57 days in Jamaica Itinerary

57 days in Jamaica Itinerary

Created using Inspirock Jamaica visit planner

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Route & dates

57 days in Jamaica Itinerary

Start: Kelowna
Fly + Drive:  16​h 30​min
1
Portland Parish
— 6 nights
taxi + bus:  2​h
2
Ocho Rios
— 15 nights
bus + Drive:  2​h 15​min
3
Saint Elizabeth Parish
— 4 nights
Drive:  1​h 45​min
4
Negril
— 14 nights
bus:  1​h 30​min
5
Montego Bay
— 16 nights
Fly:  15​h
End: Kelowna

6
nights
Portland Parish

Portland Parish ©
Tourism in Portland Parish has changed focus in recent years.
Visiting Rio Grande and San San Beach will get you outdoors. Step off the beaten path and head to Winifred Beach and Titchfield. When in Portland Parish, make a side trip to see Lyssons Beach in Morant Bay, approximately 52 minutes away. There's lots more to do: enjoy the sand and surf at Frenchman's Cove, contemplate the waterfront views at Long Bay (Northeast), take in the spiritual surroundings of Portland Parish Church, and take in the dramatic scenery at Nanny Falls.

To see maps, photos, ratings, and other tourist information, read Portland Parish trip itinerary builder site .

Kelowna, Canada to Portland Parish is an approximately 16.5-hour combination of flight and car. Due to the time zone difference, you'll lose 3 hours traveling from Kelowna to Portland Parish. In January, daily temperatures in Portland Parish can reach 36°C, while at night they dip to 27°C. Finish up your sightseeing early on the 10th (Fri) so you can travel to Ocho Rios.

Things to do in Portland Parish

Parks Beaches Outdoors

Side Trips

Lyssons Beach, Long Bay (Northeast)
Find places to stay Jan 3 — 10:
Highlights from your plan
Winifred Beach ©
Winifred Beach
Rio Grande ©
Rio Grande
Frenchman's Cove ©
Frenchman's Cove

15
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.
Step out of the city life by going to Scuba & Snorkeling and Zipline. Discover out-of-the-way places like Spas and Fishing Charters & Tours. Change things up with these side-trips from Ocho Rios: Blue Mountain Peak (in Blue Mountains National Park), St. Ann's Bay (Bob Marley's Mausoleum, H'Evans Scent, & more) and Green Grotto Caves (in Runaway Bay). Pack the 20th (Mon) with family-friendly diversions at Rainforest Adventures. Next up on the itinerary: take in the dramatic scenery at Dunn's River Falls and Park, trot along with a tour on horseback, take in nature's colorful creations at Shaw Park Gardens & Waterfalls, and stroll through Jamaica Grande Beach.

To find more things to do, reviews, where to stay, and other tourist information, you can read our Ocho Rios road trip planning website .

Do a combination of taxi and bus from Portland Parish to Ocho Rios in 2 hours. Alternatively, you can drive; or take a bus. Expect a daytime high around 36°C in January, and nighttime lows around 27°C. Cap off your sightseeing on the 25th (Sat) early enough to travel to Saint Elizabeth Parish.

Things to do in Ocho Rios

Parks Outdoors Nature

Side Trips

St. Ann's Bay, Runaway Bay, Jamaica, Blue Mountain Peak
Find places to stay Jan 10 — 25:
Highlights from your plan
Dunn's River Falls and Park ©
Dunn's River Falls and Park
Scuba & Snorkeling
Blue Mountain Peak ©
Blue Mountain Peak

4
nights
Saint Elizabeth Parish

Saint Elizabeth Parish ©
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 Treasure Beach and Black River. Step out of the city life by going to YS Falls and Bamboo Avenue. There's still lots to do: admire the sheer force of Turtle River Falls and Gardens, take in the dramatic natural features at Cockpit Country, take in the exciting artwork at The Mud Palace Gallery, and steep yourself in history at Appleton Estate.

To find more things to do, where to stay, photos, and tourist information, you can read our Saint Elizabeth Parish trip planner.

Traveling by combination of bus and car from Ocho Rios to Saint Elizabeth Parish takes 2.5 hours. Alternatively, you can drive; or take a bus. January in Saint Elizabeth Parish sees daily highs of 35°C and lows of 26°C at night. Wrap up your sightseeing on the 29th (Wed) early enough to drive to Negril.

Things to do in Saint Elizabeth Parish

Parks Nature Beaches

Side Trips

Jamaica, Turtle River Falls and Gardens
Find places to stay Jan 25 — 29:
Highlights from your plan
YS Falls ©
YS Falls
Treasure Beach ©
Treasure Beach
Black River ©
Black River

14
nights
Negril

Negril ©
Once Jamaica's hidden gem, Negril has significantly expanded its infrastructure without losing its casual way of life.
Get in touch with nature at Distillery Tours and Seven Mile Beach. We've included these beaches for you: Half Moon Beach and Bloody Bay. Explore Negril's surroundings by going to Original Mayfield Falls Jamaica (in Pennycooke) and Roaring River (in Petersfield). The adventure continues: look for all kinds of wild species at Barney's Flower & Hummingbird Garden Jamaica, take in the natural beauty of Blue Hole Mineral Spring, get where you need to go with Taxis & Shuttles, and let the river carry you with a rafting and tubing tour.

Use Inspirock's suggestions to plan your Negril trip and find the best activities and attractions for your vacation.

Getting from Saint Elizabeth Parish to Negril by car takes about 2 hours. Other options: take a bus. In January, daily temperatures in Negril can reach 35°C, while at night they dip to 26°C. Finish up your sightseeing early on the 12th (Wed) so you can catcht the bus to Montego Bay.

Things to do in Negril

Outdoors Parks Tours

Side Trips

Roaring River, Original Mayfield Falls Jamaica, Jamaica Giants Nature Tour and Sculpture Garden, Blue Hole Mineral Spring
Find places to stay Jan 29 — Feb 12:
Highlights from your plan
Half Moon Beach ©
Half Moon Beach
Seven Mile Beach ©
Seven Mile Beach

16
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.
You'll explore the less-touristy side of things at Rocklands Bird Sanctuary (Near Montego Bay) and Burwood Beach. Take a break from the city and head to Doctor's Cave Beach and Blue Waters Beach Club. Venture out of the city with trips to Good Hope Plantation (in Clarendon Parish), Tryall Golf Course (in Sandy Bay) and Falmouth (Falmouth Court House, Adrenaline & Extreme Tours, & more). Spend the 15th (Sat) wandering through the wild on a nature and wildlife tour. Next up on the itinerary: glide through the air with a parasailing or paragliding tour, play a few rounds at White Witch Golf Course, explore the activities along Martha Brae River, and get great views at Ahhh...Ras Natango Gallery and Garden.

For other places to visit, traveler tips, ratings, and other tourist information, read our Montego Bay visit planner.

Traveling by bus from Negril to Montego Bay takes 1.5 hours. Alternatively, you can drive. February in Montego Bay sees daily highs of 35°C and lows of 26°C at night. You will leave for home on the 28th (Fri).

Things to do in Montego Bay

Outdoors Parks Tours

Side Trips

Falmouth, Rastafari Indigenous Village, Tryall Golf Course, Rocklands Bird Sanctuary (Near Montego Bay), Good Hope Plantation
Find places to stay Feb 12 — 28:
Highlights from your plan
Doctor's Cave Beach ©
Doctor's Cave Beach
Parasailing & Paragliding

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