23 days in Florida Itinerary

23 days in Florida Itinerary

Created using Inspirock Florida trip planner

Make it your trip
Fly
1
Miami Beach
— 1 night
Drive
2
Everglades National Park
— 3 nights
Unknown
3
Marco Island
— 1 night
Drive
4
Key Largo
— 2 nights
Drive
5
Key West
— 4 nights
Drive
6
Big Pine Key
— 2 nights
Drive
7
Islamorada
— 2 nights
Fly
8
St. Augustine
— 2 nights
Drive
9
Orlando
— 5 nights
Fly

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Miami Beach

— 1 night

The World's Playground

Separated by water from the neighboring city of Miami, Miami Beach sits on a barrier island between Biscayne Bay and the Atlantic Ocean.
On the 15th (Wed), take a stroll through Calle Ocho, then steep yourself in history at Freedom Tower at Miami Dade College, then head outdoors with Outdoor Activities, and finally admire the majestic nature at Oleta River State Park. Keep things going the next day: explore the world behind art at Lowe Art Museum, examine the collection at Vizcaya Museum and Gardens, then take a stroll through Lincoln Road, and finally stroll through South Beach.

To see ratings, traveler tips, and other tourist information, refer to the Miami Beach day trip planning site.

Punta Cana, Dominican Republic to Miami Beach is an approximately 5.5-hour flight. The time zone difference moving from Atlantic Standard Time to Eastern Standard Time is minus 1 hour. In September, daytime highs in Miami Beach are 38°C, while nighttime lows are 29°C. Cap off your sightseeing on the 16th (Thu) early enough to travel to Everglades National Park.

Things to do in Miami Beach

Parks · Museums · Neighborhoods · Outdoors

Side Trips

Find places to stay Sep 15 — 16:

Everglades National Park

— 3 nights

Largest Subtropical Wilderness in the United States

A vast expanse of pristine wetlands, Everglades National Park holds the distinction of being the largest tropical wilderness in the U.S. Overflow from Lake Okeechobee into the Florida Bay formed these wetlands, which are home to manatees, American crocodiles, Florida panthers, and an array of wading birds, land birds, and birds of prey.
Everglades National Park is known for wildlife, trails, and parks. Your trip includes some of its best attractions: see what you can catch with Everglades City Fishing Charters, hike along Pineland Trail, contemplate the waterfront views at Mrazek Pond, and look for all kinds of wild species at Shark Valley Visitor Center.

For maps, ratings, and other tourist information, you can read our Everglades National Park trip planner.

Use the Route module to find suitable travel options from Miami Beach to Everglades National Park. In September, plan for daily highs up to 38°C, and evening lows to 30°C. Finish your sightseeing early on the 19th (Sun) to allow enough time to travel to Marco Island.

Things to do in Everglades National Park

Outdoors · Parks · Nature · Wildlife
Find places to stay Sep 16 — 19:

Marco Island

— 1 night
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 20th (Mon), contemplate the waterfront views at Capri Paddlecraft Park, catch all the local highlights with Reel Kind Fishing and Tours, and then look for gifts at Keep In Touch.

For reviews, photos, where to stay, and other tourist information, use the Marco Island trip planner.

Explore your travel options from Everglades National Park to Marco Island with the Route module. Expect a bit cooler evenings in Marco Island when traveling from Everglades National Park in September, with lows around 27°C. Wrap up your sightseeing on the 20th (Mon) to allow time to drive to Key Largo.

Things to do in Marco Island

Wildlife · Tours · Outdoors · Nature
Find places to stay Sep 19 — 20:

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.
Kick off your visit on the 21st (Tue): get a dose of the wild on Capt. Sterling's Everglades Eco-Tours, explore the gorgeous colors at Spiegel Grove, and then tour the pleasant surroundings at Florida Keys Wild Bird Rehabilitation Center. On the 22nd (Wed), you'll have a packed day of sightseeing: meet the residents at Island Dolphin Care, see some colorful creatures with a scuba or snorkeling tour, and then relax and rejuvenate at Prana.

Plan a trip to Key Largo easily and quickly by telling Inspirock to suggest an itinerary.

You can drive from Marco Island to Key Largo in 3 hours. Other options are to do a combination of taxi and bus; or do a combination of ferry and bus. Expect a daytime high around 36°C in September, and nighttime lows around 28°C. Wrap up your sightseeing on the 22nd (Wed) to allow time to drive to Key West.

Things to do in Key Largo

Wildlife · Tours · Outdoors · Parks
Find places to stay Sep 20 — 22:

Key West

— 4 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.
Key West is known for museums, adventure, and wildlife. Your trip includes some of its best attractions: examine the collection at The Ernest Hemingway Home and Museum, discover the deep blue sea with a scuba or snorkeling tour, tour the pleasant surroundings at Key West Butterfly & Nature Conservatory, and don't miss a visit to Duval Street.

To see reviews, photos, more things to do, and other tourist information, use the Key West attractions planning app.

Drive from Key Largo to Key West in 2.5 hours. Alternatively, you can take a bus. In September in Key West, expect temperatures between 36°C during the day and 31°C at night. Cap off your sightseeing on the 26th (Sun) early enough to go by car to Big Pine Key.

Things to do in Key West

Museums · Shopping · Parks · Wildlife
Find places to stay Sep 22 — 26:

Big Pine Key

— 2 nights
Big Pine Key is a census-designated place and unincorporated community in Monroe County, Florida, United States, on an island of the same name in the Florida Keys. On the 27th (Mon), see what you can catch with a fishing tour, then relax and rejuvenate at SpaTerre at Little Palm Island Resort, and then stop by Out of the Blue Gallery. On the 28th (Tue), you'll have a packed day of sightseeing: tour the pleasant surroundings at National Key Deer Refuge and then kick back and relax at Bahia Honda State Park.

To find more things to do, other places to visit, where to stay, and other tourist information, read Big Pine Key trip itinerary site.

Drive from Key West to Big Pine Key in an hour. Alternatively, you can take a shuttle; or take a bus. In September, daily temperatures in Big Pine Key can reach 38°C, while at night they dip to 30°C. Finish your sightseeing early on the 28th (Tue) so you can drive to Islamorada.

Things to do in Big Pine Key

Parks · Outdoors · Wildlife · Beaches

Side Trips

Find places to stay Sep 26 — 28:

Islamorada

— 2 nights

The Village of Islands

Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
On the 29th (Wed), head outdoors with Contagious Charters, then look for gifts at Bella Sol Fragrance Bar and Gifts, then see what you can catch with a fishing tour, and finally relax and rejuvenate at Island Flow Yoga. Here are some ideas for day two: head outdoors with Satisfaction Charters Inc. and then head outdoors with Neptune Charters.

To plan Islamorada vacation without wasting time, ask Inspirock to design an itinerary.

You can drive from Big Pine Key to Islamorada in 1.5 hours. Alternatively, you can take a bus. Expect a daytime high around 38°C in September, and nighttime lows around 30°C. Finish your sightseeing early on the 30th (Thu) to allow enough time to fly to St. Augustine.

Things to do in Islamorada

Outdoors · Tours · Spas · Wildlife
Find places to stay Sep 28 — 30:

St. Augustine

— 2 nights
St. On the 1st (Fri), walk around Rivertown Park, then stroll through St. Augustine Wild Reserve, then tee off at TPC at Sawgrass Stadium Course, and finally look for gifts at Faux Paws. On the 2nd (Sat), you'll have a packed day of sightseeing: steep yourself in history at Castillo de San Marcos National Monument, visit a coastal fixture at St. Augustine Lighthouse & Maritime Museum, Inc., then learn about all things military at Spanish Military Hospital Museum, and finally brush up on your knowledge of spirits at St. Augustine Distillery.

To see reviews and tourist information, refer to the St. Augustine trip planning tool.

You can fly from Islamorada to St. Augustine in 3.5 hours. Alternatively, you can drive; or do a combination of shuttle and bus. Traveling from Islamorada in September, things will get slightly colder in St. Augustine: highs are around 34°C and lows about 26°C. Finish your sightseeing early on the 2nd (Sat) so you can drive to Orlando.

Things to do in St. Augustine

Historic Sites · Museums · Breweries & Distilleries · Parks

Side Trips

Find places to stay Sep 30 — Oct 2:

Orlando

— 5 nights

Theme Park Capital of the World

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.
Pack the 7th (Thu) with family-friendly diversions at Universal Orlando Resort. Have a day of magic on the 5th (Tue) at Walt Disney World Resort. There's much more to do: get in on the family fun at Universal's Islands of Adventure, cool off at Discovery Cove, and make an unforgettable trip to Magic Kingdom Park.

To find reviews, ratings, and more tourist information, read Orlando trip planner.

Getting from St. Augustine to Orlando by car takes about 2 hours. Other options: take a bus. October in Orlando sees daily highs of 34°C and lows of 24°C at night. Finish up your sightseeing early on the 7th (Thu) so you can catch the flight back home.

Things to do in Orlando

Theme Parks
Find places to stay Oct 2 — 7:

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.