41 days in Jamaica Itinerary

41 days in Jamaica Itinerary

Created using Inspirock Jamaica vacation maker

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Route & dates

41 days in Jamaica Itinerary

Start: Sydney
Fly:  24​h
1
Montego Bay
— 8 nights
bus:  1​h 30​min
2
Ocho Rios
— 9 nights
Drive:  2​h
3
Port Antonio
— 4 nights
bus:  2​h
4
Kingston
— 8 nights
Drive:  3​h 45​min
5
Negril
— 8 nights
Drive:  1​h 15​min
6
Pennycooke
— 1 night
Drive + Fly:  26​h
End: Sydney

8
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.
Explore the numerous day-trip ideas around Montego Bay: Tryall Golf Course (in Sandy Bay) and Adrenaline & Extreme Tours (in Falmouth). There's lots more to do: steep yourself in history at Rose Hall Great House, get a new perspective on things with Boat Tours & Water Sports, get great views at Ahhh...Ras Natango Gallery and Garden, and contemplate the waterfront views at Martha Brae Rafting Village.

For other places to visit, more things to do, and other tourist information, use the Montego Bay road trip website .

Sydney, Australia to Montego Bay is an approximately 24-hour flight. You can also do a combination of flight and bus. The time zone difference when traveling from Sydney to Montego Bay is minus 15 hours. Traveling from Sydney in December, expect Montego Bay to be a bit warmer, temps between 36°C and 27°C. Cap off your sightseeing on the 31st (Fri) early enough to catcht the bus to Ocho Rios.

Things to do in Montego Bay

Outdoors Tours Wildlife

Side Trips

Adrenaline & Extreme Tours, Rocklands Bird Sanctuary (Near Montego Bay), Tryall Golf Course
Find places to stay Dec 23 — 31:
Highlights from your plan
Rose Hall Great House ©
Rose Hall Great House
Doctor's Cave Beach ©
Doctor's Cave Beach
Nature & Wildlife Tours

9
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 Runaway Bay (Green Grotto Caves & Scuba & Snorkeling). There's still lots to do: take in the dramatic scenery at Dunn's River Falls and Park, whizz through the canopy at some of the top local zipline courses and adventure parks, contemplate the waterfront views at White River, and tour the pleasant surroundings at Ocho Rios Bay Beach.

For maps, where to stay, photos, and other tourist information, read our Ocho Rios road trip app .

You can take a bus from Montego Bay to Ocho Rios in 1.5 hours. Another option is to drive. Expect a daytime high around 36°C in December, and nighttime lows around 28°C. Cap off your sightseeing on the 9th (Sun) early enough to go by car to Port Antonio.

Things to do in Ocho Rios

Outdoors Parks Tours

Side Trips

St. Ann's Bay, Runaway Bay, Jamaica, Columbus Park
Find places to stay Dec 31 — Jan 9:
Highlights from your plan
Dunn's River Falls and Park ©
Dunn's River Falls and Park
Horseback Riding Tours
Swim with Dolphins

4
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.
Port Antonio is known for beaches, nature, adventure, historic sites, and shopping. Your plan includes some of its best attractions: take in the dramatic scenery at Reach Falls, explore the activities along Rio Grande, kick back and relax at Boston Beach, and tour the pleasant surroundings at Frenchman's Cove.

To see where to stay, ratings, other places to visit, and tourist information, read our Port Antonio trip itinerary planning tool .

You can drive from Ocho Rios to Port Antonio in 2 hours. Alternatively, you can take a bus. January in Port Antonio sees daily highs of 36°C and lows of 27°C at night. Finish your sightseeing early on the 13th (Thu) to allow enough time to take a bus to Kingston.

Things to do in Port Antonio

Parks Nature Outdoors

Side Trips

Jamaica, Nanny Falls, Rio Grande
Find places to stay Jan 9 — 13:
Highlights from your plan
Reach Falls ©
Reach Falls
Blue Lagoon ©
Blue Lagoon
Frenchman's Cove ©
Frenchman's Cove

8
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.
Venture out of the city with trips to Hellshire Beach (in Portmore) and Blue Mountain Peak (in Blue Mountains National Park). Spend the 21st (Fri) exploring nature at Holywell Park. Next up on the itinerary: steep yourself in history at Bob Marley Museum, don't miss a visit to Fort Charles, head outdoors with Lime Cay, and walk around Emancipation Park.

To find other places to visit, where to stay, reviews, and more tourist information, use the Kingston trip planner .

Take a bus from Port Antonio to Kingston in 2 hours. Alternatively, you can drive. Expect a daytime high around 36°C in January, and nighttime lows around 27°C. Finish your sightseeing early on the 21st (Fri) so you can drive to Negril.

Things to do in Kingston

Parks Historic Sites Outdoors

Side Trips

Portmore, Jamaica, Blue Mountain Peak
Find places to stay Jan 13 — 21:
Highlights from your plan
Blue Mountain Peak ©
Blue Mountain Peak
Bob Marley Museum ©
Bob Marley Museum
Devon House ©
Devon House

8
nights
Negril

Negril ©
Once Jamaica's hidden gem, Negril has significantly expanded its infrastructure without losing its casual way of life.
You'll find plenty of places to visit near Negril: Black River (in Black River), Jamaica Giants Nature Tour and Sculpture Garden (in Little London) and YS Falls (in Saint Elizabeth Parish). There's still lots to do: kick back and relax at Seven Mile Beach, identify plant and animal life at Wildlife Areas, head off the coast to Booby Cay Island, and take in the natural beauty of Blue Hole Mineral Spring.

To find other places to visit, where to stay, photos, and more tourist information, read our Negril trip planner.

You can drive from Kingston to Negril in 4 hours. Alternatively, you can take a bus. In January in Negril, expect temperatures between 35°C during the day and 26°C at night. Wrap up your sightseeing on the 29th (Sat) to allow time to drive to Pennycooke.

Things to do in Negril

Parks Nature Outdoors

Side Trips

Saint Elizabeth Parish, Jamaica Giants Nature Tour and Sculpture Garden, Blue Hole Mineral Spring
Find places to stay Jan 21 — 29:
Highlights from your plan
Seven Mile Beach ©
Seven Mile Beach
YS Falls ©
YS Falls
Negril Cliffs ©
Negril Cliffs

1
night
Pennycooke

Pennycooke
Start off your visit on the 30th (Sun): take in nature's colorful creations at Blue Hole Gardens, head outdoors with Reggae Style Mayfield Falls, and then take in the dramatic scenery at Original Mayfield Falls Jamaica.

To see reviews, photos, traveler tips, and more tourist information, refer to the Pennycooke trip itinerary builder app .

Getting from Negril to Pennycooke by car takes about 1.5 hours. In January, daytime highs in Pennycooke are 35°C, while nighttime lows are 26°C. Finish your sightseeing early on the 30th (Sun) to allow enough time to travel back home.

Things to do in Pennycooke

Parks Outdoors Nature

Side Trip

Savanna La Mar
Find places to stay Jan 29 — 30:
Highlights from your plan
Mayfield Falls Jamaica (Original)
Mayfield Falls Jamaica (Original)
Reggae Style Mayfield Falls ©
Reggae Style Mayfield Falls

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