29 days in Florida Itinerary

29 days in Florida Itinerary

Created using Inspirock Florida journey planner

Plan created by another user. Make it yours

Route & dates

1
Pensacola
— 3 nights
2
Panama City Beach
— 3 nights
3
Crystal River
— 2 nights
4
St. Augustine
— 4 nights
5
Key Largo
— 2 nights
6
Marathon
— 2 nights
7
Key West
— 5 nights
8
Marco Island
— 2 nights
9
Naples
— 3 nights
10
Sarasota
— 2 nights

3
nights
Pensacola

Pensacola ©
Surrounded on three sides by water, Pensacola offers access to white-sand beaches and emerald-green ocean unspoiled by large resorts.
Fort Morgan State Historic Site and Pensacola Lighthouse and Museum will appeal to history buffs. Discover out-of-the-way places like Gulf State Park and Gulf Islands National Seashore. Go for a jaunt from Pensacola to Orange Beach to see Dolphin & Whale Watching about 50 minutes away. Next up on the itinerary: learn about all things military at National Naval Aviation Museum and kick back and relax at Pensacola Beach.

For reviews, maps, more things to do, and more tourist information, use the Pensacola trip maker website.

Chicago to Pensacola is an approximately 5-hour flight. You can also drive; or do a combination of train and bus. Traveling from Chicago in October, expect Pensacola to be somewhat warmer, temps between °F and °F. Finish your sightseeing early on the 17th (Thu) so you can drive to Panama City Beach.

Things to do in Pensacola

Outdoors Parks Beaches

Side Trips

Pensacola Beach, Dolphin & Whale Watching, Fort Morgan State Historic Site, Gulf State Park
Highlights from your plan
Gulf Islands National Seashore ©
Gulf Islands National Seashore
Gulf State Park ©
Gulf State Park
Fort Morgan State Historic Site ©
Fort Morgan State Historic Site

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 St. Andrews State Park and Henderson Beach State Park. Step out of the city life by going to Santa Rosa Beach and Swim with Dolphins. There's lots more to do: browse the different shops at Pier Park, kick back and relax at Panama City Beach, see majestic marine mammals with a dolphin and whale watching tour, and learn about winemaking at Panama City Beach Winery.

To find more things to do, reviews, maps, and tourist information, read our Panama City Beach tour planning app.

Getting from Pensacola to Panama City Beach by car takes about 2.5 hours. Due to the time zone difference, you'll lose 1 hour traveling from Pensacola to Panama City Beach. In October, daily temperatures in Panama City Beach can reach °F, while at night they dip to °F. Finish your sightseeing early on the 20th (Sun) to allow enough time to drive to Crystal River.

Things to do in Panama City Beach

Outdoors Parks Beaches

Side Trips

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

2
nights
Crystal River

The jewel of Florida's Nature Coast, Crystal River spreads around spring-fed Kings Bay, known for maintaining a constant 22 C (72 F) temperature all year long.
Kick off your visit on the 21st (Mon): add some adventure to your tour with a kayaking and canoeing tour and then take a memorable tour with Tours. On the 22nd (Tue), you'll have a packed day of sightseeing: immerse yourself in nature at Ellie Schiller Homosassa Springs Wildlife State Park.

To see photos, maps, and tourist information, read our Crystal River trip planner.

Drive from Panama City Beach to Crystal River in 5.5 hours. Alternatively, you can fly. In October in Crystal River, expect temperatures between °F during the day and °F at night. Finish up your sightseeing early on the 22nd (Tue) so you can go by car to St. Augustine.

Things to do in Crystal River

Tours Outdoors Wildlife

Side Trip

Ellie Schiller Homosassa Springs Wildlife State Park
Highlights from your plan
Stand-Up Paddleboarding
Scuba & Snorkeling

4
nights
St. Augustine

St. Augustine ©
St. Do some cultural sightseeing at Fort Matanzas National Monument and St. Augustine Lighthouse & Maritime Museum, Inc.. Relax by the water at Ormond Beach and Beach at Daytona Beach. Change things up with these side-trips from St. Augustine: Stetson Mansion (in DeLand) and Ponce de Leon Inlet Lighthouse & Museum (in Ponce Inlet). Next up on the itinerary: take in the spiritual surroundings of Cathedral Basilica of St. Augustine, kick back and relax at St. Augustine Beach, and brush up on your knowledge of spirits at St. Augustine Distillery.

To see ratings, other places to visit, and tourist information, read St. Augustine trip maker.

Getting from Crystal River to St. Augustine by car takes about 3 hours. Other options: take a bus. October in St. Augustine sees daily highs of °F and lows of °F at night. Cap off your sightseeing on the 26th (Sat) early enough to go by car to Key Largo.

Things to do in St. Augustine

Parks Historic Sites Outdoors

Side Trips

Beach at Daytona Beach, Stetson Mansion, Ponce de Leon Inlet Lighthouse & Museum, Ormond Beach
Highlights from your plan
Cathedral Basilica of St. Augustine ©
Cathedral Basilica of St. Augustine
Ormond Beach ©
Ormond Beach
Fort Matanzas National Monument ©
Fort Matanzas National Monument

2
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.
Start off your visit on the 27th (Sun): stroll through Spiegel Grove and then admire the majestic nature at John Pennekamp Coral Reef State Park. Get ready for a full day of sightseeing on the 28th (Mon): get interesting insight from Tours, look for all kinds of wild species at Florida Keys Wild Bird Rehabilitation Center, and then get a new perspective on things with Boat Tours & Water Sports.

For where to stay, photos, reviews, and more tourist information, go to the Key Largo trip builder tool.

Drive from St. Augustine to Key Largo in 6.5 hours. Alternatively, you can fly; or take a bus. Traveling from St. Augustine in October, expect somewhat warmer with lows of °F in Key Largo. Finish your sightseeing early on the 28th (Mon) so you can drive to Marathon.

Things to do in Key Largo

Wildlife Parks Tours

Side Trip

Fishing Charters & Tours
Highlights from your plan
Spiegel Grove ©
Spiegel Grove
Florida Keys Wild Bird Rehabilitation Center ©
Parasailing & Paragliding

2
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.
Kick off your visit on the 29th (Tue): tour the pleasant surroundings at Sombrero Beach, identify plant and animal life at The Turtle Hospital, and then enjoy the sand and surf at Bahia Honda State Park. Get ready for a full day of sightseeing on the 30th (Wed): get interesting insight from Tours, thenlook for all kinds of wild species at Dolphin Research Center, and then snap pictures at Seven Mile Bridge.

To see maps, reviews, ratings, and tourist information, you can read our Marathon trip itinerary maker tool.

Traveling by car from Key Largo to Marathon takes 1.5 hours. Alternatively, you can take a bus. In October, plan for daily highs up to °F, and evening lows to °F. Wrap up your sightseeing on the 30th (Wed) to allow time to drive to Key West.

Things to do in Marathon

Parks Outdoors Wildlife

Side Trip

Bahia Honda State Park
Highlights from your plan
Dolphin Research Center ©
Dolphin Research Center
Bahia Honda State Park ©
Bahia Honda State Park
The Turtle Hospital ©
The Turtle Hospital

5
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.
Get a sense of the local culture at U.S. Coast Guard Cutter Ingham Maritime Museum and The Ernest Hemingway Home and Museum. You'll explore and learn at Key West Lighthouse and Keeper's Quarters Museum and Mel Fisher Maritime Heritage Museum. Spend the 1st (Fri) exploring nature at Dry Tortugas National Park. There's still lots to do: identify plant and animal life at Wildlife Areas, admire the majestic nature at Fort Zachary Taylor, get a new perspective on things with Boat Tours & Water Sports, and steep yourself in history at Truman Little White House.

To find ratings, photos, other places to visit, and tourist information, read Key West driving holiday planner.

You can drive from Marathon to Key West in 1.5 hours. Alternatively, you can take a bus. Expect a daytime high around °F in October, and nighttime lows around °F. Finish up your sightseeing early on the 4th (Mon) so you can catch the ferry to Marco Island.

Things to do in Key West

Outdoors Tours Wildlife
Highlights from your plan
The Ernest Hemingway Home and Museum ©
The Ernest Hemingway Home and Museum
Dolphin & Whale Watching

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. On the 5th (Tue), surround yourself with nature on a nature and wildlife tour and then cast your line with a fishing tour. Here are some ideas for day two: see majestic marine mammals with a dolphin and whale watching tour and then get some thrills out on the water with a waterskiing or jet-skiing adventure.

Plan a trip to Marco Island easily and quickly by telling Inspirock to suggest an itinerary.

You can ride a ferry from Key West to Marco Island in 3.5 hours. Another option is to drive. Plan for slightly colder nights when traveling from Key West in November since evenings lows in Marco Island dip to °F. Finish up your sightseeing early on the 6th (Wed) so you can go by car to Naples.

Things to do in Marco Island

Tours Outdoors Wildlife

Side Trip

Nature & Wildlife Tours
Highlights from your plan
Fishing Charters & Tours
Dolphin & Whale Watching
Waterskiing & Jetskiing

3
nights
Naples

Naples ©
Get in touch with nature at Lowdermilk Beach and Dolphin & Whale Watching. Your cultural itinerary includes sights like The Bailey-Matthews National Shell Museum and Edison and Ford Winter Estates. Venture out of the city with trips to J.N. "Ding" Darling National Wildlife Refuge (in Sanibel Island) and Lovers Key State Park (in Fort Myers Beach).

To find where to stay, ratings, reviews, and other tourist information, read Naples trip planner.

Drive from Marco Island to Naples in an hour. Expect a daytime high around °F in November, and nighttime lows around °F. Finish your sightseeing early on the 9th (Sat) so you can drive to Sarasota.

Things to do in Naples

Parks Wildlife Outdoors

Side Trips

Sanibel Island, Fort Myers Beach, Edison and Ford Winter Estates
Highlights from your plan
Lowdermilk Beach ©
Lowdermilk Beach
The Bailey-Matthews National Shell Museum ©
J.N. ©

2
nights
Sarasota

Sarasota ©
Sarasota is a city in Sarasota County on the southwestern coast of the U.S. Start off your visit on the 10th (Sun): see the interesting displays at The Dali Museum, thensample the fine beverages at Siesta Key Rum, and then walk around Siesta Beach. Get ready for a full day of sightseeing on the 11th (Mon): take a stroll through Pass-a-Grille, thenstroll through Saint Pete Beach, and then explore the world behind art at The Ringling.

To find where to stay, more things to do, reviews, and other tourist information, read Sarasota itinerary site.

You can drive from Naples to Sarasota in 2 hours. Another option is to take a bus. November in Sarasota sees daily highs of °F and lows of °F at night. Wrap up your sightseeing on the 11th (Mon) to allow time to travel back home.

Things to do in Sarasota

Outdoors Parks Beaches

Side Trips

St. Pete Beach, Siesta Beach, The Dali Museum
Highlights from your plan
Siesta Key Rum ©
Siesta Key Rum
Pass-a-Grille ©
Pass-a-Grille
Siesta Beach ©
Siesta Beach

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