Holland America Line

11-Day Eastern Caribbean: Windward & Leeward Islands

05/16/2025 through 10/30/2026
05/16/2025 through 11/11/2026

Day 1

Nestled between Biscayne Bay to the east and Everglades National Park to the west, Miami, Florida is one of the Sunshine State's most vibrant, culturally diverse, and dynamic cities. Neon pink lights and tropical nights beckon you to this popular tourist destination, a favorite port for travelers on Caribbean and Trans-Atlantic cruises.

Miami’s expansive stretch of sand and sun is a beach-lover’s paradise. Lined with palm trees, Miami Beach and South Beach are excellent sites to soak up some Vitamin C, take a plunge in warm cerulean waters, and traverse the bay by boat. South Beach boasts amazing nightlife, including stunning rooftop bars with ocean views and vivid nightclubs. The LGBTQ community has contributed immensely to the city’s nightlife – several gay bars and drag clubs are some of Miami’s most sought-after spots for dancing. You’ll find the famous Art Deco district, with a delightful collection of vintage architectural masterpieces, mere steps from the sandy coastline.

A veritable melting-pot, Miami has been heavily influenced by Latin American culture. Visit the city’s Little Haiti and Little Havana neighborhoods to discover authentic Cuban and Haitian cuisine, colorful art museums, jazz bars, and robust brewed coffee. Revel in a savory bite of the classic Cubano sandwich, a staple in Miami.

Whether golfing, fishing, partying, or sun-bathing, sunny Miami, Florida has something for everyone!


Day 2 Enjoy this day at sea as you travel to your next port of call. This is an opportunity to swim, catch some sun on deck or take advantage of the many activities that are onboard your ship. Eat heartily, take a nap and get ready for the next port of call ! This is what makes cruising so great.
Day 3 Enjoy this day at sea as you travel to your next port of call. This is an opportunity to swim, catch some sun on deck or take advantage of the many activities that are onboard your ship. Eat heartily, take a nap and get ready for the next port of call ! This is what makes cruising so great.
Day 4

St. Maarten, a dazzling island in the Caribbean, is renowned for its unique blend of Dutch and French cultures, reflecting its dual governance. The capital, Philipsburg, on the Dutch side, invites visitors with its vibrant Front Street, lined with duty-free shops, colorful markets, and charming eateries. The island’s cultural tapestry is further showcased in the Museum of Sint Maarten, where artifacts and exhibits illustrate the island's rich history and heritage.

On the French side, the town of Marigot exudes a sophisticated European flair with its chic boutiques and delectable French cuisine. Stroll along the picturesque waterfront of the Marigot Marina or savor local delights at the lively outdoor markets. A visit to the Fort Louis, offering panoramic views of Marigot Bay, adds a historical touch to your experience.

For beach enthusiasts, St. Maarten's pristine shores are a paradise. The island boasts renowned beaches like Maho Beach, famous for its dramatic airplane landings just above the sand. Orient Bay, on the French side, provides a quintessential Caribbean experience with its clear turquoise waters and vibrant beach bars.

A fun fact about St. Maarten is that it is home to the world’s largest saltwater lagoon, Simpson Bay Lagoon, which is a haven for boating and water sports. To make the most of your visit, plan your trip between November and April, when the weather is pleasantly warm and ideal for exploring the island's diverse offerings.



Arrive Time: 8:00 AM – Depart Time: 5:00 PM
Day 5 Antigua and Barbuda are located in the middle of the Leeward Islands in the Eastern Caribbean. Antigua, the largest of the British Leeward Islands, is about 14 miles long and 11 miles wide, encompassing 108 square miles. Barbuda, a flat coral island with an area of only 68 square miles, lies approximately 30 miles to the north. The population is approximately 68,000 and its capital is St. John's on Antigua.

The largest of the British Leeward Islands, Antigua has warm, steady winds, a complex coastline of safe harbors, and a protective, nearly unbroken wall of coral reef. These unique characteristics have made Antigua and Barbuda in one of the Caribbean's premier tourist destinations.

The expansive, winding coastline that made Antigua difficult for sailors to navigate is where today's trekkers encounter a tremendous wealth of secluded, powdery soft beaches. The coral reefs attract snorkelers and scuba divers from all over the world. And the fascinating little island of Barbuda -- once a scavenger's paradise because so many ships wrecked on its reefs -- is now home to one of the region's most significant bird sanctuaries.


Arrive Time: 8:00 AM – Depart Time: 5:00 PM
Day 6

Arrive Time: 8:00 AM – Depart Time: 9:00 PM
Day 7 Roseau is the capital and largest city on Dominica, a small Caribbean island off the coast of Venezuela. This island getaway is renowned for its verdant rainforest landscape and natural wonders, including gorges, waterfalls, and geysers.

Arrive Time: 8:00 AM – Depart Time: 5:00 PM
Day 8 St. Kitts and Nevis is a West Indies island country and the Western Hemisphere's smallest sovereign state. Major events include Carnival (December - January), June's St. Kitts Music Festival (June), and Culturama (one week from July - August).

Arrive Time: 8:00 AM – Depart Time: 5:00 PM
Day 9 This vibrant destination in the U.S. Virgin Islands is a Caribbean paradise and the perfect tropical getaway. Colonized in the 18th century by the Danish, who established massive sugarcane plantations there, St. Thomas was later purchased by the United States in the 20th century. A popular stop on Caribbean Cruises, the island boasts a number of exciting excursions sure to impress the adventurous traveler. Hop aboard a sky gondola to find breathtaking aerial views of the island, glide through lush rainforests on a zipline, or snorkel alongside sea turtles in the crystal clear waters. Explore downtown Charlotte Amalie, the island's biggest city, to immerse yourself in St. Thomas's colonial past at Fort Christian or Blackbeard's Castle.

Arrive Time: 8:00 AM – Depart Time: 4:00 PM
Day 10 Enjoy this day at sea as you travel to your next port of call. This is an opportunity to swim, catch some sun on deck or take advantage of the many activities that are onboard your ship. Eat heartily, take a nap and get ready for the next port of call ! This is what makes cruising so great.
Day 11

Arrive Time: 8:00 AM – Depart Time: 3:00 PM
Day 12

Nestled between Biscayne Bay to the east and Everglades National Park to the west, Miami, Florida is one of the Sunshine State's most vibrant, culturally diverse, and dynamic cities. Neon pink lights and tropical nights beckon you to this popular tourist destination, a favorite port for travelers on Caribbean and Trans-Atlantic cruises.

Miami’s expansive stretch of sand and sun is a beach-lover’s paradise. Lined with palm trees, Miami Beach and South Beach are excellent sites to soak up some Vitamin C, take a plunge in warm cerulean waters, and traverse the bay by boat. South Beach boasts amazing nightlife, including stunning rooftop bars with ocean views and vivid nightclubs. The LGBTQ community has contributed immensely to the city’s nightlife – several gay bars and drag clubs are some of Miami’s most sought-after spots for dancing. You’ll find the famous Art Deco district, with a delightful collection of vintage architectural masterpieces, mere steps from the sandy coastline.

A veritable melting-pot, Miami has been heavily influenced by Latin American culture. Visit the city’s Little Haiti and Little Havana neighborhoods to discover authentic Cuban and Haitian cuisine, colorful art museums, jazz bars, and robust brewed coffee. Revel in a savory bite of the classic Cubano sandwich, a staple in Miami.

Whether golfing, fishing, partying, or sun-bathing, sunny Miami, Florida has something for everyone!


10/31/26 - 11/11/26

Starting At $2,299

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All cruise prices are per person, cruise only, and based on double occupancy. Port charges may be included. All prices are subject to change as often as daily and are based on availability at the time of the booking. Certain restrictions apply.

Taxes, fees and port expenses, as used by us, may include any and all fees, charges, tolls and taxes imposed on us by governmental or quasi-governmental authorities, as well third party fees and charges arising from a vessel’s presence in a harbor or port. Taxes, fees and port expenses may include U.S. Customs fees, head taxes, Panama Canal tolls, dockage fees, wharfage fees, inspection fees, pilotage, air taxes, hotel or VAT taxes incurred as part of a land tour, immigration and naturalization fees, and Internal Revenue Service fees, as well as fees paid to third parties for navigation, berthing, stevedoring, baggage handling/storage and security services. Taxes, fees and port expenses may be assessed per passenger, per berth, per ton or per vessel. Assessments calculated on a per ton or per vessel basis will be spread over the number of passengers on the ship. Taxes, fees and port expenses are subject to change and we reserve the right to collect any increases in effect at the time of sailing even if the fare has already been paid in full.

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