27 days in Florida Itinerary

27 days in Florida Itinerary

Created using Inspirock Florida visit planner

Make it your trip
+2
Drive to Cincinnati Northern Kentucky International Airport, Fly to Destin-Ft Walton Beach Airport, Drive to Fort Walton Beach
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Fort Walton Beach
— 3 nights
Fly
2
Key West
— 5 nights
Drive
3
Big Pine Key
— 3 nights
Drive
4
Islamorada
— 3 nights
Drive
5
Key Largo
— 3 nights
Drive
6
Miami Beach
— 2 nights
Drive
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Marco Island
— 2 nights
Drive
8
Orlando
— 3 nights
Drive
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St. Augustine
— 2 nights
+2
Drive to Jacksonville International Airport, Fly to Cincinnati Northern Kentucky International Airport, Drive to Dayton

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Fort Walton Beach

— 3 nights
Fort Walton Beach is a city in southern Okaloosa County, Florida, United States. You'll enjoy a bit of beach vacationing at Navarre Beach and Pensacola Beach. Get in touch with nature at ScubaTech and Gulf Islands National Seashore. Venture out of the city with trips to Panama City Beach (Panama City Beach Winery & Panama City Beach), Santa Rosa Beach (in Santa Rosa Beach) and Gulf Islands (in Pensacola). It doesn't end there: admire the majestic nature at Henderson Beach State Park and stroll through Okaloosa Island.

For photos, where to stay, ratings, and other tourist information, you can read our Fort Walton Beach online day trip planner.

Dayton to Fort Walton Beach is an approximately 5-hour combination of car and flight. You can also drive; or do a combination of car and flight. Due to the time zone difference, you'll gain 1 hour traveling from Dayton to Fort Walton Beach. Traveling from Dayton in July, you can expect nighttime temperatures to be somewhat warmer in Fort Walton Beach, with lows of 74°F. Cap off your sightseeing on the 8th (Thu) early enough to catch the flight to Key West.

Things to do in Fort Walton Beach

Outdoors · Parks · Beaches · Nature

Side Trips

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.
Visit Fort Zachary Taylor and Audubon House & Tropical Gardens for their historical value. The Ernest Hemingway Home and Museum and Truman Little White House will appeal to museum buffs. Next up on the itinerary: look for all kinds of wild species at Wildlife Areas, explore the gorgeous colors at Vandenberg Wreck, explore the different monuments and memorials at Key West Cemetery, and browse the exhibits of Key West Lighthouse and Keeper's Quarters Museum.

To see photos, ratings, reviews, and other tourist information, go to the Key West trip planner.

Getting from Fort Walton Beach to Key West by flight takes about 6.5 hours. Other options: drive; or do a combination of bus and shuttle. The time zone changes from Central Standard Time (CST) to Eastern Standard Time (EST), which is usually a 1 hour difference. Traveling from Fort Walton Beach in July, Key West is a bit warmer at night with lows of 81°F. Wrap up your sightseeing on the 13th (Tue) early enough to drive to Big Pine Key.

Things to do in Key West

Historic Sites · Museums · Parks · Wildlife

Big Pine Key

— 3 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. Get in touch with nature at Bahia Honda State Park and Key West Angling. Relax by the water at Calusa Beach and Long Beach. There's still lots to do: take a tour by water with Looe Key Dive Center, look for all kinds of wild species at National Key Deer Refuge, relax and rejuvenate at SpaTerre at Little Palm Island Resort, and visit a coastal fixture at American Shoal Lighthouse.

To see maps, other places to visit, and tourist information, you can read our Big Pine Key online tour planner.

Drive from Key West to Big Pine Key in an hour. Alternatively, you can take a shuttle; or take a bus. July in Big Pine Key sees daily highs of 92°F and lows of 81°F at night. Finish your sightseeing early on the 16th (Fri) to allow enough time to drive to Islamorada.

Things to do in Big Pine Key

Outdoors · Parks · Beaches · Wildlife

Side Trips

Islamorada

— 3 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.
Visiting Fishing Charters & Tours and Sombrero Beach will get you outdoors. Get out of town with these interesting Islamorada side-trips: Marathon (The Turtle Hospital & Sombrero Reef). And it doesn't end there: get to know the fascinating history of Indian Key State Historic Site, indulge your thirst for a good beer at Islamorada Brewery & Distillery, identify plant and animal life at Dolphin Research Center, and kick back and relax at Anne's Beach.

For reviews and tourist information, use the Islamorada trip itinerary planning website.

Traveling by car from Big Pine Key to Islamorada takes 1.5 hours. Alternatively, you can take a bus. In July, daily temperatures in Islamorada can reach 92°F, while at night they dip to 81°F. Finish up your sightseeing early on the 19th (Mon) so you can go by car to Key Largo.

Things to do in Islamorada

Parks · Wildlife · Outdoors · Breweries & Distilleries

Side Trip

Key Largo

— 3 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.
Get in touch with nature at Scuba & Snorkeling and Spiegel Grove. Explore the numerous day-trip ideas around Key Largo: Coral Castle (in Homestead) and Anhinga Trail (in Everglades National Park). There's much more to do: identify plant and animal life at Florida Keys Wild Bird Rehabilitation Center, see the vivid underwater world at Key Largo Undersea Park, and immerse yourself in nature at John Pennekamp Coral Reef State Park.

For photos, ratings, reviews, and more tourist information, refer to the Key Largo trip itinerary planner.

Key Largo is just a stone's throw from Islamorada. Plan for a bit cooler nights when traveling from Islamorada in July since evenings lows in Key Largo dip to 76°F. Finish up your sightseeing early on the 22nd (Thu) so you can go by car to Miami Beach.

Things to do in Key Largo

Parks · Wildlife · Outdoors · Nature

Side Trips

Miami Beach

— 2 nights

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 23rd (Fri), kick back and relax at South Beach, wander the streets of Art Deco Historic District, take in the architecture and atmosphere at Saint Francis de Sales Catholic Church, then contemplate in the serene atmosphere at St Patrick Catholic Church, and finally take a stroll through Lincoln Road. On the next day, wander the streets of Collins Avenue, enjoy the sand and surf at Haulover Beach Park, and then stroll through Crandon Park Beach.

To find traveler tips, maps, reviews, and other tourist information, use the Miami Beach road trip planning website.

You can drive from Key Largo to Miami Beach in 1.5 hours. Alternatively, you can take a bus; or take a bus. In July in Miami Beach, expect temperatures between 91°F during the day and 78°F at night. Finish your sightseeing early on the 24th (Sat) so you can drive to Marco Island.

Things to do in Miami Beach

Parks · Outdoors · Neighborhoods · Beaches

Side Trips

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. Kick off your visit on the 25th (Sun): tour the pleasant surroundings at Tigertail Beach, then tour the pleasant surroundings at South Marco Beach, and then see majestic marine mammals with Eco Endeavors. Get ready for a full day of sightseeing on the 26th (Mon): head off the coast to Cape Romano, kick back and relax at Keewaydin Island, and then look for all kinds of wild species at Capri Paddlecraft Park.

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

Drive from Miami Beach to Marco Island in 2.5 hours. Alternatively, you can do a combination of bus and taxi; or take a bus. July in Marco Island sees daily highs of 91°F and lows of 75°F at night. Wrap up your sightseeing on the 26th (Mon) to allow time to drive to Orlando.

Things to do in Marco Island

Outdoors · Parks · Beaches · Wildlife

Orlando

— 3 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.
Stetson Mansion and Seminole Rest are good opportunities to explore the local culture. Venture out of the city with trips to The Florida Key Lime Pie Company (in Cocoa Beach), NASA Kennedy Space Center Visitor Complex (in Merritt Island) and Beach Pole Fitness (in Cape Canaveral). Pack the 29th (Thu) with family-friendly diversions at Universal Orlando Resort. Next up on the itinerary: see majestic marine mammals with a dolphin and whale watching tour.

For reviews, traveler tips, more things to do, and other tourist information, go to the Orlando online travel planner.

You can drive from Marco Island to Orlando in 4.5 hours. Alternatively, you can do a combination of taxi, bus, and flight; or do a combination of taxi and bus. In July, daily temperatures in Orlando can reach 91°F, while at night they dip to 75°F. Finish your sightseeing early on the 29th (Thu) so you can drive to St. Augustine.

Things to do in Orlando

Theme Parks · Museums · Childrens Museums · Historic Sites

Side Trips

St. Augustine

— 2 nights
St. Start off your visit on the 30th (Fri): steep yourself in history at Villa Zorayda Museum, explore the galleries of St. Augustine Lighthouse & Maritime Museum, Inc., then enjoy the sand and surf at St. Augustine Beach, and finally kick back and relax at Crescent Beach Public Beach. Get ready for a full day of sightseeing on the 31st (Sat): explore the historical opulence of Castillo de San Marcos National Monument, stroll the grounds of Tolomato Cemetery, and then brush up on your knowledge of spirits at St. Augustine Distillery.

To find more things to do, ratings, maps, and other tourist information, go to the St. Augustine attractions planner.

You can drive from Orlando to St. Augustine in 2 hours. Alternatively, you can take a bus. In July in St. Augustine, expect temperatures between 90°F during the day and 75°F at night. Cap off your sightseeing on the 31st (Sat) early enough to travel back home.

Things to do in St. Augustine

Historic Sites · Outdoors · Parks · Beaches

Side Trip

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.