9 days in Jamaica Itinerary
Created using Klarna Trips Jamaica trip itinerary planner
Start: Chicago
Fly
1
Negril
— 1 night
Drive
2
Montego Bay
— 4 nights
Drive
3
Ocho Rios
— 3 nights
Fly
End: Chicago
Fri, Dec 23 - Sat, Dec 31
Edit
| S | M | T | W | T | F | S |
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18
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19
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20
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21
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22
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23
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24
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25
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26
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27
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28
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29
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30
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31
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View full calendar
Negril — 1 night
©
Once Jamaica's hidden gem, Negril has significantly expanded its infrastructure without losing its casual way of life.On the 23rd (Fri), take in the dramatic natural features at Negril Cliffs. On the next day, get a dose of the wild on Kingsley's Take Care Tours - Day Tours, then tour the pleasant surroundings at Seven Mile Beach, and then soothe aching muscles at some of the top local wellness centers.
To see photos, traveler tips, other places to visit, and more tourist information, use the Negril road trip planner.
Chicago, USA to Negril is an approximately 7-hour flight. The time zone difference when traveling from Chicago to Negril is 1 hour. Expect much hotter temperatures when traveling from Chicago in December; daily highs in Negril reach 87°F and lows reach 74°F. Wrap up your sightseeing on the 24th (Sat) to allow time to drive to Montego Bay.
Find places to stay Dec 23 — 24:
Highlights from your trip
Montego Bay — 4 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.Get outdoors at Doctor's Cave Beach and Safaris. You'll visit kid-friendly attractions like Nature & Wildlife Tours and YS Falls. Change things up with a short trip to Original Mayfield Falls Jamaica in Pennycooke (about 1h 15 min away). The adventure continues: admire the landmark architecture of Rose Hall Great House, play a few rounds at White Witch Golf Course, get a taste of the local shopping with Cinnamon Hill Golf Course, and contemplate the long history of The Cage.
To see traveler tips, reviews, where to stay, and more tourist information, you can read our Montego Bay trip itinerary builder site.
You can drive from Negril to Montego Bay in 1.5 hours. Another option is to take a bus. Expect a daytime high around 87°F in December, and nighttime lows around 74°F. Wrap up your sightseeing on the 28th (Wed) early enough to drive to Ocho Rios.
Side Trips
Find places to stay Dec 24 — 28:
Highlights from your trip
Ocho Rios — 3 nights
©
A trip to Ocho Rios, the tourist hub of Saint Ann Parish, offers travelers a staggering amount of activities and cultural attractions.Attractions like Dunn's River Falls and Park and Horseback Riding Tours make great kid-friendly stops. Escape the urban bustle at Blue Hole and Green Grotto Caves. There's lots more to do: fulfill a lifelong dream with a swim-with-the-dolphins experience, enjoy the sand and surf at Ocho Rios Bay Beach, walk around Konoko Falls, and stop by Kaya Herb House.
To see reviews, maps, other places to visit, and other tourist information, use the Ocho Rios trip planner.
Drive from Montego Bay to Ocho Rios in 2 hours. Alternatively, you can take a bus. In December, plan for daily highs up to 88°F, and evening lows to 75°F. Finish your sightseeing early on the 31st (Sat) so you can fly back home.
Side Trip
Find places to stay Dec 28 — 31:
Highlights from your trip
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Jamaica travel guide
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.
