Best Mid-Sized Cruises from Florida

Departing right from Florida, Holland America’s Caribbean cruises appeal to travelers looking for classic cruising on perfectly sized ships. With more space per guest and a quieter onboard atmosphere, these mid-sized vessels offer a refined alternative to larger resort-style ships. Our cruise specialists guide travelers through itinerary options, ship features and stateroom choices so every detail is carefully considered.

Booking through our agency means you benefit from experienced advisors who monitor sailings, compare options and help secure the best itinerary for your travel plans. Plus, we can help you take advantage of Holland America’s Anniversary Sale: Up to 30% Off + Up to US$400 Onboard Credit per stateroom + Kids Sail Free + Reduced Deposits. Enhance your cruise vacation further with their popular Have It All package, which includes Shore Excursions, a Drink Package, Specialty Dining and Wi-Fi in one simple fare.

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Caribbean itineraries designed to maximize time in port

Holland America Line itineraries focus on immersive Caribbean travel with thoughtfully planned port days and scenic sailing routes. Many sailings depart from Florida and explore the Eastern Caribbean, Southern Caribbean or the Panama Canal region. Travelers can visit historic island towns, pristine beaches and cultural landmarks across multiple destinations in one voyage.

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Popular Caribbean experiences on these itineraries include:

• Relaxing on white-sand beaches in Grand Turk and Aruba
• Exploring colonial architecture and historic forts in San Juan
• Visiting colorful Dutch Caribbean capitals like Willemstad and Oranjestad
• Experiencing wildlife and nature excursions in Costa Rica
• Cruising through the engineering marvel of the Panama Canal
• RelaxAway, Half Moon Cay™, the line’s award-winning private island in the Bahamas

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Our travel experts help you find the right sailing

Choosing the right Caribbean cruise involves more than selecting a destination. Departure dates, ship size, itinerary pace and cabin category all affect the overall experience. Our travel advisors specialize in Holland America cruises and help travelers compare options quickly and confidently.

Featured Sailings:

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7-Day Eastern Caribbean: Amber Cove & Key West

Departs October 24, 2026, aboard Eurodam

Fort Lauderdale, Florida; RelaxAway, Half Moon Cay™, Bahamas; Amber Cove, Dominican Republic; Grand Turk, Turks and Caicos; Key West, Florida; Fort Lauderdale, Florida

Verandah from $2,006 per person

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10-Day Western Caribbean: Greater Antilles, Belize & Mexico

Departs October 31, 2026,
aboard Rotterdam

Fort Lauderdale, Florida; RelaxAway, Half Moon Cay™, Bahamas; Falmouth, Jamaica; Georgetown, Cayman Islands; Mahogany Bay, Roatan, Honduras; Belize City, Belize; Cozumel, Mexico; Fort Lauderdale, Florida

Verandah from $2,689 per person

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12-Day Panama Canal Discovery: Costa Rica & Greater Antilles

Departs November 8, 2026,
aboard Nieuw Amsterdam

Fort Lauderdale, Florida; RelaxAway, Half Moon Cay™, Bahamas; Oranjestad, Aruba; Cartagena, Colombia; enter Panama Canal Cristobal; cruising Panama Canal and Gatun Lake; Gatun Lake; Cruising Gatun Lake and Panama Canal; exit Panama Canal Cristobal Colon, Panama; Puerto Limon (San Jose), Costa Rica; Ocho Rios, Jamaica; Fort Lauderdale, Florida

Verandah from $3,834 per person

★ Agency Exclusive: Enjoy the services of a Distinctive Voyages Host, a Private Welcome Reception and an Exclusive Shore Event in Cartagena, Colombia: Rhythms & Flavors of Cartagena

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7-Day Eastern Caribbean: San Juan & St. Thomas

Departs November 28, 2026,
aboard Eurodam

Fort Lauderdale, Florida; Grand Turk, Turks and Caicos; San Juan, Puerto Rico; St. Thomas, U.S. Virgin Islands; RelaxAway, Half Moon Cay™, Bahamas; Fort Lauderdale, Florida

Verandah from $2,006 per person

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7-Day Eastern Caribbean: Amber Cove & Bahamas

Departs November 28, 2026,
aboard Zuiderdam

Miami, Florida; RelaxAway, Half Moon Cay™, Bahamas; Amber Cove, Dominican Republic; Grand Turk, Turks and Caicos Island; Nassau, Bahamas; Miami, Florida

Verandah from $1,936 per person

★ Agency Exclusive: US$25 Shipboard Credit per person

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18-Day Eastern/Southern Caribbean: Amber Cove & ABC Islands

Departs March 6, 2027,
aboard Zuiderdam

Miami, Florida; RelaxAway, Half Moon Cay™, Bahamas; Amber Cove, Dominican Republic; Grand Turk, Turks and Caicos Islands; Nassau, Bahamas; Miami, Florida; RelaxAway, Half Moon Cay™, Bahamas; Grand Turk, Turks and Caicos Islands; Amber Cove, Dominican Republic; Willemstad, Curacao; Kralendijk, Bonaire; Oranjestad, Aruba; Cabo Rojo, Dominican Republic; Miami, Florida

Verandah from $5,829 per person