At a Glance
Click each day for more details.
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Day 1: Montego Bay to Negril - Arrival
Arrive at Montego Bay’s Sangster Airport and enjoy a scenic private transfer along Jamaica’s lush coast to Tensing Pen, a cliffside hideaway where handcrafted cottages overlook the Caribbean. Check into your sea-facing suite and toast your arrival with fresh coconut cocktails as the sun dips behind the horizon. Dinner is at your leisure—perhaps grilled snapper at the thatched-roof Lodge restaurant.
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Day 2: Negril - Chasing waterfalls in Ocho Rios
Venture to Ocho Rios for a guided climb up Dunn’s River Falls, ascending the 600-foot cascade hand-in-hand. Cool off in turquoise pools and refuel with roadside patties and coconut water. Return to Tensing Pen for a sunset swim from the resort’s iconic bridge, then dine cliffside on jerk chicken and grilled pineapple under flickering lanterns.
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Day 3: Negril - Snorkeling coral reefs, then dine in a candlelit grotto
Snorkel Negril’s reefs on a shared boat tour, drifting over gardens of coral where angelfish and sea fans flourish. Spend the afternoon lounging by the saltwater pool or relaxing with a deep-tissue massage. As night falls, slip into something special for a private dinner in a candlelit grotto carved into the cliffs—lobster, rum punch, and the sounds of the sea all to yourselves.
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Day 4: Negril - Champagne sipped on a sunset sail
After a slow morning of beachcombing or yoga, set sail on a private sunset catamaran cruise from Negril’s shores. Sip chilled champagne as the coastline slips by, anchoring in a hidden cove for a swim before returning under a sky ablaze with stars. Cap the night with rum cocktails and slow dancing on your private terrace.
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Day 5: Negril to Montego Bay - Grace & grandeur in iconic Montego Bay
Transfer privately to Round Hill Hotel and Villas, a heritage estate with whitewashed villas and interiors by Ralph Lauren. Check into your oceanfront suite, then head out for a guided visit to the Rose Hall Great House, steeped in myth and Georgian splendor. Return to Round Hill for a beachfront couples’ massage before dinner at The Grill, where island ingredients meet continental finesse.
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Day 6: Montego Bay - Island ease
Savor your final full day at leisure—whether you’re lounging on Round Hill’s private beach, exploring the estate’s gardens, or enjoying a final cocktail from the infinity pool. Toast your trip over grilled lobster and rum cake, watching the waves roll in as the sun sets over Montego Bay.
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Day 7: Montego Bay - Jamaica's vibrant food scene
Embark on a private Montego Bay food tour, guided through vibrant eateries to taste jerk chicken, festival dumplings, and Blue Mountain coffee, curated for an intimate culinary adventure. Return to Round Hill for a leisurely afternoon by your plunge pool or beach.
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Day 8: Montego Bay - Departure
Enjoy a final breakfast of Blue Mountain coffee and fresh fruit overlooking the sea. After a quiet morning stroll, your private driver will escort you to the airport. Depart with the island’s rhythm still pulsing through your hearts.
