59 days in Jamaica Itinerary

59 days in Jamaica Itinerary

Created using Inspirock Jamaica trip planner

Plan created by another user. Make it yours
1
Kingston
— 11 nights
2
Santa Cruz
— 7 nights
3
Montego Bay
— 13 nights
4
Negril
— 8 nights
5
Ocho Rios
— 11 nights
6
Port Antonio
— 7 nights

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11
nights
Kingston

Kingston ©
The country's capital, Kingston offers all the excitement of a lively and storied city, while also housing the services and facilities travelers need to get around and see the rest of the island.
Go for a jaunt from Kingston to Portmore to see Hellshire Beach about 40 minutes away. The adventure continues: take your sightseeing to a higher altitude at Blue Mountains, walk around Emancipation Park, take in nature's colorful creations at Devon House, and contemplate the waterfront views at Long Bay (Northeast).

For photos, where to stay, maps, and tourist information, refer to the Kingston road trip website.

Castries, St. Lucia to Kingston is an approximately 11.5-hour flight. You'll gain 1 hour traveling from Castries to Kingston due to the time zone difference. April in Kingston sees daily highs of 36°C and lows of 27°C at night. Finish up your sightseeing early on the 7th (Mon) so you can go by car to Santa Cruz.

Things to do in Kingston

Parks · Nature · Outdoors

Side Trips

Jamaica, Portmore, Turtle River Falls and Gardens
Find places to stay Apr 26 — May 7:
Highlights from your plan
Blue Mountains ©
Blue Mountains
Bob Marley Museum ©
Bob Marley Museum
Devon House ©
Devon House

7
nights
Santa Cruz

Santa Cruz ©
Santa Cruz is a town in Saint Elizabeth, Jamaica, on the A2 road connecting Black River to Mandeville. Change things up with these side-trips from Santa Cruz: The Mud Palace Gallery (in Treasure Beach) and Black River (in Black River). There's much more to do: admire the sheer force of YS Falls, cool off at Bubbling Spring Mineral Bath, take a stroll through Bamboo Avenue, and enjoy the sand and surf at Treasure Beach.

To find out how to plan a trip to Santa Cruz, use our trip itinerary maker.

You can drive from Kingston to Santa Cruz in 2.5 hours. Another option is to do a combination of bus and taxi. In May in Santa Cruz, expect temperatures between 38°C during the day and 28°C at night. On the 14th (Mon), you're off to Montego Bay.

Things to do in Santa Cruz

Parks · Nature · Neighborhoods

Side Trips

Saint Elizabeth Parish, Jamaica
Find places to stay May 7 — 14:
Highlights from your plan
YS Falls ©
YS Falls
Black River ©
Black River
Treasure Beach ©
Treasure Beach

13
nights
Montego Bay

The second largest city in Jamaica, Montego Bay boasts an international airport and a major cruise-line terminal, so it regularly receives a big influx of visitors to the island.
Change things up with these side-trips from Montego Bay: Tryall Golf Course (in Sandy Bay), Silver Sands Public Beach (in Duncans) and Falmouth (Water Square, Adrenaline & Extreme Tours, &more). Spend the 16th (Wed) wandering through the wild on a nature and wildlife tour. And it doesn't end there: stroll through Doctor's Cave Beach, get great views at Ahhh...Ras Natango Gallery and Garden, explore the activities along Martha Brae Rafting Village, and make a trip to Hip Strip.

To see where to stay, maps, ratings, and other tourist information, go to the Montego Bay tour itinerary planner.

Drive from Santa Cruz to Montego Bay in 2 hours. Alternatively, you can do a combination of taxi and bus. In May in Montego Bay, expect temperatures between 38°C during the day and 28°C at night. Finish your sightseeing early on the 27th (Sun) so you can drive to Negril.

Things to do in Montego Bay

Outdoors · Parks · Shopping

Side Trips

Falmouth, Tryall Golf Course, Roaring River, Silver Sands Public Beach, Rastafari Indigenous Village
Find places to stay May 14 — 27:
Highlights from your plan
Nature & Wildlife Tours
Doctor's Cave Beach ©
Doctor's Cave Beach
Rose Hall Great House ©
Rose Hall Great House

8
nights
Negril

Negril ©
Once Jamaica's hidden gem, Negril has significantly expanded its infrastructure without losing its casual way of life.
Venture out of the city with trips to Original Mayfield Falls (in Pennycooke) and Bluefields Beach (in Bluefields). There's still lots to do: tour the pleasant surroundings at Seven Mile Beach, visit a coastal fixture at Negril Lighthouse, kick back and relax at Bloody Bay, and Head underground at Blue Hole Mineral Spring.

For where to stay, photos, reviews, and more tourist information, use the Negril trip itinerary planner.

Traveling by car from Montego Bay to Negril takes 1.5 hours. Alternatively, you can take a bus. Expect a daytime high around 38°C in May, and nighttime lows around 28°C. Finish your sightseeing early on the 4th (Mon) to allow enough time to drive to Ocho Rios.

Things to do in Negril

Parks · Outdoors · Nature

Side Trips

Original Mayfield Falls, Blue Hole Mineral Spring, Bluefields Beach
Find places to stay May 27 — Jun 4:
Highlights from your plan
Seven Mile Beach ©
Seven Mile Beach
Original Mayfield Falls
Original Mayfield Falls
Negril Cliffs ©
Negril Cliffs

11
nights
Ocho Rios

Ocho Rios ©
A trip to Ocho Rios, the tourist hub of Saint Ann Parish, offers travelers a staggering amount of activities and cultural attractions.
You'll find plenty of places to visit near Ocho Rios: Bob Marley Museum (in St. Ann's Bay), Columbus Park (in Discovery Bay) and Green Grotto Caves (in Runaway Bay). There's lots more to do: take in the dramatic scenery at Dunn's River Falls and Park, stroll through Ocho Rios Bay Beach, stroll around Konoko Falls, and get outside with Outdoor Activities.

To see more things to do and more tourist information, you can read our Ocho Rios online trip planner.

Traveling by car from Negril to Ocho Rios takes 3 hours. Alternatively, you can take a bus. In June in Ocho Rios, expect temperatures between 38°C during the day and 30°C at night. Finish your sightseeing early on the 15th (Fri) so you can drive to Port Antonio.

Things to do in Ocho Rios

Parks · Outdoors · Tours

Side Trips

St. Ann's Bay, Jamaica, Columbus Park, Green Grotto Caves
Find places to stay Jun 4 — 15:
Highlights from your plan
Dunn's River Falls and Park ©
Dunn's River Falls and Park
Swim with Dolphins
Horseback Riding Tours

7
nights
Port Antonio

Port Antonio ©
A coastal getaway from coastal getaways, Port Antonio offers a break from the more touristy retreats in the west of the island.
Step out of Port Antonio to go to Hillside and see Reggae Falls, which is approximately 2h 30 min away. Next up on the itinerary: tour the pleasant surroundings at Boston Beach, admire the sheer force of Reach Falls, enjoy the sand and surf at Frenchman's Cove, and take in the waterfront activity at Errol Flynn Marina.

For ratings, reviews, where to stay, and tourist information, refer to the Port Antonio trip planner.

Traveling by car from Ocho Rios to Port Antonio takes 2 hours. Alternatively, you can take a bus. In June, daily temperatures in Port Antonio can reach 38°C, while at night they dip to 30°C. Wrap up your sightseeing by early afternoon on the 22nd (Fri) to allow enough time to travel back home.

Things to do in Port Antonio

Parks · Nature · Beaches

Side Trips

Nanny Falls, Reggae Falls, Rio Grande, Castleton Gardens
Find places to stay Jun 15 — 22:
Highlights from your plan
Frenchman's Cove ©
Frenchman's Cove
Boston Beach ©
Boston Beach
Reach Falls ©
Reach Falls

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