Holland America 2027-28 Caribbean Season: Everything Cruise Travelers Need to Know Wait, let me redo that properly: Holland America Reveals Its 2027

Holland America Line just dropped some exciting news for Caribbean cruise fans. Here’s what you need to know about their upcoming 2027-28 season.

Holland America Line Opens 2027-28 Caribbean Season

The new season runs from October 2027 through March 2028. It features 29 itineraries across 47 departures. You’ll have the chance to visit 35 ports in 25 countries and territories.

The season covers the Eastern, Western, and Southern Caribbean, plus the Panama Canal. That’s a lot of ground to cover!

Something for Every Type of Traveler

Holland America has clearly put thought into building a season with options for everyone. “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 of deployment and revenue planning.

Short trips start at five days. Longer voyages stretch up to 28 days. No matter your schedule or budget, there’s likely a fit for you.

The Reimagined Oosterdam Makes Its Debut

One of the biggest highlights of the season is the freshly updated Oosterdam. The ship has gone through a major makeover and will be sailing longer routes through the Southern Caribbean and Panama Canal.

Guests can look forward to new stateroom and suite categories. There’s also a brand-new all-day dining spot called the Grand Dutch Café. It draws inspiration from Holland America’s Dutch roots.

Half Moon Cay Gets a Big Upgrade

Nearly every itinerary includes a stop at Half Moon Cay, Holland America’s private island destination called RelaxAway. The island is getting some serious upgrades for this season.

A new beach club will offer waiter service and priority tendering. You’ll also get exclusive food and drink options and upgraded seating. It sounds like a much more relaxing experience than your typical private island stop.

The fun doesn’t stop there. The Lobster Shack has been refreshed with new island-exclusive menu items. There are also new beverage experiences, expanded cabanas and villas, new shops, and upgraded beach facilities. Pickleball fans will be happy to know it’s on the activity list too!

Shore excursions range from kayaking and snorkeling with stingrays to horseback riding on the beach.

A Special Voyage for History Buffs

A standout sailing this season is the 28-Day “Pan Am 100th Anniversary Legendary Voyage” aboard the Zuiderdam. It departs October 30, 2027, roundtrip from Miami, Florida.

This unique cruise was created in partnership with Pan Am. It retraces the historic Clipper flying boat routes the airline once flew across the Caribbean. Stops include Nassau, Bahamas, and San Juan, Puerto Rico. It’s a truly one-of-a-kind itinerary for travelers who love history.

Holland America also offers eight holiday cruises during this season if you want to celebrate Thanksgiving or the winter holidays at sea.

Highlighted Itineraries for 2027-28

Here’s a quick look at some of the featured sailings:

• 5-day Eastern Caribbean & Bahamas Getaway
• 6-day Eastern Caribbean: Amber Cove & Bahamas
• 7-day Eastern Caribbean: Amber Cove & Key West
• 7-day Eastern Caribbean: Amber Cove & Bahamas
• 7-day Eastern Caribbean: San Juan & St. Thomas
• 8-day Eastern Caribbean: San Juan & St. Thomas
• 9-, 10-, or 11-day Southern Caribbean: ABC Islands
• 10- or 11-day Western Caribbean: Greater Antilles, Belize & Mexico
• 10- or 11-day Eastern Caribbean: Windward & Leeward Islands
• 12-day Panama Canal Discovery: Costa Rica & Greater Antilles
• 12-day Eastern Caribbean: Barbados, St. Lucia & St. Kitts

With so many options, the 2027-28 Holland America Caribbean season has something for just about every kind of cruiser.