The line first sailed in the region on February 18, 1926, when its then ship Veendam II departed from New York, making the company among the first to offer regularly scheduled departures to the Caribbean. The cruise visited Havana, Cuba; Kingston, Jamaica; Colon/Cristóbal, Panama; Cartagena, Colombia; San Juan, Puerto Rico; and Bermuda.
Voyages to the Caribbean are included in Holland America Line’s ongoing ‘Start Your Journey Sale’, which runs until February 26, 2026.
Guests who book applicable voyages with ‘Have it All’ fares will benefit from a free stateroom upgrade and reduced fares for children aged 18 and under travelling as the third and fourth guests. The ‘Have it All’ benefits include a Signature Beverage Package, shore excursion credit, speciality dining, Wi-Fi and prepaid crew appreciation.
The offer is valid for bookings on more than 500 cruises departing from summer 2026 to spring 2027, including Caribbean itineraries.
Karen Farndell, associate vice-president of sales and marketing for the UK and Ireland at Holland America Line, said: “Celebrating 100 years of cruising in the Caribbean is a proud moment for Holland America Line and a testament to our deep roots in the region. From our very first Caribbean sailing in 1926, we’ve been committed to offering thoughtfully curated itineraries that connect guests with the culture, history and natural beauty of these destinations.”
Holland America Line's Caribbean highlights include:
* 1926: first Caribbean (then “West Indies”) cruise on Veendam II
* 1927: first calls at Willemstad, Curaçao and St. Thomas, U.S. Virgin Islands
* 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 private island in the Bahamas, with Ryndam III making the first call
