Journey to a Jamaica You’ve Never Seen Before
Say goodbye to your preconceived notions of Jamaica as we journey around the island on a 10-night itinerary to show you a side of this slice of paradise you would not have imagined existed.
Stunning scenery on the Pantrepant estate (photo credit: Dominique DeBay Collection)
Perhaps when you think of a trip to Jamaica, all you can imagine is warm weather and sandy beaches, maybe even crowded all-inclusive resorts. While there is plenty of that to go around, we have a stunning ten-night itinerary around Jamaica featuring some beautiful hotels (all owned by Chris Blackwell of Island Records fame) and fabulous activity suggestions along the way that will show you a trip to Jamaica can be so much more if you want it to be. This is Jamaica as you have never seen or imagined, from adventures in the mountains to kayaking lagoons to private dinners in secret caves.
Begin your virtual journey around this island below, which is sure to set you daydreaming about your in-person journey sometime soon, which we are more than happy to arrange for you!
Day 1
Arrival Day
The two-bedroom villa at Strawberry Hill, nestled in the Blue Mountains (photo credit: Dominique DeBay Collection)
Welcome to Kingston, the capital of Jamaica! On arrival, meet your private driver, who will take you up the Blue Mountains to Strawberry Hill, your intimate mountaintop retreat.
This afternoon, sit back on your balcony with your feet soaking, finding yourself surrounded by the lush landscape as your spa therapist prepares your customized in-room treatment, perfect after a day of traveling.
This evening, sip on sunset cocktails poolside as you overlook the sparkling lights of the city, followed by a sumptuous dinner on the veranda. Retire early to your charming wood-framed cottage.
Hotel Spotlight
Strawberry Hill
A unique hilltop hotel in the heart of the Blue Mountains—a UNESCO World Heritage Site, we might add—Strawberry Hill is truly a magical mountain village. It is comprised of unique and exquisite cottages nestled into the mountain’s contours, looking down at Jamaica’s capital city of Kingston, only a 30-minute drive away. The way the cottages are situated in the mountain ensures privacy, and the verandas are all angled to capture their own ravishing views. There are 16 cottages in all, made up of five Studio Suites, four Studio Cottages, one Two-Bedroom Cottage, one One-Bedroom Villa, and two One-Bedroom Villas. The variation in accommodation size means there is something for everyone. Here, you can enjoy a cool mountain breeze, learn all about Blue Mountain coffee, and enjoy hiking to explore a different side of Jamaica than most travelers ever experience. Along with bird watching and nature hiking in the Blue Mountains, you can also have a little fun playing backgammon or finding your center on the yoga deck. Easy excursions include the Blue Mountain Coffee Estates, Holywell National Park, the National Gallery, and Kingston music and cultural tours, many of which we have included in this itinerary.
Day 2
Hike for the Wine & Coffee
A local guide (photo credit: Dominique DeBay Collection)
This morning, listen to the sounds of the chirping birds during a peaceful breakfast on the veranda looking out at the hills. Afterwards, hike with a native and explore nature’s bounty on The Gordon Town Trail, passing beautiful waterfalls and quaint churches.
This afternoon, relax with a bottle of wine, some cheese, and a breathtaking view of the forest at Holywell. Learn about (and taste!) the world’s best coffee on a tour of the Craighton House Coffee Estate.
For the evening, we recommend a garden stroll around the property’s legendary grounds to explore hundreds of exotic plant species before enjoying a quiet dinner and then a nightcap at the bar’s fireplace.
Accommodations: Strawberry Hill
Day 3
Get to Know Kingston
Start your day by surveying the vast open vistas with a private yoga session on the lawn and a fresh plate of fruit.
This afternoon, savor incredible organic cuisine at EITS on your drive into Kingston. Once you have arrived into the city, take in picturesque Kingston Waterfront, Fleet Street, and Life Yard on your way to visit the National Gallery, Jamaica’s art museum. This is a commercial and cultural center on Kingston Harbor.
Before heading back up the hill, head to Devon House for an ice cream. Or, for a more “reggae route,” check out the Bob Marley Museum, Trenchtown Culture Yard, Heroes Park, or Tuff Gong Studio. Please note, we can arrange a private driver and guide for all of today’s touring if you’d like!
This evening, return to Strawberry Hill for a final dinner overlooking the capital along with a soundtrack of great music.
Accommodations: Strawberry Hill
Day 4
Off to GoldenEye You Go!
The rooftop lounge of Shabeen, where you can enjoy rum cocktails on arrival at GoldenEye (photo credit: Dominique DeBay Collection)
This morning, absorb your last breaths of cool mountain air and sips of heavenly coffee from your classic Colonial-style home, which has served as your first stop on this not-so-standard Caribbean escape.
Depart for the illustrious GoldenEye north via Buff Bay—because the scenic route is the best route.
Stop by Twyman’s family-run Old Tavern Coffee Estate for more world-renowned gourmet coffee or sample festive street food along the way as you say your proper goodbyes to the Blue Mountains. Please note, we can arrange a private driver and guide for today’s transfer and any touring you might wish to do en-route if you’d like!
This evening, arrive at GoldenEye, where refreshing Blackwell Rum cocktails await at Shabeen, a chill spot with a rooftop lounge that is the perfect spot to take in panoramic views of the sea. Dine on fresh seafood at Gazebo, a hip open-air treehouse-style lounge and restaurant looking out at Low Cay Beach and the Lagoon.
Hotel Spotlight
GoldenEye
Once the Jamaican home of author Ian Fleming, the creator of James Bond, GoldenEye was opened as a hotel in 2011 by Chris Blackwell. The 52-acre seafront estate is home to secret coves, lagoons, and private beaches. True fans of 007 will want to stay in the villa where 14 James Bond novels were written. Other fabulous accommodation options include the 1- and 2-bedroom Beach and Lagoon Villas, Lagoon Cottages, or Beach Huts. With two beaches, three restaurants, and four bars, there are plenty of places for you to relax as well as eat, drink, and be merry! Activities include weekly barbecues and cocktail parties, bonfire nights, a spa with yoga and meditation, three pools, paddle-boarding, snorkeling (some say GoldenEye enjoys the best snorkeling in Jamaica, in fact!), glass-bottom boat tours, turtle hatching, tree planting, and tennis. The resort also enjoys access to Noel Coward’s former estate, Firefly. Here’s a little top tip: if you stay in a Lagoon Cottage, you will have direct access to the 6-acre lagoon from your deck and can kayak over to the Field Spa for a massage. Dreamy!
Poe Perks at GoldenEye:
Upgrade on arrival, subject to availability (Only applicable in the Beach Hut category)
Full breakfast daily
$100 USD equivalent resort/hotel credit to be utilized during stay (not combinable, not valid on room rate, no cash value if not redeemed in full)
Early check-in/late check-out, subject to availability
Complimentary Wi-Fi
Day 5
Wellness & Learning the Lay of the Land
Start your morning off with a private yoga session at GoldenEye, followed by a low-key breakfast at Bizot, steps from the sea and swimming pool. Afterwards, enjoy a glass bottom boat tour to visit the fish sanctuary and learn what is being done to save the coral reef.
Lunch on rustic Button Beach to enjoy the smoky flavors of Jamaican jerk barbecue and fresh grilled fish. Afterwards, partake in some stand-up paddle-boarding around Oracabessa Bay and the Lagoon. Next, why not pamper yourself with a restorative spa treatment at Field Spa, or perhaps you’d like to plant a tree with a donation to the local Oracabessa Foundation.
Enjoy sunset cocktails this evening at Firefly, home of former British playwright Noel Coward, which enjoys the most stunning view of the Caribbean and is only 15 minutes from Goldeneye. We recommend a barbecue dinner back at Bizot, which is the perfect opportunity to mingle with other guests.
Accommodations: GoldenEye
Day 6
Snorkeling & Activities Farther Afield
This morning, partake in a private fitness session at Playscape, a meditative destination between Bizot and the beach huts, followed by breakfast at nearby Bizot. After breakfast, head out for a guided snorkeling tour to discover the various fish and extensive coral gardens surrounding GoldenEye.
Horseback riding on the beach at GoldenEye (photo credit: Dominique DeBay Collection)
This afternoon, pick between two itineraries. In the first, you can enjoy Stush in the Bush in St. Ann, a farm-to-table lunch, organic farm walking tour, and optional cooking as well as yoga and Pilates classes (1 hour 15 minutes away). Alternatively, you can enjoy rafting and lunch in Port Antonio, a full-day adventure in the town of Port Antonio in which you can experience the Blue Lagoon and rafting on the Rio Grande (2 hours away). Or, if you’d prefer, simply relax at GoldenEye and perhaps enjoy a spa treatment if you didn’t find the time yesterday, or you could even choose to ride horseback on the beach.
In the evening, return to GoldenEye if you ventured farther field, to change for dinner. We recommend enjoying dinner at a local restaurant in Oracabessa to get a feel for local cuisine—the concierge can of course help with recommendations. We also recommend a final evening cocktail at Gazebo.
Accommodations: GoldenEye
Day 7
Be Whisked Away to a Family Farm
Unforgettable meals are the only kind at Pantrepant (photo credit: Dominique DeBay Collection)
Begin your morning at GoldenEye, where you can kayak around the serene lagoon to start the day before enjoying a final breakfast at Bizot, enjoying fresh food from the farm you’re about to visit. You can depart for the farm, called Pantrepant, via car or helicopter, both of which we can arrange for you.
This afternoon, arrive to Pantrepant and your private cottage. Lunch under the centuries-old guango tree, quite possibly the best homecooked meal you’ll ever eat. Afterwards, relax on your veranda, taking in the tranquil surroundings of Cockpit County.
This evening, enjoy dinner followed by homemade ice cream and good tunes coming from your living room.
Hotel Spotlight
Pantrepant
This section is a little bit of a misnomer, as Pantrepant is not a hotel but is in fact Chris Blackwell’s private Jamaican estate, which he has opened up to guests. After making stars of Bob Marley and Grace Jones, this is where Blackwell came to tune out the noise of his everyday life, and now you can experience the peace on this estate as well. Blackwell opened the estate up for farm-to-table lunches in 2013, but it was only a couple of years ago that he opened up the estate’s two-bedroom guesthouse for overnight stays. The farm-to-table cuisine remains a major highlight of guest stays. The look is simple and organic, described as “country Caribbean.” The 200-year-old guango tree that towers behind Blackwell’s home is the star of the estate. He actually described it as the reason he bought Pantrepant in the first place, so it is unsurprising that guests love to enjoy lunch under its shade. Pantrepant has been called by Conde Nast Traveller “the best villa to rent in Jamaica.” You can read Conde Nast Travellers’ beautiful feature on Pantrepant here.
Day 8
Exploring the Farm & Surrounds
This morning we recommend a private yoga session with the calming sounds of the farm as your backdrop. After yoga, enjoy a quiet breakfast under the almond tree outside your cottage, followed by a farm tour with Conroy to learn about the delicious food you’re eating and where it comes from.
This afternoon, it’s time to saddle up as you head out on a guided horseback riding tour through the fields and forest. Take a trip down to the watering hole, a slice of heaven, to bathe in the Martha Brae River and float in a tube. Lunch under the magnificent guango tree.
This evening, enjoy a spa treatment with botanicals harvested from the Pantrepant garden, and once you’re relaxed from your pampering, enjoy your final dinner on the farm.
Accommodations: Pantrepant
Day 9
Off to The Caves!
This morning, enjoy your final breakfast on the farm on the veranda as you watch the cattle come through. Afterwards, you can depart for The Caves via car or helicopter, either of which we can arrange or you. If you go by car, we recommend visiting the David Pinto Studio along the way. He is Jamaica’s leading ceramic artist.
In the afternoon, arrive at The Caves and enjoy lunch at the Gazebo, a laidback thatched-roof pavilion.
This evening, enjoy sunset cocktails at Blackwell Rum Bar, located down a coral staircase at the water’s edge, across a wooden footbridge in a secret cave. How gloriously mysterious! Afterwards, enjoy dinner in the dining room under the stars.
Hotel Spotlight
The Caves
Perched on the limestone cliffs of Negril’s scenic West End in Jamaica (a perfect spot for jumping into the sea), The Caves is a two-acre oceanfront sanctuary with 12 exclusive cliffside accommodations. Located close to Negril’s stunning seven-mile beachfront, one of the stars of this hotel is the Blackwell Rum grotto bar, which is nestled inside a cave. Similarly, you can arrange private cave dining for a special evening (see tomorrow’s itinerary!). Their Aveda Spa enjoys a stunning sea view, as does their saltwater pool. Activities include kayaking, snorkeling, adrenaline-inducing cliff jumping, cooking and cocktail-making classes, nature walks, and weekly Jamaican themed dinner at The Sands with live music.
Day 10
Grand Finale
Cliff diving at The Caves (photo credit: Dominique DeBay Collection)
Enjoy breakfast at Gazebo with fresh fruit and made-to-order omelets. Afterwards, meet Paul for kayaking and snorkeling to discover the species of the sea just beyond the volcanic cliffs.
This afternoon, enjoy lunch with a refreshing drink followed by a spa treatment looking out at the ocean. Swoon. Next, learn how to make a delicious drink in a cocktail-making class, because what’s a trip to the Caribbean without delicious cocktails?!
On your final evening, end your trip in style with a private dinner in the cave surrounded by candles and the ocean waves. Ooh, la la!
Accommodations: The Caves
Day 11
Goodbye’s the Saddest Word
Try to enjoy your final breakfast overlooking the blue Caribbean Sea, not letting your end-of-vacation blues get in the way! Depart for Montego Bay Airport via car or helicopter, either of which we can arrange for you. As a final treat to yourself, we recommend the VIP Club Mobay Departure Service as a treat to yourself at the airport.
COVID-19 Requirements for Jamaica
You can find the most up-to-date travel requirements on Visit Jamaica’s website. All residents of the USA that are 12 years of age or older are required to present a negative COVID-19 PCR or antigen test result in order to check-in for your flight to Jamaica. Tests must be done by a medical laboratory that has a CLIA or ISO 15189 certification. The date of the sample collection must be less than 10 days from the travel date to Jamaica. See Visit Jamaica’s website for specific test requirements. You will also be required to fill out a travel authorization form.
Please note, some activities may not be operating or may be slightly altered to accommodate for COVID-19 regulations. Details on specific activities can be provided when we create a travel proposal for you.
If you would like to get away to Jamaica (or anywhere else in the world), simply contact us, and we will set you on your way.