30 days in Florida Itinerary

30 days in Florida Itinerary

Created using Inspirock Florida trip planner

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Route & dates

30 days in Florida Itinerary

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

1
night
Miami Beach

Miami Beach ©
Separated by water from the neighboring city of Miami, Miami Beach sits on a barrier island between Biscayne Bay and the Atlantic Ocean.
Kick off your visit on the 1st (Sun): walk around Lincoln Road, shop like a local with Aventura Mall, and then see the interesting displays at Lock & Load Museum. On your second day here, enjoy the sand and surf at Hollywood Beach, appreciate the extensive heritage of Art Deco Historic District, and then wander the streets of Collins Avenue.

Inspirock's itinerary builder makes planning a Miami Beach trip simple and quick.

Miami to Miami Beach is an approximately half hour car ride. Expect a daytime high around 90°F in September, and nighttime lows around 77°F. Wrap up your sightseeing on the 2nd (Mon) to allow time to drive to Islamorada.

Things to do in Miami Beach

Shopping Neighborhoods Parks

Side Trips

Hollywood Beach, Aventura Mall, Lock & Load Museum
Highlights from your plan
Hollywood Beach ©
Hollywood Beach
Art Deco Historic District ©
Art Deco Historic District
Aventura Mall ©
Aventura Mall

2
nights
Islamorada

Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
On the 3rd (Tue), see some colorful creatures with a scuba or snorkeling tour, then get a new perspective on things with Boat Tours & Water Sports, and then sample the tasty concoctions at Islamorada Beer Company. Get ready for a full day of sightseeing on the 4th (Wed): glide through the air with a parasailing or paragliding tour, look for all kinds of wild species at Florida Keys Wild Bird Rehabilitation Center, take an in-depth tour of History of Diving Museum, then view the masterpieces at Pasta Pantaleo Signature Gallery, and finally shop like a local with Lobster Trap Art Gallery.

To find more things to do, ratings, reviews, and other tourist information, you can read our Islamorada sightseeing planning tool .

Getting from Miami Beach to Islamorada by car takes about 2 hours. Other options: take a bus. September in Islamorada sees daily highs of 90°F and lows of 79°F at night. Wrap up your sightseeing on the 4th (Wed) to allow time to drive to Marathon.

Things to do in Islamorada

Outdoors Tours Wildlife

Side Trip

Key Largo
Highlights from your plan
Scuba & Snorkeling
Fishing Charters & Tours

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 5th (Thu): enjoy the sand and surf at Sombrero Beach, then identify plant and animal life at The Turtle Hospital, and then admire the majestic nature at Bahia Honda State Park. Get ready for a full day of sightseeing on the next day: get a new perspective on things with Boat Tours & Water Sports, identify plant and animal life at Dolphin Research Center, and then snap pictures at Seven Mile Bridge.

To find maps, ratings, other places to visit, and more tourist information, refer to the Marathon road trip planning website .

Traveling by car from Islamorada to Marathon takes an hour. Alternatively, you can take a bus. In September in Marathon, expect temperatures between 90°F during the day and 79°F at night. Wrap up your sightseeing on the 6th (Fri) early enough to take a bus to Key West.

Things to do in Marathon

Parks Outdoors Wildlife

Side Trip

Bahia Honda State Park
Highlights from your plan
The Turtle Hospital ©
The Turtle Hospital
Dolphin Research Center ©
Dolphin Research Center
Fishing Charters & Tours

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.
Eschew the tourist crowds and head to Dolphin & Whale Watching and Scuba & Snorkeling. Escape the urban bustle at Dry Tortugas National Park and Waterskiing & Jetskiing. There's still lots to do: examine the collection at The Ernest Hemingway Home and Museum, look for gifts at Isle Cook Key West, shop like a local with Alan S. Maltz Gallery, and view the masterpieces at 7 Artists & Friends.

To find more things to do, photos, maps, and tourist information, you can read our Key West journey planner .

Traveling by bus from Marathon to Key West takes 1.5 hours. Alternatively, you can drive. In September in Key West, expect temperatures between 88°F during the day and 80°F at night. Finish your sightseeing early on the 10th (Tue) to allow enough time to ride a ferry to Marco Island.

Things to do in Key West

Outdoors Tours Wildlife
Highlights from your plan
Dry Tortugas National Park ©
Dry Tortugas National Park
Dolphin & Whale Watching
Scuba & Snorkeling

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 11th (Wed): look for all kinds of wild species at Wildlife Areas, zoom along the surf with a waterskiing or jet-skiing adventure, and then look for gifts at Keep In Touch. Get ready for a full day of sightseeing on the 12th (Thu): cast your line with a fishing tour, get up close to creatures of the deep with a dolphin and whale watching tour, and then take in the exciting artwork at Malenda Trick Art Gallery.

To see ratings, more things to do, and tourist information, read our Marco Island trip builder site .

Traveling by ferry from Key West to Marco Island takes 2.5 hours. Alternatively, you can drive. Traveling from Key West in September, expect little chillier with lows of 74°F in Marco Island. Finish your sightseeing early on the 12th (Thu) to allow enough time to drive to Naples.

Things to do in Marco Island

Outdoors Tours Wildlife

Side Trip

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

3
nights
Naples

Naples is a city in Collier County, Florida, United States. Get some cultural insight at Edison & Ford Winter Estates and Fifth Avenue South. Step out of the city life by going to Dolphin & Whale Watching and Lowdermilk Beach. Explore Naples' surroundings by going to Miromar Outlets (in Estero) and Lovers Key State Park (in Fort Myers Beach). Next up on the itinerary: zoom along the surf with a waterskiing or jet-skiing adventure.

To find other places to visit, maps, more things to do, and other tourist information, refer to the Naples online journey maker .

You can drive from Marco Island to Naples in an hour. Expect a daytime high around 89°F in September, and nighttime lows around 76°F. Finish your sightseeing early on the 15th (Sun) to allow enough time to drive to Crystal River.

Things to do in Naples

Parks Outdoors Wildlife

Side Trips

Fort Myers Beach, Edison and Ford Winter Estates, Miromar Outlets
Highlights from your plan
Dolphin & Whale Watching
Lovers Key State Park ©
Lovers Key State Park
Edison and Ford Winter Estates ©
Edison and Ford Winter Estates

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.
Start off your visit on the 16th (Mon): paddle through the water with a kayaking and canoeing tour and then see some colorful creatures with a scuba or snorkeling tour. Keep things going the next day: see majestic marine mammals with a dolphin and whale watching tour and then identify plant and animal life at Ellie Schiller Homosassa Springs Wildlife State Park.

To see other places to visit, more things to do, photos, and other tourist information, go to the Crystal River online road trip planner .

Traveling by car from Naples to Crystal River takes 4.5 hours. Alternatively, you can take a bus; or take a bus. Expect a bit cooler evenings in Crystal River when traveling from Naples in September, with lows around 71°F. Finish your sightseeing early on the 17th (Tue) to allow enough time to drive to Orlando.

Things to do in Crystal River

Outdoors Tours Wildlife

Side Trips

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

4
nights
Orlando

Orlando ©
For most people, any mention of Orlando immediately conjures up images of sprawling theme parks filled with characters plucked right out of popular animated movies.
Get a sense of the local culture at Stetson Mansion and Timothy's Gallery. Visiting Fishing Charters & Tours and Cocoa Beach will get you outdoors. Get out of town with these interesting Orlando side-trips: Ron Jon Surf Shop (in Cocoa Beach) and Ponce de Leon Inlet Lighthouse & Museum (in Ponce Inlet). The adventure continues: take a stroll through International Drive, get some fabulous bargains at Orlando Vineland Premium Outlets, take in a show at Happily Ever After Fireworks, and explore the world behind art at Charles Hosmer Morse Museum of American Art.

For photos, traveler tips, other places to visit, and more tourist information, you can read our Orlando visit planner .

You can drive from Crystal River to Orlando in 2 hours. Other options are to take a bus; or do a combination of bus and train. In September, plan for daily highs up to 89°F, and evening lows to 74°F. Finish up your sightseeing early on the 21st (Sat) so you can go by car to St. Augustine.

Things to do in Orlando

Shopping Outdoors Neighborhoods

Side Trips

Cocoa Beach, Winter Park, Ponce de Leon Inlet Lighthouse & Museum, Stetson Mansion, Fishing Charters & Tours
Highlights from your plan
Stetson Mansion ©
Stetson Mansion
Fishing Charters & Tours

4
nights
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. Your cultural itinerary includes sights like Fort Matanzas National Monument and Memorial Presbyterian Church. Eschew the tourist crowds and head to Vilano Beach and St. Augustine Alligator Farm Zoological Park. Change things up with these side-trips from St. Augustine: Ormond Beach (in Ormond Beach) and Beach at Daytona Beach (in Daytona Beach). There's still lots to do: kick back and relax at St. Augustine Beach, take in the spiritual surroundings of Cathedral Basilica of St. Augustine, view the masterpieces at High Tide Gallery Art & Gifts, and see the interesting displays at Lightner Museum.

To see maps, ratings, and more tourist information, use the St. Augustine road trip website .

Getting from Orlando to St. Augustine by car takes about 2 hours. Other options: take a bus. In September, daytime highs in St. Augustine are 85°F, while nighttime lows are 73°F. Wrap up your sightseeing on the 25th (Wed) to allow time to drive to Panama City Beach.

Things to do in St. Augustine

Parks Outdoors Beaches

Side Trips

Ormond Beach, Beach at Daytona Beach
Highlights from your plan
Vilano Beach ©
Vilano Beach
St. Augustine Beach ©
St. Augustine Beach
Ormond Beach ©
Ormond Beach

5
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.
Get some cultural insight at Panama City Beach Winery and Panama City CENTER for the ARTS. Museum-lovers will appreciate Fusion Art Glass Gallery and The Blue Giraffe. Venture out of the city with trips to 30A Farmers Market (in Rosemary Beach) and Navarre Beach (in Navarre). There's still lots to do: immerse yourself in nature at Henderson Beach State Park, buy something for everyone on your list at Pier Park, tour the pleasant surroundings at St. Andrews State Park, and cool off at Panama City Beach.

For where to stay, other places to visit, photos, and tourist information, read our Panama City Beach day trip site .

You can drive from St. Augustine to Panama City Beach in 5.5 hours. Other options are to do a combination of bus and flight; or do a combination of bus, flight, and taxi. In September, daytime highs in Panama City Beach are 89°F, while nighttime lows are 70°F. Finish your sightseeing early on the 30th (Mon) to allow enough time to travel back home.

Things to do in Panama City Beach

Outdoors Parks Beaches

Side Trips

Santa Rosa Beach, Henderson Beach State Park, Fusion Art Glass Gallery, Navarre Beach, 30A Farmers Market
Highlights from your plan
Swim with Dolphins
Navarre Beach ©
Navarre Beach
Dolphin & Whale Watching

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