34 days in Florida Itinerary

34 days in Florida Itinerary

Created using Inspirock Florida journey maker

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Route & dates

34 days in Florida Itinerary

Start: Ocala
+2
bus + taxi + ferry:  9​h 30​min
1
Key West
— 2 nights
Fly + taxi:  6​h 45​min
2
Panama City Beach
— 2 nights
Drive:  2​h 15​min
3
Pensacola Beach
— 2 nights
Drive:  6​h 45​min
4
St. Augustine
— 2 nights
Drive:  6​h 45​min
5
Pensacola
— 3 nights
Fly + bus:  5​h 45​min
6
Marco Island
— 3 nights
Drive:  2​h 30​min
7
Sarasota
— 3 nights
Fly:  5​h 15​min
8
Fort Walton Beach
— 3 nights
+2
taxi + Fly + bus:  5​h 45​min
9
Naples
— 3 nights
Drive:  1​h 15​min
10
Sanibel Island
— 3 nights
Drive:  5​h
11
Ormond Beach
— 3 nights
Drive:  1​h 45​min
12
Kissimmee
— 3 nights
Drive:  1​h 45​min
End: Ocala

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.
Start off your visit on the 18th (Thu): pause for some photo ops at Florida Keys Historical Military Memorial, make a trip to Mallory Square, get a new perspective on things with Boat Tours & Water Sports, look for all kinds of wild species at Key West Butterfly & Nature Conservatory, then see the interesting displays at The Ernest Hemingway Home and Museum, and finally don't miss a visit to Duval Street. Keep things going the next day: find your balance on the water with some of the best stand-up paddleboarding in the area, take a memorable tour with Tours, and then stroll the grounds of Key West Cemetery.

To find photos, where to stay, other places to visit, and other tourist information, read Key West day trip app .

Ocala to Key West is an approximately 6.5-hour combination of bus and flight. You can also drive; or do a combination of bus and ferry. Expect a bit warmer evenings in Key West when traveling from Ocala in July, with lows around 81°F. Finish up your sightseeing early on the 19th (Fri) so you can travel to Panama City Beach.

Things to do in Key West

Tours Outdoors Wildlife
Highlights from your plan
The Ernest Hemingway Home and Museum ©
Parasailing & Paragliding

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.
On the 20th (Sat), get up close to creatures of the deep with a dolphin and whale watching tour, get close to the beloved marine mammals with a swim-with-the-dolphins experience, then kick back and relax at Panama City Beach, and finally observe the fascinating underwater world at Gulf World Marine Park. Here are some ideas for day two: get your game on at Kartona The Electric Speedway, head off the coast to Shell Island, stroll through St. Andrews State Park, then learn about winemaking at Panama City Beach Winery, and finally buy something for everyone on your list at Pier Park.

Start your trip to Panama City Beach by creating a personalized itinerary on Inspirock.

Traveling by combination of flight and taxi from Key West to Panama City Beach takes 7 hours. Alternatively, you can fly; or drive. Plan for little chillier nights when traveling from Key West in July since evenings lows in Panama City Beach dip to 74°F. Cap off your sightseeing on the 21st (Sun) early enough to go by car to Pensacola Beach.

Things to do in Panama City Beach

Outdoors Parks Nature
Highlights from your plan
Swim with Dolphins
Dolphin & Whale Watching
Panama City Beach ©
Panama City Beach

2
nights
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 22nd (Mon): steep yourself in history at Fort Pickens Area, then tour the pleasant surroundings at Gulf Islands National Seashore, then enjoy the sand and surf at Pensacola Beach, and finally get up close to creatures of the deep with a dolphin and whale watching tour. On the next day, learn about wildlife with up-close encounters at The Gulf Breeze ZOO, look for gifts at Innerlight Surf Shop, sample the fine beverages at Rollins Distillery, then tour the pleasant surroundings at Pensacola Beach Gulf Pier, and finally get interesting insight from Tours.

To find traveler tips, reviews, maps, and other tourist information, use the Pensacola Beach driving holiday planner.

Getting from Panama City Beach to Pensacola Beach by car takes about 2.5 hours. You'll gain 1 hour traveling from Panama City Beach to Pensacola Beach due to the time zone difference. Expect a daytime high around 91°F in July, and nighttime lows around 76°F. Finish your sightseeing early on the 23rd (Tue) to allow enough time to drive to St. Augustine.

Things to do in Pensacola Beach

Outdoors Parks Beaches

Side Trip

Gulf Breeze
Highlights from your plan
Dolphin & Whale Watching
Gulf Islands National Seashore ©
Gulf Islands National Seashore
Pensacola Beach ©
Pensacola Beach

2
nights
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. Kids will enjoy St. Augustine Beach and St. Augustine Pirate & Treasure Museum. Take a break from St. Augustine with a short trip to Jacksonville Zoo & Gardens in Jacksonville, about 1h 10 min away. There's much more to do: brush up on your knowledge of spirits at St. Augustine Distillery, explore the galleries of St. Augustine Lighthouse & Maritime Museum, Inc., steep yourself in history at Old Jail, and gain insight at Flagler College.

To see where to stay, maps, and more tourist information, read our St. Augustine road trip planning app .

You can drive from Pensacola Beach to St. Augustine in 7 hours. Alternatively, you can do a combination of car, flight, and bus; or do a combination of taxi, flight, and bus. The time zone difference moving from Central Standard Time (CST) to Eastern Standard Time (EST) is 1 hour. In July, daytime highs in St. Augustine are 90°F, while nighttime lows are 75°F. Wrap up your sightseeing on the 26th (Fri) early enough to drive to Pensacola.

Things to do in St. Augustine

Parks Museums Wildlife

Side Trip

Jacksonville Zoo & Gardens
Highlights from your plan
St. Augustine Beach ©
St. Augustine Beach
Jacksonville Zoo & Gardens ©
Jacksonville Zoo & Gardens

3
nights
Pensacola

Surrounded on three sides by water, Pensacola offers access to white-sand beaches and emerald-green ocean unspoiled by large resorts.
Kick off your visit on the 27th (Sat): explore the galleries of Pensacola Lighthouse and Museum, then look for gifts at Perdido Key Seafood, then get up close to creatures of the deep with a dolphin and whale watching tour, and finally see what you can catch with a fishing tour. Keep things going the next day: brush up on your military savvy at National Naval Aviation Museum, then learn about wildlife with up-close encounters at Alabama Gulf Coast Zoo, and then glide through the air with a parasailing or paragliding tour.

To see traveler tips, photos, reviews, and tourist information, refer to the Pensacola online trip itinerary maker .

Traveling by car from St. Augustine to Pensacola takes 7 hours. Alternatively, you can do a combination of bus and flight; or do a combination of bus, flight, and taxi. Traveling from St. Augustine to Pensacola, you'll gain 1 hour due to the time zone difference. In July, daily temperatures in Pensacola can reach 91°F, while at night they dip to 76°F. Wrap up your sightseeing by early afternoon on the 29th (Mon) to allow enough time to travel to Marco Island.

Things to do in Pensacola

Tours Outdoors Wildlife

Side Trips

Orange Beach, Alabama Gulf Coast Zoo, Perdido Key Seafood
Highlights from your plan
Dolphin & Whale Watching
Fishing Charters & Tours
Waterskiing & Jetskiing

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. Kick off your visit on the 30th (Tue): surround yourself with nature on a nature and wildlife tour, find your balance on the water with some of the best stand-up paddleboarding in the area, then get up close to creatures of the deep with a dolphin and whale watching tour, and finally look for gifts at Keep In Touch. Here are some ideas for day two: zoom along the surf with a waterskiing or jet-skiing adventure, then take a memorable tour with Tours, then kick back and relax at South Marco Beach, and finally tour the pleasant surroundings at Tigertail Beach.

For ratings, traveler tips, other places to visit, and other tourist information, go to the Marco Island visit planning site .

Traveling by combination of flight and bus from Pensacola to Marco Island takes 6 hours. Alternatively, you can do a combination of taxi, flight, and bus; or drive. The time zone difference moving from Central Standard Time to Eastern Standard Time is 1 hour. In July in Marco Island, expect temperatures between 91°F during the day and 75°F at night. Wrap up your sightseeing by early afternoon on the 1st (Thu) to allow time for the car ride to Sarasota.

Things to do in Marco Island

Outdoors Tours Wildlife

Side Trip

Speed Boats Tours
Highlights from your plan
Dolphin & Whale Watching
South Marco Beach ©
South Marco Beach
Tigertail Beach ©
Tigertail Beach

3
nights
Sarasota

Sarasota ©
Sarasota is a city in Sarasota County on the southwestern coast of the U.S. Bring the kids along to Mote Marine Laboratory and Aquarium and Sarasota Jungle Gardens. There's still lots to do: find your balance on the water with some of the best stand-up paddleboarding in the area, kick back and relax at South Lido Park, explore the different monuments and memorials at Sarasota National Cemetery, and appreciate the extensive heritage of Marie Selby Botanical Gardens.

For traveler tips, ratings, where to stay, and other tourist information, use the Sarasota trip planner.

You can drive from Marco Island to Sarasota in 2.5 hours. Alternatively, you can take a bus. In August, daily temperatures in Sarasota can reach 92°F, while at night they dip to 76°F. Finish your sightseeing early on the 4th (Sun) to allow enough time to travel to Fort Walton Beach.

Things to do in Sarasota

Parks Outdoors Zoos & Aquariums
Highlights from your plan
Mote Marine Laboratory and Aquarium ©
Sarasota Jungle Gardens ©
Sarasota Jungle Gardens

3
nights
Fort Walton Beach

Fort Walton Beach ©
Fort Walton Beach is a city in southern Okaloosa County, Florida, United States. Kick off your visit on the 5th (Mon): get a taste of the local shopping with The Boardwalk on Okaloosa Island, learn about all things military at Air Force Armament Museum, then step off the mainland to explore Okaloosa Island, then observe the fascinating underwater world at Gulfarium Marine Adventure Park, and finally take in the waterfront at Okaloosa Island Pier. Get ready for a full day of sightseeing on the 6th (Tue): kick back and relax at Navarre Beach, then get up close to creatures of the deep with a dolphin and whale watching tour, and then enjoy the sand and surf at Henderson Beach State Park.

For photos, where to stay, and more tourist information, refer to the Fort Walton Beach day trip app .

Traveling by flight from Sarasota to Fort Walton Beach takes 5.5 hours. Alternatively, you can do a combination of flight and taxi; or drive. Traveling from Sarasota to Fort Walton Beach, you'll gain 1 hour due to the time zone difference. In August, plan for daily highs up to 89°F, and evening lows to 74°F. Wrap up your sightseeing by early afternoon on the 7th (Wed) to allow enough time to drive back home.

Things to do in Fort Walton Beach

Outdoors Parks Beaches

Side Trips

Destin, Navarre Beach
Highlights from your plan
Okaloosa Island ©
Okaloosa Island
Navarre Beach ©
Navarre Beach
Henderson Beach State Park ©
Henderson Beach State Park

3
nights
Naples

Naples is a city in Collier County, Florida, United States. Kick off your visit on the 8th (Thu): see what you can catch with a fishing tour, learn about wildlife with up-close encounters at Naples Zoo at Caribbean Gardens, and then take in the waterfront at Naples Pier. Here are some ideas for day two: get up close to creatures of the deep with a dolphin and whale watching tour, explore the engaging exhibits at Golisano Children's Museum of Naples, then kick back and relax at Lowdermilk Beach, and finally wander the streets of Fifth Avenue South.

For other places to visit, ratings, maps, and more tourist information, read Naples road trip planner .

Traveling by combination of taxi, flight, and bus from Fort Walton Beach to Naples takes 6 hours. Alternatively, you can do a combination of flight and bus; or drive. The time zone difference moving from Central Standard Time to Eastern Standard Time is 1 hour. In August, plan for daily highs up to 91°F, and evening lows to 76°F. On the 10th (Sat), wrap the sightseeing up by early afternoon so you can drive to Sanibel Island.

Things to do in Naples

Wildlife Outdoors Tours
Highlights from your plan
Fishing Charters & Tours
Naples Zoo at Caribbean Gardens ©
Naples Zoo at Caribbean Gardens
Lowdermilk Beach ©
Lowdermilk Beach

3
nights
Sanibel Island

Sanibel Island ©
Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.
Kids will appreciate attractions like Fishing Charters & Tours and Cape Coral. You'll find plenty of places to visit near Sanibel Island: Fort Myers (Edison & Ford Winter Estates & Lakes Regional Park). There's still lots to do: look for all kinds of wild species at J.N. "Ding" Darling National Wildlife Refuge, enjoy the sand and surf at Blind Pass Beach Park, see the interesting displays at The Bailey-Matthews National Shell Museum, and hunt for treasures at Sanibel Island Farmer's Market.

To find more things to do, ratings, other places to visit, and other tourist information, refer to the Sanibel Island driving holiday site .

You can drive from Naples to Sanibel Island in 1.5 hours. Expect a daytime high around 92°F in August, and nighttime lows around 75°F. Cap off your sightseeing on the 13th (Tue) early enough to go by car to Ormond Beach.

Things to do in Sanibel Island

Parks Outdoors Beaches

Side Trips

Fort Myers, Cape Coral, Captiva Beach
Highlights from your plan
Bowman's Beach ©
Bowman's Beach
Fishing Charters & Tours
Captiva Beach ©
Captiva Beach

3
nights
Ormond Beach

Ormond Beach ©
Ormond Beach is a city in Volusia County, Florida, United States. On the 14th (Wed), enjoy the sand and surf at Ormond Beach, then stroll through Andy Romano Beachfront Park, then try for a hole-in-one at Pirate's Cove Adventure Golf, and finally admire the majestic nature at Tomoka State Park. On the 15th (Thu), you'll have a packed day of sightseeing: pause for some serene contemplation at St. Brendan Catholic Church, take a leisurely stroll along Flagler Beach Municipal Pier, then stroll around Waterfront Park, and finally immerse yourself in nature at De Leon Springs State Park.

For where to stay, more things to do, other places to visit, and more tourist information, read our Ormond Beach vacation builder app .

Traveling by car from Sanibel Island to Ormond Beach takes 5 hours. Alternatively, you can do a combination of bus, flight, and shuttle; or do a combination of bus and train. In August, daily temperatures in Ormond Beach can reach 88°F, while at night they dip to 74°F. On the 16th (Fri), wrap the sightseeing up by early afternoon so you can drive to Kissimmee.

Things to do in Ormond Beach

Parks Outdoors Nature

Side Trips

De Leon Springs State Park, Waterfront Park, Flagler Beach Municipal Pier
Highlights from your plan
Ormond Beach ©
Ormond Beach
St. Brendan Catholic Church ©
St. Brendan Catholic Church
Pirate's Cove Adventure Golf ©
Pirate's Cove Adventure Golf

3
nights
Kissimmee

Kissimmee ©
A popular vacation destination in the central part of Florida, Kissimmee's major claim to fame remains its sunny weather and proximity to a large Disney entertainment complex.
Kids will appreciate attractions like Old Town and Disney's Fantasia Gardens Miniature Golf Course. And it doesn't end there: find something for the whole family at Fun Spot America Kissimmee, enjoy some diversion at Congo River Golf, have some family-friendly fun at Kissimmee Go-Karts, and examine the collection at Museum of Military History.

For where to stay, traveler tips, and other tourist information, refer to the Kissimmee trip itinerary maker website .

You can drive from Ormond Beach to Kissimmee in 2 hours. Alternatively, you can do a combination of taxi and train; or take a bus. In August, daily temperatures in Kissimmee can reach 91°F, while at night they dip to 76°F. On the 19th (Mon), you'll have the morning to explore before heading back home.

Things to do in Kissimmee

Fun & Games Theme Parks Neighborhoods
Highlights from your plan
Congo River Golf ©
Congo River Golf
Fun Spot America Kissimmee ©
Fun Spot America Kissimmee
Old Town ©
Old Town

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