Holland America Line have revealed its 2027–2028 Caribbean season with a range of itineraries designed to explore the region while offering quick escapes to long journeys.
Starting in December of 2027 the Oosterdam is returning to duty following it’s renovations and improvements as part of Holland America’s new Evolution investment.
Here are the options available during the 2027-2028 season!
Five-to-Six Day Itineraries:
December 18, 2027 – 5-Day Eastern Caribbean & Bahamas Getaway with ports of calls including Nassau; RelaxAway, Half Moon Cay; and Grand Turk.
March 26, 2028 – 5-Day Eastern Caribbean, Amber Cove & Bahamas Getaway with ports of calls including RelaxAway, Half Moon Cay; Amber Cove, and Grand Turk.
Seven- to Eight-Day Itineraries
October 23, 2027 – 7-Day Eastern Caribbean, Amber Cove & Key West Getaway with ports of calls including RelaxAway, Half Moon Cay, Amber Cove, Key West, Florida, and Grand Turk.
November 27, 2027 Through March 25, 2028 – 7-Day Eastern Caribbean, Amber Cove & Bahamas Getaway with ports of call of RelaxAway, Half Moon Cay, Grand Turk, and Amber Cove.
December 4, 2027 Through March 18, 2028 – 7-Day Eastern Caribbean, San Juan & St. Thomas Getaway with ports of calls including RelaxAway, Half Moon Cay, Grand Turk, San Juan, and St. Thomas.
November 13, 2027 – 8-Day Eastern Caribbean, San Juan & St. Thomas Getaway with ports of calls including RelaxAway, Half Moon Cay, Grand Turk, San Juan, St. Thomas, and St. Marten.
Nine-to-Twelve Day Itineraries
December 22, 2027 Through March 17, 2028 – 9/10/11-Day Southern Caribbean Getaway with ports of calls including RelaxAway, Half Moon Cay, Aruba, Curaçao, Bonaire (9-10 day only), Cabo Rojo, Dominican Republic (10 day only), Grand Cayman and Cartagena (11 day only).
December 12, 2027 Through March 4, 2028 – 10/11-Day Western Caribbean, Greater Antilles, Belize & Mexico Getaway with ports of calls including RelaxAway, Half Moon Cay, Falmouth, Ocho Rios or Montego Bay, Jamaica, Grand Cayman, Mahogany Bay, Honduras, Belize City, Belize, and Cozumel, Mexico.
December 1, 2027 Through March 15, 2028 – 10/11-Day Eastern Caribbean, Windward & Leeward Islands Getaway with ports of calls including St. Maarten, Antigua, Martinique, St. Kitts, San Juan, and Dominica (11 day only).
December 11, 2027 Through March 26, 2028 – 12-Day Panama Canal Discovery Getaway with ports of calls including RelaxAway, Half Moon Cay, Aruba or Curaçao, Cartagena, Colón, Puerto Limón, Costa Rica, Grand Cayman, Panama Canal transit, and Gatun Lake.
December 23, 2027 – 12-Day Eastern Caribbean, Barbados, St. Lucia & St. Kitts Getaway with ports of calls including RelaxAway, Half Moon Cay, St. Maarten, St. Kitts, Martinique, Barbados, St. Lucia, and Tobago.
In honor of Pan Am 100th Anniversary, Holland America will run a 28-Day cruise aboard the Zuiderdamand departing on October 30, 2027. The cruise will follow the airline’s historic Clipper flying boat routes across the Caribbean, Mexico and Latin America, visiting 19 ports in 13 countries.
Additionally, during the 2027-2028 season there will be eight holiday cruises which will see the ships decorated for the season with festive dining, live music, holiday programming with traditions from around the world
For the new 2027-2028 season, Holland America is bringing longer port stays, longer journeys, immersive experiences, and private island escapes. If you are thinking about planning your next Caribbean cruise, then you can do so Here!
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