Season explores more of the Caribbean with longer port stays, immersive experiences, private island escapes and a longer journey tracing Pan Am’s historic routes

Key Points:

• 2027–2028 Caribbean season features 29 itineraries across 47 departures, with more nine-day-or-longer voyages than any other cruise line
• Range of itineraries spans five- and six-day getaways to extended journeys across the Eastern, Western and Southern Caribbean, as well as the Panama Canal
• Season includes diverse experiences, from relaxing escapes at RelaxAway, Half Moon Cay to the 28-day Pan Am Legendary Voyage tracing historic Clipper flying boat routes
• Enhanced guest experience features upgrades across the fleet, including the debut of the reimagined Oosterdam with new staterooms and onboard venues

Holland America Line, a leader in destination-rich travel and personalized service, is opening its 2027–2028 Caribbean season with a range of itineraries designed to give guests more ways to explore the region — from quick five- and six-day getaways to longer voyages that spend more time in port than any other cruise line sailing the Caribbean. Nearly every itinerary includes a call at RelaxAway, Half Moon Cay, the line’s award-winning private island.

Sailing October 2027 through March 2028, the season includes 29 itineraries across 47 departures, visiting 35 ports in 25 countries and territories throughout the Eastern, Western and Southern Caribbean, as well as the Panama Canal. The season also introduces enhanced onboard and shoreside experiences, including the debut of the reimagined Oosterdam as part of the line’s broader Evolution investment across the fleet.

“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.”

Throughout the season, guests can expect experiences designed to connect more deeply with the region, both on board and ashore. Shore excursions curated with The HISTORY Channel and locally focused “Meet the Makers” tours bring each destination to life, while Destination Dining™ and the line’s Global Fresh Fish Program reflect the flavors of the Caribbean. On board, guests can unwind in spaces like the adults-only aft pool, where live music, poolside service and ocean views create a more relaxed atmosphere.

A New Chapter for Oosterdam in the Caribbean

Guests sailing in the Caribbean beginning December 2027 will also have the opportunity to experience the reimagined Oosterdam, the first ship to debut as part of Holland America Line’s Evolution investment. Following its transformation, the ship introduces new stateroom and suite categories designed to reflect how guests travel today, along with expanded access to signature venues.

New accommodations include Solo Verandah staterooms with private balconies and dedicated workspace, as well as premium options such as Bridgeview Suites with panoramic ocean views and expanded living space, and Vista Suites debuting on the ship for the first time. The transformation also adds Grand Dutch Café, an all-day venue inspired by the line’s Dutch heritage. During the 2027–2028 Caribbean season, Oosterdam will sail longer itineraries across the Southern Caribbean and Panama Canal.

RelaxAway, Half Moon Cay: A Signature Caribbean Experience

RelaxAway, Half Moon Cay is included on nearly every Caribbean itinerary and is being enhanced with new offerings that elevate the private island experience. A new beach club features waiter service, priority tendering, exclusive food and beverage options, and upgraded seating, along with indoor and outdoor spaces with ship views.

Guests will also find a refreshed Lobster Shack, island-exclusive menu items and new beverage experiences including Aperol spritz tricycles and Bacardi beach buggies. Additional upgrades include expanded cabanas and villas, new shopping venues, enhanced beach facilities and activities such as pickleball. Shore excursions range from kayaking and snorkeling with stingrays to horseback riding along the beach.

Holidays at Sea

Holland America Line offers eight holiday cruises during the season, giving guests a range of options to celebrate at sea. Guests can spend the holidays aboard Rotterdam on a Dec. 22, 2027, roundtrip from Fort Lauderdale, Florida, seven-day Eastern Caribbean Holiday itinerary, sailing to Grand Turk, Turks & Caicos; RelaxAway, Half Moon Cay; Charlotte, Amalie; St. Thomas; and a late-night stay in San Juan, Puerto Rico. For a longer holiday escape, guests can sail aboard the newly reimagined Oosterdam on an 11-day Southern Caribbean Holiday voyage, also departing Dec. 22, roundtrip from Fort Lauderdale, with calls at RelaxAway, Half Moon Cay; George Town, Grand Cayman; and Cartagena, Colombia, along with late-night stays in Aruba and Curaçao.

Ships are decorated for the season and feature festive dining, live music and holiday programming that bring together traditions from around the world, giving guests the opportunity to celebrate without the stress of planning.

Reliving the Golden Age of Travel at Sea

A highlight of the season is the 28-Day Pan Am 100th Anniversary Legendary Voyage aboard Zuiderdam, departing Oct. 30, 2027, roundtrip from Miami, Florida. Created in partnership with Pan Am, the sailing traces the airline’s historic Clipper flying boat routes across the Caribbean, Mexico and Latin America, visiting 19 ports in 13 countries. Nearly half of the itinerary features destinations that were part of Pan Am’s original network, offering guests the opportunity to follow in the footsteps of one of travel’s most iconic brands while exploring both well-known and less frequently visited ports throughout the region.

The itinerary includes stops in Nassau, Bahamas, and San Juan, two early hubs in Pan Am’s Caribbean network, along with ports such as Willemstad, Curaçao; Cartagena; and Colón, Panama. The voyage also includes multiple consecutive port days in parts of the Caribbean, giving guests more time in the destination compared to shorter itineraries.

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, Florida; 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 (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- 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; Falmouth, Ocho Rios or Montego Bay, Jamaica; Grand Cayman; Mahogany Bay, Honduras; Belize City, Belize; Cozumel, Mexico
  • 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, Costa Rica; 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

FAQ

• What is new for Holland America Line’s 2027–2028 Caribbean season?

  The season features 29 itineraries across 47 departures from October 2027 through March 2028, with more nine-day-or-longer Caribbean cruises than any other cruise line, plus enhanced ship experiences and upgrades to RelaxAway, Half Moon Cay.

• What cruise lengths are available?

  Guests can choose cruises that range from five to 28 days, shorter from five- to eight-day voyages, and longer itineraries of nine to 12 days, along with a 28-day Pan Am Legendary Voyage. Collectors’ Voyages combine non-repeating, back-to-back cruises, forming an extended Caribbean experience.

• Where do the cruises travel?

  Itineraries span the Eastern, Western and Southern Caribbean, including stops in Grand Turk, San Juan, St. Thomas, St. Maarten, the ABC Islands (Aruba, Bonaire and Curaçao), Colombia and the Panama Canal.

• Do the cruises include RelaxAway, Half Moon Cay?

  Nearly every sailing includes a visit to RelaxAway, Half Moon Cay, Holland America Line’s private island in the Bahamas, now featuring a new beach club, expanded cabanas and upgraded dining and beverage experiences.

• Are there holiday cruises available?

  Yes. Eight holiday sailings are offered, including Thanksgiving, Christmas and New Year itineraries with festive décor, seasonal dining and special onboard programming.

Guests booking 2027-2028 Caribbean cruises with the Have It All premium package receive standard amenities—shore excursions, specialty dining, Signature Beverage Package, and Wi-Fi. For more information about Holland America Line or to book a cruise, consult a travel advisor, call 1-877-SAIL HAL (877-724-5425) or visit hollandamerica.com.