Top Caribbean Tours & Cruises in 2029

Experience a 15-day exploration of the Dominican Republic, from the historic streets of Santo Domingo to the remote shores of the Samaná Peninsula. Wander the oldest colonial city in the Americas before driving north to discover secluded beaches, vibrant marine life, and lush national parks. Retreat to eco-lodges and pristine coastal villages.

Travel with a private driver-guide across the Dominican Republic for 15 days of nature, history, and coastal relaxation. Explore the colonial center of Santo Domingo before heading inland to the mountains of Jarabacoa. Discover hidden beaches, snorkel vibrant coral reefs, and rest each night in comfortable eco-lodges and boutique hotels.

Spend 15 days driving the Dominican Republic's north coast, from the colonial streets of Santo Domingo to the fishing village of Punta Rucia, the surfer town of Cabarete, and the beaches of Las Terrenas on the Samana Peninsula. This self-drive tour combines a guided city tour, snorkeling, and open coastal roads with free time at each stop.

This 8-day tour crosses the Dominican Republic, blending historic city exploration with lush mountain landscapes and pristine coastline. Wander the colonial streets of Santo Domingo, visit thriving highland plantations, and snorkel the coral reefs of Cayo Arena. Uncover local history and relax on white sand beaches along the way.

This 15-day self-drive tour crosses the Dominican Republic from Santo Domingo's Colonial Zone to the cool highlands of Jarabacoa, the surf town of Cabarete, and the beaches of the Samaná Peninsula. Along the way, you raft rivers, hike to waterfalls, bike through history, and explore secluded coves reachable only by boat.

Pick up your 4x4 and set off into the Dominican Republic's central mountains for an active 8-day adventure. You drive over high mountain passes, explore coffee plantations, and rappel down canyons. The trip culminates in a challenging 2-day trek to the summit of Pico Duarte, the highest peak in the Caribbean.

Set sail on an 8-day Caribbean cruise aboard the Emerald Sakara, starting in Philipsburg, Sint Maarten. Visit Anguilla's coral reefs, explore Virgin Gorda's grottos, and enjoy local cuisine while discovering unique island architecture.

Set sail on an 8-day Eastern Caribbean cruise from Bridgetown on Emerald Sakara, visiting St. Lucia's mud baths, Antigua's Nelson's Dockyard, and the stunning beaches of Iles des Saintes. End your journey in Philipsburg, the lively capital of Dutch Sint Maarten.

Set sail on a 15-day Caribbean cruise from Barbados aboard the Emerald Sakara, visiting Saint Lucia for its mud baths, Antigua's historic dockyard, and Anguilla's vibrant coral reefs. Conclude your journey in Philipsburg, Sint Maarten, enjoying the region's rich culture and cuisine.

Set sail on a 15-day Caribbean cruise aboard the Emerald Sakara, visiting islands like Anguilla for snorkeling and Virgin Gorda for stunning rock formations. Explore vibrant Gustavia in Saint Barthelemy, enjoy the charm of the Iles des Saintes, relax in Saint Lucia's hot springs, and experience the colonial beauty of Barbados.

Set sail on an 8-day Caribbean cruise aboard the Emerald Kaia from San Juan, Puerto Rico, exploring Vieques, Cruz Bay, and Jost Van Dyke's stunning beaches. Visit Gustavia in Saint Barthelemy, experiencing its unique French culture before concluding the journey in St. John's, Antigua.

Set sail on an 8-day Caribbean cruise aboard the Emerald Kaia from Antigua, visiting St. Kitts, Guadeloupe, and Saint-Barthelemy, before exploring the British Virgin Islands' iconic sites. End your journey in San Juan, Puerto Rico, the oldest European settlement in the Americas.