30 days in Florida & Jamaica Itinerary

30 days in Florida & Jamaica Itinerary

Created using Inspirock trip planner

Make it your trip
Fly
1
Key West, United States
— 4 nights
Drive
2
Marathon, United States
— 4 nights
Drive
3
Islamorada, United States
— 3 nights
Drive
4
Key Largo, United States
— 3 nights
Fly
5
Ocho Rios, Jamaica
— 3 nights
Drive
6
Montego Bay, Jamaica
— 4 nights
Fly
7
Orlando, United States
— 5 nights
Fly
8
Fort Walton Beach, United States
— 3 nights
Drive

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Key West, United States

— 4 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, identify plant and animal life at Key West Butterfly & Nature Conservatory, make a trip to Southernmost Point, and get engrossed in the history at Key West Firehouse Museum.

To see photos, traveler tips, more things to do, and tourist information, go to the Key West online sightseeing planner.

Montgomery to Key West is an approximately 5.5-hour flight. You can also drive; or do a combination of bus, subway, taxi, and ferry. Due to the time zone difference, you'll lose 1 hour traveling from Montgomery to Key West. Traveling from Montgomery in June, plan for a bit warmer nights in Key West, with lows around 79°F. Cap off your sightseeing on the 5th (Sat) early enough to go by car to Marathon.

Things to do in Key West

Museums · Parks · Wildlife · Shopping
Find places to stay Jun 1 — 5:

Marathon, United States

— 4 nights

Heart of the Florida Keys

A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
Go for a jaunt from Marathon to Little Torch Key to see SpaTerre at Little Palm Island Resort about 34 minutes away. There's much more to do: enjoy the sand and surf at Bahia Honda State Park, snap pictures at Old Seven Mile Bridge, look for all kinds of wild species at National Key Deer Refuge, and see the vivid underwater world at Sombrero Reef.

To find photos, maps, more things to do, and more tourist information, read our Marathon road trip tool.

Traveling by car from Key West to Marathon takes 1.5 hours. Alternatively, you can take a bus. In June, plan for daily highs up to 90°F, and evening lows to 79°F. Cap off your sightseeing on the 9th (Wed) early enough to go by car to Islamorada.

Things to do in Marathon

Parks · Wildlife · Outdoors · Beaches

Side Trips

Find places to stay Jun 5 — 9:

Islamorada, United States

— 3 nights

The Village of Islands

Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
Islamorada is known for wildlife, adventure, and museums. Your plan includes some of its best attractions: cast your line with a fishing tour, sample the tasty concoctions at Florida Keys Brewing Company, get outside with Contagious Charters, and shop like a local with Lobster Trap Art Gift Shop and Gallery.

To see ratings, more things to do, where to stay, and more tourist information, use the Islamorada trip planner.

Traveling by car from Marathon to Islamorada takes an hour. Alternatively, you can take a bus. Expect a daytime high around 90°F in June, and nighttime lows around 79°F. Cap off your sightseeing on the 12th (Sat) early enough to go by car to Key Largo.

Things to do in Islamorada

Outdoors · Museums · Historic Sites · Breweries & Distilleries
Find places to stay Jun 9 — 12:

Key Largo, United States

— 3 nights

Diving Capital of the World

The northernmost island of the Florida Keys, Key Largo provides stunning scenery, a number of watersports opportunities, and plenty of areas to relax on vacation.
Key Largo is known for wildlife, nature, and adventure. Your plan includes some of its best attractions: take a tour by water with Boat Tours & Water Sports, see the vivid underwater world at Spiegel Grove, immerse yourself in nature at John Pennekamp Coral Reef State Park, and admire nature's wide array of creatures at Island Dolphin Care.

For reviews, ratings, more things to do, and more tourist information, read Key Largo day trip planning tool.

Key Largo is just a short distance from Islamorada. June in Key Largo sees daily highs of 88°F and lows of 75°F at night. Finish up your sightseeing early on the 15th (Tue) so you can catch the flight to Ocho Rios.

Things to do in Key Largo

Parks · Wildlife · Nature · Tours
Find places to stay Jun 12 — 15:

Ocho Rios, Jamaica

— 3 nights
A trip to Ocho Rios, the tourist hub of Saint Ann Parish, offers travelers a staggering amount of activities and cultural attractions.
You'll find plenty of places to visit near Ocho Rios: Bob Marley Museum (in St. Ann's Bay) and Green Grotto Caves (in Runaway Bay). And it doesn't end there: take in the dramatic scenery at Dunn's River Falls and Park, take in the architecture and atmosphere at Our Lady of Fatima Catholic Church, stroll around Konoko Falls, and take a pleasant ride with a tour on horseback.

To see maps, traveler tips, reviews, and tourist information, refer to the Ocho Rios trip planner.

You can fly from Key Largo to Ocho Rios in 5 hours. Expect a daytime high around 90°F in June, and nighttime lows around 78°F. Finish your sightseeing early on the 18th (Fri) so you can drive to Montego Bay.

Things to do in Ocho Rios

Parks · Nature · Outdoors · Trails

Side Trips

Find places to stay Jun 15 — 18:

Montego Bay, Jamaica

— 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 out of town with these interesting Montego Bay side-trips: Tryall Golf Course (in Sandy Bay), Original Mayfield Falls Jamaica (in Pennycooke) and Seven Mile Beach (in Negril). Spend the 22nd (Tue) wandering through the wild on a nature and wildlife tour. The adventure continues: play a few rounds at Cinnamon Hill Golf Course, see exotic creatures in open habitats at Rastasafari Experience, tour the pleasant surroundings at Doctor's Cave Beach, and steep yourself in history at Rose Hall Great House.

To see reviews, ratings, photos, and more tourist information, read our Montego Bay driving holiday planning site.

Traveling by car from Ocho Rios to Montego Bay takes 2 hours. Alternatively, you can take a bus. Expect a daytime high around 91°F in June, and nighttime lows around 77°F. Finish your sightseeing early on the 22nd (Tue) to allow enough time to fly to Orlando.

Things to do in Montego Bay

Outdoors · Wildlife · Tours · Parks

Side Trips

Find places to stay Jun 18 — 22:

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.
Pack the 23rd (Wed) with family-friendly diversions at Universal Orlando Resort. Plan for a day of cool, family-friendly fun on the 25th (Fri) at Discovery Cove. Next up on the itinerary: get in on the family fun at Universal's Islands of Adventure, cool off at Disney's Typhoon Lagoon Water Park, and make an unforgettable trip to Walt Disney World Resort.

To find maps, other places to visit, ratings, and other tourist information, read Orlando online trip planner.

You can fly from Montego Bay to Orlando in 5 hours. June in Orlando sees daily highs of 91°F and lows of 73°F at night. Finish up your sightseeing early on the 27th (Sun) so you can catch the flight to Fort Walton Beach.

Things to do in Orlando

Theme Parks
Find places to stay Jun 22 — 27:

Fort Walton Beach, United States

— 3 nights
Fort Walton Beach is a city in southern Okaloosa County, Florida, United States. Change things up with these side-trips from Fort Walton Beach: Island Style (in Navarre), Pensacola (National Naval Aviation Museum & Gulf Islands) and Pensacola Beach (Chase-N-Fins, Pensacola Beach, &more). The adventure continues: kick back and relax at Navarre Beach and hike along Turkey Creek Nature Trail.

To see maps, where to stay, traveler tips, and other tourist information, go to the Fort Walton Beach road trip website.

You can fly from Orlando to Fort Walton Beach in 3.5 hours. Other options are to drive; or take a bus. Traveling from Orlando to Fort Walton Beach, you'll gain 1 hour due to the time zone difference. While traveling from Orlando, expect little chillier days and about the same nights in Fort Walton Beach, ranging from highs of 86°F to lows of 72°F. Finish your sightseeing early on the 30th (Wed) to allow enough time to drive back home.

Things to do in Fort Walton Beach

Parks · Outdoors · Beaches · Museums

Side Trips

Find places to stay Jun 27 — 30:

Florida travel guide

4.4
Disney Parks & Activities · Beaches · Theme Parks
The Sunshine State
The “Sunshine State,” Florida became a favorite winter destination for the affluent crowd over a century ago. Today, the state attracts visitors from around the world with its golden beaches and modern theme parks. You can spend your entire vacation enjoying the state's highly developed seaside areas, but remember that some of Florida's best-kept secrets are in secluded locations. Visit the big cities and their comfortable resorts offering top-notch dining and nightlife, but leave some time to see the peninsula's swampy landscape, filled with wild creatures and native plants. Farther away from the tourist-packed urban areas, the untamed wetlands of Florida offer a selection of things to do, such as kayaking, boat rides, and numerous other outdoor activities.

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.