29 days in Florida Itinerary

29 days in Florida Itinerary

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Route & dates

29 days in Florida Itinerary

Start: Orlando
1
Orlando
— 3 nights
Drive:  4​h 15​min
2
Marco Island
— 2 nights
ferry:  2​h 30​min
3
Key West
— 4 nights
bus:  1​h 15​min
4
Marathon
— 4 nights
Drive:  45​min
5
Islamorada
— 3 nights
Drive:  45​min
6
Key Largo
— 4 nights
Drive:  1​h 15​min
7
Coral Gables
— 4 nights
Fly + Drive:  4​h 30​min
8
Panama City Beach
— 2 nights
Drive:  2​h 15​min
9
Pensacola Beach
— 2 nights
Drive + Fly:  5​h
End: Orlando

3
nights
Orlando

Orlando ©
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.
Visiting Discovery Cove and Audubon Center for Birds of Prey will get you outdoors. There's still lots to do: get in on the family fun at Walt Disney World Resort, have some family-friendly fun at The Escape Game Orlando, admire the masterpieces at Charles Hosmer Morse Museum of American Art, and admire the natural beauty at Harry P. Leu Gardens.

To see where to stay, maps, and more tourist information, refer to the Orlando trip tool .

The Route module can give you travel options from your home to Orlando. In August in Orlando, expect temperatures between 92°F during the day and 76°F at night. Cap off your sightseeing on the 5th (Mon) early enough to go by car to Marco Island.

Things to do in Orlando

Theme Parks Parks Outdoors

Side Trips

Audubon Center for Birds of Prey, Charles Hosmer Morse Museum of American Art
Highlights from your plan
Walt Disney World Resort ©
Walt Disney World Resort
Discovery Cove ©
Discovery Cove
Audubon Center for Birds of Prey ©
Audubon Center for Birds of Prey

2
nights
Marco Island

Marco Island is a city in Collier County, Florida, United States, located on an island by the same name in the Gulf of Mexico off the coast of Southwest Florida. Kick off your visit on the 6th (Tue): zoom along the surf with a waterskiing or jet-skiing adventure, then glide through the air with a parasailing or paragliding tour, and then see majestic marine mammals with a dolphin and whale watching tour. Here are some ideas for day two: get some thrills on the water with a speed boat tour, find your balance on the water with some of the best stand-up paddleboarding in the area, and then stop by Keep In Touch.

For more things to do, ratings, where to stay, and tourist information, read our Marco Island journey planning site .

Traveling by car from Orlando to Marco Island takes 4.5 hours. Alternatively, you can do a combination of flight and bus; or take a bus. August in Marco Island sees daily highs of 92°F and lows of 76°F at night. Finish your sightseeing early on the 7th (Wed) to allow enough time to ride a ferry to Key West.

Things to do in Marco Island

Outdoors Tours Adventure

Side Trip

Speed Boats Tours
Highlights from your plan
Dolphin & Whale Watching
Waterskiing & Jetskiing
Stand-Up Paddleboarding

4
nights
Key West

Key West ©
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.
Visiting Dolphin & Whale Watching and Dry Tortugas National Park will get you outdoors. Next up on the itinerary: identify plant and animal life at Key West Butterfly & Nature Conservatory, glide peacefully along the water with some of the best stand-up paddleboarding in the area, see the interesting displays at The Ernest Hemingway Home and Museum, and take in nature's colorful creations at Audubon House & Tropical Gardens.

To find ratings, maps, photos, and tourist information, go to the Key West travel planner .

Traveling by ferry from Marco Island to Key West takes 2.5 hours. Alternatively, you can drive. August in Key West sees daily highs of 90°F and lows of 81°F at night. Cap off your sightseeing on the 11th (Sun) early enough to catcht the bus to Marathon.

Things to do in Key West

Parks Wildlife Outdoors
Highlights from your plan
Dry Tortugas National Park ©
Dry Tortugas National Park
Parasailing & Paragliding

4
nights
Marathon

Marathon ©
A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
Step out of the city life by going to Bahia Honda State Park and National Key Deer Refuge. There's lots more to do: get answers to all your questions at Pigeon Key Foundation, look for all kinds of wild species at Dolphin Research Center, take in the architecture and atmosphere at San Pablo Catholic Church, and cast your line with a fishing tour.

To see other places to visit, maps, traveler tips, and more tourist information, read Marathon road trip app .

Traveling by bus from Key West to Marathon takes 1.5 hours. Alternatively, you can drive. In August, daily temperatures in Marathon can reach 92°F, while at night they dip to 80°F. Wrap up your sightseeing on the 15th (Thu) early enough to drive to Islamorada.

Things to do in Marathon

Wildlife Parks Outdoors

Side Trip

Big Pine Key
Highlights from your plan
National Key Deer Refuge ©
National Key Deer Refuge
Bahia Honda State Park ©
Bahia Honda State Park
Scuba & Snorkeling

3
nights
Islamorada

Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
Get outdoors at Fishing Charters & Tours and Parasailing & Paragliding. There's much more to do: glide peacefully along the water with some of the best stand-up paddleboarding in the area, see the vivid underwater world at Alligator Reef Light House, enjoy the sand and surf at Anne's Beach, and sample the tasty concoctions at Islamorada Beer Company.

To find maps, traveler tips, photos, and tourist information, you can read our Islamorada holiday planning website .

You can drive from Marathon to Islamorada in an hour. Another option is to take a bus. In August in Islamorada, expect temperatures between 92°F during the day and 80°F at night. Wrap up your sightseeing on the 18th (Sun) to allow time to drive to Key Largo.

Things to do in Islamorada

Outdoors Tours Wildlife
Highlights from your plan
Fishing Charters & Tours
Scuba & Snorkeling
Parasailing & Paragliding

4
nights
Key Largo

Key Largo ©
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.
Step out of the city life by going to Scuba & Snorkeling and John Pennekamp Coral Reef State Park. When in Key Largo, make a side trip to see Anhinga Trail in Everglades National Park, approximately 48 minutes away. There's still lots to do: see the vivid underwater world at Spiegel Grove, identify plant and animal life at Florida Keys Wild Bird Rehabilitation Center, fly like a bird with a parasailing or paragliding tour, and zoom along the surf with a waterskiing or jet-skiing adventure.

To find ratings, reviews, other places to visit, and more tourist information, read our Key Largo tour itinerary builder app .

You can drive from Islamorada to Key Largo in an hour. Another option is to do a combination of bus and taxi. In August, daytime highs in Key Largo are 90°F, while nighttime lows are 77°F. Finish your sightseeing early on the 22nd (Thu) so you can drive to Coral Gables.

Things to do in Key Largo

Parks Wildlife Outdoors

Side Trip

Anhinga Trail
Highlights from your plan
Spiegel Grove ©
Spiegel Grove
Scuba & Snorkeling
Anhinga Trail ©
Anhinga Trail

4
nights
Coral Gables

Coral Gables ©
Coral Gables, officially the City of Coral Gables, is a city in Miami-Dade County, Florida, United States, located southwest of Downtown Miami. Escape the urban bustle at Shark Valley Visitor Center and Mrazek Pond. Change things up with these side-trips from Coral Gables: Everglades National Park (in Florida City), Everglades National Park (Long Pine Key, Slough Slog, & more) and Homestead Historic Town Hall Museum (in Homestead). It doesn't end there: get outside with Venetian Pool.

For photos, maps, traveler tips, and other tourist information, read Coral Gables trip planner .

Traveling by car from Key Largo to Coral Gables takes 1.5 hours. Alternatively, you can take a bus. Expect a daytime high around 91°F in August, and nighttime lows around 78°F. Cap off your sightseeing on the 26th (Mon) early enough to travel to Panama City Beach.

Things to do in Coral Gables

Parks Nature Outdoors

Side Trips

Everglades National Park, Everglades National Park, Homestead Historic Town Hall Museum
Highlights from your plan
Shark Valley Visitor Center ©
Shark Valley Visitor Center
Gumbo Limbo Trail ©
Gumbo Limbo Trail
Everglades National Park ©
Everglades National Park

2
nights
Panama City Beach

Boasting 43 km (27 mi) of white sandy beaches and plenty of sunshine, Panama City Beach is an ideal choice for a relaxing holiday.
Kick off your visit on the 27th (Tue): do a tasting at Panama City Beach Winery, then get close to the beloved marine mammals with a swim-with-the-dolphins experience, then view the masterpieces at Panama City CENTER for the ARTS, and finally look for all kinds of wild species at Bear Creek Feline Center. Get ready for a full day of sightseeing on the 28th (Wed): kick back and relax at Santa Rosa Beach and then get up close to creatures of the deep with a dolphin and whale watching tour.

For traveler tips, maps, ratings, and tourist information, go to the Panama City Beach driving holiday planning site .

Traveling by combination of flight and car from Coral Gables to Panama City Beach takes 4.5 hours. Alternatively, you can fly; or drive. In August, daytime highs in Panama City Beach are 91°F, while nighttime lows are 74°F. Wrap up your sightseeing on the 28th (Wed) to allow time to drive to Pensacola Beach.

Things to do in Panama City Beach

Outdoors Wildlife Tours

Side Trips

Panama City, Santa Rosa Beach
Highlights from your plan
Swim with Dolphins
Dolphin & Whale Watching
Panama City Beach Winery ©
Panama City Beach Winery

2
nights
Pensacola Beach

Pensacola Beach ©
Pensacola Beach is an unincorporated community located on Santa Rosa Island, a barrier island, in Escambia County, Florida, United States. Start off your visit on the 29th (Thu): contemplate the waterfront views at Navarre Beach Marine Sanctuary and then tour the pleasant surroundings at Navarre Beach. On the next day, get up close to creatures of the deep with a dolphin and whale watching tour and then enjoy the sand and surf at Gulf Islands National Seashore.

To find maps, more things to do, reviews, and other tourist information, read Pensacola Beach online trip maker .

You can drive from Panama City Beach to Pensacola Beach in 2.5 hours. Traveling from Panama City Beach to Pensacola Beach, you'll gain 1 hour due to the time zone difference. In August, daily temperatures in Pensacola Beach can reach 90°F, while at night they dip to 75°F. Wrap up your sightseeing on the 30th (Fri) to allow time to travel back home.

Things to do in Pensacola Beach

Parks Outdoors Beaches

Side Trip

Navarre
Highlights from your plan
Navarre Beach ©
Navarre Beach
Gulf Islands National Seashore ©
Gulf Islands National Seashore

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