Holland America Line is expanding its Caribbean program for the 2027–2028 season with a strong focus on longer port stays, immersive destination experiences, and a wide range of itineraries from short escapes to extended voyages. Sailing from October 2027 through March 2028, the season includes 29 itineraries and 47 departures visiting 35 ports across 25 countries and territories in the Caribbean and Panama Canal region.
Nearly every itinerary includes a visit to the line’s private island, RelaxAway, Half Moon Cay.
Guests can choose from quick five- and six-day getaways or longer sailings designed to spend more time in destination than any other cruise line in the Caribbean.
“We’ve built this season to give guests more ways to experience the Caribbean, whether they are looking for a quick getaway or a longer journey that explores more of the region,” said Paul Grigsby, vice president, deployment and revenue planning for Holland America Line. “With more Caribbean itineraries of nine days or longer than any other cruise line, guests have more time to explore each destination and relax at our private island and with signature experiences on board.”
Onboard and ashore programming continues to expand with The HISTORY Channel–curated shore excursions, locally focused “Meet the Makers” experiences, and culinary offerings through Destination Dining and the Global Fresh Fish Program.
A key highlight of the season is the introduction of the reimagined Oosterdam, the first ship to debut under Holland America Line’s Evolution investment. From December 2027, guests will find new stateroom categories including Solo Verandah staterooms, Bridgeview Suites, and Vista Suites, alongside refreshed venues such as the Grand Dutch Café.
Private island experiences at RelaxAway, Half Moon Cay are also being enhanced with a new beach club offering priority tendering, dedicated service, and exclusive food and beverage options, as well as expanded cabanas, upgraded beach facilities, and new recreational activities.
Holiday sailings remain a key feature of the season, including eight festive departures across the Caribbean. Highlights include a 7-day Eastern Caribbean holiday cruise aboard Rotterdam and an 11-day Southern Caribbean holiday voyage aboard Oosterdam, featuring Aruba, Curaçao, Cartagena, and Grand Cayman. Seasonal entertainment, themed dining, and onboard celebrations are offered fleetwide.
A standout itinerary is the 28-day Pan Am 100th Anniversary Legendary Voyage aboard Zuiderdam, retracing historic Clipper routes across the Caribbean, Mexico, and Latin America with 19 ports in 13 countries and extended time in key destinations.
Full Itinerary Highlights
Five- to Six-Day Itineraries
- 5-Day Eastern Caribbean & Bahamas Getaway, onboard Zuiderdam, roundtrip from Fort Lauderdale
Calls at Nassau; RelaxAway, Half Moon Cay; Grand Turk
Sails Dec. 18, 2027
- 6-Day Eastern Caribbean: Amber Cove & Bahamas, onboard Eurodam, roundtrip from Fort Lauderdale
Calls at RelaxAway, Half Moon Cay; Amber Cove, Dominican Republic; Grand Turk
Sails March 26, 2028
Seven- to Eight-Day Itineraries
- 7-Day Eastern Caribbean: Amber Cove & Key West, onboard Eurodam, roundtrip from Fort Lauderdale
Calls at RelaxAway, Half Moon Cay; Amber Cove; Key West; Grand Turk
Sails Oct. 23, 2027
- 7-Day Eastern Caribbean: Amber Cove & Bahamas, onboard Rotterdam or Zuiderdam, roundtrip from Fort Lauderdale or Miami
Calls at Nassau; RelaxAway, Half Moon Cay; Grand Turk; Amber Cove
Departs Nov. 27, 2027 (Miami), Dec. 11, 2027; Jan. 15, Jan. 29, Feb. 12, Feb. 26, March 11, March 25, 2028
Holiday departure: Dec. 23, 2027 (Zuiderdam)
- 7-Day Eastern Caribbean: San Juan & St. Thomas, onboard Eurodam, Rotterdam or Zuiderdam, roundtrip from Fort Lauderdale or Miami
Calls at RelaxAway, Half Moon Cay; Grand Turk; San Juan; St. Thomas
Departs Dec. 4, 2027 (Miami); Jan. 8, Jan. 22, Jan. 29, Feb. 5, Feb. 19, March 4, March 18, 2028
Holiday departures: Dec. 22, 2027 (Rotterdam); Dec. 30, 2027 (Zuiderdam)
- 8-Day Eastern Caribbean: San Juan & St. Thomas, onboard Eurodam, roundtrip from Fort Lauderdale
Calls at RelaxAway, Half Moon Cay; Grand Turk; San Juan; St. Thomas; St. Maarten
Sails Nov. 13, 2027
Nine- to 12-Day Itineraries
- 9-, 10- or 11-Day Southern Caribbean: ABC Islands, onboard Oosterdam, Rotterdam or Eurodam, roundtrip from Fort Lauderdale
Calls at RelaxAway, Half Moon Cay; Aruba; Curaçao
9-day and 10-day include Bonaire; 10-day includes Cabo Rojo (Dominican Republic); 11-day includes Grand Cayman and Cartagena
Departs Jan. 14, Feb. 4, Feb. 23, Feb. 25, March 17, 2028
Holiday departures: Dec. 22, 2027 (Oosterdam); Dec. 29, 2027 (Rotterdam)
- 10- or 11-Day Western Caribbean: Greater Antilles, Belize & Mexico, onboard Eurodam, roundtrip from Fort Lauderdale
Calls at RelaxAway, Half Moon Cay; Jamaica (Falmouth, Ocho Rios or Montego Bay); Grand Cayman; Mahogany Bay; Belize City; Cozumel
Departs Dec. 12, 2027; Jan. 2; March 4, 2028
Holiday departure: Nov. 21, 2027 (Eurodam)
- 10- or 11-Day Eastern Caribbean: Windward & Leeward Islands, onboard Eurodam, roundtrip from Fort Lauderdale
Calls at St. Maarten; Antigua; Martinique; St. Kitts; San Juan
11-day includes Dominica
Departs Dec. 1, 2027; Jan. 12, Feb. 12, March 15, 2028
Holiday departure: Dec. 22, 2027 (Oosterdam)
- 12-Day Panama Canal Discovery: Costa Rica & Greater Antilles, onboard Volendam or Oosterdam, roundtrip from Fort Lauderdale
Calls at RelaxAway, Half Moon Cay; Aruba or Curaçao; Cartagena; Colón; Puerto Limón; Grand Cayman
Features partial Panama Canal transit and Gatun Lake
Departs Dec. 11, 2027; Jan. 2; Jan. 23; Feb. 13; March 5; March 26, 2028
- 12-Day Eastern Caribbean: Barbados, St. Lucia & St. Kitts, onboard Volendam, roundtrip from Fort Lauderdale
Calls at RelaxAway, Half Moon Cay; St. Maarten; St. Kitts; Martinique; Barbados; St. Lucia; Tobago
Sails Dec. 23, 2027
Guests booking 2027–2028 Caribbean cruises with the Have It All premium package receive included amenities such as shore excursions, specialty dining, Signature Beverage Package, and Wi-Fi.
Pictures courtesy of Holland America Line.
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