Luxury Caribbean Cruise from Miami to San Juan | A Journey of Endless Sophistication and Island Charm - JWT Travel

Luxury Caribbean Cruise from Miami to San Juan | A Journey of Endless Sophistication and Island Charm

Special
  • 27 November 2025
  • 8 Nights
  • From 4,400 Per Person
  • Dublin
  • Explora I
Sail onboard this stunning luxury Caribbean Cruise from Miami to San Juan, Puerto Rico, onboard the exquisite Explora I visiting the vibrant ports of Charlotte Amalie,  Terre-de-Haut, Fort-de-France, Bridgetown and San Juan!

Sailing between Miami and Heaven with two days at sea leads you into an Ocean State of Mind of curated wellness and culinary experiences.

Heart-shaped Magen’s Bay, beloved beach in Charlotte Amalie, rises to undulating mountains dotted with thriving gardens. In Terre-de-Haute and Fort-de-France find boulangeries selling croissants before rising with dawn to peer into the mile-wide crater near Basseterre.

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 of Endless Sophistication and Island Charm

Sail onboard this stunning luxury Caribbean Cruise from Miami to San Juan, Puerto Rico, onboard the exquisite Explora I visiting the vibrant ports of Charlotte Amalie,  Terre-de-Haut, Fort-de-France, Bridgetown and San Juan!

Sailing between Miami and Heaven with two days at sea leads you into an Ocean State of Mind of curated wellness and culinary experiences.

Heart-shaped Magen’s Bay, beloved beach in Charlotte Amalie, rises to undulating mountains dotted with thriving gardens. In Terre-de-Haute and Fort-de-France find boulangeries selling croissants before rising with dawn to peer into the mile-wide crater near Basseterre.

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 – AT SEA

DAY 4 -CHARLOTTE AMALIE – SAINT THOMAS

Savour a fusion of heritage in sparkly St Thomas. Roam a flawless Capital teeming with local culture, smart boutiques, American hallmarks, streets bearing Danish names, and former hideouts for the notorious pirates of Blackbeard and Bluebeard. Climb up to historic landmarks, catch the cable car for serious views and savour the Frenchtown quarter famed for its restaurants. Ferry to scenic conservatory of St. John, float around diamond-sand beaches with limpid blue waters and venture on forested yomps through rugged hilltops. Dreamy Caribbean warmth soaked in Danish roots and American influence – this USVI is a curious culture clash with plenty of personality.

DAY 5 – TERRE-DE-HAUT – ILES DES SAINTES

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 6 – BRIDGETOWN

Gently breeze into the vibrant capital of Barbados. Steeped in fascinating history, with architecture to match, uncover the wonderfully laid-back West Indian ambiance. Embrace the slow Bajan rhythm of this welcoming island; surf, snorkel and try spotting turtles in balmy azure waters. Explore subterranean Harrison’s Cave, Jacobean St Nicholas Abbey and zipline high above bountiful tropical flora. Then return to restore on pastel pink sands at palm-studded beaches, where you’ll discover cocktail hour is endless, and measures of rum are copious.

DAY 7 – FORT-DE-FRANCE

Follow the French flag waving over the hulking fortress that gave the city its name then dive into the island’s Afro-French-West Indies culture. Green is the island’s colour for sustainability, spicy is its flavour, and Creole is its soul. This “island of flowers” lives up to her name as one of the world’s 35 biodiversity hotspots. Hike beside waterfalls, ponder the flying buttresses at Cathédrale St-Louis, and savour cocoa farms, local rum, and artisan sorbet in the shade of one of the island’s enchanting gardens.

DAY 8 – BASSETERRE

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 9 – 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.

  • 10 night fly cruise
  • 1 night hotel Miami included
  • 8 nights Ocean Terrace Suite – All Inclusive Explora 1
  • Subject to availability
  • T&C’s apply

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