Luxury Jamaica Itinerary

Jamaica: Where Every Little Thing is Going to be Alright

The home of Bob Marley is, of course, known for its music and Caribbean beats, and part of the thrill of our Jamaica itinerary is to hear those rhythms wherever you go as well as the gospel sounds pouring from churches. In addition to its rich culture and feel-good cuisine, Jamaica is a picturesque island of waterfalls, sandy beaches and exquisite coral reefs.  

Jamaica’s history, immortalized in sites like Rose Hall Great House and the Bob Marley Museum, adds depth to the island’s allure, and visitors can delve into its past while exploring the island. And of course, this is the perfect destination for scuba-diving, snorkelling, bamboo rafting, caving, and hiking.  

For adventure seekers, the island provides a playground for activities like zip-lining through rainforests, exploring hidden waterfalls, or horseback riding along the shore. Jamaican spas, often sought out for their holistic healing techniques, offer rejuvenating therapies set against the backdrop of serene beaches and tropical gardens. 

Jamaica tantalizes the senses with its vibrant culture, and exquisite Creole food – yam, rice, plantain and local fish washed down with rum is often accompanied by the rhythm of reggae in chic beachfront restaurants. But whether it’s sipping cocktails at sunset, indulging in spa treatments, or exploring the island’s natural wonders, Montego Bay provides an enchanting mix of all the luxury, culture, and adventure Jamaica has to offer. 


December - April


From GBP £4,850 USD $5,965 pp excl. flights


8 days


9 hours 45 mins from London
4 hours From NYC


Jamaican Dollar



When to go

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Jamaican cuisine is a delightful fusion of flavours from various cultures, including African, European, and Asian influences. Known for its vibrant street food culture, try tasty snacks and dishes like beef patties and ackee and saltfish.

The itinerary

Kayaking at Round Hill Retreat

Kayaking at Round Hill offers an exhilarating aquatic adventure amidst the Caribbean’s crystal-clear waters. Paddlers glide along the coast, exploring hidden coves, vibrant coral reefs, and lush mangrove forests. With warm tropical breezes and ultra-clear waters, kayakers often encounter diverse marine life, including colourful fish and sea turtles. Whether navigating tranquil bays or riding gentle waves, Round Hill’s kayaking experiences cater to both beginners and seasoned enthusiasts.

Montego Bay Cultural Centre

History buffs can head to Sam Sharpe Square, where revolving museum exhibits and historic monuments at the Montego Bay Cultural Centre tell Jamaica’s complex stories. While you’re there, make sure to enjoy a meal at Ol’ Joe, a beloved eatery serving traditional Jamaican cuisine!

Snorkelling at Round Hill Retreat

Snorkelling at Round Hill offers a captivating journey into a realm of vibrant marine life and brilliant coral formations. Warm Caribbean waters offer excellent visibility for snorkelers, and you can explore a kaleidoscope of colours beneath the surface. Along the coastline, coral gardens are filled with exotic fish, sea fans and sponges creating a surreal aquatic paradise.

The Spa at Round Hill

The resort’s spa is a tranquil haven where you can indulge in a variety of spa treatments, including massages, facials, and body therapies to promote relaxation and rejuvenation. There is also the opportunity to join yoga and wellness classes, all of which are hosted in carefully selected settings, allowing you to benefit from the tranquillity and rejuvenating atmosphere.

Paddleboarding at Round Hill

Paddleboarding at Round Hill invites adventure-seekers to catch a wave, or those seeking something less challenging to glide gracefully over the Caribbean’s turquoise waters. Standing atop a stable board, paddlers novice and experienced alike can explore the island’s coastal beauty and tranquil bays.

Walking Trail at Round Hill Retreat

Sitting at the top of Round Hill is the exclusive walking/running trail – also known as the Fit-trail. Paired with the incredible views of the Caribbean Sea, the Fit-trail path is approximately three quarters of a mile through the resplendent mangrove forest. Along the way, you’ll discover workout stations which guide you through upper and lower body workouts for all fitness levels.

The itinerary


Where to stay

Nothing but the best. On this suggested Jamaica itinerary these are our handpicked, tried-and-tested choices.

Roundhill, Montego Bay

Round Hill is a luxurious retreat that captures the essence of Caribbean elegance. This 110-acre private enclave features individually designed guestrooms, suites and villas, each with stunning ocean views.

With its classic architecture and lush gardens, Round Hill exudes timeless charm, complete with a private beach, infinity pool, award-winning spa and a diverse range of water activities.


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Our tailor-made journeys include:

  • A dedicated Destination Expert who will curate your itinerary from scratch, tailoring it to your preferences + interests
  • Private + extraordinary under-the-radar experiences
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