2027–2028 Holland America Caribbean Cruises Are Ready to Explore
Experience Holland America’s Caribbean
Set your sights on Holland America’s 2027–2028 Caribbean season, featuring relaxing days on our award-winning private island and peaceful moments at our adults-only Signature Pool Experience. Designed for travelers who want to experience the Caribbean refreshingly free of overcrowded beaches, amusement parks, and boring buffets.
With itineraries ranging from immersive island explorations to extended Caribbean journeys, look forward to more time to unwind, discover, and connect with the destinations you’ll visit.
Ready for your next vacation? Find 2027–2028 Caribbean itineraries here.
More Time in the Caribbean
Among the highlights are 10- and 11-day itineraries that allow you to experience more of the region at a comfortable pace. Sail through the Eastern, Western, or Southern Caribbean while enjoying signature Holland America experiences, including:
- More time in port to explore each destination
- Curated cultural experiences that bring the Caribbean to life
- Locally inspired cuisine and regional flavors
- Perfectly sized ships that help you avoid the crowds
- Thoughtfully crafted journeys that balance discovery and relaxation
With more Caribbean voyages of nine days or longer than any other cruise line, you’ll have more opportunities to explore ashore, savor local flavors and soak in the beauty of each destination without feeling rushed.
RelaxAway, Half Moon Cay™ and Pickleball in Paradise
Nearly every 2027–2028 Caribbean sailing includes a call at RelaxAway, Half Moon Cay™, our award-winning private island. Spend the day stretched out on uncrowded beaches, enjoying enhanced dining options or simply embracing a slower pace beneath swaying palms. For pickleball enthusiasts, the island now features four dedicated pickleball courts, bringing one of the world’s fastest-growing sports to our spectacular beachfront setting.
Relaxation Continues On Board
Between ports, you can enjoy signature Holland America experiences on ships designed for effortless relaxation. Lounge at the adults-only Signature Pool Experience, enjoy destination-inspired dining and personalized service, and take in ocean views from perfectly sized ships built for Caribbean exploration.
Plan Your Caribbean Escape
Whether you’re dreaming of colorful island capitals, crystal-clear waters, or a relaxing day at RelaxAway, Half Moon Cay™, now is the time to secure your spot.
Learn more about our 2027–2028 Caribbean itineraries and find available departures.
