Cruise line was among first in the region when it sailed to the Caribbean in 1926

 When Holland America Line’s Veendam II sailed from New York in February 1926, it charted a course that would help define Caribbean cruising, making the company among the first to offer regularly scheduled vacations to the region for guests seeking a warm-weather getaway. A century later, Holland America Line is commemorating 100 years of Caribbean cruising with a limited time promotion that includes a $100 onboard credit for a party of two.

From Feb. 3–9, 2026, guests can escape the cold by booking select Caribbean sailings departing now through April 30 to receive up to 50% off fares and a $50 per guest onboard credit with Free Fares for Kids (18 and under on select sailings). Travelers can enjoy a refreshingly free style of Caribbean cruising — no oversized ships, amusement parks at sea, or overcrowded beaches and decks. Instead, guests are able to unwind, enjoy quiet moments and truly savor time together while indulging in fresh, globally inspired cuisine and exploring ports at a comfortable pace — creating a more relaxed, spacious and genuinely rejuvenating way to experience the Caribbean.

“Our first Caribbean voyage in 1926 marked a defining moment for Holland America Line and for the evolution of modern cruise travel,” said Beth Bodensteiner, president of Holland America Line. “As we celebrate 100 years, we wanted to offer something both meaningful and memorable — $100 for 100 years, with added ways for guests to save. It’s our way of honoring the milestone while inviting travelers to experience what sets us apart in the Caribbean: perfectly sized ships designed for guests to relax and connect, a premium onboard experience and time ashore at our private island RelaxAway, Half Moon Cay.”

Eligible departures include a variety of Caribbean cruises from Fort Lauderdale and Miami, Florida, including:

• 10-day Westerdam Caribbean: Greater Antilles, Belize and Mexico on Koningsdam, departing Feb. 25, 2026, roundtrip from Fort Lauderdale.
• 7-day Western Caribbean: Greater Antilles and Mexico on Eurodam, departing March 22, 2026, roundtrip from Fort Lauderdale.
• 10-day Southern Caribbean: Amber Cove and ABC Islands on Zuiderdam, departing March 25, 2026, roundtrip from Miami.
• 7-day Eastern Caribbean: Amber Cove and Bahamas on Eurodam, departing March 29, 2026, roundtrip from Fort Lauderdale.
• 12-day Eastern Caribbean: U.S. and British Virgin Islands on Koningsdam, departing March 29, 2026, roundtrip from Fort Lauderdale.
• 7-day Eastern Caribbean: Amber Cove and Bahamas on Zuiderdam, departing April 4, 2026, roundtrip from Miami.

A History of Caribbean Cruising

A pioneer in the industry for more than 150 years, Holland America Line has a history of firsts in the Caribbean that continue to set the standard for cruise travel:

• 1926: First Caribbean (then “West Indies”) cruise by Veendam II.
• 1927: First calls at Willemstad, Curaçao and St. Thomas, U.S. Virgin Islands.
• 1938: First dedicated cruise call to Cristóbal/Colón, Panama.
• 1959: First calls at Aruba once larger docks were developed.
• 1964: First calls at St. Maarten as the island became a growing tourism destination.
• 1997: Opening of Half Moon Cay, Holland America Line’s award‑winning private island in the Bahamas, with Ryndam III making the first call.

Holland America Line’s maiden Caribbean cruise was a ground-breaking 26-day itinerary that departed New York Feb. 18, 1926, and visited Havana, Cuba; Kingston, Jamaica; Colon/Cristóbal, Panama; Cartagena, Colombia; San Juan, Puerto Rico; and Bermuda before returning to New York.

The cruise line’s Caribbean voyages were introduced during the North Atlantic off-season and quickly gained popularity throughout the 1920s and 1930s. As demand grew, the company expanded its Caribbean presence with multiple ships, including Veendam, Statendam and Volendam, bringing warm-weather cruising to more guests.

In the years leading up to World War II, the line’s flagship vessels, including Nieuw Amsterdam II, joined Caribbean itineraries, further strengthening Holland America Line’s leadership in the region. Following the war, winter Caribbean cruises resumed and expanded, ushering in a new era that reflected the evolving tastes of travelers.

By the 1970s, the rise of commercial air travel reshaped Caribbean cruising, allowing Florida — particularly Fort Lauderdale — to emerge as Holland America Line’s primary gateway to the region. One hundred years after its first Caribbean sailing, the company continues to build on this legacy, honoring more than a century of innovation.