29 days in Florida Itinerary

29 days in Florida Itinerary

Created using Inspirock Florida journey planner

This plan was created by another user.  Make it your plan

Route & dates

29 days in Florida Itinerary

Start: Chicago
Fly:  4​h 30​min
1
Pensacola
— 3 nights
Drive:  2​h 15​min
2
Panama City Beach
— 3 nights
Drive:  5​h 15​min
3
Crystal River
— 2 nights
Drive:  2​h 45​min
4
St. Augustine
— 4 nights
+2
Drive + Fly + shuttle:  5​h 15​min
5
Key Largo
— 2 nights
Drive:  1​h 15​min
6
Marathon
— 2 nights
bus:  1​h 15​min
7
Key West
— 5 nights
ferry:  2​h 30​min
8
Marco Island
— 2 nights
Drive:  45​min
9
Naples
— 3 nights
Drive:  2​h
10
Sarasota
— 2 nights
Fly:  5​h
End: Chicago

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.
Your inner history buff will appreciate Pensacola Lighthouse and Museum and Fort Morgan State Historic Site. Get in touch with nature at Gulf Islands National Seashore and Dolphin & Whale Watching. When in Pensacola, make a side trip to see Gulf State Park in Gulf Shores, approximately 56 minutes away. There's still lots to do: brush up on your military savvy at National Naval Aviation Museum and enjoy the sand and surf at Pensacola Beach.

To find maps, more things to do, traveler tips, and more tourist information, go to the Pensacola trip planning tool .

Chicago to Pensacola is an approximately 4.5-hour flight. You can also do a combination of flight and taxi; or drive. Traveling from Chicago in October, things will get a bit warmer in Pensacola: highs are around 82°F and lows about 63°F. Cap off your sightseeing on the 17th (Thu) early enough to go by car to Panama City Beach.

Things to do in Pensacola

Outdoors Parks Beaches

Side Trips

Pensacola Beach, Fort Morgan State Historic Site, Dolphin & Whale Watching, Gulf State Park
Highlights from your plan
Pensacola Lighthouse and Museum ©
Pensacola Lighthouse and Museum
Gulf Islands National Seashore ©
Gulf Islands National Seashore
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.
Explore hidden gems such as Santa Rosa Beach and Swim with Dolphins. Visit Henderson Beach State Park and Panama City Beach for some beach relaxation. There's still lots to do: kick back and relax at St. Andrews State Park, see majestic marine mammals with a dolphin and whale watching tour, buy something for everyone on your list at Pier Park, and do a tasting at Panama City Beach Winery.

To plan Panama City Beach vacation without wasting time, ask Inspirock to design an itinerary.

Traveling by car from Pensacola to Panama City Beach takes 2.5 hours. You'll lose 1 hour traveling from Pensacola to Panama City Beach due to the time zone difference. In October, plan for daily highs up to 83°F, and evening lows to 59°F. Wrap up your sightseeing on the 20th (Sun) early enough 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
Henderson Beach State Park ©
Henderson Beach State Park
Swim with Dolphins
Panama City Beach Winery ©
Panama City Beach Winery

2
nights
Crystal River

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.
On the 21st (Mon), add some adventure to your tour with a kayaking and canoeing tour and then look for all kinds of wild species at Wildlife Areas. Get ready for a full day of sightseeing on the next day: see majestic marine mammals with a dolphin and whale watching tour and then immerse yourself in nature at Ellie Schiller Homosassa Springs Wildlife State Park.

For traveler tips, where to stay, and other tourist information, go to the Crystal River holiday planner .

You can drive from Panama City Beach to Crystal River in 5.5 hours. Alternatively, you can do a combination of car, flight, and bus; or do a combination of flight, bus, and taxi. Expect a daytime high around 83°F in October, and nighttime lows around 62°F. Wrap up your sightseeing on the 22nd (Tue) to allow time to drive to St. Augustine.

Things to do in Crystal River

Tours Outdoors Wildlife

Side Trips

Ellie Schiller Homosassa Springs Wildlife State Park, Dolphin & Whale Watching
Highlights from your plan
Dolphin & Whale Watching
Scuba & Snorkeling

4
nights
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. Relax by the water at Ormond Beach and Beach at Daytona Beach. Fort Matanzas National Monument and Ponce de Leon Inlet Lighthouse & Museum will appeal to history buffs. When in St. Augustine, make a side trip to see Stetson Mansion in DeLand, approximately 1h 35 min away. And it doesn't end there: take in the spiritual surroundings of Cathedral Basilica of St. Augustine, brush up on your knowledge of spirits at St. Augustine Distillery, kick back and relax at St. Augustine Beach, and enjoy the sea views from St. Augustine Lighthouse & Maritime Museum, Inc..

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

Traveling by car from Crystal River to St. Augustine takes 3 hours. Alternatively, you can take a bus. In October, plan for daily highs up to 80°F, and evening lows to 67°F. Finish your sightseeing early on the 26th (Sat) to allow enough time to travel to Key Largo.

Things to do in St. Augustine

Parks Historic Sites Outdoors

Side Trips

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

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.
On the 27th (Sun), see the vivid underwater world at Spiegel Grove and then immerse yourself in nature at John Pennekamp Coral Reef State Park. Keep things going the next day: fly like a bird with a parasailing or paragliding tour, then look for all kinds of wild species at Florida Keys Wild Bird Rehabilitation Center, and then get interesting insight from Tours.

For where to stay, more things to do, ratings, and more tourist information, go to the Key Largo online trip itinerary planner .

You can do a combination of car, flight, and shuttle from St. Augustine to Key Largo in 5.5 hours. Alternatively, you can drive; or do a combination of bus, flight, and shuttle. Traveling from St. Augustine in October, Key Largo is a bit warmer at night with lows of 73°F. Finish your sightseeing early on the 28th (Mon) to allow enough time to 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
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.
Start off your visit on the 29th (Tue): enjoy the sand and surf at Sombrero Beach, then look for all kinds of wild species at The Turtle Hospital, and then immerse yourself in nature at Bahia Honda State Park. On the next day, see what you can catch with a fishing tour, identify plant and animal life at Dolphin Research Center, and then snap pictures at Seven Mile Bridge.

To see ratings, reviews, more things to do, and more tourist information, refer to the Marathon tour itinerary planner .

You can drive from Key Largo to Marathon in 1.5 hours. Another option is to take a bus. In October in Marathon, expect temperatures between 87°F during the day and 77°F at night. Finish your sightseeing early on the 30th (Wed) so you can take a bus 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.
You'll explore and learn at The Ernest Hemingway Home and Museum and Key West Lighthouse and Keeper's Quarters Museum. Discover out-of-the-way places like U.S. Coast Guard Cutter Ingham Maritime Museum and Key West Garden Club. Spend the 1st (Fri) exploring nature at Dry Tortugas National Park. The adventure continues: identify plant and animal life at Key West Butterfly & Nature Conservatory, stroll through Fort Zachary Taylor, cast your line with a fishing tour, and take a memorable drive along The Overseas Highway.

For reviews, where to stay, maps, and other tourist information, use the Key West journey website .

You can take a bus from Marathon to Key West in 1.5 hours. Alternatively, you can drive. In October, daytime highs in Key West are 86°F, while nighttime lows are 77°F. Wrap up your sightseeing on the 4th (Mon) early enough to ride a ferry to Marco Island.

Things to do in Key West

Outdoors Tours Wildlife
Highlights from your plan

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. Kick off your visit on the 5th (Tue): surround yourself with nature on a nature and wildlife tour and then cast your line with a fishing tour. On your second day here, look for all kinds of wild species at Wildlife Areas and then zoom along the surf with a waterskiing or jet-skiing adventure.

To find ratings, reviews, where to stay, and tourist information, use the Marco Island online trip maker .

You can ride a ferry from Key West to Marco Island in 2.5 hours. Alternatively, you can drive. Plan for a bit cooler 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

Side Trip

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

3
nights
Naples

Naples ©
Naples is a city in Collier County, Florida, United States. Let the collections at The Bailey-Matthews National Shell Museum and Edison & Ford Winter Estates capture your imagination. Discover out-of-the-way places like Lowdermilk Beach and Lovers Key State Park. You'll find plenty of places to visit near Naples: J.N. "Ding" Darling National Wildlife Refuge (in Sanibel Island) and Dolphin & Whale Watching (in Fort Myers Beach).

To see reviews, maps, and more tourist information, read Naples trip itinerary maker tool .

Drive from Marco Island to Naples in an hour. November in Naples sees daily highs of 82°F and lows of 65°F at night. Finish up your sightseeing early on the 9th (Sat) so you can go by car to Sarasota.

Things to do in Naples

Parks Wildlife Outdoors

Side Trips

Fort Myers Beach, Sanibel Island, Edison and Ford Winter Estates
Highlights from your plan
Lowdermilk Beach ©
Lowdermilk Beach
Dolphin & Whale Watching

2
nights
Sarasota

Sarasota ©
Sarasota is a city in Sarasota County on the southwestern coast of the U.S. On the 10th (Sun), examine the collection at The Dali Museum, sample the fine beverages at Siesta Key Rum, and then walk around Siesta Beach. On the 11th (Mon), you'll have a packed day of sightseeing: take a stroll through Pass-a-Grille, kick back and relax at Saint Pete Beach, and then get engrossed in the history at The Ringling.

For maps, photos, and tourist information, read Sarasota road trip planner.

Traveling by car from Naples to Sarasota takes 2 hours. Alternatively, you can take a bus. Expect a daytime high around 80°F in November, and nighttime lows around 62°F. Finish up your sightseeing early on the 11th (Mon) so you can travel back home.

Things to do in Sarasota

Outdoors Parks Beaches

Side Trips

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

Similar Plans

31 days in Florida BY A USER FROM UNITED KINGDOM July, popular sights PREFERENCES: July ATTRACTION STYLE: Popular sights PACE: Medium 30 days in Florida & Philadelphia BY A USER FROM UNITED STATES July, fast-paced, popular sights PREFERENCES: July ATTRACTION STYLE: Popular sights PACE: Fast-paced 31 days in United States BY A USER FROM AUSTRALIA May, popular sights PREFERENCES: May ATTRACTION STYLE: Popular sights PACE: Medium 30 days in Florida BY A USER FROM UNITED STATES September, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: September, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 31 days in United States BY A USER FROM AUSTRALIA May, culture, beaches, shopping, wildlife, popular & hidden gems PREFERENCES: May, culture, beaches, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 10 days in Florida BY A USER FROM UNITED STATES July, teens, kids, popular sights PREFERENCES: July, teens, kids ATTRACTION STYLE: Popular sights PACE: Medium 3 days in Florida BY A USER FROM UNITED STATES July, teens, kids, popular sights PREFERENCES: July, teens, kids ATTRACTION STYLE: Popular sights PACE: Medium 5 days in Florida BY A USER FROM UNITED STATES July, teens, kids, popular sights PREFERENCES: July, teens, kids ATTRACTION STYLE: Popular sights PACE: Medium 6 days in Florida BY A USER FROM UNITED STATES January, teens, kids, popular sights PREFERENCES: January, teens, kids ATTRACTION STYLE: Popular sights PACE: Medium 17 days in Florida BY A USER FROM UNITED KINGDOM April, teens, kids, popular sights PREFERENCES: April, teens, kids ATTRACTION STYLE: Popular sights PACE: Medium 2 days in Florida BY A USER FROM UNITED STATES July, teens, kids, popular sights PREFERENCES: July, teens, kids ATTRACTION STYLE: Popular sights PACE: Medium
View more plans