60 days in Jamaica Itinerary

60 days in Jamaica Itinerary

Created using Inspirock Jamaica trip planner

Make it your trip
Fly
1
Montego Bay
— 15 nights
Drive
2
Ocho Rios
— 12 nights
Drive
3
Port Antonio
— 6 nights
Drive
4
Kingston
— 10 nights
Drive
5
Saint Elizabeth Parish
— 5 nights
Drive
6
Negril
— 9 nights
Drive
7
Pennycooke
— 2 nights
Drive to Sangster International Airport, Fly to Chicago Midway International Airport

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Montego Bay

— 15 nights
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.
Eschew the tourist crowds and head to Rastasafari Experience and Ahhh...Ras Natango Gallery and Garden. Get out of town with these interesting Montego Bay side-trips: Good Hope Plantation (in Clarendon Parish), Falmouth (Jamaica Swamp Safari Village, Red Stripe Beach, &more) and Savanna La Mar (Blue Hole Gardens & Reggae Style Mayfield Falls). Spend the 3rd (Sat) wandering through the wild on a nature and wildlife tour. On the 4th (Sun), enjoy an adventurous day among the treetops at some of the top local zipline courses and adventure parks. There's much more to do: relax in the rural setting at Croydon Plantation, get to know the fascinating history of Rastafari Indigenous Village, get the lay of the land with Walking tours, and take an in-depth tour of Greenwood Great House.

For where to stay, photos, more things to do, and other tourist information, go to the Montego Bay online trip builder.

Chicago, USA to Montego Bay is an approximately 8-hour flight. Traveling from Chicago to Montego Bay, you'll lose 1 hour due to the time zone difference. Prepare for much warmer weather when traveling from Chicago in April: high temperatures in Montego Bay hover around 89°F and lows are around 75°F. Cap off your sightseeing on the 16th (Fri) early enough to go by car to Ocho Rios.

Things to do in Montego Bay

Outdoors · Parks · Tours · Wildlife

Side Trips

Ocho Rios

— 12 nights
A trip to Ocho Rios, the tourist hub of Saint Ann Parish, offers travelers a staggering amount of activities and cultural attractions.
You'll discover tucked-away gems like Coyaba River Garden and Museum and Stush in the Bush. Explore Ocho Rios' surroundings by going to Joe James Gallery (in Rio Bueno), Runaway Bay (Woolery Kitchen & Green Grotto Caves) and Bob Marley Museum (in St. Ann's Bay). Pack the 25th (Sun) with family-friendly diversions at Rainforest Adventures. And it doesn't end there: take in the dramatic scenery at Dunn's River Falls and Park, see Off-Road Tours, don't miss a visit to Firefly House, and get outside with Outdoor Activities.

For traveler tips, more things to do, other places to visit, and more tourist information, use the Ocho Rios trip app.

You can drive from Montego Bay to Ocho Rios in 2 hours. Another option is to take a bus. In April, daily temperatures in Ocho Rios can reach 88°F, while at night they dip to 74°F. Wrap up your sightseeing on the 28th (Wed) to allow time to drive to Port Antonio.

Things to do in Ocho Rios

Parks · Outdoors · Nature · Tours

Side Trips

Port Antonio

— 6 nights
A coastal getaway from coastal getaways, Port Antonio offers a break from the more touristy retreats in the west of the island.
Eschew the tourist crowds and head to Winifred Beach and Sir Henry Morgan Angling Association, De Ole Marina Pub, Restaurant & Marina. There's still lots to do: contemplate the waterfront views at Rio Grande, kick back and relax at Long Bay Beach, contemplate in the serene atmosphere at Portland Parish Church, and tour the pleasant surroundings at Frenchman's Cove.

To find reviews, maps, ratings, and tourist information, refer to the Port Antonio planner.

Traveling by car from Ocho Rios to Port Antonio takes 2 hours. Alternatively, you can take a bus. April in Port Antonio sees daily highs of 88°F and lows of 74°F at night. Wrap up your sightseeing on the 4th (Tue) early enough to drive to Kingston.

Things to do in Port Antonio

Parks · Outdoors · Beaches · Nature

Side Trips

Kingston

— 10 nights
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.
Discover out-of-the-way places like Lime Cay and Jamaica National Gallery. Explore the numerous day-trip ideas around Kingston: Blue Mountain Peak (in Blue Mountains National Park), Craighton Estate Great House (in Irish Town) and Hellshire Beach (in Portmore). There's lots more to do: take your sightseeing to a higher altitude at Blue Mountains, steep yourself in history at Bob Marley Museum, take in the architecture and atmosphere at St. Jago De La Vega Cathedral, and examine the collection at Trench Town Culture Yard.

To find ratings, other places to visit, maps, and other tourist information, read our Kingston tour itinerary planner.

Drive from Port Antonio to Kingston in 2.5 hours. Alternatively, you can take a bus. May in Kingston sees daily highs of 89°F and lows of 77°F at night. Finish up your sightseeing early on the 14th (Fri) so you can go by car to Saint Elizabeth Parish.

Things to do in Kingston

Parks · Historic Sites · Outdoors · Nature

Side Trips

Saint Elizabeth Parish

— 5 nights
Ecotourism and beach break activities dominate most Saint Elizabeth Parish itineraries, as this wild and relatively undeveloped region offers a wealth of natural environments.
Explore hidden gems such as Captain Joseph Treasure Beach Adventures and Lovers' Leap. Change things up with a short trip to Island Routes Caribbean Adventures - South Coast in White House (about 46 minutes away). The adventure continues: contemplate the waterfront views at Black River, visit Alligator Pond, admire the sheer force of YS Falls, and tour the pleasant surroundings at Treasure Beach.

To see ratings, where to stay, maps, and more tourist information, use the Saint Elizabeth Parish road trip site.

Drive from Kingston to Saint Elizabeth Parish in 2.5 hours. Alternatively, you can take a bus. In May, plan for daily highs up to 90°F, and evening lows to 75°F. Finish up your sightseeing early on the 19th (Wed) so you can go by car to Negril.

Things to do in Saint Elizabeth Parish

Parks · Nature · Outdoors · Wildlife

Side Trips

Negril

— 9 nights
Once Jamaica's hidden gem, Negril has significantly expanded its infrastructure without losing its casual way of life.
Discover out-of-the-way places like Half Moon Beach and Barney's Flower & Hummingbird Garden Jamaica. Take a break from Negril with a short trip to Zentropia Palladium Spa & Wellness in Lucea, about 44 minutes away. Plan for a day of cool, family-friendly fun on the 26th (Wed) at Kool Runnings Waterpark. The adventure continues: tour the pleasant surroundings at Seven Mile Beach, step off the mainland to explore Booby Cay Island, explore the activities along Bloody Bay, and take in the natural beauty of Blue Hole Mineral Spring.

To see other places to visit, photos, more things to do, and tourist information, read Negril road trip planning website.

You can drive from Saint Elizabeth Parish to Negril in 2 hours. Another option is to take a bus. In May, daily temperatures in Negril can reach 90°F, while at night they dip to 75°F. Finish your sightseeing early on the 28th (Fri) so you can drive to Pennycooke.

Things to do in Negril

Parks · Outdoors · Nature · Beaches

Side Trips

Pennycooke

— 2 nights
Kick off your visit on the 29th (Sat): contemplate the waterfront views at Roaring River, then take in nature's colorful creations at Blue Hole Gardens, and then play a few rounds at Tryall Golf Course. On the 30th (Sun), you'll have a packed day of sightseeing: admire the sheer force of Original Mayfield Falls.

For other places to visit, traveler tips, maps, and more tourist information, read Pennycooke vacation tool.

Getting from Negril to Pennycooke by car takes about 1.5 hours. Other options: do a combination of bus and taxi. May in Pennycooke sees daily highs of 90°F and lows of 75°F at night. You will have some time to spend on the 30th (Sun) before leaving for home.

Things to do in Pennycooke

Parks · Nature · Golf · Outdoors

Side Trips

Jamaica travel guide

4.1
Waterfalls · Beaches · Nightlife
The third most populous English-speaking country in the Americas, Jamaica remains a member of the Commonwealth of Nations, with the British monarch its official head of state. Jamaica tourism thrives thanks to the island nation's reputation for natural beauty, outstanding cuisine, and lively music scene. The country's landscape is as diverse as its population, its tropical climate supporting varied ecosystems that include everything from savannahs to rugged mountain slopes. For most visitors, a holiday in Jamaica is a largely outdoor affair, with hiking, fishing, golfing, camping, snorkeling, horseback riding, and kite surfing among the most popular things to do.