59 days in Jamaica Itinerary

59 days in Jamaica Itinerary

Created using Inspirock Jamaica trip planner

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Route & dates

59 days in Jamaica Itinerary

Start: Castries, St. Lucia
Fly:  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
Drive:  1​h 30​min
4
Negril
— 8 nights
bus:  1​h 45​min
5
Ocho Rios
— 11 nights
Drive:  2​h
6
Port Antonio
— 7 nights
Fly:  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.
Get out of town with these interesting Kingston side-trips: Portmore (Two Sisters Cave & Hellshire Beach). And it doesn't end there: take your sightseeing to a higher altitude at Blue Mountains, appreciate the history behind Devon House, take in the architecture and design of University Of The West Indies - Mona, and explore and take pictures at Sabina Park Cricket Stadium.

To find where to stay, reviews, ratings, and other tourist information, go to the Kingston trip itinerary builder website .

Castries, St. Lucia to Kingston is an approximately 14.5-hour flight. The time zone difference moving from Atlantic Standard Time to Eastern Standard Time is minus 1 hour. 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. Explore Santa Cruz's surroundings by going to The Mud Palace Gallery (in Treasure Beach) and Black River (in Black River). There's lots more to do: take in the dramatic scenery at YS Falls, explore the striking landscape at Lovers' Leap, meet the residents at Jamaica Zoo, and sample the fine beverages at Appleton Estate.

Plan my day in Santa Cruz using traveler tips and tourist information provided by Inspirock.

Traveling by car from Kingston to Santa Cruz takes 2 hours. Alternatively, you can do a combination of flight and taxi; or do a combination of bus and taxi. May in Santa Cruz sees daily highs of 38°C and lows of 28°C at night. You will leave for Montego Bay on the 14th (Mon).

Things to do in Santa Cruz

Parks Nature Outdoors

Side Trips

Jamaica, The Mud Palace Gallery, Jamaica Zoo, Black River, YS Falls
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

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.
Get out of town with these interesting Montego Bay side-trips: Tryall Golf Course (in Sandy Bay), Falmouth (Water Square, Adrenaline & Extreme Tours, & more) and Silver Sands Public Beach (in Duncans). Spend the 16th (Wed) wandering through the wild on a nature and wildlife tour. And it doesn't end there: enjoy the sand and surf at Doctor's Cave Beach, contemplate the waterfront views at Martha Brae River, take an in-depth tour of Greenwood Great House, and play a few rounds at Cinnamon Hill Golf Course.

For other places to visit, maps, reviews, and other tourist information, read Montego Bay trip itinerary planning tool .

Drive from Santa Cruz to Montego Bay in 1.5 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) to allow enough time to drive to Negril.

Things to do in Montego Bay

Outdoors Parks Tours

Side Trips

Falmouth, Tryall Golf Course, Silver Sands Public Beach, Rocklands Bird Sanctuary (Near Montego Bay), Rastafari Indigenous Village
Find places to stay May 14 — 27:
Highlights from your plan
Rose Hall Great House ©
Rose Hall Great House
Doctor's Cave Beach ©
Doctor's Cave Beach
Nature & Wildlife Tours

8
nights
Negril

Negril ©
Once Jamaica's hidden gem, Negril has significantly expanded its infrastructure without losing its casual way of life.
Step out of Negril with an excursion to Bluefields Beach in Bluefields--about 1h 10 min away. The adventure continues: stroll through Seven Mile Beach, explore the activities along Bloody Bay, take in the natural beauty of Blue Hole Mineral Spring, and take in the dramatic natural features at Negril Cliffs.

To see where to stay, other places to visit, traveler tips, and tourist information, refer to the Negril journey planning website .

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. Wrap up your sightseeing on the 4th (Mon) early enough to take a bus to Ocho Rios.

Things to do in Negril

Parks Outdoors Nature

Side Trips

Bluefields Beach, Blue Hole Mineral Spring, Original Mayfield Falls Jamaica
Find places to stay May 27 — Jun 4:
Highlights from your plan
Seven Mile Beach ©
Seven Mile Beach
Original Mayfield Falls Jamaica
Original Mayfield Falls Jamaica
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.
Explore Ocho Rios' surroundings by going to Green Grotto Caves (in Runaway Bay), Bob Marley's Mausoleum (in St. Ann's Bay) and Columbus Park (in Discovery Bay). There's still lots to do: admire the sheer force of Dunn's River Falls and Park, get in on the family fun at Rainforest Adventures Jamaica, take a pleasant ride with a tour on horseback, and take a memorable tour with Tours.

To see reviews, maps, other places to visit, and tourist information, read Ocho Rios trip planner.

Traveling by bus from Negril to Ocho Rios takes 2 hours. Alternatively, you can drive. June in Ocho Rios sees daily highs of 38°C and lows of 30°C at night. Wrap up your sightseeing on the 15th (Fri) early enough to drive to Port Antonio.

Things to do in Ocho Rios

Parks Outdoors Beaches

Side Trips

Jamaica, St. Ann's Bay, 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
Blue Hole ©
Blue Hole
Rainforest Adventures Jamaica ©
Rainforest Adventures Jamaica

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 50 minutes away. And it doesn't end there: tour the pleasant surroundings at Frenchman's Cove, explore the activities along Blue Lagoon, admire the sheer force of Somerset Falls, and go for a stroll along the water at Errol Flynn Marina.

Find out how to plan Port Antonio trip without stress by asking Inspirock to help create an itinerary.

You can drive from Ocho Rios to Port Antonio in 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. Cap off your sightseeing on the 22nd (Fri) early enough to travel back home.

Things to do in Port Antonio

Parks Outdoors Beaches

Side Trips

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

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