Luxury Caribbean Cruise from Miami to San Juan | A Journey through Stunning Scenery and Charming Caribbean Culture - JWT Travel

Luxury Caribbean Cruise from Miami to San Juan | A Journey through Stunning Scenery and Charming Caribbean Culture

  • 29 January 2027
  • 7 Nights
  • From €3,975 Per Person
  • Explora I

Embark on an extraordinary luxury Caribbean cruise from Miami to San Juan, Puerto Rico, aboard the exquisite Explora I. Discover a captivating collection of island destinations, from the vibrant shores of Puerto Plata and the colourful streets of Philipsburg to the French-Caribbean charm of Terre-de-Haut, the natural beauty of Basseterre and the historic allure of San Juan.

Between Miami and the Caribbean’s sun-kissed islands, enjoy two blissful days at sea, embracing an Ocean State of Mind through thoughtfully curated wellness experiences, exceptional cuisine and moments of pure relaxation.

Your journey begins in Miami, where cosmopolitan energy meets tropical beauty, before sailing to Puerto Plata to discover waterfalls and breathtaking mountain landscapes. Enjoy a leisurely day at sea before arriving in Philipsburg, Sint Maarten, where colourful waterfront streets and island charm invite exploration.

Continue to Terre-de-Haut, a picturesque gem where French-Caribbean culture and a laid-back island atmosphere create an irresistible escape. In Basseterre, discover lush landscapes, fascinating wildlife and dramatic volcanic scenery before concluding your voyage in San Juan, Puerto Rico, where vibrant markets, elegant colonial architecture and rich cultural heritage provide a memorable finale.

Contact your JWT Cruise team for more information on this beautiful ship and ultimate luxury Caribbean Cruise from Miami to San Juan with EXPLORA JOURNEYS.

Luxury Caribbean Cruise from Miami to San Juan | A Journey through Stunning Scenery and Charming Caribbean Culture

Embark on an extraordinary luxury Caribbean cruise from Miami to San Juan, Puerto Rico, aboard the exquisite Explora I. Discover a captivating collection of island destinations, from the vibrant shores of Puerto Plata and the colourful streets of Philipsburg to the French-Caribbean charm of Terre-de-Haut, the natural beauty of Basseterre and the historic allure of San Juan.

Between Miami and the Caribbean’s sun-kissed islands, enjoy two blissful days at sea, embracing an Ocean State of Mind through thoughtfully curated wellness experiences, exceptional cuisine and moments of pure relaxation.

Your journey begins in Miami, where cosmopolitan energy meets tropical beauty, before sailing to Puerto Plata to discover waterfalls and breathtaking mountain landscapes. Enjoy a leisurely day at sea before arriving in Philipsburg, Sint Maarten, where colourful waterfront streets and island charm invite exploration.

Continue to Terre-de-Haut, a picturesque gem where French-Caribbean culture and a laid-back island atmosphere create an irresistible escape. In Basseterre, discover lush landscapes, fascinating wildlife and dramatic volcanic scenery before concluding your voyage in San Juan, Puerto Rico, where vibrant markets, elegant colonial architecture and rich cultural heritage provide a memorable finale.

Contact your JWT Cruise team for more information on this beautiful ship and ultimate luxury Caribbean Cruise from Miami to San Juan with EXPLORA JOURNEYS.

Itinerary

CARIBBEAN CRUISE FROM MIAMI TO SAN JUAN ITINERARY

Day 1 – Miami

Welcome to Miami and the sweep of South Beach – backdrop to every iconic Miami movie, and forefront of Latin American culture. Stroll through pastel-hued geometric buildings in the art deco district, to graffiti mural masterpieces at Wynwood Walls. Watch Latino life unfold in Little Havana – the heartbeat of this great city – where walk-up windows sell café cortadito, sweet sugarcane juice, hatuey beer and guava ice-cream. Watch passionate locals discuss politics, play dominoes and smoke cigars. Shimmy at a salsa class, shop designer boutiques and race marlin and sharks by speedboat. Then slow your pace to uncover rare and endangered species at the Everglades National Park outdoor oasis. You’ll find the Miami dream is real – and it’s not just Cuban heels that will give you a spring in your step.

Day 2 – At Sea

Day 3 – Puerto Plata, Dominican Republic

The queen of the “Silver Coast”, Puerto Plata is treasured for her soaring cloud-shrouded peaks and stunning shining beaches. Once famously plundered by pirates — you too can storm the 16th-century Fortaleza San Felipe fort — now is coveted by modern-day aficionados seeking her bounty of aged rum, robust cigars, and rich chocolate. Adventurers can soar to the top of the Pico Isabel de Torres 793m (2,602 ft), dare to off-road to the Waterfalls of Damajagua, or kite-surf, catamaran, and zip-line over the ocean. Pro tip: save time for a buzzy beach club to chill with coconut-fused libations.

Day 4 – At Sea

Day 5 – Philipsburg, Sint Marteen

Princely Philipsburg reigns as the capital of the Dutch side of the dual-nation island of Sint Maarten/ and French Saint Martin. Lounging beside aptly named Great Bay, the seaside city weaves colourful streets lined with Dutch emporiums brimming with chocolates, cheeses and coveted luxuries. Kayak lapis-blue waters, dive amongst a kaleidoscope of reefs or gallop on horseback along shaded plantation trails. Play ‘lady luck’ in winning casinos or a round of golf beside an eternally blue sea. Every moment embraces the idea that a day in Philipsburg is royal.

Day 6 – Terre-de-Haut (Îles des Saintes), Guadeloupe

In dainty Terre-de-Haute, diminutive sibling of Guadeloupe and queen of the Îles des Saintes, French charm and Caribbean culture are woven together in laid-back towns and sleepy fishing villages. High above, Fort Napoleon and Le Chameau peak are flanked by fragrant forests of fern and frangipani, overlooking picture-perfect landscapes bathed in golden sunlight and sailboats afloat on gin-clear bays.

Day 7 – Basseterre, Saint Kitts and Nevis

Formed by volcanoes, St Kitts fertile soil is so rich it turns monkeys green. Trek through miles of rainforest amongst colourful wildlife to conquer the highest peak of Mount Liamuiga so you can peer into the mile-wide crater, or bravely descend to sniff the sulphur. Experience a train ride, sailing trip, cooking class, sky safari zip-line, or creative batik fabric workshops. Visit sugarcane plantations, the Narrows between St Kitts and Nevis and the UNESCO Brimstone Hill Fortress for spectacular views of neighbouring islands. You’ll find this special island small in size yet tall in standing, as well as big on charm.

Day 8 – San Juan, Puerto Rico

Explore the oldest US city for a dose of Caribbean history, slice of Spanish culture and twist of American dream. Roam historic Old San Juan alleyways to glimpse centuries-old forts and colourful colonial buildings. Learn how to move, as locals sashay out the salsa to rhythmic reggae beats. Shop the boho streets or glamorous boutiques for artisan goods, decadent designers and hand-rolled cigars. Experience world-class surfing, explore a tropical rainforest, attend a private rum cocktail tasting and polish off empanadas. Then retire to one of the beautiful beaches to soak up crystal clear waters and, perhaps, one last rum cocktail.

  • All Inclusive
  • 7 nights Ocean Terrace Suite
  • Onboard gratuities
  • Shuttle services from port to city centre (where required / available)
  • Wi-Fi
  • Subject to availability
  • T&C’s apply

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