Eastern & Western Caribbean: Leeward Islands & Mexico Cruise

Day 1 - Miami

Arrive: Sat 31 October 2026 / Depart: Sat 31 October 2026 at 16:00

Because of its many canals and waterways, Ft. Lauderdale is sometimes called the Venice of America. It's home to the annual Fort Lauderdale International Boat Show, one of the largest in-water boat shows in the world; which is one of the many reasons our Fort Lauderdale cruise guests love visiting here. Guests can easily get a taste of the area's nautical lifestyle by cruising the Intracoastal Waterway on an old-fashioned paddle wheeler. Other options include hopping aboard one of the popular water taxis or Venetian gondolas that glide down the historic New River, which flows right through town. While Ft. Lauderdale is often overshadowed by its flashy neighbor, Miami, the port city is expanding rapidly as major developers and high-end resorts build up the beachfront and surrounding neighborhoods. Visitors will find world-class shopping on famous Las Olas Boulevard, celebrated restaurants and a cultural explosion in the Riverwalk Arts & Entertainment District. It's clear that Ft. Lauderdale is solidifying its place as a sophisticated destination, and one of the reasons our Fort Lauderdale cruises are a popular choice for many vacation goers.

Day 2 - At Sea

Day 3 - At Sea

Day 4 - Philipsburg, St Maarten

Arrive: Tue 03 November 2026 at 08:00 / Depart: Tue 03 November 2026 at 17:00

Philipsburg is the capital of Sint Maarten, the Dutch side of the Caribbean island Saint Martin. Beachfront bars line the boardwalk along Great Bay. Voorstraat, or Front Street, has duty-free shops and casinos. The St. Maarten Zoo is home to parrots, monkeys and a playground. Sint Maarten Museum displays artifacts from the indigenous Arawak people. The ruins of 17th-century Fort Amsterdam stand on a nearby peninsula.

Day 5 - St John's, Antigua

Arrive: Wed 04 November 2026 at 08:00 / Depart: Wed 04 November 2026 at 17:00

Antigua is a Caribbean paradise, with sun-drenched beaches and lush rainforests. Explore the capital city of St. John’s, where the baroque towers of St. John’s Cathedral stand guard. Visit the Museum of Antigua and Barbuda and see Arawak and colonial antiquities. Glimpse rarely-seen species in the rainforest canopy. Nearby, Barbuda is home to one of the region's most significant bird sanctuaries. Sample shore excursions: Kayak & Snorkel Adventure; Five Star Bird Island.

Day 6 - Fort de France, Martinique

Arrive: Thu 05 November 2026 at 08:00 / Depart: Thu 05 November 2026 at 21:00

Stunning volcanic history (in 1902 Mont Pelee blew open with catastrophic force), rum distilleries and blooms in every tropical hue await on this verdant "Island of Flowers."

Day 7 - Roseau

Arrive: Fri 06 November 2026 at 08:00 / Depart: Fri 06 November 2026 at 17:00

Wonderfully untouched. Take in the thunder of Trafalgar Falls, breathtaking in triplicate; watch for the rare and beautiful Sisserou parrot, found only here.

Day 8 - St. Kitts

Arrive: Sat 07 November 2026 at 08:00 / Depart: Sat 07 November 2026 at 17:00

St. Kitts and Nevis are a pair of islands that form a single Eastern Caribbean nation. Ripe with historical sites, the larger St. Kitts passed hands among the Spanish, French and English, with the latter establishing the strongest foothold. The architecture and layout of its capital city, Basseterre, are all typically British. And the island's sprawling, colonial-era plantations are a reminder of the tumultuous history of the tobacco, rum, sugar and slave trades that were here for generations. Beyond its rich past, St. Kitts offers golden-sand beaches for relaxing, a lush jungle interior that welcomes heart-pumping adventure, laid-back bars with fantastic sunset views and restaurants serving up über-local fare.

Day 9 - St. Thomas (US Virgin Islands)

Arrive: Sun 08 November 2026 at 08:00 / Depart: Sun 08 November 2026 at 16:00

The lovely, European-influenced port of Charlotte Amalie wins the prize for Caribbean shopping thrills. Cameras, jewelry, watches, perfumes are all here. So are beautiful beaches, undersea gardens and tales of Blackbeard. Sample shore excursions: Sea Trekking Helmet Dive & Coral World; Champagne Catamaran Sail & Snorkel to St. John; St. Thomas Ocean Racing; Ultimate Island Experience.

Day 10 - At Sea

Day 11 - Half Moon Cay

Arrive: Tue 10 November 2026 at 08:00 / Depart: Tue 10 November 2026 at 15:00

The Caribbean is full of tropical wonders and natural beauty. But there’s nothing like Half Moon Cay, our pristine private island paradise in the Bahamas. Cruise to the Bahamas with Holland America Line and discover the most stunning, highest-rated private-island experience in the region, Half Moon Cay. This island has won Porthole Cruise Magazine’s Best Private Island award 17 consecutive years, and was also named the best in Travel Weekly's Readers' Choice Awards. As soon as your toes touch that powdery white sand and your eyes settle on the perfect blue-crystal clear water, you’ll understand why this island is one of the most sought out destinations. Whether you are planning a romantic getaway or a family vacation, book a Bahamas cruise and explore Half Moon Cay's beautiful beaches, exciting cruise excursions, exclusive beach cabanas and more.

Day 12 - Miami

Arrive: Wed 11 November 2026 at 07:00 / Depart: Wed 11 November 2026 at 16:00

Because of its many canals and waterways, Ft. Lauderdale is sometimes called the Venice of America. It's home to the annual Fort Lauderdale International Boat Show, one of the largest in-water boat shows in the world; which is one of the many reasons our Fort Lauderdale cruise guests love visiting here. Guests can easily get a taste of the area's nautical lifestyle by cruising the Intracoastal Waterway on an old-fashioned paddle wheeler. Other options include hopping aboard one of the popular water taxis or Venetian gondolas that glide down the historic New River, which flows right through town. While Ft. Lauderdale is often overshadowed by its flashy neighbor, Miami, the port city is expanding rapidly as major developers and high-end resorts build up the beachfront and surrounding neighborhoods. Visitors will find world-class shopping on famous Las Olas Boulevard, celebrated restaurants and a cultural explosion in the Riverwalk Arts & Entertainment District. It's clear that Ft. Lauderdale is solidifying its place as a sophisticated destination, and one of the reasons our Fort Lauderdale cruises are a popular choice for many vacation goers.

Day 13 - Key West

Arrive: Thu 12 November 2026 at 07:00 / Depart: Thu 12 November 2026 at 16:00

One of the first things you’ll notice on your Key West cruise is the colorful gingerbread wooden houses and the amazing sunsets, and the constant crowing of roosters. Hundreds of the noisy birds—along with their quieter-clucking mates—roam the streets at all hours, and are nearly as synonymous with Key West cruises as its six-toed cats, the famous furry residents of Ernest Hemingway’s mansion in the Old Town district. They’re all part of the quirky charm of the United States' southernmost point, whose compact 11 square kilometers (4.2 square miles) pack in everything from gorgeous historic architecture and spectacular fishing and sailing to a raucous party scene along famed Duval Street. All of which is truly enjoyed by vacationers who cruise to Key West, Florida.

Day 14 - At Sea

Day 15 - Falmouth,Jamaica

Arrive: Sat 14 November 2026 at 08:00 / Depart: Sat 14 November 2026 at 17:00

Noted for being one of the Caribbean's best-preserved Georgian towns, Falmouth boasts a rich 18th and early 19th century history. Explore Saint Peter's Anglican Church, built in 1795; shop for local crafts at the Albert George Shopping and Historical Centre, and visit Greenwood Great House; built in 1760, this house was once owned by poet Elizabeth Barrett Browning's family and today is home to the finest antique museum in the Caribbean.

Day 16 - George Town, Cayman Islands

Arrive: Sun 15 November 2026 at 08:00 / Depart: Sun 15 November 2026 at 17:00

Crystalline waters, snorkeling with tame stingrays, civilian submarines: This duty-free port has it all, plus Seven Mile Beach and a charming turtle farm. Sample shore excursions: Stingray City Cruise & Island Drive; Reef & Wreck Snorkel by Boat; Scuba Adventure; Nautilus One Semi-submarine.

Day 17 - At Sea

Day 18 - Mahogany Bay

Arrive: Tue 17 November 2026 at 07:00 / Depart: Tue 17 November 2026 at 16:00

Located just 40 miles northeast of mainland Honduras, Roatán Island is a Western Caribbean paradise. Enjoy the ease of Mahogany Bay’s new state of the art cruise ship terminal; relax on a soft sand beach; and explore the Carambola Botanical Gardens and nature trails in search of iguana, parrot, and archaeological sites dating back to Mayan times. Sample shore excursions: Roatán West Side Island Tour; Submarine Boat Ride & West End Village.

Day 19 - Cozumel

Arrive: Wed 18 November 2026 at 08:00 / Depart: Wed 18 November 2026 at 16:00

A cruise to Cozumel will take you , anto an island in the Caribbean off the eastern coast of Mexico's Yucatán Peninsula. Cozumel is a popular destination as , drawsit draws many scuba divers, snorkelers and seekers of sand and sun who are attracted by the reliably sunny and tropical climate. The island and its environs also offer all other manner of on- and around-the-water attractions, many of which are quite unique, such as underwater sculpture gardens, a submarine excursion to see a shipwreck and a sailboat-racing experience that's second only to the America's Cup. For visitors who are intrigued by Mexico's Maya culture, there are several archaeological sites in and around Cozumel, including the UNESCO-inscribed Chichén Itzá and, on Cozumel itself, San Gervasio, once a site where women made offerings to the goddess of fertility and childbirth. When you're done sightseeing on your cruise to Cozumel, there's shopping for traditional Mexican crafts, jewelry and leather goods, including custom-made sandals, and excellent food (the seafood, of course, is stellar).

Day 20 - At Sea

Day 21 - Half Moon Cay

Arrive: Fri 20 November 2026 at 09:00 / Depart: Fri 20 November 2026 at 16:00

The Caribbean is full of tropical wonders and natural beauty. But there’s nothing like Half Moon Cay, our pristine private island paradise in the Bahamas. Cruise to the Bahamas with Holland America Line and discover the most stunning, highest-rated private-island experience in the region, Half Moon Cay. This island has won Porthole Cruise Magazine’s Best Private Island award 17 consecutive years, and was also named the best in Travel Weekly's Readers' Choice Awards. As soon as your toes touch that powdery white sand and your eyes settle on the perfect blue-crystal clear water, you’ll understand why this island is one of the most sought out destinations. Whether you are planning a romantic getaway or a family vacation, book a Bahamas cruise and explore Half Moon Cay's beautiful beaches, exciting cruise excursions, exclusive beach cabanas and more.

Day 22 - Miami

Arrive: Sat 21 November 2026 at 07:00 / Depart: Sat 21 November 2026

Because of its many canals and waterways, Ft. Lauderdale is sometimes called the Venice of America. It's home to the annual Fort Lauderdale International Boat Show, one of the largest in-water boat shows in the world; which is one of the many reasons our Fort Lauderdale cruise guests love visiting here. Guests can easily get a taste of the area's nautical lifestyle by cruising the Intracoastal Waterway on an old-fashioned paddle wheeler. Other options include hopping aboard one of the popular water taxis or Venetian gondolas that glide down the historic New River, which flows right through town. While Ft. Lauderdale is often overshadowed by its flashy neighbor, Miami, the port city is expanding rapidly as major developers and high-end resorts build up the beachfront and surrounding neighborhoods. Visitors will find world-class shopping on famous Las Olas Boulevard, celebrated restaurants and a cultural explosion in the Riverwalk Arts & Entertainment District. It's clear that Ft. Lauderdale is solidifying its place as a sophisticated destination, and one of the reasons our Fort Lauderdale cruises are a popular choice for many vacation goers.