29 days in Florida Itinerary

29 days in Florida Itinerary

Created using Inspirock Florida journey planner

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

S M T W T F S
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16

Pensacola

— 3 nights

Western Gate to the Sunshine State

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

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

Chicago to Pensacola is an approximately 4-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 82°F and 63°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 · Museums

Side Trips

Panama City Beach

— 3 nights

World's Most Beautiful Beaches

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: learn about winemaking at Panama City Beach Winery, kick back and relax at Panama City Beach, see majestic marine mammals with a dolphin and whale watching tour, and browse the different shops at Pier Park.

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 83°F, while at night they dip to 59°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 · Tours

Side Trips

Crystal River

— 2 nights

The Gem of the Nature Coast

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): get a new perspective on things with Boat Tours & Water Sports and then get outside with Outdoor Activities. 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 do a combination of car and flight. In October in Crystal River, expect temperatures between 83°F during the day and 62°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 · Adventure

Side Trip

St. Augustine

— 4 nights
St. Do some cultural sightseeing at Ponce de Leon Inlet Lighthouse & Museum and St. Augustine Lighthouse & Maritime Museum, Inc.. Relax by the water at Ormond Beach and Beach at Daytona Beach. Go for a jaunt from St. Augustine to DeLand to see Stetson Mansion about 1h 25 min away. Spend the 26th (Sat) exploring nature at Fort Matanzas National Monument. There's lots more to do: pause for some serene contemplation at Cathedral Basilica of St. Augustine, enjoy the sand and surf at St. Augustine Beach, and brush up on your knowledge of spirits at St. Augustine Distillery.

To see other places to visit, photos, ratings, and other tourist information, go to the St. Augustine vacation site.

Drive from Crystal River to St. Augustine in 3 hours. Alternatively, you can take a bus. October in St. Augustine sees daily highs of 80°F and lows of 67°F at night. Finish up your sightseeing early on the 26th (Sat) so you can catch the flight to Key Largo.

Things to do in St. Augustine

Parks · Historic Sites · Nature · Beaches

Side Trips

Key Largo

— 2 nights

Diving Capital of the World

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): admire all the interesting features of 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): head outdoors with Outdoor Activities, stroll through 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.

Fly from St. Augustine to Key Largo in 3 hours. Alternatively, you can drive; or take a bus. Traveling from St. Augustine in October, expect somewhat warmer with lows of 73°F in Key Largo. Finish your sightseeing early on the 28th (Mon) so you can drive to Marathon.

Things to do in Key Largo

Parks · Wildlife · Tours · Outdoors

Side Trip

Marathon

— 2 nights

Heart of the Florida Keys

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, tour the pleasant surroundings 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): head outdoors with Outdoor Activities, then stroll through 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 87°F, and evening lows to 77°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 · Beaches

Side Trip

Key West

— 5 nights

Conch Republic

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 much more to do: identify plant and animal life at Wildlife Areas, take in the pleasant sights at Key West Garden Club, see what you can catch with a fishing tour, and tour the pleasant surroundings at Key West Butterfly & Nature Conservatory.

To find traveler tips, where to stay, other places to visit, and tourist information, refer to the Key West trip planner.

Traveling by car from Marathon to Key West takes 1.5 hours. Alternatively, you can take a bus. In October in Key West, expect temperatures between 86°F during the day and 77°F at night. Wrap up your sightseeing on the 4th (Mon) to allow time to ride a ferry to Marco Island.

Things to do in Key West

Outdoors · Tours · Wildlife · Parks

Marco Island

— 2 nights
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 4 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 64°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 · Adventure

Side Trip

Naples

— 3 nights
Get in touch with nature at Dolphin & Whale Watching and Lovers Key State Park. Your cultural itinerary includes sights like The Bailey-Matthews National Shell Museum and Edison and Ford Winter Estates. Change things up with a short trip to J.N. "Ding" Darling National Wildlife Refuge in Sanibel Island (about 1h 20 min away).

For traveler tips, reviews, and other tourist information, you can read our Naples visit site.

Naples is just a short distance from Marco Island. Expect a daytime high around 82°F in November, and nighttime lows around 65°F. Finish your sightseeing early on the 9th (Sat) so you can drive to Sarasota.

Things to do in Naples

Parks · Wildlife · Outdoors · Museums

Side Trips

Sarasota

— 2 nights
Sarasota is a city in Sarasota County on the southwestern coast of the U.S. state of Florida. Start off your visit on the 10th (Sun): see the interesting displays at The Dali Museum, then sample 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 Beach, Florida, then stroll through St. 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. Other options are to take a bus; or do a combination of bus and taxi. November in Sarasota sees daily highs of 80°F and lows of 62°F at night. Wrap up your sightseeing on the 11th (Mon) to allow time to fly back home.

Things to do in Sarasota

Parks · Beaches · Outdoors · Museums

Side Trips

Florida travel guide

4.4
Disney Parks & Activities · Beaches · Theme Parks
The Sunshine State
The “Sunshine State,” Florida became a favorite winter destination for the affluent crowd over a century ago. Today, the state attracts visitors from around the world with its golden beaches and modern theme parks. You can spend your entire vacation enjoying the state's highly developed seaside areas, but remember that some of Florida's best-kept secrets are in secluded locations. Visit the big cities and their comfortable resorts offering top-notch dining and nightlife, but leave some time to see the peninsula's swampy landscape, filled with wild creatures and native plants. Farther away from the tourist-packed urban areas, the untamed wetlands of Florida offer a selection of things to do, such as kayaking, boat rides, and numerous other outdoor activities.