Pick Your Paradise — A Guide to 4 Caribbean Regions and Their Signature Experiences
Our regional breakdown of the Caribbean might spark immediate wanderlust and we’re totally here for it!
The Caribbean feels magical — white-sand beaches, turquoise waters, and the rhythm of steel drums echoing through sun-washed streets. But the enchantment of this destination lies in its diversity. Each Caribbean region and island tells a uniquely beautiful story.
Whether you’re eager to relax on a private island, explore ancient ruins, or hike through lush rainforests, there’s a Caribbean itinerary right for you. With departures from Ft. Lauderdale and Miami, a Holland America Caribbean cruise gives you the chance to conveniently island hop through the Caribbean regions.
What islands do eastern Caribbean cruises visit? Spanning from Key West to Trinidad and Tobago, this area also includes Puerto Rico plus the Bahamas, Dominican Republic, U.S. Virgin Islands, and smaller islands of the Lesser Antilles. Ports include San Juan, St. Thomas, Grand Turk, St. Maarten, and our award-winning private island, RelaxAway, Half Moon Cay™.
Why Cruise to the Eastern Caribbean
The Eastern Caribbean offers lush jungles and fascinating history. Whether you’re horseback riding along the gentle surf on our private island or exploring the centuries-old forts and color-washed streets of Old San Juan, there’s something special to experience.
Things to See & Do in the Eastern Caribbean:
- Swim beneath cascading waterfalls in Amber Cove’s Damajagua
- Stroll the streets of Old San Juan and peruse artisan shops or visit the U.S.’s only rainforest at El Yunque National Park
- Lounge on the sugar-white sands of our private island
- Climb the ramparts of St. Thomas’ Blackbeard’s Castle and sip rum with a view
Explore Eastern Caribbean cruises
Explore the Western Caribbean
This diverse Caribbean region includes Jamaica, the Cayman Islands, Belize, and Mexico’s Yucatán Peninsula — home to idyllic beaches, colorful coral, intriguing Mayan ruins, and more. Ports include Cozumel, Belize City, Roatán, and Key West.
For those craving adventure and ancient wonders, the Western Caribbean delivers a blend of ancient and modern cultures with stunning natural wonders. From snorkeling the second-largest barrier reef in the world in Belize to exploring mysterious Mayan ruins in Mexico, this region gives you a wonderful blend of outdoor adventures, ancient wonders, and stunning natural beauty.
Things to See & Do in the Western Caribbean:
- Explore ancient Mayan ruins in Cozumel and enjoy a delicious tasting at the Mayan Cacao Company
- Drift through Belize’s limestone caves on a river tubing tour
- Zip-line through tropical jungles of Roatán
- Channel Hemingway in Key West with conch fritters and a cold mojito
Discover Western Caribbean cruises
Ready for an island-hopping adventure? Check out our Caribbean cruises.
Southern Caribbean — A Colorful Escape
Less travelled and undeniably vibrant, the Southern Caribbean is a kaleidoscope of color, cultures, and celebrations. From the exciting Bonaire Regatta and the popular Curaçao North Sea Jazz Festival to the exuberant Carnivals that kick off the Lent season, there’s always magical awaiting your discovery. Snorkel vibrant coral reefs in Bonaire, explore pastel-colored towns in Curaçao, and visit rugged volcanic peaks in St. Lucia.
The Southern Caribbean comprises the “ABC” Islands—Aruba, Bonaire, and Curaçao. Ports include Bridgetown, Georgetown, and Montego Bay.
Things to See & Do in the Southern Caribbean:
- Submerge beneath the waves on a submarine excursion in Barbados
- Hike the rugged Pitons in verdant St. Lucia
- Wander through the candy-colored towns of Curaçao and explore floating markets
- Experience the power of nature at the Baby Natural Bridge, naturally carved out of solid coral from the crashing surf
Unwind with Southern Caribbean cruises
Panama Canal Discovery
More than a passage between two oceans, the Panama Canal is a testament to human ingenuity and determination. Watch from the deck as your ship rises and falls with the massive locks, then walk in the footsteps of literary legends such as Gabriel García Márquez in Cartagena, hike the vast and lush jungles of Costa Rica, and more. Select cruises offer a chance to experience a partial transit through the Panama Canal — a wondrous engineering marvel.
Things to See & Do on Panama Canal Discovery Cruises:
- Hike Santa Ana Volcano in El Salvador
- Spot scarlet macaws in Costa Rica’s wildlife sanctuaries
- Roam the walled streets of Cartagena and discover its storied past
- Soar on an aerial tram through the rainforest canopy in Puerto Caldera
Venture to the Panama Canal
Best Time to Cruise the Caribbean
The best time to visit the Caribbean is usually from December to April. However, it mainly depends on what you’re most excited about. Savvy travelers often go during the shoulder seasons, usually April to June, and again from late October to early December. During these times, you’ll enjoy warm weather without the peak season rush.
Time to Set Sail?
Ready to trade your everyday routine for rum punch and snorkeling reefs? Holland America’s Save on Sunshine sale offers up to 50% off select Caribbean sailings, so now is the time to chase sun and adventure!
