41 days in Florida Itinerary

41 days in Florida Itinerary

Created using Inspirock Florida trip itinerary planner

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Route & dates

41 days in Florida Itinerary

Start: Ocala
+2
bus + foot + Fly:  6​h 15​min
1
Key West
— 4 nights
bus:  45​min
2
Big Pine Key
— 1 night
Fly:  5​h 45​min
3
Panama City Beach
— 2 nights
Drive:  2​h 15​min
4
Pensacola Beach
— 2 nights
Drive:  6​h 45​min
5
St. Augustine
— 2 nights
Drive:  4​h 15​min
6
Siesta Key
— 3 nights
Drive:  2​h 30​min
7
Marco Island
— 3 nights
Drive:  5​h 15​min
8
Ormond Beach
— 3 nights
Fly + Drive:  5​h 30​min
9
Navarre
— 3 nights
Fly:  6​h
10
Sarasota
— 2 nights
Drive:  2​h
11
Naples
— 3 nights
+2
bus + Fly + taxi:  5​h 45​min
12
Fort Walton Beach
— 3 nights
Drive:  1​h
13
Pensacola
— 3 nights
Drive:  8​h 30​min
14
Jensen Beach
— 3 nights
Drive:  4​h 15​min
End: Ocala

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.
Attractions like Key West Butterfly & Nature Conservatory and Fort Zachary Taylor make great kid-friendly stops. There's lots more to do: see the interesting displays at The Ernest Hemingway Home and Museum, get interesting insight from Tours, steep yourself in history at Truman Little White House, and take a leisurely stroll along Mallory Square.

To see other places to visit, maps, more things to do, and other tourist information, read our Key West tour planning site .

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. Traveling from Ocala in July, Key West is a bit warmer at night with lows of 81°F. Finish your sightseeing early on the 22nd (Mon) to allow enough time to take a bus to Big Pine Key.

Things to do in Key West

Outdoors Parks Nature
Highlights from your plan
The Ernest Hemingway Home and Museum ©
Fort Zachary Taylor ©
Fort Zachary Taylor

1
night
Big Pine Key

Big Pine Key ©
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. On the 23rd (Tue), look for all kinds of wild species at National Key Deer Refuge, tour the pleasant surroundings at Bahia Honda State Park, and then enjoy the sand and surf at Calusa Beach.

For other places to visit, more things to do, reviews, and tourist information, refer to the Big Pine Key visit website .

Traveling by bus from Key West to Big Pine Key takes an hour. Alternatively, you can drive. In July, daytime highs in Big Pine Key are 92°F, while nighttime lows are 81°F. Cap off your sightseeing on the 23rd (Tue) early enough to travel to Panama City Beach.

Things to do in Big Pine Key

Parks Beaches Outdoors
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
National Key Deer Refuge ©
National Key Deer Refuge

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 24th (Wed), see majestic marine mammals with a dolphin and whale watching tour, then take a memorable tour with Tours, then observe the fascinating underwater world at Gulf World Marine Park, and finally take advantage of the amenities at Panama City Beach. On your second day here, enjoy the sand and surf at Santa Rosa Beach, immerse yourself in nature at St. Andrews State Park, and then step off the mainland to explore Shell Island.

For maps, other places to visit, photos, and tourist information, read Panama City Beach online tour itinerary planner .

Traveling by flight from Big Pine Key to Panama City Beach takes 6 hours. Alternatively, you can do a combination of flight and car; or drive. Traveling from Big Pine Key in July, you can expect nighttime temperatures to be little chillier in Panama City Beach, with lows of 74°F. Cap off your sightseeing on the 25th (Thu) early enough to go by car to Pensacola Beach.

Things to do in Panama City Beach

Outdoors Parks Beaches

Side Trip

Santa Rosa Beach
Highlights from your plan
Swim with Dolphins
Panama City Beach ©
Panama City Beach
St. Andrews State Park ©
St. Andrews State Park

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. Kick off your visit on the 26th (Fri): identify plant and animal life at Wildlife Areas, look for gifts at Innerlight Surf Shop, then enjoy the sand and surf at Gulf Islands National Seashore, and finally enjoy the sand and surf at Pensacola Beach. Get ready for a full day of sightseeing on the next day: stroll through Park West, steep yourself in history at Fort Pickens Area, then take a leisurely stroll along Pensacola Beach Gulf Pier, and finally get interesting insight from Tours.

To see reviews, photos, more things to do, and more tourist information, you can read our Pensacola Beach trip planner .

You can drive from Panama City Beach to Pensacola Beach in 2.5 hours. The time zone difference when traveling from Panama City Beach to Pensacola Beach is minus 1 hour. Expect a daytime high around 91°F in July, and nighttime lows around 76°F. Finish up your sightseeing early on the 27th (Sat) so you can go by car to St. Augustine.

Things to do in Pensacola Beach

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

2
nights
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. Attractions like St. Augustine Beach and Vilano Beach make great kid-friendly stops. There's much more to do: brush up on your knowledge of spirits at St. Augustine Distillery, do a tasting at San Sebastian Winery, see the interesting displays at St. Augustine Pirate & Treasure Museum, and enjoy the sand and surf at Frank Butler County Park West.

For photos, where to stay, other places to visit, and more tourist information, go to the St. Augustine tour itinerary planner.

Traveling by car from Pensacola Beach to St. Augustine takes 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 when traveling from Pensacola Beach to St. Augustine is 1 hour. In July, plan for daily highs up to 90°F, and evening lows to 75°F. Wrap up your sightseeing on the 30th (Tue) to allow time to drive to Siesta Key.

Things to do in St. Augustine

Parks Beaches Outdoors
Highlights from your plan
St. Augustine Beach ©
St. Augustine Beach
St. Augustine Distillery ©
St. Augustine Distillery
Vilano Beach ©
Vilano Beach

3
nights
Siesta Key

Siesta Key ©
Siesta Key draws most of its visitors with soft, white-quartz sand beaches and translucent ocean water.
On the 31st (Wed), enjoy the sand and surf at Turtle Beach, take in the dramatic natural features at Point of Rocks, then kick back and relax at Siesta Beach, and finally tour the pleasant surroundings at Siesta Key Beach. Keep things going the next day: indulge in some personalized pampering at some of the best spas, stroll through Crescent Beach, then enjoy the sand and surf at Nokomis Beach, and finally tour the pleasant surroundings at Caspersen Beach.

Make your Siesta Key itinerary with Inspirock to find out what to see and where to go.

Traveling by car from St. Augustine to Siesta Key takes 4.5 hours. Alternatively, you can take a bus; or do a combination of bus and flight. In July, daytime highs in Siesta Key are 91°F, while nighttime lows are 76°F. On the 2nd (Fri), wrap the sightseeing up by early afternoon so you can drive to Marco Island.

Things to do in Siesta Key

Beaches Outdoors Parks

Side Trips

Caspersen Beach, Nokomis Beach, Manasota Key Beach
Highlights from your plan
Turtle Beach ©
Turtle Beach
Siesta Beach ©
Siesta Beach
Crescent Beach ©
Crescent Beach

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. Kids will enjoy Dolphin & Whale Watching and Tigertail Beach. You'll enjoy a bit of beach vacationing at Keewaydin Island and Cape Romano. Change things up with a short trip to Speed Boats Tours in Everglades City (about 38 minutes away). There's still lots to do: get some thrills out on the water with a waterskiing or jet-skiing adventure, kick back and relax at South Marco Beach, relax and rejuvenate at some of the best spas, and get interesting insight from Tours.

To see where to stay, reviews, ratings, and tourist information, read Marco Island online route planner .

Traveling by car from Siesta Key to Marco Island takes 2.5 hours. Alternatively, you can take a bus. In August, daily temperatures in Marco Island can reach 92°F, while at night they dip to 76°F. Finish up your sightseeing early on the 5th (Mon) so you can go by car to Ormond Beach.

Things to do in Marco Island

Outdoors Tours Beaches

Side Trip

Speed Boats Tours
Highlights from your plan
Dolphin & Whale Watching
Keewaydin Island ©
Keewaydin Island
Tigertail Beach ©
Tigertail Beach

3
nights
Ormond Beach

Ormond Beach ©
Ormond Beach is a city in Volusia County, Florida, United States. On the 6th (Tue), kick back and relax at Andy Romano Beachfront Park, view the masterpieces at Ocean Art Gallery, try for a hole-in-one at Pirate's Cove Adventure Golf, then do a tasting at Flagler Beachfront Winery, and finally explore and take pictures at The Loop. Here are some ideas for day two: contemplate the long history of The Casements, take in the waterfront at Flagler Beach Municipal Pier, then take a stroll through European village, and finally immerse yourself in nature at De Leon Springs State Park.

To see photos, maps, where to stay, and tourist information, read our Ormond Beach trip planner.

You can drive from Marco Island to Ormond Beach in 5.5 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. Wrap up your sightseeing by early afternoon on the 8th (Thu) to allow time for travel to Navarre.

Things to do in Ormond Beach

Parks Outdoors Beaches

Side Trips

Flagler Beach, De Leon Springs State Park, European village
Highlights from your plan
Ormond Beach ©
Ormond Beach
Flagler Beachfront Winery ©
Flagler Beachfront Winery
Ormond Scenic Loop & Trail ©
Ormond Scenic Loop & Trail

3
nights
Navarre

Navarre ©
Navarre is an unincorporated community in Santa Rosa County in the northwest Florida Panhandle. Bring the kids along to Navarre Beach and Navarre Beach Sea Turtle Conservation Center. Get out of town with these interesting Navarre side-trips: Blackwater River State Park (in Holt) and Blackwater Heritage State Trail (in Milton). The adventure continues: see what you can catch with a fishing tour, see the vivid underwater world at Navarre Beach Marine Sanctuary, tee off at Hidden Creek Golf Club, and get to know the resident critters at The Gulf Breeze ZOO.

To find maps, where to stay, ratings, and more tourist information, refer to the Navarre route planner .

Do a combination of flight and car from Ormond Beach to Navarre in 5.5 hours. Alternatively, you can do a combination of shuttle and flight; or drive. The time zone changes from Eastern Standard Time (EST) to Central Standard Time (CST), which is usually a -1 hour difference. In August, plan for daily highs up to 89°F, and evening lows to 74°F. Cap off your sightseeing on the 11th (Sun) early enough to travel to Sarasota.

Things to do in Navarre

Parks Outdoors Wildlife

Side Trips

Blackwater Heritage State Trail, The Gulf Breeze ZOO, Blackwater River State Park
Highlights from your plan
Navarre Beach ©
Navarre Beach
Fishing Charters & Tours
The Gulf Breeze ZOO ©
The Gulf Breeze ZOO

2
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 South Lido Park. There's much more to do: find your balance on the water with some of the best stand-up paddleboarding in the area, relax and rejuvenate at some of the best spas, explore the different monuments and memorials at Sarasota National Cemetery, and brush up on your knowledge of spirits at As Good As It Gets.

To see ratings, reviews, and tourist information, refer to the Sarasota itinerary planning site .

Getting from Navarre to Sarasota by flight takes about 6 hours. Other options: do a combination of car and flight; or drive. Due to the time zone difference, you'll lose 1 hour traveling from Navarre to Sarasota. August in Sarasota sees daily highs of 92°F and lows of 76°F at night. Wrap up your sightseeing on the 14th (Wed) early enough to drive to Naples.

Things to do in Sarasota

Parks Outdoors Wildlife
Highlights from your plan
Siesta Key Rum ©
Siesta Key Rum
Mote Marine Laboratory and Aquarium ©
Spas

3
nights
Naples

Naples ©
Naples is a city in Collier County, Florida, United States. Start off your visit on the 15th (Thu): relax and rejuvenate at some of the best spas, learn about wildlife with up-close encounters at Naples Zoo at Caribbean Gardens, enjoy the sand and surf at Lowdermilk Beach, then take a leisurely stroll along Naples Pier, and finally take a stroll through Fifth Avenue South. On the 16th (Fri), you'll have a packed day of sightseeing: see majestic marine mammals with a dolphin and whale watching tour and then cast your line with a fishing tour.

Plan my trip to Naples with suggested itineraries provided by Inspirock.

Getting from Sarasota to Naples by car takes about 2 hours. Other options: take a bus. In August, plan for daily highs up to 91°F, and evening lows to 76°F. Wrap up your sightseeing by early afternoon on the 17th (Sat) to allow time for travel to Fort Walton Beach.

Things to do in Naples

Outdoors Wildlife Tours
Highlights from your plan
Lowdermilk Beach ©
Lowdermilk Beach
Naples Zoo at Caribbean Gardens ©
Naples Zoo at Caribbean Gardens
Spas

3
nights
Fort Walton Beach

Fort Walton Beach ©
Fort Walton Beach is a city in southern Okaloosa County, Florida, United States. Relax by the water at Henderson Beach State Park and Okaloosa Island. Attractions like Crystal Sands Beach and Village of Baytowne Wharf make great kid-friendly stops. There's still lots to do: get up close to creatures of the deep with a dolphin and whale watching tour, get in on the family fun at Wild Willy's Adventure Zone, walk around John C Beasley Park, and don't miss a visit to Destin Harbor Boardwalk.

To see photos, more things to do, maps, and more tourist information, read our Fort Walton Beach trip itinerary builder site .

Traveling by combination of bus, flight, and taxi from Naples to Fort Walton Beach takes 6 hours. Alternatively, you can do a combination of bus and flight; or drive. You'll gain 1 hour traveling from Naples to Fort Walton Beach due to the time zone difference. Expect a daytime high around 89°F in August, and nighttime lows around 74°F. Finish your sightseeing early on the 20th (Tue) to allow enough time to drive to Pensacola.

Things to do in Fort Walton Beach

Outdoors Parks Beaches

Side Trip

Destin
Highlights from your plan
Henderson Beach State Park ©
Henderson Beach State Park
Air Force Armament Museum ©
Air Force Armament Museum
The Village of Baytowne Wharf ©
The Village of Baytowne Wharf

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 21st (Wed): look for all kinds of wild species at Wildlife Areas, look for gifts at Perdido Key Seafood, then brush up on your military savvy at National Naval Aviation Museum, and finally deepen your knowledge of military history at Pensacola Naval Air Station. Here are some ideas for day two: enjoy the sea views from Pensacola Lighthouse and Museum, stroll through Gulf State Park, and then take a leisurely stroll along Gulf State Park Fishing Pier.

To find reviews, traveler tips, photos, and more tourist information, go to the Pensacola trip planner .

Traveling by car from Fort Walton Beach to Pensacola takes an hour. Alternatively, you can take a bus; or take a bus. August in Pensacola sees daily highs of 90°F and lows of 75°F at night. On the 23rd (Fri), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Pensacola

Outdoors Beaches Nature

Side Trips

Orange Beach, Gulf Shores, Perdido Key Seafood
Highlights from your plan
Dolphin & Whale Watching
Gulf State Park ©
Gulf State Park
Parasailing & Paragliding

3
nights
Jensen Beach

Jensen Beach ©
Jensen Beach is a census-designated place (CDP) in Martin County, Florida, United States. Start off your visit on the 24th (Sat): kick back and relax at Herman’s Bay Beach, kick back and relax at Walton Rocks Beach, tour the pleasant surroundings at Walton Rocks Beach/ Dog Park, browse for treasures at Then & Now Gallery, then explore the engaging exhibits at The Children's Museum of the Treasure Coast, and finally walk around Indian Riverside Park. On the 25th (Sun), you'll have a packed day of sightseeing: tour the pleasant surroundings at Normandy Beach, then kick back and relax at Waveland Beach, then stroll through Jensen Beach Park, and finally kick back and relax at Jensen Beach Causeway Park.

To find traveler tips, photos, and other tourist information, read Jensen Beach route app .

You can drive from Pensacola to Jensen Beach in 8.5 hours. Alternatively, you can do a combination of car and flight. Traveling from Pensacola to Jensen Beach, you'll lose 1 hour due to the time zone difference. Expect a daytime high around 89°F in August, and nighttime lows around 76°F. On the 26th (Mon), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Jensen Beach

Parks Beaches Outdoors
Highlights from your plan
Indian Riverside Park ©
Indian Riverside Park
Then & Now Gallery ©
Then & Now Gallery

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