Coastal Bliss in Jamaica

  • Trip Type
  • Mid-Luxury
  • Length
  • 7 Days / 6 Nights
  • When to Go
  • November-June
Soulful rhythms, emerald cascades, and barefoot elegance

Jamaica’s rugged cliffs, coral reefs, and colonial echoes set the stage for a romantic journey steeped in rhythm and soul. This 6-night luxury escape blends Negril’s wild edge with Montego Bay’s timeless grace. Climb Dunn’s River Falls, snorkel sapphire waters, and toast the horizon on a private sunset sail. Dine in a hidden cliffside grotto, unwind with a seaside massage, and retreat to two of the island’s most iconic boutique properties. Designed for couples craving connection and Caribbean color, this is Jamaica at its most intimate and alive.

Trip Highlights

  • Guided climb of Dunn’s River Falls
  • Private sunset catamaran sail with champagne
  • Snorkeling Negril’s coral reefs
  • Candlelit grotto dinner on the cliffs
  • Tour of Rose Hall Great House
  • Beachfront couples’ massage
  • Private Montego Bay street food adventure

similar trips per person from:

$3,575.00 low season (May - Oct)
$4,700.00 high season (Nov - Apr)
prices vary based on departure season.

At a Glance

Click each day for more details

  • 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.

  • 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.

  • 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.

  • 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.

  • 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.

  • 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.

  • 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.

  • 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.

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Accommodations

Rockhouse Hotel, Negril

Carved into the cliffs of Negril’s West End, Rockhouse is a soulful boutique retreat where thatched-roof villas meet the sea. With ladders to the turquoise water, a world-class spa, and farm-to-table cuisine, it’s a place for unplugged romance, barefoot luxury, and laid-back island rhythm. Hotel website.

Round Hill Hotel, Montego Bay

Timeless and elegant, Round Hill Villas offer classic Caribbean luxury with a private, residential feel. Each villa is uniquely designed with ocean views, private pools, and dedicated staff, all set within a lush, secluded estate just outside Montego Bay. Ideal for couples, families, or groups seeking refined comfort with five-star service. Hotel website.

What's Included?

Your trip includes everything you want & need, plus a few surprises along the way. Unique, unforgettable destinations; tours with local experts; authentic local cuisine; lessons, demonstrations & new cultural insights; more adventure than you can handle; blissful relaxation; romantic touches; and a feeling of total freedom. ROAM takes care of everything so that you can enjoy a hassle-free journey without worrying about a thing.

  • Airport pickup
  • All hotel accommodation
  • All breakfasts, 1 lunch, all dinners
  • Detailed maps and trip preparation guide
  • All special events and tours
  • All vehicle and regional air transportation from rendezvous to drop-off
  • All baggage transportation
  • All gratuities for baggage, porters and hotel service

Know Before You Go

  • Itinerary prices are dependent on season of departure. Christmas, New Years and Easter (Semana Santa) are peak season, and prices during these periods are significantlky higher than other times of year. High season runs from November through April, and green season from May through September.

  • Arrival: hotel check-in times are at 3:00pm, but you may arrive at any time during the day. If you arrive prior to the scheduled check-in time, we will arrange for early check-in wherever possible.

  • Departure: hotel check-out times are at 9:00am. International flights on your departure day should be arranged to depart after 1:30pm.

  • All prices in USD.

  • For vaccination recommendations, please visit the CDC website.

  • For American, Canadian, and British citizens, a valid passport with 6+ months remaining is required for entry to Belize.

  • Debit cards may not work in Central America, but most establishments accept major credit cards.

  • Please ensure you have immediate access to a minimum of USD $250 as an emergency fund to be used if circumstances outside our control (e.g. a natural disaster) require changes to your planned route.

  • If departing Belize by air, most major airlines include exit taxes in the price of your airfare.

  • It is customary to tip service providers (waiters) around 10% depending on service. Tipping taxi drivers is not required.

  • Gratuities for guides and drivers are deeply appreciated, and provide an important supplement to their income. If you are pleased with the tour services you've received, a guideline for tipping in Central America is USD $8-10 per person per day for multiple-day tours, or USD $5-10 per person for day tours.

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Getting There

From North America: several airlines offer direct and connecting flights to Belize’s international airport: Philip S. W. Goldson International Airport in Belize City (airport code: BZE). Including connection time, flights from the USA typically range from 2.5-9 hours in duration, while most flights from Canada range from 9-15 hours in duration.

From the UK: there are currently no direct flights to Belize from the UK, but there are several flight options connecting in the United States and/or Canada. Including connection time, flights from the UK typically range from 12-18 hours in duration.

When you arrive in BZE, there will be an airport transfer waiting to take you to your first destination. If you have questions about flights, or require assistance booking, please contact us here. We're here to help!

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How it Works

Step 1: Get Inspired

Browse our trip ideas. We specialize in creating custom trips centered around your special event, so this is a starting point - your trip will be unique! Then, we want to get to know you and your travel companions better. Once you send us your inquiry, our team will reach out to you within 48 hours to schedule an intake call.

Step 2: Plan

We'll discuss your trip ideas, what matters to you, and your budget. We take your vision, and our ideas, and turn it into a tangible plan.

No idea what you want? No problem! Have as little or as much input as you want to. You can select your dream resorts and activities, or leave it to us. We've got you.

Step 3: Experience

From here, the process is simple. We refine your itinerary until it's perfect, then you pay a deposit, and we get to work behind the scenes to prepare & arrange your trip.

We'll be here if you have any questions before your departure. Next thing you know, you're in paradise!

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