27 days in Florida Itinerary

27 days in Florida Itinerary

Created using Inspirock Florida trip itinerary planner
Make it your trip
Fly
1
Orlando
— 3 nights
Fly
2
Hollywood
— 3 nights
Drive
3
Marco Island
— 2 nights
Ferry
4
Key West
— 3 nights
Ferry
5
Fort Myers Beach
— 5 nights
Drive
6
Siesta Key
— 4 nights
Drive
7
St. Pete Beach
— 3 nights
Drive
8
Clearwater
— 3 nights
Drive

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Orlando — 3 nights

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.
You'll visit kid-friendly attractions like Universal's Islands of Adventure and Disney's Animal Kingdom Theme Park. There's more to do: get in on the family fun at Universal Orlando Resort and discover the magic at Magic Kingdom Park.

To see where to stay, other places to visit, and more tourist information, read Orlando trip planner.

Phoenix to Orlando is an approximately 6.5-hour flight. You can also drive; or take a bus. The time zone changes from Mountain Standard Time (MST) to Eastern Standard Time (EST), which is usually a 2 hour difference. Traveling from Phoenix in June, expect Orlando to be a bit cooler, temps between 91°F and 73°F. Wrap up your sightseeing on the 18th (Sat) early enough to fly to Hollywood.
Theme Parks

Hollywood — 3 nights

The city of Hollywood is a classic Florida beach town and popular vacation spot, attracting visitors with its picturesque beaches, lively nightlife, and laid-back vibe.
Kids will appreciate attractions like South Beach and Art Deco Historic District. Explore the numerous day-trip ideas around Hollywood: Miami Beach (Espanola Way, Lincoln Road, &more). Next up on the itinerary: head outdoors with JP Outfitters Inc., kick back and relax at Fort Lauderdale Beach, take a leisurely stroll along Hollywood Beach Broadwalk, and stroll through Hollywood Beach.

For traveler tips, maps, reviews, and tourist information, use the Hollywood trip itinerary planner.

Fly from Orlando to Hollywood in 3 hours. Alternatively, you can drive; or take a bus. In June, plan for daily highs up to 89°F, and evening lows to 77°F. Wrap up your sightseeing on the 21st (Tue) early enough to drive to Marco Island.
Outdoors · Parks · Beaches · Neighborhoods
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. Kids will enjoy Dolphin & Whale Watching and Capri Paddlecraft Park. And it doesn't end there: take an in-depth tour of Marco Island Historical Museum, indulge in some personalized pampering at some of the best spas, kick back and relax at South Marco Beach, and tour the pleasant surroundings at Tigertail Beach.

For maps, other places to visit, and more tourist information, read our Marco Island trip planning tool.

Traveling by car from Hollywood to Marco Island takes 2.5 hours. Alternatively, you can do a combination of train, bus, and taxi; or do a combination of bus and taxi. In June, daytime highs in Marco Island are 90°F, while nighttime lows are 74°F. Wrap up your sightseeing on the 23rd (Thu) to allow time to ride a ferry to Key West.
Outdoors · Parks · Wildlife · Beaches

Key West — 3 nights

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.
Kick off your visit on the 24th (Fri): see some colorful creatures with a scuba or snorkeling tour, explore the world behind art at Fort East Martello Museum, then stroll through Key West Butterfly & Nature Conservatory, then examine the collection at The Ernest Hemingway Home and Museum, and finally get a tailor-made plan with Key West Local Luxe -Jewelry Store. Get ready for a full day of sightseeing on the 25th (Sat): observe the fascinating underwater world at Florida Keys Eco-Discovery Center, make a trip to Duval Street, and then take a leisurely stroll along Mallory Square.

To see other places to visit, traveler tips, photos, and more tourist information, use the Key West road trip website.

Getting from Marco Island to Key West by ferry takes about 4 hours. Other options: drive. Expect a daytime high around 88°F in June, and nighttime lows around 79°F. Finish up your sightseeing early on the 26th (Sun) so you can catch the ferry to Fort Myers Beach.
Parks · Wildlife · Museums · Tours

Fort Myers Beach — 5 nights

Fort Myers Beach is a town located on Estero Island in Lee County, Florida, United States. Family-friendly places like Parasailing & Paragliding and Fort Myers Beach will thrill your kids. Change things up with these side-trips from Fort Myers Beach: Bowman's Beach (in Sanibel Island) and Fort Myers (Edison and Ford Winter Estates & IMAG History & Science Center). And it doesn't end there: tour the pleasant surroundings at J.N. "Ding" Darling National Wildlife Refuge, enjoy the sand and surf at Bonita Springs Public Beach, look for gifts at The Goodz, and don't miss a visit to Times Square.

To find where to stay, ratings, reviews, and tourist information, go to the Fort Myers Beach day trip planning site.

Traveling by ferry from Key West to Fort Myers Beach takes 4.5 hours. Alternatively, you can drive; or take a bus. Traveling from Key West in June, Fort Myers Beach is a bit cooler at night with lows of 74°F. Finish your sightseeing early on the 1st (Fri) so you can drive to Siesta Key.
Parks · Outdoors · Beaches · Museums
Side Trips

Siesta Key — 4 nights

Siesta Key draws most of its visitors with soft, white-quartz sand beaches and translucent ocean water.
Kids will enjoy Stand-Up Paddleboarding and Spas. There's lots more to do: kick back and relax at Siesta Beach, stroll through Crescent Beach, don't miss a visit to Siesta Key Village, and get the adrenaline pumping with an extreme tour.

For more things to do, reviews, traveler tips, and other tourist information, you can read our Siesta Key trip itinerary tool.

Traveling by car from Fort Myers Beach to Siesta Key takes 2 hours. Alternatively, you can do a combination of taxi and bus. July in Siesta Key sees daily highs of 91°F and lows of 76°F at night. Finish up your sightseeing early on the 5th (Tue) so you can go by car to St. Pete Beach.
Parks · Outdoors · Beaches · Shopping
Side Trip

St. Pete Beach — 3 nights

St. Attractions like Parasailing & Paragliding and Pass-a-Grille Beach, Florida make great kid-friendly stops. There's still lots to do: kick back and relax at St. Pete Beach, stroll through Madeira Beach, explore the world behind art at The Dali Museum, and admire the majestic nature at Fort De Soto Park.

To find more things to do, other places to visit, photos, and more tourist information, you can read our St. Pete Beach trip builder.

Drive from Siesta Key to St. Pete Beach in 1.5 hours. Alternatively, you can do a combination of bus and taxi. July in St. Pete Beach sees daily highs of 90°F and lows of 79°F at night. Finish your sightseeing early on the 8th (Fri) so you can drive to Clearwater.
Parks · Outdoors · Beaches · Neighborhoods
Side Trips

Clearwater — 3 nights

Holding the record for most consecutive days of sunshine in a single year, Clearwater offers long sandy beaches and proximity to other major cities in the Tampa Bay area.
You'll visit kid-friendly attractions like Busch Gardens Tampa Bay and Waterskiing & Jetskiing. The adventure continues: kick back and relax at Clearwater Beach, meet the residents at Clearwater Marine Aquarium, deepen your understanding at Church of Scientology Information Center, and take a leisurely stroll along Pier 60.

To see ratings, more things to do, where to stay, and tourist information, go to the Clearwater tour itinerary planner.

Traveling by car from St. Pete Beach to Clearwater takes an hour. Alternatively, you can take a bus. In July, daily temperatures in Clearwater can reach 90°F, while at night they dip to 76°F. Wrap up your sightseeing by early afternoon on the 11th (Mon) to allow enough time to drive back home.
Theme Parks · Parks · Outdoors · Beaches
Side Trip

Florida travel guide

4.3
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.