* CAD
    Taxes & fees included
  • 7 night Caribbean Cruise

    7 night Caribbean Cruise
    Depart: Sat, Nov 28, 2026
    Returns: Sat, Dec 5, 2026
    Depart – Ft Lauderdale, United States
    Fort Lauderdale, Florida, US | Grand Turk, Turks and Caicos | San Juan, Puerto Rico | St Thomas, USVI | RelaxAway Half Moon Cay, Bahamas | Fort Lauderdale, Florida, US
    Returns – Ft Lauderdale, United States
    Fort Lauderdale, Florida, US | Grand Turk, Turks and Caicos | San Juan, Puerto Rico | St Thomas, USVI | RelaxAway Half Moon Cay, Bahamas | Fort Lauderdale, Florida, US
    Expedia® Extras* (Extras vary and apply to select staterooms and prices)
    • Exclusive! $50 Onboard Credit & Pinnacle Grill Lunch
    • Have It All - Includes Drinks, Shore Excursions, Dining, and Wi-Fi
    • Up to 50% Off
    • show more 
    from
    $785* CAD
    Taxes & fees included
  • 7 night Caribbean Cruise

    7 night Caribbean Cruise
    Depart: Sat, Oct 24, 2026
    Returns: Sat, Oct 31, 2026
    Depart – Ft Lauderdale, United States
    Fort Lauderdale, Florida, US | RelaxAway Half Moon Cay, Bahamas | Amber Cove, Dominican Republic | Grand Turk, Turks and Caicos | Key West, Florida, US | Fort Lauderdale, Florida, US
    Returns – Ft Lauderdale, United States
    Fort Lauderdale, Florida, US | RelaxAway Half Moon Cay, Bahamas | Amber Cove, Dominican Republic | Grand Turk, Turks and Caicos | Key West, Florida, US | Fort Lauderdale, Florida, US
    Expedia® Extras* (Extras vary and apply to select staterooms and prices)
    • Have It All - Includes Drinks, Shore Excursions, Dining, and Wi-Fi
    • Up to 50% Off
    • Up to $200 Onboard Credit per stateroom
    • show more 
    from
    $842* CAD
    Taxes & fees included
  • 10 night Caribbean Cruise

    10 night Caribbean Cruise
    Depart: Sat, Oct 31, 2026
    Returns: Tue, Nov 10, 2026
    Depart – Ft Lauderdale, United States
    Fort Lauderdale, Florida, US | RelaxAway Half Moon Cay, Bahamas | Falmouth, Jamaica | Georgetown, Cayman Islands | Mahogany Bay, Roatan, Honduras | Belize City, Belize | Cozumel, Mexico | Fort Lauderdale, Florida, US
    Returns – Ft Lauderdale, United States
    Fort Lauderdale, Florida, US | RelaxAway Half Moon Cay, Bahamas | Falmouth, Jamaica | Georgetown, Cayman Islands | Mahogany Bay, Roatan, Honduras | Belize City, Belize | Cozumel, Mexico | Fort Lauderdale, Florida, US
    Expedia® Extras* (Extras vary and apply to select staterooms and prices)
    • Have It All - Includes Drinks, Shore Excursions, Dining, and Wi-Fi
    • Up to 50% Off
    • Up to $200 Onboard Credit per stateroom
    • show more 
    from
    $1,182* CAD
    Taxes & fees included
  • 9 night Caribbean Cruise

    9 night Caribbean Cruise
    Depart: Fri, Oct 30, 2026
    Returns: Sun, Nov 8, 2026
    Depart – Ft Lauderdale, United States
    Fort Lauderdale, Florida, US | Cabo Rojo, Dominican Republic | Willemstad, Curacao | Oranjestad, Aruba | RelaxAway Half Moon Cay, Bahamas | Fort Lauderdale, Florida, US
    Returns – Ft Lauderdale, United States
    Fort Lauderdale, Florida, US | Cabo Rojo, Dominican Republic | Willemstad, Curacao | Oranjestad, Aruba | RelaxAway Half Moon Cay, Bahamas | Fort Lauderdale, Florida, US
    Expedia® Extras* (Extras vary and apply to select staterooms and prices)
    • Have It All - Includes Drinks, Shore Excursions, Dining, and Wi-Fi
    • Up to 50% Off
    • Up to $200 Onboard Credit per stateroom
    • show more 
    from
    $1,217* CAD
    Taxes & fees included
  • 11 night Caribbean Cruise

    11 night Caribbean Cruise
    Depart: Tue, Dec 1, 2026
    Returns: Sat, Dec 12, 2026
    Depart – Ft Lauderdale, United States
    Fort Lauderdale, Florida, US | Philipsburg, Sint Maarten | St Johns, Antigua and Barbuda | Roseau, Dominica | Castries, Saint Lucia | Basseterre, St Kitts and Nevis | St Thomas, USVI | RelaxAway Half Moon Cay, Bahamas | Fort Lauderdale, Florida, US
    Returns – Ft Lauderdale, United States
    Fort Lauderdale, Florida, US | Philipsburg, Sint Maarten | St Johns, Antigua and Barbuda | Roseau, Dominica | Castries, Saint Lucia | Basseterre, St Kitts and Nevis | St Thomas, USVI | RelaxAway Half Moon Cay, Bahamas | Fort Lauderdale, Florida, US
    Expedia® Extras* (Extras vary and apply to select staterooms and prices)
    • Have It All - Includes Drinks, Shore Excursions, Dining, and Wi-Fi
    • Up to 50% Off
    • Up to $200 Onboard Credit per stateroom
    • show more 
    from
    $1,461* CAD
    Taxes & fees included
  • 9 night Caribbean Cruise

    9 night Caribbean Cruise
    Depart: Fri, Jan 8, 2027
    Returns: Sun, Jan 17, 2027
    Depart – Ft Lauderdale, United States
    Fort Lauderdale, Florida, US | Kralendijk, Bonaire | Willemstad, Curacao | Oranjestad, Aruba | RelaxAway Half Moon Cay, Bahamas | Fort Lauderdale, Florida, US
    Returns – Ft Lauderdale, United States
    Fort Lauderdale, Florida, US | Kralendijk, Bonaire | Willemstad, Curacao | Oranjestad, Aruba | RelaxAway Half Moon Cay, Bahamas | Fort Lauderdale, Florida, US
    Expedia® Extras* (Extras vary and apply to select staterooms and prices)
    • Exclusive! $50 Onboard Credit & Pinnacle Grill Lunch
    • Have It All - Includes Drinks, Shore Excursions, Dining, and Wi-Fi
    • Up to 50% Off
    • show more 
    from
    $1,582* CAD
    Taxes & fees included
  • 12 night Caribbean Cruise

    12 night Caribbean Cruise
    Depart: Sun, Nov 29, 2026
    Returns: Fri, Dec 11, 2026
    Depart – Ft Lauderdale, United States
    Fort Lauderdale, Florida, US | Philipsburg, Sint Maarten | Fort-De-France, Martinique | Bridgetown, Barbados | Scarborough, Trinidad and Tobago | Castries, Saint Lucia | Basseterre, St Kitts and Nevis | Key West, Florida, US | Fort Lauderdale, Florida, US
    Returns – Ft Lauderdale, United States
    Fort Lauderdale, Florida, US | Philipsburg, Sint Maarten | Fort-De-France, Martinique | Bridgetown, Barbados | Scarborough, Trinidad and Tobago | Castries, Saint Lucia | Basseterre, St Kitts and Nevis | Key West, Florida, US | Fort Lauderdale, Florida, US
    Expedia® Extras* (Extras vary and apply to select staterooms and prices)
    • Exclusive! $75 Onboard Credit
    • Have It All - Includes Drinks, Shore Excursions, Dining, and Wi-Fi
    • Up to 50% Off
    • show more 
    from
    $1,695* CAD
    Taxes & fees included
  • 12 night Caribbean Cruise

    12 night Caribbean Cruise
    Depart: Sun, Oct 18, 2026
    Returns: Fri, Oct 30, 2026
    Depart – Ft Lauderdale, United States
    Fort Lauderdale, Florida, US | RelaxAway Half Moon Cay, Bahamas | Oranjestad, Aruba | Cartagena, Colombia | Enter Panama Canal Cristobal | Gatun Lake, Panama | Exit Panama Canal Cristobal | Colon, Panama | Puerto Limon (San Jose), Costa Rica | Georgetown, Cayman Islands | Fort Lauderdale, Florida, US
    Returns – Ft Lauderdale, United States
    Fort Lauderdale, Florida, US | RelaxAway Half Moon Cay, Bahamas | Oranjestad, Aruba | Cartagena, Colombia | Enter Panama Canal Cristobal | Gatun Lake, Panama | Exit Panama Canal Cristobal | Colon, Panama | Puerto Limon (San Jose), Costa Rica | Georgetown, Cayman Islands | Fort Lauderdale, Florida, US
    Expedia® Extras* (Extras vary and apply to select staterooms and prices)
    • Exclusive! $75 Onboard Credit
    • Have It All - Includes Drinks, Shore Excursions, Dining, and Wi-Fi
    • Up to 50% Off
    • show more 
    from
    $1,771* CAD
    Taxes & fees included
  • 11 night Caribbean Cruise

    11 night Caribbean Cruise
    Depart: Tue, Feb 2, 2027
    Returns: Sat, Feb 13, 2027
    Depart – Ft Lauderdale, United States
    Fort Lauderdale, Florida, US | Philipsburg, Sint Maarten | St Johns, Antigua and Barbuda | Roseau, Dominica | Fort-De-France, Martinique | Basseterre, St Kitts and Nevis | Road Town (Tortola), British Virgin Islands | RelaxAway Half Moon Cay, Bahamas | Fort Lauderdale, Florida, US
    Returns – Ft Lauderdale, United States
    Fort Lauderdale, Florida, US | Philipsburg, Sint Maarten | St Johns, Antigua and Barbuda | Roseau, Dominica | Fort-De-France, Martinique | Basseterre, St Kitts and Nevis | Road Town (Tortola), British Virgin Islands | RelaxAway Half Moon Cay, Bahamas | Fort Lauderdale, Florida, US
    Expedia® Extras* (Extras vary and apply to select staterooms and prices)
    • Exclusive! $75 Onboard Credit
    • Have It All - Includes Drinks, Shore Excursions, Dining, and Wi-Fi
    • Up to 50% Off
    • show more 
    from
    $1,868* CAD
    Taxes & fees included
  • 11 night Caribbean Cruise

    11 night Caribbean Cruise
    Depart: Tue, Dec 22, 2026
    Returns: Sat, Jan 2, 2027
    Depart – Ft Lauderdale, United States
    Fort Lauderdale, Florida, US | Philipsburg, Sint Maarten | Basseterre, St Kitts and Nevis | Roseau, Dominica | Castries, Saint Lucia | St Johns, Antigua and Barbuda | St Thomas, USVI | RelaxAway Half Moon Cay, Bahamas | Fort Lauderdale, Florida, US
    Returns – Ft Lauderdale, United States
    Fort Lauderdale, Florida, US | Philipsburg, Sint Maarten | Basseterre, St Kitts and Nevis | Roseau, Dominica | Castries, Saint Lucia | St Johns, Antigua and Barbuda | St Thomas, USVI | RelaxAway Half Moon Cay, Bahamas | Fort Lauderdale, Florida, US
    Expedia® Extras* (Extras vary and apply to select staterooms and prices)
    • Exclusive! $75 Onboard Credit
    • Have It All - Includes Drinks, Shore Excursions, Dining, and Wi-Fi
    • Up to 50% Off
    • show more 
    from
    $2,402* CAD
    Taxes & fees included
  • 14 night Caribbean Cruise

    14 night Caribbean Cruise
    Depart: Tue, Dec 22, 2026
    Returns: Tue, Jan 5, 2027
    Depart – Ft Lauderdale, United States
    Fort Lauderdale, Florida, US | Key West, Florida, US | Oranjestad, Aruba | Charlotteville, Trinidad and Tobago | Saint Georges, Grenada | Bridgetown, Barbados | Castries, Saint Lucia | San Juan, Puerto Rico | RelaxAway Half Moon Cay, Bahamas | Fort Lauderdale, Florida, US
    Returns – Ft Lauderdale, United States
    Fort Lauderdale, Florida, US | Key West, Florida, US | Oranjestad, Aruba | Charlotteville, Trinidad and Tobago | Saint Georges, Grenada | Bridgetown, Barbados | Castries, Saint Lucia | San Juan, Puerto Rico | RelaxAway Half Moon Cay, Bahamas | Fort Lauderdale, Florida, US
    Expedia® Extras* (Extras vary and apply to select staterooms and prices)
    • Exclusive! $75 Onboard Credit
    • Have It All - Includes Drinks, Shore Excursions, Dining, and Wi-Fi
    • Up to 50% Off
    • show more 
    from
    $2,483* CAD
    Taxes & fees included
  • 20 night Caribbean Cruise

    20 night Caribbean Cruise
    Depart: Sun, Feb 14, 2027
    Returns: Sat, Mar 6, 2027
    Depart – Miami, United States
    Miami, Florida, US | RelaxAway Half Moon Cay, Bahamas | San Juan, Puerto Rico | St Thomas, USVI | Road Town (Tortola), British Virgin Islands | Philipsburg, Sint Maarten | St Johns, Antigua and Barbuda | Castries, Saint Lucia | Roseau, Dominica | Bridgetown, Barbados | Saint Georges, Grenada | Scarborough, Trinidad and Tobago | Kralendijk, Bonaire | Oranjestad, Aruba | Willemstad, Curacao | Falmouth, Jamaica | Miami, Florida, US
    Returns – Miami, United States
    Miami, Florida, US | RelaxAway Half Moon Cay, Bahamas | San Juan, Puerto Rico | St Thomas, USVI | Road Town (Tortola), British Virgin Islands | Philipsburg, Sint Maarten | St Johns, Antigua and Barbuda | Castries, Saint Lucia | Roseau, Dominica | Bridgetown, Barbados | Saint Georges, Grenada | Scarborough, Trinidad and Tobago | Kralendijk, Bonaire | Oranjestad, Aruba | Willemstad, Curacao | Falmouth, Jamaica | Miami, Florida, US
    Expedia® Extras* (Extras vary and apply to select staterooms and prices)
    • Have It All - Includes Drinks, Shore Excursions, Dining, and Wi-Fi
    • Up to 50% Off
    • Up to $200 Onboard Credit per stateroom
    • show more 
    from
    $3,725* CAD
    Taxes & fees included
  • 28 night Caribbean Cruise

    28 night Caribbean Cruise
    Depart: Sat, Oct 30, 2027
    Returns: Sat, Nov 27, 2027
    Depart – Miami, United States
    Miami, Florida, US | Nassau, Bahamas | RelaxAway Half Moon Cay, Bahamas | Ocho Rios, Jamaica | Santo Domingo, Dominican Republic | San Juan, Puerto Rico | St Thomas, USVI | St Johns, Antigua and Barbuda | Castries, Saint Lucia | Port-of-Spain, Trinidad and Tobago | Willemstad, Curacao | Oranjestad, Aruba | Santa Marta, Colombia | Cartagena, Colombia | Colon, Panama | Puerto Limon (San Jose), Costa Rica | Belize City, Belize | Cozumel, Mexico | Progreso (Merida), Yucatan, Mexico | Miami, Florida, US
    Returns – Miami, United States
    Miami, Florida, US | Nassau, Bahamas | RelaxAway Half Moon Cay, Bahamas | Ocho Rios, Jamaica | Santo Domingo, Dominican Republic | San Juan, Puerto Rico | St Thomas, USVI | St Johns, Antigua and Barbuda | Castries, Saint Lucia | Port-of-Spain, Trinidad and Tobago | Willemstad, Curacao | Oranjestad, Aruba | Santa Marta, Colombia | Cartagena, Colombia | Colon, Panama | Puerto Limon (San Jose), Costa Rica | Belize City, Belize | Cozumel, Mexico | Progreso (Merida), Yucatan, Mexico | Miami, Florida, US
    Expedia® Extras* (Extras vary and apply to select staterooms and prices)
    • Exclusive! $100 Onboard Credit & Sparkling wine
    • Have It All - Includes Drinks, Shore Excursions, Dining, and Wi-Fi
    • Earn OneKeyCash
    from
    $5,464* CAD
    Taxes & fees included

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Terms & Conditions

Travel by Sea Sale (“Offer”): Featured fares are per person based on double occupancy. Advertised fares include Taxes and Fees. Cruises available in connection with this Offer are subject to availability and Offer and its parts are available only while space is available. Offer is available for 1st/2nd guests in a stateroom on new bookings only. Offer and its parts are neither transferable nor redeemable for cash. Offer is applicable on select 2026–2027 departures and excludes Grand Voyages and any cruise lasting three days or less. Crew Appreciation: Receive free prepaid stateroom gratuities on board. Gratuities for other services, including bar, dining room, wine accounts, and Spa & Salon services, are not included. Free & Reduced Kids’ Fares: Additional guests 18 and under in a stateroom are eligible to travel with free and reduced fares when booked as a 3rd and/or 4th guest on select cruises. Cruise fare is $0. Price shown reflects all non-Government fees and expenses. Limit up to two free or reduced fares per eligible booking. Free and Reduced Fares for Kids are available only when booked with promotion code Z3* with a 1st/2nd guest booking with promotion code VH & OL*. 50% Reduced Deposit is a reduced per-person booking deposit available for 1st/2nd guests in a stateroom on new bookings only for select cruises booked outside of the final payment date. Balance is due on final payment of the booking. Offer is available only on select cruises unless sold out or otherwise withdrawn. Standard refund and cancellation conditions apply. A deposit is required for all stateroom guests and the amount of deposit varies, even if deposit is reduced per Offer. Onboard Credit is available only in the following amounts: US$75 per person (US$150 per stateroom) for guests booked on a 7-day Caribbean cruise in a Verandah stateroom or Suite; US$150 per person (US$300 per stateroom) for guests booked on a 9+ day Caribbean cruise in a Verandah stateroom or Suite. Limit: One (1) Onboard Credit per guest. Onboard Credit is in USD, is neither refundable nor transferable, and has no cash value. Onboard Credit expires at the end of the Eligible Cruise and may not be used in the Casino or on any other specified fees or items. Use code CBBONUS26 to redeem at checkout or with your Travel Advisor. Promotion Code: VH & OL*. Offer and/or its terms may be modified or withdrawn without prior notice. Offer expires on July 23, 2026. Other restrictions and exclusions may apply. Fares are based on Promo(s) N1/U1. Featured fares are per person based on double occupancy (cruise or cruisetours only). Advertised fares include Taxes and Fees. Have It All amenities are subject to availability, available for new bookings only, available for 1st/2nd guests in a stateroom only, applicable only to the cruise portion of Alaska cruisetours, and neither transferable nor refundable. Have It All fares are applicable on select departures and exclude Grand Voyages and any cruise lasting three days or less. Signature Beverage Package has a daily limit of 15 beverages, which includes all beverages priced at US$12 or less and beverage service charges. Beverage packages include non-alcoholic beverages such as sodas and specialty coffees. Guests must order beverages one at a time and be 21 years or older for alcoholic beverages. Sharing is not permitted. Management reserves the right to revoke the package if misused and refuse service for any reason, including service of alcoholic beverages to intoxicated guests. Package excludes purchases made in The Shops, from the mini-bar, through 24-hour room service, or on RelaxAway, Half Moon Cay™. Specialty Dining is based on cruise duration and ship type. For 4- to 9-day cruises, guests will receive one night at Pinnacle Grill, Rudi’s Sel de Mer, Canaletto, or Tamarind. For ships without Rudi’s Sel de Mer or Tamarind, guests will receive one night at Pinnacle Grill or Canaletto. For 10- to 20-day cruises, guests will receive two nights:

*Expedia Extras offers are per stateroom (unless otherwise stated) on select sailings, based on double occupancy, apply to new bookings only, are not combinable with any other offer, are capacity controlled and may be withdrawn without notice. Certain restrictions may apply. For full terms and conditions, click the specific Expedia Extra offer or contact your Expedia Cruises Vacation Consultant.

Prices are per traveller, available within last 24 hours and valid for US and Canadian residents only. Taxes, fees, and port expenses are included. Fuel supplement may apply. Savings advertised and Expedia Extras are based on specific cabin types and sailing dates and may not be available for all cabin types/sailings. Availability & prices can change frequently, please continue with the booking to check latest availability & prices.

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At Expedia Cruises, we are navigators of spectacular vacation experiences. As part of the number one brand in travel, this is our promise to you:


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