The Greater Antilles comprises the larger islands of the Caribbean, including Cuba, Jamaica, Hispaniola, and Puerto Rico. With a dynamic fusion of cultural influences—most notably from the Caribbean and South America—the Greater Antilles offers diverse landscapes. This destination is also perfect for a winter escape aboard a superyacht because it combines warm, tropical weather with various unique experiences best enjoyed from the water.

Hispaniola, located at the heart of the Greater Antilles, is divided between two nations—the Dominican Republic and Haiti. The Dominican Republic is known for its colourful year-round festivals, while Haiti has some of the most beautiful beaches. From the deck of your luxury superyacht, you can admire the dramatic scenery, including five mountain ranges that stretch across its length and neighbouring white sand beaches.

Jamaica has long been a favorite escape for the glitterati, attracting everyone from Hollywood icons to European royalty and earning a special place in the hearts of its visitors. In the 17th century, Port Royal in the south was the largest city in the Caribbean and a bustling haven for pirates. These days, the island has an abundance of barefoot luxury resorts sitting comfortably alongside rustic beach huts. Meanwhile, the island's north coast is home to various dive sites, while its interior is a playground of waterfalls, forests, rivers, and caves.

If you're a party lover or a die-hard reggae fan, you can't miss the Reggae Sumfest. Montego Bay comes alive every July with the sweet sounds of Jamaica's iconic music. As the biggest music festival in the Caribbean, it attracts superstars from across the reggae spectrum, from digital dancehall legends to the soulful queens of lover's rock.

Located between the Virgin Islands and Hispaniola, Puerto Rico combines cultural influences, from Taino and Creole to Spanish, African, and South American. Highlights include the El Yunque National Rainforest, home to over 400 wildlife species, and the contrasting arid, rocky landscapes in the south. Puerto Rico boasts casinos, nightclubs, and historic sites like the 400-year-old San Felipe del Morro fortress for those looking for excitement ashore.

From the comfort of your luxury yacht, dock at Guayama Marina and take a 30-minute trip to Guavate, also known as La Ruta del Lechón or "The Pork Highway." On weekend afternoons, this spot comes alive with the irresistible aroma of lechón asado (roast suckling pig), hailed as the best in the world. Along the roadside, lechoneras serve mouthwatering plates of tender pork paired with rice, pigeon peas, cold cervezas, lively salsa and merengue music.

Cuba is the answer for adventurous charterers ready to trade the glitz of upscale destinations for something more authentic. Dance salsa in lively backstreet nightclubs, savour local rum straight from the distillery barrels or wander the same streets that once inspired Hemingway. Cuba is surrounded by over 200 bays and nearly 300 sun-kissed beaches, ideal for onshore excursions. Its mountainous landscapes and off-lying islands, like Isla de la Juventud (Island of Youth), offer endless opportunities for exploration.

View all the Caribbean luxury charter yachts available to rent and let a trusted yacht charter broker help craft your perfect getaway in the Greater Antilles.