Tailor-Made Holiday

Jamaica - Highlights of Jamaica

14 days

from £4,775pp

This classic 14-day island exploration takes you to the four corners of Jamaica, staying in small boutique hotels with character and charm. Jamaica is the Caribbean’s third largest island offering a variety of landscapes, wildlife, birdlife and golden Caribbean beaches. Snorkel, visit rural fishing villages, hike, mountain bike and participate in a range of cultural tours and activities. From cool mountain top to balmy beach, this trip suggestion offers a great introduction to Jamaica.

  • Dine in a candle lit cave with views of the sun setting over the Caribbean sea
  • Search for manatees and crocodiles on a boat tour along the south coast rivers
  • Hike and bike forest trails through Jamaica’s beautiful Blue Mountains
  • Explore sleepy fishing villages in Treasure Beach

All of the small hotels that we use are terrifically comfortable bases offering spa services and are great places to relax in their own right. Perched on a rocky outcrop The Caves has 12 suites with wonderful views. Jakes is nestled away on the sandy south coast in Treasure Beach, and Strawberry Hill will take you back to the colonial era, as a beautiful plantation house on a coffee estate in the misty Blue Mountains. This classic holiday finishes at the glamorous GoldenEye beach resort on the north coast. 

For a more detailed itinerary with great ideas on what to do and where to stay, please get in touch with our experts.

  Click here to see what is included/excluded

what is included

  • All accommodation
  • Internal flights
  • International flights as detailed
  • Sightseeing with private guide as per the itinerary
  • Transfers as detailed

what is excluded

  • Gratuities
  • Travel Insurance
  • Visas


Itinerary at a glance

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Day 1

Fly London to Montego Bay

Drive from Montego Bay to Negril

Negril is a lively, seven mile strip of sand, lined with jerk chicken shacks and local bars. It is also a centre for various outdoor activities, from scuba diving to mountain biking. To get away from it all, head inland to the Royal Palm Reserve or south to the scenic, low cliffs where the area's exclusive retreats are tucked away.

You will be staying at The Caves

Day 2

Several Days of Activities
Days at leisure to relax or choose from a wide range of locally bookable activities and excursions;

- Take a morning fishing trip to catch Mahi Mahi, tee off at Negril Hills Golf Club (one of Jamaica’s finest courses)

- Horseback ride through Paradise Park, a beautiful farm that encompasses a number of rivers and sprawling fields.

- Take a tour of the Royal Palm Reserve, the second largest wetland in Jamaica, created to protect the endangered swamp cabbage palm in 1989. A mile-long board walk meanders through the morass and is a good place to spot ospreys, herons, egrets and the endangered black billed parrot.

- Bird lovers will want to visit Rocklands Estate, outside the town of Anchovy, where you can hand feed hummingbirds (including the doctor bird, Jamaica’s national bird) who will perch on your finger while they drink from a hand held bottle.

If you fancy a little nightlife then Rick’s Cafe is the famous watering hole of choice, reputed to be the best place in Negril to enjoy the sunset and a fun place to sup on a red stripe while you watch the cliff divers take to the air.

You will be staying at The Caves

Day 3

You will be staying at The Caves

Day 4

Drive from Negril to Treasure Beach

You will be staying at Jakes

Day 5

You will be staying at Jakes

Day 6

You will be staying at Jakes

Day 7

Drive from Treasure Beach to the Blue Mountains

You will be staying at Strawberry Hill

Day 8

Several Days at Leisure
Days at leisure to soak up the views and unwind in the pristine hills of the Blue Mountains. For further exploration, activities include hiking trails, guided walks and tours of the beautiful gardens on the Strawberry Hill estate.

Kingston, just 45 minutes away also has a huge amount to offer, particularly in the way of museums and art galleries. A combination of the Arawak, Spanish, British, Chinese, Indian and African influences have culminated in a rich and varied Jamaica, whose customs, traditions and beliefs are depicted in Kingston's downtown cultural centres.

You will be staying at Strawberry Hill

Day 9

You will be staying at Strawberry Hill

Day 10

Drive from the Blue Mountains to Oracabessa

A journey time of approximately two hours.

You will be staying at Goldeneye

Day 11

Goldeye - Several Days to Explore
Free days to relax at Goldeneye and explore the surrounding countryside. Bond fans may wish to visit the stunning private beach of Laughing Waters, where Ursula Andress made her unforgettable appearance from the sea in Dr. No.

You will be staying at Goldeneye

Day 12

You will be staying at Goldeneye

Day 13

Drive from Oracabessa to Kingston

Fly Kingston to London


Below you can see some of the wonderful places we recommend you stay on your journey.



Jakes is a charming seaside resort nestled in the quaint fishing village of Treasure Beach, offering a mix of adobe-like cottages, guestrooms and villas....

View Accommodation

Strawberry Hill

Strawberry Hill

Originally a coffee estate, Strawberry Hill is located 3,100ft....

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The Caves

The Caves

The Caves are a colourful collection of 12 Cottages, Suites and a Four-bedroom Villa....

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The former estate of James Bond author, Ian Fleming, GoldenEye is one of Jamaica's most luxurious and exclusive coastal resorts....

View Accommodation

For a more detailed itinerary with great ideas on what to do and where to stay, please get in touch with our experts.

Destination Experts

Our experts have unrivalled firsthand knowledge of Jamaica

John Faithfull, Travel Expert

"Personalised service. Seemed to really want to get it right for us. Very impressed when I first called and John spent 40 minutes finding out what we wanted to do and tailoring it for us."

"The expertise that John has really gave us faith in where we were going, the regions, the hotels, the trips. John knew about it all, he described them in detail, and when we asked for different regions he was straight in there with suggestions and ideas. The way the whole trip was planned and presented to us, never any pressure to book or any problem to change plans /ideas."

"John Faithful was wonderfully helpful and conscientious in arranging the itinerary and was always ready to suggest alternatives or rearrange matters without any hesitation; this and his detailed knowledge gave one great confidence."

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For a more detailed itinerary with great ideas on what to do and where to stay, please get in touch with our experts.

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Holiday Ideas in Jamaica

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