18 days in Florida Itinerary

18 days in Florida Itinerary

Created using Inspirock Florida trip itinerary builder

Make it your trip
Fly to Fort Lauderdale, Shuttle to Islamorada
1
Islamorada
— 2 nights
Drive
2
Big Pine Key
— 1 night
Drive
3
Key West
— 3 nights
Drive
4
Key Largo
— 1 night
Bus
5
Everglades National Park
— 1 night
Drive
6
Miami Beach
— 2 nights
Drive
7
Siesta Key
— 1 night
Drive
8
Tampa
— 2 nights
Drive
9
Orlando
— 2 nights
Drive
10
St. Augustine
— 1 night
Bus to Orlando, Fl, Fly to Dubai

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Islamorada

— 2 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.
Give yourself a bit of retail therapy at Pasta Pantaleo Signature Gallery and Shady Palm Art Gallery & Photography. Museum-lovers will get to explore Crane Point Museum & Nature Center and Old Road Gallery. Get out of town with these interesting Islamorada side-trips: Marathon (San Pablo Catholic Church, The Turtle Hospital, &more) and Sunset Park Beach (in Key Colony Beach). There's much more to do: see what you can catch with a fishing tour, enjoy the sand and surf at Anne's Beach, identify plant and animal life at Dolphin Research Center, and view the masterpieces at Lobster Trap Art Gift Shop and Gallery.

To see reviews, photos, more things to do, and other tourist information, refer to the Islamorada holiday planner.

Dubai, United Arab Emirates to Islamorada is an approximately 19.5-hour combination of flight and shuttle. You'll gain 9 hours traveling from Dubai to Islamorada due to the time zone difference. Traveling from Dubai in May, things will get a bit cooler in Islamorada: highs are around 36°C and lows about 29°C. Wrap up your sightseeing on the 16th (Sun) early enough to drive to Big Pine Key.

Things to do in Islamorada

Parks · Wildlife · Outdoors · Museums

Side Trips

Find places to stay May 14 — 16:

Big Pine Key

— 1 night
Big Pine Key is a census-designated place and unincorporated community in Monroe County, Florida, United States, on an island of the same name in the Florida Keys. Kick off your visit on the 17th (Mon): tour the pleasant surroundings at Long Beach, get a new perspective on things with Boat Tours & Water Sports, then look for all kinds of wild species at National Key Deer Refuge, and finally kick back and relax at Bahia Honda State Park.

To find reviews, ratings, maps, and more tourist information, use the Big Pine Key online road trip planner.

Drive from Islamorada to Big Pine Key in 1.5 hours. Alternatively, you can take a bus. In May, daily temperatures in Big Pine Key can reach 36°C, while at night they dip to 29°C. Wrap up your sightseeing on the 17th (Mon) to allow time to drive to Key West.

Things to do in Big Pine Key

Parks · Outdoors · Wildlife · Beaches
Find places to stay May 16 — 17:

Key West

— 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.
Museum-lovers will get to explore The Ernest Hemingway Home and Museum and 7 Artists & Friends Gallery. Get some historical perspective at Truman Little White House and Key West Cemetery. There's still lots to do: identify plant and animal life at Key West Butterfly & Nature Conservatory, admire the natural beauty at Audubon House & Tropical Gardens, see the vivid underwater world at Vandenberg Wreck, and pause for some serene contemplation at Saint Mary Star of the Sea.

To see ratings, where to stay, maps, and other tourist information, use the Key West travel route builder site.

Traveling by car from Big Pine Key to Key West takes an hour. Alternatively, you can take a shuttle; or take a bus. In May, daily temperatures in Key West can reach 34°C, while at night they dip to 29°C. Finish up your sightseeing early on the 20th (Thu) so you can go by car to Key Largo.

Things to do in Key West

Historic Sites · Museums · Parks · Wildlife
Find places to stay May 17 — 20:

Key Largo

— 1 night

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.
Start off your visit on the 21st (Fri): take a memorable tour with Florida Keys Flats Fishing, then get a dose of the wild on Capt. Sterling's Everglades Eco-Tours, then identify plant and animal life at Spiegel Grove, and finally indulge in some personalized pampering at Prana.

To find ratings, photos, more things to do, and more tourist information, go to the Key Largo trip itinerary planner.

You can drive from Key West to Key Largo in 2.5 hours. Alternatively, you can take a bus. Traveling from Key West in May, you can expect nighttime temperatures to be slightly colder in Key Largo, with lows of 26°C. Finish up your sightseeing early on the 21st (Fri) so you can catch the bus to Everglades National Park.

Things to do in Key Largo

Wildlife · Outdoors · Tours · Spas
Find places to stay May 20 — 21:

Everglades National Park

— 1 night

Largest Subtropical Wilderness in the United States

A vast expanse of pristine wetlands, Everglades National Park holds the distinction of being the largest tropical wilderness in the U.S. Overflow from Lake Okeechobee into the Florida Bay formed these wetlands, which are home to manatees, American crocodiles, Florida panthers, and an array of wading birds, land birds, and birds of prey.
On the 22nd (Sat), look for all kinds of wild species at Shark Valley Visitor Center, then hike along Pineland Trail, then identify plant and animal life at Anhinga Trail, and finally look for all kinds of wild species at Mahogany Hammock.

To see reviews, other places to visit, and tourist information, use the Everglades National Park sightseeing tool.

Traveling by bus from Key Largo to Everglades National Park takes 2.5 hours. In May, plan for daily highs up to 36°C, and evening lows to 29°C. Wrap up your sightseeing on the 22nd (Sat) early enough to travel to Miami Beach.

Things to do in Everglades National Park

Parks · Wildlife · Trails · Outdoors
Find places to stay May 21 — 22:

Miami Beach

— 2 nights

The World's Playground

Separated by water from the neighboring city of Miami, Miami Beach sits on a barrier island between Biscayne Bay and the Atlantic Ocean.
Start off your visit on the 23rd (Sun): wander the streets of Lincoln Road, then take in the architecture and atmosphere at Saint Francis de Sales Catholic Church, then kick back and relax at Haulover Beach Park, and finally shop like a local with Aventura Mall. Here are some ideas for day two: take a stroll through Collins Avenue, don't miss a visit to Bayside Marketplace, enjoy the sand and surf at 12th Street Beach, then stroll through South Beach, and finally stop by Art Deco Historic District.

For ratings, maps, other places to visit, and more tourist information, use the Miami Beach itinerary builder website.

The Route module can help you plan travel from Everglades National Park to Miami Beach. In May in Miami Beach, expect temperatures between 36°C during the day and 27°C at night. Finish your sightseeing early on the 24th (Mon) to allow enough time to drive to Siesta Key.

Things to do in Miami Beach

Shopping · Parks · Neighborhoods · Beaches

Side Trips

Find places to stay May 22 — 24:

Siesta Key

— 1 night
Siesta Key draws most of its visitors with soft, white-quartz sand beaches and translucent ocean water.
Kick off your visit on the 25th (Tue): kick back and relax at Siesta Beach, enjoy the sand and surf at Crescent Beach, then stroll the grounds of Sarasota National Cemetery, then stop by Sunshine & Sand Hidden Treasures, and finally enjoy the sand and surf at Turtle Beach.

For traveler tips, ratings, photos, and more tourist information, read our Siesta Key trip itinerary maker tool.

Drive from Miami Beach to Siesta Key in 4 hours. Alternatively, you can take a bus; or fly. Expect little chillier evenings in Siesta Key when traveling from Miami Beach in May, with lows around 23°C. Finish your sightseeing early on the 25th (Tue) so you can drive to Tampa.

Things to do in Siesta Key

Parks · Beaches · Outdoors · Historic Sites

Side Trip

Find places to stay May 24 — 25:

Tampa

— 2 nights

Big Guava

Tampa ranks among the country's most livable cities, attracting newcomers with its growing economy and status as a major port on the Gulf of Mexico.
Start off your visit on the 26th (Wed): stop by The St. Pete Store and Visitor Center, admire the masterpieces at Duncan McClellan Gallery, then kick back and relax at Clearwater Beach, and finally immerse yourself in nature at Honeymoon Island State Park. On the 27th (Thu), you'll have a packed day of sightseeing: cast your line with a fishing tour, then kick back and relax at Treasure Island Beach, and then kick back and relax at Saint Pete Beach.

To see maps, ratings, photos, and tourist information, read our Tampa itinerary planner.

Traveling by car from Siesta Key to Tampa takes 1.5 hours. Alternatively, you can take a bus. In May in Tampa, expect temperatures between 37°C during the day and 25°C at night. Finish your sightseeing early on the 27th (Thu) to allow enough time to drive to Orlando.

Things to do in Tampa

Outdoors · Parks · Beaches · Wildlife

Side Trips

Find places to stay May 25 — 27:

Orlando

— 2 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.
Start off your visit on the 28th (Fri): get in on the family fun at Walt Disney World Resort. Get ready for a full day of sightseeing on the next day: take in the exciting artwork at Crealde School of Art, admire the masterpieces at Charles Hosmer Morse Museum of American Art, then stop by MacroBaby, and finally buy something for everyone on your list at Disney Springs.

To find more things to do, traveler tips, ratings, and more tourist information, you can read our Orlando trip itinerary planner.

You can drive from Tampa to Orlando in 1.5 hours. Alternatively, you can take a bus; or take a train. In May, daily temperatures in Orlando can reach 36°C, while at night they dip to 24°C. Finish your sightseeing early on the 29th (Sat) so you can drive to St. Augustine.

Things to do in Orlando

Theme Parks · Shopping · Museums

Side Trip

Find places to stay May 27 — 29:

St. Augustine

— 1 night
St. On the 30th (Sun), explore the historical opulence of Castillo de San Marcos National Monument, enjoy the sea views from St. Augustine Lighthouse & Maritime Museum, Inc., kick back and relax at St. Augustine Beach, then enjoy the sand and surf at Crescent Beach Public Beach, and finally sample the fine beverages at St. Augustine Distillery.

To find out how to plan a trip to St. Augustine, use our trip itinerary maker.

Traveling by car from Orlando to St. Augustine takes 2 hours. Alternatively, you can take a bus. Traveling from Orlando in May, expect nights in St. Augustine to be about the same, around 22°C, while days are slightly colder, around 33°C. Finish up your sightseeing early on the 30th (Sun) so you can travel back home.

Things to do in St. Augustine

Parks · Beaches · Outdoors · Historic Sites

Side Trip

Find places to stay May 29 — 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.