16 days in Orlando, Key West & Jamaica Itinerary

16 days in Orlando, Key West & Jamaica Itinerary

Created using Inspirock journey planner

Make it your trip
Fly
1
Orlando, United States
— 4 nights
Fly
2
Key West, United States
— 3 nights
Fly
3
Ocho Rios, Jamaica
— 2 nights
Drive
4
Negril, Jamaica
— 2 nights
Drive
5
Montego Bay, Jamaica
— 3 nights
Fly

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Orlando, United States

— 4 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.
Have a day of magic on the 11th (Mon) at Walt Disney World Resort. Pack the 12th (Tue) with family-friendly diversions at Universal Orlando Resort. The adventure continues: find something for the whole family at Universal's Islands of Adventure and explore the world behind art at Charles Hosmer Morse Museum of American Art.

Quickly create a custom-made itinerary for Orlando using our trip planner.

Cairo, Egypt to Orlando is an approximately 21-hour flight. The time zone changes from Eastern European Standard Time (EET) to Eastern Standard Time (EST), which is usually a -7 hour difference. In October, plan for daily highs up to 34°C, and evening lows to 24°C. Cap off your sightseeing on the 14th (Thu) early enough to travel to Key West.

Things to do in Orlando

Theme Parks · Museums

Side Trip

Key West, United States

— 3 nights

Conch Republic

Located just 140 km (90 mi) from Cuba, Key West is an island only about 6.4 km (4 mi) long and 1.6 km (1 mi) wide.
Key West is known for wildlife, adventure, and museums. Your plan includes some of its best attractions: see the interesting displays at The Ernest Hemingway Home and Museum, take a tour by water with Boat Tours & Water Sports, take in the exciting artwork at 7 Artists & Friends Gallery, and make a trip to Southernmost Point.

To find reviews, traveler tips, other places to visit, and tourist information, go to the Key West trip maker app.

Traveling by flight from Orlando to Key West takes 4.5 hours. Alternatively, you can drive; or take a bus. Plan for somewhat warmer nights when traveling from Orlando in October since evenings lows in Key West dip to 29°C. Finish your sightseeing early on the 17th (Sun) so you can travel to Ocho Rios.

Things to do in Key West

Museums · Historic Sites · Parks · Shopping

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.
Kick off your visit on the 18th (Mon): stop by Jewels & Time Duty Free Jewelers, admire the sheer force of Dunn's River Falls and Park, then relax and float downstream with a rafting and tubing tour, and finally pause for some serene contemplation at Our Lady of Fatima Catholic Church. On the 19th (Tue), you'll have a packed day of sightseeing: admire the sheer force of Blue Hole and then take in nature's colorful creations at Shaw Park Gardens & Waterfalls.

For maps, other places to visit, traveler tips, and more tourist information, read our Ocho Rios itinerary builder website.

Fly from Key West to Ocho Rios in 9 hours. In October, daily temperatures in Ocho Rios can reach 38°C, while at night they dip to 30°C. Finish your sightseeing early on the 19th (Tue) so you can drive to Negril.

Things to do in Ocho Rios

Parks · Nature · Outdoors · Adventure

Negril, Jamaica

— 2 nights
Once Jamaica's hidden gem, Negril has significantly expanded its infrastructure without losing its casual way of life.
Start off your visit on the 20th (Wed): enjoy the sand and surf at Seven Mile Beach, then stroll through Bloody Bay, and then soothe aching muscles at some of the top local wellness centers. On the 21st (Thu), you'll have a packed day of sightseeing: explore the striking landscape at Negril Cliffs, then look for gifts at Irie Art, and then Head underground at Blue Hole Mineral Spring.

For maps, other places to visit, reviews, and more tourist information, read Negril online tour planner.

You can drive from Ocho Rios to Negril in 3 hours. Other options are to drive; or take a bus. In October, daily temperatures in Negril can reach 38°C, while at night they dip to 28°C. Cap off your sightseeing on the 21st (Thu) early enough to go by car to Montego Bay.

Things to do in Negril

Parks · Nature · Beaches · Outdoors

Side Trip

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.
Spend the 23rd (Sat) wandering through the wild on a nature and wildlife tour. Next up on the itinerary: tee off at White Witch Golf Course, contemplate the long history of Rose Hall Great House, enjoy the sand and surf at Doctor's Cave Beach, and tour the pleasant surroundings at Rocklands Bird Sanctuary.

To see traveler tips, maps, ratings, and more tourist information, refer to the Montego Bay itinerary website.

Getting from Negril to Montego Bay by car takes about 1.5 hours. Other options: take a bus. In October, daily temperatures in Montego Bay can reach 38°C, while at night they dip to 28°C. Wrap up your sightseeing on the 24th (Sun) to allow time to travel back home.

Things to do in Montego Bay

Outdoors · Wildlife · Tours · Parks

Side Trip

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.