36 days in Florida Itinerary

36 days in Florida Itinerary

Created using Inspirock Florida journey planner

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Route & dates

36 days in Florida Itinerary

Start: New York City
bus + Fly:  5​h 45​min
1
Sanibel Island
— 3 nights
Drive:  1​h 15​min
2
Naples
— 2 nights
Drive:  30​min
3
Marco Island
— 1 night
ferry:  3​h
4
Key West
— 2 nights
bus:  1​h 15​min
5
Marathon
— 3 nights
Drive:  45​min
6
Islamorada
— 3 nights
Drive:  1​h 45​min
7
Miami
— 3 nights
Fly + Drive:  5​h 15​min
8
St. Augustine
— 3 nights
Drive:  2​h
9
Orlando
— 5 nights
Drive:  2​h 30​min
10
Bradenton Beach, Anna Maria Island
— 2 nights
bus + Fly:  5​h 15​min
11
Pensacola Beach
— 1 night
Drive:  3​h 30​min
12
Apalachicola
— 2 nights
Drive:  1​h 45​min
13
Panama City Beach
— 3 nights
Drive:  1​h 15​min
14
Destin
— 1 night
+2
taxi + Fly + bus:  5​h
End: New York City

3
nights
Sanibel Island

Sanibel Island ©
Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.
Start off your visit on the 1st (Fri): get lost in a book at Sanibel Public Library and then stop by Bailey's General Store. Keep things going the next day: get engrossed in the history at Sanibel Historical Museum and Village, then kick back and relax at Gulfside Beach, and then get up close to creatures of the deep with a dolphin and whale watching tour.

To find where to stay, reviews, photos, and tourist information, read our Sanibel Island online tour itinerary planner .

New York City to Sanibel Island is an approximately 6-hour combination of bus, flight, and taxi. You can also do a combination of train, flight, and taxi; or drive. Traveling from New York City in June, things will get a bit warmer in Sanibel Island: highs are around 91°F and lows about 73°F. Wrap up your sightseeing on the 4th (Mon) to allow time to drive to Naples.

Things to do in Sanibel Island

Outdoors Parks Beaches

Side Trip

Captiva Beach
Highlights from your plan
Sanibel Historical Museum and Village ©
Captiva Beach ©
Captiva Beach
Gulfside Beach ©
Gulfside Beach

2
nights
Naples

Naples ©
Naples is a city in Collier County, Florida, United States. On the 4th (Mon), stop by Mercato and then stroll through Vanderbilt Beach. Keep things going the next day: find your balance on the water with some of the best stand-up paddleboarding in the area, explore the engaging exhibits at Golisano Childrens Museum of Naples, then examine the collection at The Revs Institute, and finally browse the different shops at Coastland Center.

To find photos and other tourist information, read Naples online trip maker .

Traveling by car from Sanibel Island to Naples takes 1.5 hours. Expect a daytime high around 90°F in June, and nighttime lows around 74°F. Finish up your sightseeing early on the 6th (Wed) so you can go by car to Marco Island.

Things to do in Naples

Shopping Outdoors Museums

Side Trip

Vanderbilt Beach
Highlights from your plan
Revs Institute ©
Revs Institute
Stand-Up Paddleboarding
Golisano Children's Museum of Naples ©

1
night
Marco Island

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. Start off your visit on the 6th (Wed): hunt for treasures at Marco Island Farmers Market-Wednesday, see majestic marine mammals with a dolphin and whale watching tour, then take in the exciting artwork at Malenda Trick Art Gallery, and finally head off the coast to Cape Romano.

For more things to do, where to stay, traveler tips, and more tourist information, refer to the Marco Island day trip planning site .

Marco Island is just a short distance from Naples. In June in Marco Island, expect temperatures between 90°F during the day and 72°F at night. Finish your sightseeing early on the 7th (Thu) to allow enough time to travel to Key West.

Things to do in Marco Island

Outdoors Parks Nature
Highlights from your plan
Cape Romano ©
Cape Romano
Malenda Trick Art Gallery ©
Malenda Trick Art Gallery

2
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.
Mel Fisher Maritime Museum and Key West Lighthouse and Keeper's Quarters Museum are good opportunities to explore the local culture. Shop till you drop at Alan S Maltz Gallery and 7 Artists & Friends. And it doesn't end there: see majestic marine mammals with a dolphin and whale watching tour, look for gifts at Peppers Of Key West, see some colorful creatures with a scuba or snorkeling tour, and stroll the grounds of Key West Cemetery.

Discover how to plan a Key West trip in just a few steps with Inspirock's itinerary builder.

You can do a combination of taxi and flight from Marco Island to Key West in 3 hours. Alternatively, you can ride a ferry; or drive. Traveling from Marco Island in June, expect a bit warmer with lows of 79°F in Key West. Wrap up your sightseeing on the 9th (Sat) early enough to drive to Marathon.

Things to do in Key West

Outdoors Tours Wildlife
Highlights from your plan
7 Artists & Friends Gallery ©
7 Artists & Friends Gallery
Alan S. Maltz Gallery ©
Alan S. Maltz Gallery

3
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.
On the 10th (Sun), admire nature's wide array of creatures at Florida Keys Aquarium Encounters, take in the architecture and atmosphere at San Pablo Catholic Church, stop by The Tackle Box, then snap pictures at Old Seven Mile Bridge, and finally see the interesting displays at EAA Air Museum. Here are some ideas for day two: identify plant and animal life at Sombrero Reef, look for all kinds of wild species at Crane Point Museum & Nature Center, and then tour the water at your own pace with Captain Hook's Marina & Dive Center.

To find where to stay, traveler tips, maps, and tourist information, go to the Marathon tour builder site .

You can drive from Key West to Marathon in 1.5 hours. Another option is to take a bus. In June in Marathon, expect temperatures between 90°F during the day and 79°F at night. Wrap up your sightseeing on the 12th (Tue) to allow time to drive to Islamorada.

Things to do in Marathon

Wildlife Parks Tours
Highlights from your plan
Florida Keys Aquarium Encounters ©
Florida Keys Aquarium Encounters
Crane Point Museum & Nature Center ©
San Pablo Catholic Church ©
San Pablo Catholic Church

3
nights
Islamorada

Islamorada ©
Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
Old Road Gallery and History of Diving Museum will appeal to museum buffs. Family-friendly places like Molasses Reef and Anne's Beach will thrill your kids. There's much more to do: find your balance on the water with Key Largo Adventures - an Islamorada Boat Charter, identify plant and animal life at Spiegel Grove, look for gifts at Shell World, and take a memorable tour with A1A Watersports.

To see traveler tips, other places to visit, maps, and other tourist information, go to the Islamorada tour itinerary planner.

Drive from Marathon to Islamorada in an hour. Alternatively, you can take a shuttle; or take a bus. In June, daily temperatures in Islamorada can reach 90°F, while at night they dip to 79°F. Wrap up your sightseeing on the 15th (Fri) to allow time to drive to Miami.

Things to do in Islamorada

Outdoors Adventure Tours

Side Trip

Key Largo
Highlights from your plan
History of Diving Museum ©
History of Diving Museum
Spiegel Grove ©
Spiegel Grove

3
nights
Miami

Miami ©
Florida’s mecca of fun in the sun, the lively tropical metropolis of Miami is one of the world’s top vacation spots.
Eschew the tourist crowds and head to Las Olas Beach and Robert Is Here Fruit Stand. Family-friendly places like Anhinga Trail and Haulover Beach Park will thrill your kids. Explore Miami's surroundings by going to Homestead (Coral Castle & Everglades Alligator Farm), Mizner Park (in Boca Raton) and Morikami Museum and Japanese Gardens (in Delray Beach). There's lots more to do: shop like a local with Bal Harbour Shops, appreciate the extensive heritage of Art Deco Tours, and explore the world behind art at Pérez Art Museum Miami.

To find maps, where to stay, other places to visit, and tourist information, read Miami journey maker .

Traveling by car from Islamorada to Miami takes 2 hours. Alternatively, you can take a shuttle; or take a bus. In June, daily temperatures in Miami can reach 89°F, while at night they dip to 77°F. Wrap up your sightseeing on the 18th (Mon) to allow time to drive to St. Augustine.

Things to do in Miami

Parks Outdoors Beaches

Side Trips

Homestead, Bal Harbour, Morikami Museum & Japanese Gardens, Anhinga Trail, Las Olas Beach
Highlights from your plan
Anhinga Trail ©
Anhinga Trail
Las Olas Beach ©
Las Olas Beach
Haulover Beach Park ©
Haulover Beach Park

3
nights
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. Appreciate the collections at World Golf Hall of Fame and High Tide Gallery. Get some historical perspective at Memorial Presbyterian Church and Old St. Augustine Village. Step out of St. Augustine with an excursion to Jacksonville Beach in Jacksonville Beach--about 50 minutes away. Next up on the itinerary: enjoy the sand and surf at Vilano Beach, explore the galleries of St. Photios Greek Orthodox National Shrine, see the interesting displays at Ximenez-Fatio House Museum, and stop by Claude's Chocolate.

Plan my day in St. Augustine using traveler tips and tourist information provided by Inspirock.

Traveling by car from Miami to St. Augustine takes 5.5 hours. Alternatively, you can do a combination of tram, flight, and bus; or take a bus. In June, plan for daily highs up to 89°F, and evening lows to 73°F. Finish your sightseeing early on the 21st (Thu) so you can drive to Orlando.

Things to do in St. Augustine

Museums Parks Outdoors

Side Trip

Jacksonville Beach
Highlights from your plan
Memorial Presbyterian Church ©
Memorial Presbyterian Church
Vilano Beach ©
Vilano Beach
Jacksonville Beach ©
Jacksonville Beach

5
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.
Kids will appreciate attractions like Ponce de Leon Inlet Lighthouse & Museum and Ellie Schiller Homosassa Springs Wildlife State Park. Museum-lovers will appreciate Madame Tussauds and The Charles Hosmer Morse Museum of American Art. Explore the numerous day-trip ideas around Orlando: Cocoa Beach (in Cocoa Beach), Oakland Nature Preserve (in Oakland) and Florida Artists Gallery (in Floral City). There's lots more to do: make an unforgettable trip to World of Disney, take an in-depth tour of Enterprise Heritage Center and Museum, see the interesting displays at American Space Museum and Walk of Fame, and wander the streets of Old Town.

For maps, other places to visit, more things to do, and tourist information, use the Orlando visit planning app .

Drive from St. Augustine to Orlando in 2 hours. Alternatively, you can take a bus. In June, daytime highs in Orlando are 90°F, while nighttime lows are 73°F. Wrap up your sightseeing on the 26th (Tue) to allow time to drive to Bradenton Beach.

Things to do in Orlando

Museums Parks Shopping

Side Trips

Titusville, Ponce Inlet, Florida Artists Gallery, Ellie Schiller Homosassa Springs Wildlife State Park, Cocoa Beach
Highlights from your plan
Marine Science Center ©
Marine Science Center
Oakland Nature Preserve ©
Oakland Nature Preserve

2
nights
Bradenton Beach, Anna Maria Island

Bradenton Beach ©
Bradenton Beach is a city on Anna Maria Island in Manatee County, Florida, United States. Kick off your visit on the 27th (Wed): look for gifts at AMI Outfitters Coastal Gear & Apparel, then get engrossed in the history at Anna Maria Island Historical Society, then tour the pleasant surroundings at Coquina Baywalk, and finally enjoy the sand and surf at Coquina Beach. Get ready for a full day of sightseeing on the next day: tour the pleasant surroundings at Bean Point, relax and rejuvenate at some of the top local wellness centers, then take in the waterfront at Bradenton Beach City Pier, and finally have some family-friendly fun at The Fish Hole Miniature Golf.

For ratings, reviews, photos, and more tourist information, read Bradenton Beach tour itinerary maker website .

Drive from Orlando to Bradenton Beach in 2.5 hours. Alternatively, you can do a combination of train, bus, and taxi. June in Bradenton Beach sees daily highs of 89°F and lows of 73°F at night. Wrap up your sightseeing on the 28th (Thu) early enough to travel to Pensacola Beach.

Things to do in Bradenton Beach

Parks Outdoors Beaches

Side Trip

Anna Maria
Highlights from your plan
Bean Point ©
Bean Point
Anna Maria Island Historical Museum ©
The Fish Hole Miniature Golf ©
The Fish Hole Miniature Golf

1
night
Pensacola Beach

Pensacola Beach ©
Pensacola Beach is an unincorporated community located on Santa Rosa Island, a barrier island, in Escambia County, Florida, United States. On the 29th (Fri), kick back and relax at Gulf Islands National Seashore - Florida District, then get interesting insight from Dolphin Express, and then stroll through Pensacola Beach.

To find more things to do, ratings, reviews, and tourist information, you can read our Pensacola Beach trip planning site .

Traveling by combination of bus, flight, and taxi from Bradenton Beach to Pensacola Beach takes 5.5 hours. Alternatively, you can drive; or do a combination of bus and taxi. Due to the time zone difference, you'll gain 1 hour traveling from Bradenton Beach to Pensacola Beach. Expect a daytime high around 89°F in June, and nighttime lows around 74°F. Finish your sightseeing early on the 29th (Fri) to allow enough time to travel to Apalachicola.

Things to do in Pensacola Beach

Outdoors Parks Beaches
Highlights from your plan
Gulf Islands National Seashore ©
Gulf Islands National Seashore
Pensacola Beach ©
Pensacola Beach

2
nights
Apalachicola

Apalachicola ©
Apalachicola is a city in Franklin County, Florida, United States, on the shore of Apalachicola Bay, an inlet of the Gulf of Mexico. On the 30th (Sat), get engrossed in the history at John Gorrie State Museum, then relax and rejuvenate at some of the top local wellness centers, then stop by Shell Shack, and finally kick back and relax at Mexico Beach. On the 1st (Sun), you'll have a packed day of sightseeing: stroll the grounds of Chestnut Street Cemetery, then see the interesting displays at Raney House Museum, then identify plant and animal life at Apalachicola National Estuarine Research Reserve, and finally enjoy the sea views from Crooked River Lighthouse.

For traveler tips, reviews, and more tourist information, refer to the Apalachicola online attractions planner .

You can drive from Pensacola Beach to Apalachicola in 4 hours. Due to the time zone difference, you'll lose 1 hour traveling from Pensacola Beach to Apalachicola. In June, daily temperatures in Apalachicola can reach 89°F, while at night they dip to 73°F. Cap off your sightseeing on the 1st (Sun) early enough to travel to Panama City Beach.

Things to do in Apalachicola

Parks Outdoors Wildlife

Side Trips

Mexico Beach, Crooked River Lighthouse, Apalachicola National Estuarine Research Reserve
Highlights from your plan
Mexico Beach ©
Mexico Beach
Crooked River Lighthouse ©
Crooked River Lighthouse

3
nights
Panama City Beach

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.
You'll discover tucked-away gems like Eden Gardens State Park and Shell Island Blue Dolphin Tours. Get some cultural insight at Fusion Art Glass Gallery and Man in the Sea Museum. You'll find plenty of places to visit near Panama City Beach: Bear Creek Feline Center (in Panama City) and Seaside (Seaside Beach & Sundog Books). There's lots more to do: try for a hole-in-one at Pirate's Island Adventure Golf, bet on your favorite at Hidden Lagoon Golf and Racetrack, and have some family-friendly fun at Goofy Golf.

To see photos, reviews, more things to do, and tourist information, use the Panama City Beach itinerary maker app .

You can drive from Apalachicola to Panama City Beach in 2 hours. In July, plan for daily highs up to 90°F, and evening lows to 74°F. Wrap up your sightseeing on the 4th (Wed) early enough to drive to Destin.

Things to do in Panama City Beach

Parks Fun & Games Wildlife

Side Trips

Seaside, Panama City, Eden Gardens State Park
Highlights from your plan
Pirate's Island Adventure Golf ©
Pirate's Island Adventure Golf
Eden Gardens State Park ©
Eden Gardens State Park
Hidden Lagoon Golf and Racetrack ©

1
night
Destin

Destin ©
With emerald water and white beaches, Destin is one of America's favorite vacation destinations.
Kick off your visit on the 5th (Thu): get a new perspective on things with Boat Tours & Water Sports, then take an in-depth tour of Destin History & Fishing Museum, then relax and rejuvenate at some of the top local wellness centers, and finally browse the different shops at Destin Commons.

Use Inspirock's suggestions to plan your Destin trip and find the best activities and attractions for your vacation.

Traveling by car from Panama City Beach to Destin takes 1.5 hours. Alternatively, you can do a combination of bus and taxi. The time zone difference moving from Eastern Standard Time (EST) to Central Standard Time (CST) is minus 1 hour. In July in Destin, expect temperatures between 89°F during the day and 77°F at night. Cap off your sightseeing on the 5th (Thu) early enough to travel back home.

Things to do in Destin

Shopping Museums
Highlights from your plan
Destin Commons ©
Destin Commons
Destin History & Fishing Museum ©
Destin History & Fishing Museum

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