37 days in Jamaica Itinerary

37 days in Jamaica Itinerary

Created using Inspirock Jamaica sightseeing planner

Make it your trip
Fly
1
Ocho Rios
— 9 nights
Drive
2
Port Antonio
— 3 nights
Drive
3
Kingston
— 6 nights
Drive
4
Saint Elizabeth Parish
— 3 nights
Drive
5
Negril
— 6 nights
Drive
6
Montego Bay
— 9 nights
Fly

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Ocho Rios

— 9 nights
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 Runaway Bay (Woolery Kitchen & Green Grotto Caves) and Bob Marley Museum (in St. Ann's Bay). Next up on the itinerary: take in the dramatic scenery at Dunn's River Falls and Park, get in on the family fun at Rainforest Adventures, explore the activities along White River, and get close to the beloved marine mammals with a swim-with-the-dolphins experience.

For where to stay, traveler tips, photos, and more tourist information, read our Ocho Rios trip itinerary maker site.

Orlando, USA to Ocho Rios is an approximately 5-hour flight. In September, daily temperatures in Ocho Rios can reach 91°F, while at night they dip to 79°F. Cap off your sightseeing on the 2nd (Fri) early enough to go by car to Port Antonio.

Things to do in Ocho Rios

Parks · Outdoors · Nature · Tours

Side Trips

Find places to stay Sep 23 — Oct 2:

Port Antonio

— 3 nights
A coastal getaway from coastal getaways, Port Antonio offers a break from the more touristy retreats in the west of the island.
Port Antonio is known for beaches, nature, and historic sites. Your trip includes some of its best attractions: take in the dramatic scenery at Reach Falls, contemplate the waterfront views at Long Bay (Northeast), pick up some local products at Boston Jerk Centre, and enjoy the sand and surf at Frenchman's Cove.

To see more things to do, other places to visit, where to stay, and other tourist information, refer to the Port Antonio itinerary tool.

Traveling by car from Ocho Rios to Port Antonio takes 2 hours. Alternatively, you can take a bus. In October, plan for daily highs up to 90°F, and evening lows to 78°F. Cap off your sightseeing on the 5th (Mon) early enough to go by car to Kingston.

Things to do in Port Antonio

Parks · Nature · Beaches · Outdoors

Side Trips

Find places to stay Oct 2 — 5:

Kingston

— 6 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.
Change things up with these side-trips from Kingston: Hellshire Beach (in Portmore) and Blue Mountain Peak (in Blue Mountains National Park). There's much more to do: make a short side trip with Loose Cannon Boat Charters and Tours Limited, don't miss a visit to 41 Fleet Street, get outside with Lime Cay, and go for a stroll along the water at Port Royal.

To see traveler tips, more things to do, where to stay, and more tourist information, use the Kingston road trip tool.

You can drive from Port Antonio to Kingston in 2.5 hours. Another option is to take a bus. In October, daily temperatures in Kingston can reach 90°F, while at night they dip to 78°F. Cap off your sightseeing on the 11th (Sun) early enough to go by car to Saint Elizabeth Parish.

Things to do in Kingston

Outdoors · Parks · Tours · Historic Sites

Side Trips

Find places to stay Oct 5 — 11:

Saint Elizabeth Parish

— 3 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.
Saint Elizabeth Parish is known for nature, nightlife, and wildlife. Your trip includes some of its best attractions: take in the dramatic scenery at YS Falls, get a new perspective on things with Black River Safari Cruise, tour the pleasant surroundings at Bamboo Avenue, and relax and rejuvenate at Shirley's Steam Bath & Massage.

For reviews, other places to visit, and more tourist information, use the Saint Elizabeth Parish attractions planner.

Traveling by car from Kingston to Saint Elizabeth Parish takes 2.5 hours. Alternatively, you can take a bus. In October in Saint Elizabeth Parish, expect temperatures between 90°F during the day and 76°F at night. Finish your sightseeing early on the 14th (Wed) to allow enough time to drive to Negril.

Things to do in Saint Elizabeth Parish

Parks · Nature · Tours · Outdoors

Side Trip

Find places to stay Oct 11 — 14:

Negril

— 6 nights
Once Jamaica's hidden gem, Negril has significantly expanded its infrastructure without losing its casual way of life.
Explore Negril's surroundings by going to Original Mayfield Falls Jamaica (in Pennycooke) and Roaring River (in Petersfield). The adventure continues: kick back and relax at Seven Mile Beach, head off the coast to Booby Cay Island, Head underground at Blue Hole Mineral Spring, and explore the activities along Bloody Bay.

To see photos, other places to visit, and other tourist information, read Negril journey planner.

You can drive from Saint Elizabeth Parish to Negril in 2 hours. Another option is to take a bus. In October, daily temperatures in Negril can reach 90°F, while at night they dip to 76°F. Finish your sightseeing early on the 20th (Tue) to allow enough time to drive to Montego Bay.

Things to do in Negril

Parks · Outdoors · Nature · Tours

Side Trips

Find places to stay Oct 14 — 20:

Montego Bay

— 9 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.
Venture out of the city with trips to Blue Hole Gardens (in Savanna La Mar) and Tryall Golf Course (in Sandy Bay). Spend the 22nd (Thu) wandering through the wild on a nature and wildlife tour. There's much more to do: contemplate the long history of Rose Hall Great House, don't miss a visit to Hip Strip, get great views at Ahhh...Ras Natango Gallery and Garden, and tour the pleasant surroundings at Doctor's Cave Beach.

To find maps, more things to do, traveler tips, and more tourist information, read our Montego Bay day trip planner.

Drive from Negril to Montego Bay in 1.5 hours. Alternatively, you can take a bus. October in Montego Bay sees daily highs of 90°F and lows of 76°F at night. Wrap up your sightseeing on the 29th (Thu) early enough to fly back home.

Things to do in Montego Bay

Outdoors · Tours · Parks · Wildlife

Side Trips

Find places to stay Oct 20 — 29:

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.