14 days in Orlando & Jamaica Itinerary

14 days in Orlando & Jamaica Itinerary

Created using Inspirock vacation maker

Make it your trip
1
Orlando, United States
— 5 nights
Fly
2
Montego Bay, Jamaica
— 3 nights
Drive
3
Negril, Jamaica
— 1 night
Drive
4
Saint Elizabeth Parish, Jamaica
— 1 night
Drive
5
Kingston, Jamaica
— 1 night
Drive
6
Ocho Rios, Jamaica
— 2 nights
Fly

S M T W T F S
26
27
28
29
30
31
1
2
3
4
5
6
7
8

Orlando, United States

— 5 nights

Theme Park Capital of the World

For most people, any mention of Orlando immediately conjures up images of sprawling theme parks filled with characters plucked right out of popular animated movies.
Explore the numerous day-trip ideas around Orlando: DeLand (Stetson Mansion & Stetson University). Have a day of magic on the 31st (Fri) at Walt Disney World Resort. Pack the 27th (Mon) with family-friendly diversions at Universal's Islands of Adventure. Next up on the itinerary: get in on the family fun at Universal Orlando Resort, make an unforgettable trip to Epcot, see Enchanted Tales With Belle, and laugh and play at World of Disney.

To see maps, ratings, where to stay, and more tourist information, go to the Orlando trip builder site.

If you are flying in from United States, the closest major aiports are Orlando International Airport, Orlando Sanford International Airport, Daytona Beach International Airport, Leesburg International Airport and Lakeland Linder International Airport. Expect a daytime high around 77°F in December, and nighttime lows around 59°F. Wrap up your sightseeing on the 31st (Fri) to allow time to fly to Montego Bay.

Things to do in Orlando

Theme Parks · Historic Sites · Shopping · Fun & Games

Side Trip

Find places to stay Dec 26 — 31:

Montego Bay, Jamaica

— 3 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.
You'll find plenty of places to visit near Montego Bay: Tryall Golf Course (in Sandy Bay) and Original Mayfield Falls Jamaica (in Pennycooke). There's much more to do: contemplate the long history of Rose Hall Great House, relax and rejuvenate at Half Moon Rosehall, A Rock Resort, kick back and relax at Doctor's Cave Beach, and look for gifts at White Witch Golf Course.

Plan my day in Montego Bay using traveler tips and tourist information provided by Inspirock.

Traveling by flight from Orlando to Montego Bay takes 5 hours. In December, Montego Bay is somewhat warmer than Orlando - with highs of 87°F and lows of 74°F. Wrap up your sightseeing on the 3rd (Mon) to allow time to drive to Negril.

Things to do in Montego Bay

Outdoors · Golf · Parks · Shopping

Side Trips

Find places to stay Dec 31 — Jan 3:

Negril, Jamaica

— 1 night
Once Jamaica's hidden gem, Negril has significantly expanded its infrastructure without losing its casual way of life.
Kick off your visit on the 4th (Tue): identify plant and animal life at Kingsley's Take Care Tours - Day Tours, then stroll through Seven Mile Beach, and then relax and rejuvenate at some of the top local wellness centers.

For where to stay, photos, reviews, and other tourist information, read our Negril driving holiday planner.

Traveling by car from Montego Bay to Negril takes 1.5 hours. Alternatively, you can take a bus. January in Negril sees daily highs of 86°F and lows of 73°F at night. Finish your sightseeing early on the 4th (Tue) to allow enough time to drive to Saint Elizabeth Parish.

Things to do in Negril

Outdoors · Parks · Beaches · Wildlife
Find places to stay Jan 3 — 4:

Saint Elizabeth Parish, Jamaica

— 1 night
Ecotourism and beach break activities dominate most Saint Elizabeth Parish itineraries, as this wild and relatively undeveloped region offers a wealth of natural environments.
Start off your visit on the 5th (Wed): take in the dramatic scenery at YS Falls and then surround yourself with nature on Captain Joseph Treasure Beach Adventures.

To find photos, traveler tips, where to stay, and tourist information, you can read our Saint Elizabeth Parish trip itinerary planning website.

You can drive from Negril to Saint Elizabeth Parish in 2 hours. Another option is to take a bus. In January, plan for daily highs up to 86°F, and evening lows to 73°F. Finish your sightseeing early on the 5th (Wed) to allow enough time to drive to Kingston.

Things to do in Saint Elizabeth Parish

Wildlife · Tours · Outdoors · Nature
Find places to stay Jan 4 — 5:
Highlights from your trip

Kingston, Jamaica

— 1 night
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.
Kick off your visit on the 6th (Thu): take in the awesome beauty at Blue Mountains.

To see traveler tips and other tourist information, refer to the Kingston driving holiday planner.

Traveling by car from Saint Elizabeth Parish to Kingston takes 2.5 hours. Alternatively, you can take a bus. In January in Kingston, expect temperatures between 87°F during the day and 74°F at night. Wrap up your sightseeing on the 6th (Thu) early enough to drive to Ocho Rios.

Things to do in Kingston

Nature · Parks
Find places to stay Jan 5 — 6:
Highlights from your trip

Ocho Rios, Jamaica

— 2 nights
A trip to Ocho Rios, the tourist hub of Saint Ann Parish, offers travelers a staggering amount of activities and cultural attractions.
On the 7th (Fri), admire the sheer force of Blue Hole, then take in the dramatic scenery at Dunn's River Falls and Park, and then take in nature's colorful creations at Shaw Park Gardens & Waterfalls. On the next day, explore the fascinating underground world of Green Grotto Caves and then take a pleasant ride with a tour on horseback.

To see photos, ratings, other places to visit, and more tourist information, use the Ocho Rios travel route builder website.

Traveling by car from Kingston to Ocho Rios takes 1.5 hours. Alternatively, you can take a bus. In January, daytime highs in Ocho Rios are 87°F, while nighttime lows are 74°F. Wrap up your sightseeing on the 8th (Sat) to allow time to fly back home.

Things to do in Ocho Rios

Parks · Nature · Tours · Outdoors

Side Trip

Find places to stay Jan 6 — 8:

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.