59 days in Jamaica Itinerary

59 days in Jamaica Itinerary

Created using Inspirock Jamaica trip planner

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Route & dates

Start: Castries, St. Lucia
+2
Fly + Foot + Bus:  14 h 30 min
1
Kingston
— 11 nights
Drive:  2 h
2
Santa Cruz
— 7 nights
Drive:  1 h 30 min
3
Montego Bay
— 13 nights
Bus:  1 h 30 min
4
Negril
— 8 nights
Drive:  1 h 45 min
5
Ocho Rios
— 11 nights
Drive:  2 h
6
Port Antonio
— 7 nights
+2
Drive + Fly + Drive:  15 h 30 min
End: Castries, St. Lucia

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. And it doesn't end there: take your sightseeing to a higher altitude at Blue Mountains, take in the architecture and design of University Of The West Indies - Mona, take in nature's colorful creations at Devon House, and steep yourself in history at Fort Charles.

For traveler tips, maps, more things to do, and more tourist information, use the Kingston tour itinerary app.

Castries, St. Lucia to Kingston is an approximately 9- hour combination of flight and bus. You can also do a combination of bus and flight. Traveling from Castries to Kingston, you'll gain 1 hour due to the time zone difference. In April in Kingston, expect temperatures between 36°C during the day and 27°C at night. Finish your sightseeing early on the 7th (Mon) so you can drive 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: Black River (in Black River) and The Mud Palace Gallery (in Treasure Beach). 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 take a bus. 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: Silver Sands Public Beach (in Duncans), Tryall Golf Course (in Sandy Bay) and Falmouth (Water Square, Adrenaline & Extreme Tours, &more). Spend the 16th (Wed) wandering through the wild on a nature and wildlife tour. There's lots more to do: stroll through Doctor's Cave Beach, tee off at Cinnamon Hill Golf Course, admire the natural beauty at Ahhh...Ras Natango Gallery and Garden, and explore the activities along Martha Brae Rafting Village.

For maps, where to stay, more things to do, and other tourist information, you can read our Montego Bay sightseeing planner.

Traveling by car from Santa Cruz to Montego Bay takes 2 hours. Alternatively, you can take a bus. In May in Montego Bay, expect temperatures between 38°C during the day and 28°C at night. Wrap up your sightseeing on the 27th (Sun) early enough to take a bus to Negril.

Things to do in Montego Bay

Outdoors Parks Shopping

Side Trips

Falmouth, Silver Sands Public Beach, Rastafari Indigenous Village, Rocklands Bird Sanctuary, Tryall Golf Course
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 Mayfield Falls Jamaica (Original) (in Pennycooke) and Bluefields Beach (in Bluefields). There's lots more to do: explore the striking landscape at Negril Cliffs, head off the coast to Booby Cay Island, take in nature's colorful creations at Barney's Flower & Hummingbird Garden Jamaica, and tour the pleasant surroundings at Half Moon Beach.

To see where to stay, traveler tips, more things to do, and more tourist information, use the Negril route planner.

You can take a bus from Montego Bay to Negril in 1.5 hours. Alternatively, you can drive. May in Negril sees daily highs of 38°C and lows of 28°C at night. Wrap up your sightseeing on the 4th (Mon) to allow time to drive to Ocho Rios.

Things to do in Negril

Parks Outdoors Nature

Side Trips

Blue Hole Mineral Spring, Mayfield Falls Jamaica (Original), Bluefields Beach
Find places to stay May 27 — Jun 4:
Highlights from your plan
Seven Mile Beach ©
Seven Mile Beach
Mayfield Falls Jamaica (Original)
Mayfield Falls Jamaica (Original)
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: Green Grotto Caves (in Runaway Bay), Columbus Park (in Discovery Bay) and Bob Marley Museum (in St. Ann's Bay). There's lots more to do: fulfill a lifelong dream with a swim-with-the-dolphins experience, don't miss a visit to Nine Miles, walk around Konoko Falls, and take in the dramatic scenery at Dunn's River Falls and Park.

To see maps, where to stay, more things to do, and other tourist information, you can read our Ocho Rios trip itinerary planner.

Drive from Negril to Ocho Rios in 3 hours. Alternatively, you can take a bus. In June, daytime highs in Ocho Rios are 38°C, while nighttime lows are 30°C. 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

Jamaica, St. Ann's Bay, Green Grotto Caves, Columbus Park
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: stroll through Frenchman's Cove, contemplate the waterfront views at Blue Lagoon, enjoy the sand and surf at Winifred Beach, and admire the sheer force of Somerset Falls.

To find ratings, reviews, where to stay, and other tourist information, go to the Port Antonio trip planning tool.

Traveling by car from Ocho Rios to Port Antonio takes 2 hours. Alternatively, you can take a bus. June in Port Antonio sees daily highs of 38°C and lows of 30°C at night. Finish your sightseeing early on the 22nd (Fri) so you can travel back home.

Things to do in Port Antonio

Parks Outdoors Nature

Side Trips

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

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