29 days in Florida Itinerary

29 days in Florida Itinerary

Created using Inspirock Florida trip planner

Make it your trip
Drive
1
Siesta Key
— 2 nights
Bus to Ft. Myers, Fly to Key West
2
Key West
— 4 nights
Drive
3
Marathon
— 4 nights
Fly
4
Clearwater
— 3 nights
Fly
5
Fort Walton Beach
— 5 nights
Drive
6
St. Augustine
— 3 nights
Drive
7
Merritt Island
— 1 night
Drive
8
Orlando
— 6 nights
Drive

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Siesta Key

— 2 nights
Siesta Key draws most of its visitors with soft, white-quartz sand beaches and translucent ocean water.
Kick off your visit on the 2nd (Fri): enjoy the sand and surf at Siesta Beach, then kick back and relax at Crescent Beach, then soothe aching muscles at some of the top local wellness centers, and finally enjoy the sand and surf at Stump Pass Beach State Park. Get ready for a full day of sightseeing on the next day: enjoy the sand and surf at Turtle Beach, find your balance on the water with some of the best stand-up paddleboarding in the area, and then observe the fascinating underwater world at Mote Marine Laboratory & Aquarium.

For other places to visit, ratings, maps, and other tourist information, refer to the Siesta Key day trip planner.

Ocala to Siesta Key is an approximately 3-hour car ride. You can also drive; or do a combination of bus and taxi. Expect a bit warmer evenings in Siesta Key when traveling from Ocala in October, with lows around 68°F. Finish your sightseeing early on the 3rd (Sat) so you can fly to Key West.

Things to do in Siesta Key

Outdoors · Parks · Beaches · Adventure

Side Trips

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.
Family-friendly places like Fort Zachary Taylor and Scuba & Snorkeling will thrill your kids. And it doesn't end there: see the interesting displays at The Ernest Hemingway Home and Museum, make a trip to Southernmost Point, look for gifts at Peppers of Key West, and see the world from above with Air Adventures Helicopter Tours.

For traveler tips, more things to do, other places to visit, and tourist information, read our Key West trip builder tool.

You can do a combination of bus and flight from Siesta Key to Key West in 7.5 hours. Alternatively, you can fly; or drive; or do a combination of bus, taxi, and ferry. Traveling from Siesta Key in October, expect a bit warmer with lows of 77°F in Key West. Finish your sightseeing early on the 7th (Wed) to allow enough time to drive to Marathon.

Things to do in Key West

Museums · Historic Sites · Parks · Tours

Marathon

— 4 nights

Heart of the Florida Keys

A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
You'll get in some beach time at Bahia Honda State Park and Sombrero Beach. Kids will appreciate attractions like Sunset Park Beach and Crane Point Museum & Nature Center. Venture out of the city with trips to Island Dolphin Care (in Key Largo), Islamorada (Theater of the Sea & Island Flow Yoga) and Florida Keys Wild Bird Rehabilitation Center (in Tavernier). There's lots more to do: stroll through The Turtle Hospital, take in the exciting artwork at Shady Palm Art Gallery & Photography, take in the views from Seven Mile Bridge, and relax in the rural setting at Grimal Grove.

To see where to stay, photos, traveler tips, and tourist information, you can read our Marathon day trip planning site.

You can drive from Key West to Marathon in 1.5 hours. Other options are to drive; or take a bus. In October in Marathon, expect temperatures between 87°F during the day and 77°F at night. Finish your sightseeing early on the 11th (Sun) so you can travel to Clearwater.

Things to do in Marathon

Parks · Wildlife · Outdoors · Beaches

Side Trips

Clearwater

— 3 nights

Fun and Sun for All

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.
Visit Clearwater Beach and Treasure Island Beach for some beach relaxation. You'll visit kid-friendly attractions like St. Pete Beach and Honeymoon Island State Park. Venture out of the city with trips to Tampa (Sunshine Skyway Bridge, The Florida Aquarium, &more) and Two Friend's Closet (in St. Pete Beach). Next up on the itinerary: kick back and relax at Madeira Beach, meet the residents at Clearwater Marine Aquarium, head outdoors with Outdoor Activities, and contemplate in the serene atmosphere at Church of Scientology Information Center.

To find ratings, maps, reviews, and more tourist information, refer to the Clearwater visit planner.

You can fly from Marathon to Clearwater in 5.5 hours. Alternatively, you can do a combination of bus and flight; or drive; or do a combination of bus, train, and taxi. Traveling from Marathon in October, expect little chillier with lows of 71°F in Clearwater. Cap off your sightseeing on the 14th (Wed) early enough to catch the flight to Fort Walton Beach.

Things to do in Clearwater

Parks · Outdoors · Beaches · Theme Parks

Side Trips

Fort Walton Beach

— 5 nights
Fort Walton Beach is a city in southern Okaloosa County, Florida, United States. Relax by the water at Navarre Beach and Pensacola Beach. Bring the kids along to Gulf Islands National Seashore and St. Andrews State Park. Get out of town with these interesting Fort Walton Beach side-trips: Santa Rosa Beach (in Santa Rosa Beach), Panama City Beach (Panama City Beach & Abc Fine Wine And Spirits) and Gail Walsh Massage & Skincare Co. (in Gulf Breeze). There's lots more to do: enjoy the sand and surf at Okaloosa Island, play a few rounds at Goofy Golf, see some colorful creatures with Cattywampus, and brush up on your military savvy at Air Force Armament Museum.

To see photos, other places to visit, reviews, and other tourist information, go to the Fort Walton Beach vacation builder site.

Getting from Clearwater to Fort Walton Beach by flight takes about 5 hours. Other options: fly; or drive; or do a combination of taxi and bus. You'll gain 1 hour traveling from Clearwater to Fort Walton Beach due to the time zone difference. Plan for slightly colder temperatures traveling from Clearwater in October, with highs in Fort Walton Beach at 80°F and lows at 60°F. Wrap up your sightseeing on the 19th (Mon) to allow time to fly to St. Augustine.

Things to do in Fort Walton Beach

Outdoors · Parks · Beaches · Nature

Side Trips

St. Augustine

— 3 nights
St. Family-friendly places like St. Augustine Beach and Ormond Beach will thrill your kids. We've included these beaches for you: Andy Romano Beachfront Park and Jacksonville Beach. There's still lots to do: learn about wildlife with up-close encounters at St. Augustine Wild Reserve, enjoy the sea views from St. Augustine Lighthouse & Maritime Museum, Inc., immerse yourself in nature at Anastasia State Park, and stroll through St. Augustine Alligator Farm Zoological Park.

To find more things to do, traveler tips, where to stay, and tourist information, read St. Augustine day trip app.

Traveling by car from Fort Walton Beach to St. Augustine takes 6.5 hours. Alternatively, you can fly; or drive; or take a bus. Due to the time zone difference, you'll lose 1 hour traveling from Fort Walton Beach to St. Augustine. Traveling from Fort Walton Beach in October, plan for somewhat warmer nights in St. Augustine, with lows around 67°F. Cap off your sightseeing on the 22nd (Thu) early enough to go by car to Merritt Island.

Things to do in St. Augustine

Parks · Beaches · Outdoors · Museums

Side Trips

Merritt Island

— 1 night
Start off your visit on the 23rd (Fri): push the limits with Jump Right In Flyboarding, look and learn at NASA Kennedy Space Center Visitor Complex, then engage your brain at Space Shuttle Atlantis, and finally kick back and relax at Jetty Park Beach & Pier.

To find maps, reviews, ratings, and other tourist information, you can read our Merritt Island road trip planning app.

Traveling by car from St. Augustine to Merritt Island takes 2.5 hours. Alternatively, you can drive; or do a combination of bus and car; or do a combination of bus and taxi. Traveling from St. Augustine in October, expect somewhat warmer with lows of 73°F in Merritt Island. Wrap up your sightseeing on the 23rd (Fri) early enough to drive to Orlando.

Things to do in Merritt Island

Childrens Museums · Museums · Outdoors · Beaches

Side Trip

Orlando

— 6 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.
Attractions like Magic Kingdom Park and Universal Orlando Resort make great kid-friendly stops. Step out of Orlando with an excursion to Boat Tours & Water Sports in Saint Cloud--about 38 minutes away. Have a day of magic on the 24th (Sat) at Walt Disney World Resort. There's lots more to do: find something for the whole family at SeaWorld, stop by M&M'S World Disney Springs, discover the magic at Avatar Flight of Passage, and take in the architecture and atmosphere at St James Roman Catholic Cathedral.

To see where to stay, traveler tips, ratings, and more tourist information, read Orlando road trip website.

Traveling by car from Merritt Island to Orlando takes 1.5 hours. Alternatively, you can drive; or take a shuttle. Expect a daytime high around 85°F in October, and nighttime lows around 69°F. Finish your sightseeing early on the 29th (Thu) so you can drive back home.

Things to do in Orlando

Theme Parks · Outdoors · Tours · Shopping

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.