8 days in Jamaica Itinerary

8 days in Jamaica Itinerary

Created using Inspirock Jamaica holiday planner

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Route & dates

8 days in Jamaica Itinerary

Start: Winnipeg
Fly:  11​h 30​min
1
Kingston
— 1 night
Drive:  1​h 30​min
2
Ocho Rios
— 2 nights
Drive:  3​h
3
Negril
— 2 nights
bus:  1​h 30​min
4
Montego Bay
— 2 nights
Fly:  8​h 45​min
End: Winnipeg

1
night
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.
On the 3rd (Sun), go for a stroll along the water at Port Royal, then walk around Emancipation Park, then look for gifts at Chocolate Dreams, and finally pause for some photo ops at Devon House.

To find where to stay, traveler tips, more things to do, and other tourist information, refer to the Kingston road trip planning website .

Winnipeg, Canada to Kingston is an approximately 11.5-hour flight. The time zone changes from Central Standard Time (CST) to Eastern Standard Time (EST), which is usually a 1 hour difference. Expect much warmer temperatures when traveling from Winnipeg in November; daily highs in Kingston reach 37°C and lows reach 28°C. Finish your sightseeing early on the 3rd (Sun) so you can drive to Ocho Rios.

Things to do in Kingston

Parks Historic Sites Shopping
Find places to stay Nov 2 — 3:
Highlights from your plan
Devon House ©
Devon House
Port Royal ©
Port Royal
Emancipation Park ©
Emancipation Park

2
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.
Kick off your visit on the 4th (Mon): admire the sheer force of Blue Hole, then admire the sheer force of Dunn's River Falls and Park, and then get interesting insight from Tours. Here are some ideas for day two: enjoy the sand and surf at Bamboo Beach Club, take a pleasant ride with a tour on horseback, and then take in the architecture and atmosphere at Our Lady of Fatima Catholic Church.

To find ratings, photos, other places to visit, and more tourist information, refer to the Ocho Rios day trip planning website .

Traveling by car from Kingston to Ocho Rios takes 1.5 hours. Alternatively, you can take a bus. In November, plan for daily highs up to 37°C, and evening lows to 28°C. Cap off your sightseeing on the 5th (Tue) early enough to go by car to Negril.

Things to do in Ocho Rios

Parks Outdoors Nature
Find places to stay Nov 3 — 5:
Highlights from your plan
Dunn's River Falls and Park ©
Dunn's River Falls and Park
Horseback Riding Tours
Swim with Dolphins

2
nights
Negril

Negril ©
Once Jamaica's hidden gem, Negril has significantly expanded its infrastructure without losing its casual way of life.
Start off your visit on the 6th (Wed): kick back and relax at Bloody Bay, then kick back and relax at Seven Mile Beach, and then enjoy the sea views from Negril Lighthouse. Get ready for a full day of sightseeing on the next day: take in the dramatic natural features at Negril Cliffs, then fulfill a lifelong dream with a swim-with-the-dolphins experience, and then indulge in some personalized pampering at some of the best spas.

To see reviews, maps, traveler tips, and tourist information, use the Negril trip planner .

You can drive from Ocho Rios to Negril in 3 hours. Alternatively, you can take a bus. In November, plan for daily highs up to 36°C, and evening lows to 28°C. Finish your sightseeing early on the 7th (Thu) so you can take a bus to Montego Bay.

Things to do in Negril

Parks Beaches Outdoors
Find places to stay Nov 5 — 7:
Highlights from your plan
Seven Mile Beach ©
Seven Mile Beach
Negril Cliffs ©
Negril Cliffs
Bloody Bay ©
Bloody Bay

2
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.
Start off your visit on the 8th (Fri): enjoy the sand and surf at Doctor's Cave Beach, then contemplate the long history of Rose Hall Great House, and then tee off at Cinnamon Hill Golf Course. On the 9th (Sat), you'll have a packed day of sightseeing: surround yourself with nature on a nature and wildlife tour.

Plan a trip to Montego Bay easily and quickly by telling Inspirock to suggest an itinerary.

Traveling by bus from Negril to Montego Bay takes 1.5 hours. Alternatively, you can drive. In November in Montego Bay, expect temperatures between 36°C during the day and 28°C at night. Finish your sightseeing early on the 9th (Sat) so you can travel back home.

Things to do in Montego Bay

Outdoors Tours Wildlife
Find places to stay Nov 7 — 9:
Highlights from your plan
Rose Hall Great House ©
Rose Hall Great House
Doctor's Cave Beach ©
Doctor's Cave Beach
Nature & Wildlife Tours

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