34 days in Florida Itinerary

34 days in Florida Itinerary

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Route & dates

34 days in Florida Itinerary

Start: Portland
Drive:  28​h
1
Everglades City
— 1 night
Drive:  45​min
2
Marco Island
— 3 nights
Drive:  1​h 45​min
3
Sanibel Island
— 2 nights
taxi + Fly:  3​h
4
Key West
— 5 nights
bus:  1​h 15​min
5
Marathon
— 4 nights
Drive:  45​min
6
Islamorada
— 3 nights
+2
shuttle + Fly + Drive:  5​h 30​min
7
St. Augustine
— 4 nights
bus:  1​h
8
Daytona Beach
— 2 nights
Fly + Drive:  5​h 15​min
9
Pensacola Beach
— 2 nights
Drive:  2​h 15​min
10
Panama City Beach
— 5 nights
taxi + Fly:  7​h 30​min
End: Portland

1
night
Everglades City

Everglades City is a city in Collier County, Florida, United States, of which it is the former county seat. Start off your visit on the 20th (Tue): get a dose of the wild on a nature and wildlife tour and then get a new perspective on things with Boat Tours & Water Sports.

Plan trip to Everglades City with our itinerary maker to find out where to go and what to do.

Portland to Everglades City is an approximately 7-hour combination of flight and car. You can also do a combination of bus, flight, and car; or drive. Plan for somewhat warmer temperatures traveling from Portland in August, with highs in Everglades City at 92°F and lows at 76°F. Finish up your sightseeing early on the 20th (Tue) so you can go by car to Marco Island.

Things to do in Everglades City

Outdoors Tours Wildlife

Side Trip

Nature & Wildlife Tours
Highlights from your plan
Nature & Wildlife Tours

3
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. Appreciate the collections at Marco Island Historical Museum and Malenda Trick Art Gallery. Discover out-of-the-way places like Dolphin & Whale Watching and Parasailing & Paragliding. There's lots more to do: find your balance on the water with some of the best stand-up paddleboarding in the area, take in the architecture and atmosphere at San Marco Catholic Church, don't miss a visit to Marco Island Center for the Arts, and head off the coast to Cape Romano.

To find maps, photos, reviews, and other tourist information, read Marco Island journey planner.

You can drive from Everglades City to Marco Island in an hour. In August, daytime highs in Marco Island are 92°F, while nighttime lows are 76°F. Finish your sightseeing early on the 23rd (Fri) so you can drive to Sanibel Island.

Things to do in Marco Island

Outdoors Tours Adventure
Highlights from your plan
Dolphin & Whale Watching
Fishing Charters & Tours
Waterskiing & Jetskiing

2
nights
Sanibel Island

Sanibel Island ©
Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.
On the 24th (Sat), take in the exciting artwork at Tower Gallery, don't miss a visit to The Hirdie-Girdie Gallery, then enjoy the sand and surf at Bowman's Beach, and finally take in nature's colorful creations at Edison & Ford Winter Estates. On the next day, examine the collection at The Bailey-Matthews National Shell Museum, take in the architecture and atmosphere at St. Isabel Catholic Church, and then see majestic marine mammals with a dolphin and whale watching tour.

For more things to do, where to stay, maps, and tourist information, go to the Sanibel Island vacation maker app .

Drive from Marco Island to Sanibel Island in 2 hours. August in Sanibel Island sees daily highs of 92°F and lows of 75°F at night. Finish your sightseeing early on the 25th (Sun) so you can travel to Key West.

Things to do in Sanibel Island

Outdoors Parks Museums

Side Trip

Edison and Ford Winter Estates
Highlights from your plan
Bowman's Beach ©
Bowman's Beach
St. Isabel Catholic Church ©
St. Isabel Catholic Church

5
nights
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.
Relax by the water at Smathers Beach and Higgs Beach. Take a break from the city and head to Dolphin & Whale Watching and Vandenberg Wreck. There's still lots to do: find your balance on the water with some of the best stand-up paddleboarding in the area, glide through the air with a parasailing or paragliding tour, examine the collection at The Ernest Hemingway Home and Museum, and pause for some serene contemplation at Saint Mary Star of the Sea.

To see traveler tips, photos, more things to do, and more tourist information, read our Key West travel route website .

Traveling by combination of taxi and flight from Sanibel Island to Key West takes 3 hours. Alternatively, you can ride a ferry; or drive. Traveling from Sanibel Island in August, expect somewhat warmer with lows of 81°F in Key West. Wrap up your sightseeing on the 30th (Fri) to allow time to take a bus to Marathon.

Things to do in Key West

Outdoors Parks Tours
Highlights from your plan
Stand-Up Paddleboarding
Dolphin & Whale Watching
Vandenberg Wreck ©
Vandenberg Wreck

4
nights
Marathon

A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
Get some cultural insight at San Pablo Catholic Church and Shady Palm Art Gallery & Photography. Step off the beaten path and head to Sombrero Reef and Scuba & Snorkeling. There's lots more to do: see what you can catch with a fishing tour, look for all kinds of wild species at Crane Point Museum & Nature Center, kick back and relax at Sunset Park Beach, and get all the information you need at Pigeon Key Foundation.

For more things to do, other places to visit, maps, and more tourist information, read our Marathon trip itinerary builder site .

Traveling by bus from Key West to Marathon takes 1.5 hours. Alternatively, you can drive. August in Marathon sees daily highs of 92°F and lows of 80°F at night. Finish your sightseeing early on the 3rd (Tue) so you can drive to Islamorada.

Things to do in Marathon

Outdoors Wildlife Parks

Side Trips

Key Colony Beach, Bahia Honda State Park
Highlights from your plan
Fishing Charters & Tours
Scuba & Snorkeling
Crane Point Museum & Nature Center ©

3
nights
Islamorada

Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
Museum-lovers will get to explore Florida Keys History & Discovery Center and Michelle Nicole Lowe Art Gallery. Discover out-of-the-way places like Scuba & Snorkeling and Alligator Reef Light House. And it doesn't end there: look for all kinds of wild species at Florida Keys Wild Bird Rehabilitation Center, stroll around Harry Harris Park, get interesting insight from Tours, and get some thrills out on the water with a waterskiing or jet-skiing adventure.

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

Getting from Marathon to Islamorada by car takes about an hour. Other options: take a bus. In September, daily temperatures in Islamorada can reach 90°F, while at night they dip to 79°F. Wrap up your sightseeing on the 6th (Fri) to allow time to travel to St. Augustine.

Things to do in Islamorada

Outdoors Wildlife Tours

Side Trip

Key Largo
Highlights from your plan
Scuba & Snorkeling
Waterskiing & Jetskiing

4
nights
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. St. Photios Greek Orthodox National Shrine and Florida Museum of Natural History will appeal to museum buffs. Your itinerary includes some good beach time at Vilano Beach and Jacksonville Beach. Explore St. Augustine's surroundings by going to Marjorie Kinnan Rawlings Historic State Park (in Hawthorne), Gainesville (Butterfly Rainforest & University of Florida Bat House) and Island Grove Wine Company Tasting House (in Island Grove). The adventure continues: contemplate the long history of Mission of Nombre de Dios, examine the collection at Potter's Wax Museum, kick back and relax at Crescent Beach Public Beach, and explore the different monuments and memorials at Tolomato Cemetery.

For ratings, photos, where to stay, and tourist information, you can read our St. Augustine trip planner.

Do a combination of shuttle, flight, and car from Islamorada to St. Augustine in 5.5 hours. Alternatively, you can drive; or do a combination of shuttle, flight, and bus. In September, St. Augustine is little chillier than Islamorada - with highs of 85°F and lows of 73°F. Finish your sightseeing early on the 10th (Tue) to allow enough time to take a bus to Daytona Beach.

Things to do in St. Augustine

Parks Historic Sites Beaches

Side Trips

Gainesville, Marjorie Kinnan Rawlings Historic State Park, Island Grove Wine Company Tasting House, Jacksonville Beach, Crescent Beach Public Beach
Highlights from your plan
Vilano Beach ©
Vilano Beach
Jacksonville Beach ©
Jacksonville Beach

2
nights
Daytona Beach

Daytona Beach ©
The iconic seaside destination of Daytona Beach once supported sugar mill plantations, but now entertains up to 8 million visitors a year.
Start off your visit on the 11th (Wed): enjoy the sand and surf at Beach at Daytona Beach, take in the architecture and atmosphere at Our Lady of Lourdes Catholic Church, then steep yourself in history at Heritage Preservation Trust, and finally visit a coastal fixture at Ponce de Leon Inlet Lighthouse & Museum. Get ready for a full day of sightseeing on the 12th (Thu): enjoy the sand and surf at Apollo Beach, then make a trip to Arts on Douglas, then examine the collection at MOAS - Museum of Arts and Sciences, and finally steep yourself in history at Mary Bethune Home.

To see maps, ratings, traveler tips, and more tourist information, read our Daytona Beach trip itinerary maker app .

Take a bus from St. Augustine to Daytona Beach in an hour. Alternatively, you can drive. In September, daily temperatures in Daytona Beach can reach 88°F, while at night they dip to 73°F. Finish your sightseeing early on the 12th (Thu) so you can travel to Pensacola Beach.

Things to do in Daytona Beach

Parks Beaches Outdoors

Side Trips

New Smyrna Beach, Ponce de Leon Inlet Lighthouse & Museum
Highlights from your plan
MOAS - Museum of Arts and Sciences ©
Beach at Daytona Beach ©
Beach at Daytona Beach

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 13th (Fri): contemplate the long history of Fort Pickens Area, enjoy the sand and surf at Gulf Islands National Seashore, and then enjoy the sand and surf at Pensacola Beach. On the next day, get up close to creatures of the deep with a dolphin and whale watching tour and then tour the pleasant surroundings at Navarre Beach.

To see where to stay, maps, photos, and tourist information, refer to the Pensacola Beach planner .

You can do a combination of flight and car from Daytona Beach to Pensacola Beach in 5.5 hours. Alternatively, you can do a combination of flight and taxi; or drive. Traveling from Daytona Beach to Pensacola Beach, you'll gain 1 hour due to the time zone difference. In September, daytime highs in Pensacola Beach are 88°F, while nighttime lows are 72°F. Wrap up your sightseeing on the 14th (Sat) to allow time to drive to Panama City Beach.

Things to do in Pensacola Beach

Outdoors Parks Beaches

Side Trip

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

5
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.
Step off the beaten path and head to Dolphin & Whale Watching and Swim with Dolphins. You'll get in some beach time at St. Andrews State Park and Seaside Beach. Venture out of the city with trips to Bear Creek Feline Center (in Panama City), Eden Gardens State Park (in Point Washington) and 30A Farmers Market (in Rosemary Beach). There's lots more to do: take a tour by water with Boat Tours & Water Sports, see what you can catch with a fishing tour, enjoy the sand and surf at Panama City Beach, and get a taste of the local shopping with Panama City CENTER for the ARTS.

To find where to stay, more things to do, maps, and more tourist information, read our Panama City Beach tour planner .

Traveling by car from Pensacola Beach to Panama City Beach takes 2.5 hours. Traveling from Pensacola Beach to Panama City Beach, you'll lose 1 hour due to the time zone difference. Expect a daytime high around 89°F in September, and nighttime lows around 70°F. Finish your sightseeing early on the 19th (Thu) so you can travel back home.

Things to do in Panama City Beach

Outdoors Wildlife Parks

Side Trips

Panama City, Seaside Beach, Blue Mountain Beach, Eden Gardens State Park, 30A Farmers Market
Highlights from your plan
Dolphin & Whale Watching
Swim with Dolphins
St. Andrews State Park ©
St. Andrews State Park

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