23 days in Florida Itinerary

23 days in Florida Itinerary

Created using Inspirock Florida tour itinerary builder

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Route & dates

23 days in Florida Itinerary

Start: Chicago
Fly:  5​h
1
Sanibel Island
— 2 nights
Drive:  30​min
2
Fort Myers Beach
— 2 nights
Drive:  45​min
3
Naples
— 2 nights
Drive:  30​min
4
Marco Island
— 2 nights
Drive:  2​h 15​min
5
Fort Lauderdale
— 2 nights
Drive:  45​min
6
Miami Beach
— 3 nights
bus:  3​h 30​min
7
Everglades National Park
— 3 nights
+3
bus + train + foot + bus:  4​h 45​min
8
Islamorada
— 2 nights
Drive:  45​min
9
Marathon
— 2 nights
bus:  1​h 15​min
10
Key West
— 2 nights
Fly:  6​h
End: Chicago

2
nights
Sanibel Island

Sanibel Island ©
Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.
Start off your visit on the 22nd (Fri): see majestic marine mammals with a dolphin and whale watching tour and then stop by The Bait Box. On the next day, hunt for treasures at Sanibel Island Farmer's Market, then stop by Finnimore's Cycle Shop, then buy something for everyone on your list at Periwinkle Place, and finally stroll through Gulfside Beach.

For traveler tips, more things to do, other places to visit, and other tourist information, refer to the Sanibel Island day trip planner .

Chicago to Sanibel Island is an approximately 5-hour combination of flight and taxi. You can also drive; or do a combination of bus and taxi. The time zone difference moving from Central Standard Time to Eastern Standard Time is 1 hour. Plan for warmer temperatures traveling from Chicago in December, with highs in Sanibel Island at 80°F and lows at 61°F. Wrap up your sightseeing on the 24th (Sun) to allow time to drive to Fort Myers Beach.

Things to do in Sanibel Island

Outdoors Parks Shopping
Highlights from your plan
Gulfside Beach ©
Gulfside Beach
Sanibel Island Farmer's Market ©
Sanibel Island Farmer's Market
Periwinkle Place ©
Periwinkle Place

2
nights
Fort Myers Beach

Fort Myers Beach ©
Fort Myers Beach is a town located on Estero Island in Lee County, Florida, United States. Get ready for a full day of sightseeing on the 25th (Mon): hunt for treasures at Trico Shrimp Co, try for a hole-in-one at JungleGolf, and then stroll through Little Hickory Beach Park.

For maps, ratings, where to stay, and other tourist information, refer to the Fort Myers Beach road trip planner .

Fort Myers Beach is just a stone's throw from Sanibel Island. In December in Fort Myers Beach, expect temperatures between 76°F during the day and 57°F at night. Cap off your sightseeing on the 26th (Tue) early enough to go by car to Naples.

Things to do in Fort Myers Beach

Parks Wildlife Beaches

Side Trips

Octagon Wildlife Sanctuary And Rehabilitation Center, Little Hickory Beach Park, Four Mile Cove Ecological Preserve
Highlights from your plan
Four Mile Cove Ecological Preserve ©
Trico Shrimp Co ©
Trico Shrimp Co

2
nights
Naples

Naples ©
Naples is a city in Collier County, Florida, United States. Kick off your visit on the 27th (Wed): buy something for everyone on your list at Coastland Center, find your balance on the water with some of the best stand-up paddleboarding in the area, and then buy something for everyone on your list at The Village Shops on Venetian Bay.

For ratings, maps, more things to do, and other tourist information, read our Naples itinerary app .

Getting from Fort Myers Beach to Naples by car takes about an hour. Other options: do a combination of bus and taxi. In December, plan for daily highs up to 80°F, and evening lows to 62°F. Wrap up your sightseeing on the 28th (Thu) early enough to drive to Marco Island.

Things to do in Naples

Shopping Tours Adventure
Highlights from your plan
Coastland Center ©
Coastland Center
Stand-Up Paddleboarding
The Village Shops on Venetian Bay ©
The Village Shops on Venetian Bay

2
nights
Marco Island

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. Start off your visit on the 28th (Thu): look for all kinds of wild species at Big Cypress National Preserve and then see what you can catch with a fishing tour. On the 29th (Fri), you'll have a packed day of sightseeing: take an in-depth tour of Marco Island Historical Museum, then head off the coast to Cape Romano, and then soothe aching muscles at some of the top local wellness centers.

To find traveler tips, where to stay, maps, and tourist information, refer to the Marco Island trip planner .

Marco Island is just a short distance from Naples. December in Marco Island sees daily highs of 80°F and lows of 60°F at night. Finish your sightseeing early on the 30th (Sat) to allow enough time to drive to Fort Lauderdale.

Things to do in Marco Island

Outdoors Wildlife Parks

Side Trips

Fishing Charters & Tours, Big Cypress National Preserve
Highlights from your plan
Big Cypress National Preserve ©
Big Cypress National Preserve
Cape Romano ©
Cape Romano
Spas & Wellness

2
nights
Fort Lauderdale

Fort Lauderdale ©
Known as the "Venice of America" because of its extensive network of navigable waterways, Fort Lauderdale welcomes over 10 million annual visitors, most of them attracted by the city's popular beaches and marinas.
On the 30th (Sat), enjoy the sand and surf at Lake Worth Beach and then look for all kinds of wild species at Green Cay Nature Center and Wetlands. Here are some ideas for day two: stroll through Fort Lauderdale Beach Park, browse the different shops at Town Center at Boca Raton, and then stop by Coral Square.

To see traveler tips, where to stay, and tourist information, refer to the Fort Lauderdale trip itinerary planner .

You can drive from Marco Island to Fort Lauderdale in 2.5 hours. Another option is to do a combination of taxi and bus. Expect a daytime high around 77°F in December, and nighttime lows around 64°F. Finish your sightseeing early on the 1st (Mon) to allow enough time to drive to Miami Beach.

Things to do in Fort Lauderdale

Parks Beaches Outdoors

Side Trips

Lake Worth Beach, Coral Square, Green Cay Nature Center and Wetlands, Town Center at Boca Raton
Highlights from your plan
Green Cay Nature Center and Wetlands ©
Fort Lauderdale Beach Park ©
Fort Lauderdale Beach Park
Town Center at Boca Raton ©
Town Center at Boca Raton

3
nights
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.
Take a break from the city and head to Haulover Beach Park and Surfside Beach. You'll discover tucked-away gems like Bal Harbor Beach and Bal Harbour Shops. Venture out of the city with trips to Miami International Mall (in Doral), Dadeland Mall (in Kendall) and R F Orchids (in Homestead). The adventure continues: take a stroll through Lincoln Road, stop by Perfect Gifts South Beach, shop like a local with Miami Design District, and browse the different shops at Shops at Merrick Park.

To find photos, reviews, maps, and more tourist information, you can read our Miami Beach journey planning tool .

Traveling by car from Fort Lauderdale to Miami Beach takes an hour. Alternatively, you can take a bus. In January, plan for daily highs up to 77°F, and evening lows to 62°F. Cap off your sightseeing on the 4th (Thu) early enough to travel to Everglades National Park.

Things to do in Miami Beach

Shopping Parks Beaches

Side Trips

Miami, Bal Harbour, Dadeland Mall, Village of Merrick Park, Miami International Mall
Highlights from your plan
Surfside Beach ©
Surfside Beach
Haulover Beach Park ©
Haulover Beach Park
Bal Harbour Shops ©
Bal Harbour Shops

3
nights
Everglades National Park

Everglades National Park ©
A vast expanse of pristine wetlands, Everglades National Park holds the distinction of being the largest tropical wilderness in the U.S.
On the 5th (Fri), take a leisurely stroll along West Lake Trail, then get some fabulous bargains at Florida Keys Premium Outlets, and then do a tasting at Schnebly Redland's Winery & Brewery. Keep things going the next day: trek along Pa-hay-okee Trail and then look for all kinds of wild species at Mahogany Hammock.

To find reviews, other places to visit, photos, and other tourist information, read our Everglades National Park tour planner.

Traveling by bus from Miami Beach to Everglades National Park takes 3.5 hours. In January in Everglades National Park, expect temperatures between 77°F during the day and 67°F at night. Finish your sightseeing early on the 7th (Sun) so you can travel to Islamorada.

Things to do in Everglades National Park

Parks Wildlife Trails

Side Trips

Schnebly Redland's Winery, Florida Keys Outlet Marketplace
Highlights from your plan
Mahogany Hammock ©
Mahogany Hammock
Pa-hay-okee Trail ©
Pa-hay-okee Trail
West Lake Trail ©
West Lake Trail

2
nights
Islamorada

Islamorada ©
Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
Kick off your visit on the 7th (Sun): look for gifts at Ocean Gardens, indulge your thirst for a good beer at Islamorada Beer Company Brewery and Tasting Room, take in the exciting artwork at Old Road Gallery, then stop by Petals With Pizzazz, and finally kick back and relax at Anne's Beach. Get ready for a full day of sightseeing on the next day: look for all kinds of wild species at Molasses Reef, then explore the gorgeous colors at Spiegel Grove, and then look for gifts at Shell World.

Use Inspirock's suggestions to plan your Islamorada trip and find the best activities and attractions for your vacation.

You can take a bus from Everglades National Park to Islamorada in 5 hours. Alternatively, you can do a combination of bus and shuttle. In January, daytime highs in Islamorada are 75°F, while nighttime lows are 64°F. Wrap up your sightseeing on the 9th (Tue) early enough to drive to Marathon.

Things to do in Islamorada

Parks Wildlife Shopping

Side Trip

Key Largo
Highlights from your plan
Molasses Reef ©
Molasses Reef
Spiegel Grove ©
Spiegel Grove
Anne's Beach ©
Anne's Beach

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 9th (Tue): choose your vessel at Captain Hook's Marina & Dive Center, look for all kinds of wild species at Crane Point Museum & Nature Center, and then identify plant and animal life at National Key Deer Refuge. Get ready for a full day of sightseeing on the 10th (Wed): kick back and relax at Sunset Park Beach, stop by Hawks Cay Marina Dockside Store, then stop by The Tackle Box, and finally take in the views from Old Seven Mile Bridge.

For where to stay, ratings, reviews, and more tourist information, read our Marathon trip planner.

You can drive from Islamorada to Marathon in an hour. Alternatively, you can take a shuttle; or take a bus. Expect a daytime high around 76°F in January, and nighttime lows around 65°F. Wrap up your sightseeing on the 11th (Thu) early enough to drive to Key West.

Things to do in Marathon

Parks Wildlife Outdoors

Side Trips

National Key Deer Refuge, Sunset Park Beach
Highlights from your plan
Crane Point Museum & Nature Center ©
Sunset Park Beach ©
Sunset Park Beach
The Tackle Box ©
The Tackle Box

2
nights
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.
Take a break from the city and head to Dolphin & Whale Watching and Scuba & Snorkeling. Head to Peppers Of Key West and Uva Wine Shop & Barfor plenty of shopping. And it doesn't end there: glide peacefully along the water with some of the best stand-up paddleboarding in the area, relax and rejuvenate at some of the top local wellness centers, immerse yourself in nature at Fort Zachary Taylor, and enjoy the sand and surf at Smathers Beach.

To see where to stay, ratings, and more tourist information, read our Key West trip maker website .

Drive from Marathon to Key West in 1.5 hours. Alternatively, you can take a bus. In January, plan for daily highs up to 76°F, and evening lows to 67°F. Finish your sightseeing early on the 13th (Sat) so you can travel back home.

Things to do in Key West

Outdoors Tours Wildlife
Highlights from your plan
Dolphin & Whale Watching
Stand-Up Paddleboarding
Smathers Beach ©
Smathers Beach

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