31 days in Florida Itinerary

31 days in Florida Itinerary

Created using Inspirock Florida travel route planner

Make it your trip
Drive
1
Clearwater
— 3 nights
Drive
2
Siesta Key
— 2 nights
Fly
3
Miami Beach
— 3 nights
Drive
4
Marathon
— 3 nights
Drive
5
Key West
— 5 nights
Fly
6
Fort Walton Beach
— 5 nights
Fly
7
St. Augustine
— 2 nights
Drive
8
Merritt Island
— 1 night
Drive
9
Orlando
— 6 nights

S M T W T F S
27
28
29
30
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31

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.
You'll enjoy a bit of beach vacationing at Clearwater Beach and Bean Point. Kids will appreciate attractions like St. Pete Beach and Madeira Beach. Venture out of the city with trips to Tampa (Busch Gardens Tampa Bay & 9/11 Fallen Heroes Memorial) and Treasure Island Beach (in Treasure Island). There's lots more to do: take a tour by water with Sea N Things, LLC, enjoy the sand and surf at Redington Shores Beach Access, relax in the rural setting at Horse Power for Kids & Animal Sanctuary, and stroll through Indian Shores Beach.

To see traveler tips, maps, reviews, and tourist information, use the Clearwater trip planner.

Orlando to Clearwater is an approximately 2-hour car ride. You can also do a combination of train and taxi; or take a bus. In October, daily temperatures in Clearwater can reach 85°F, while at night they dip to 71°F. Wrap up your sightseeing on the 4th (Sun) to allow time to drive to Siesta Key.

Things to do in Clearwater

Outdoors · Parks · Beaches · Theme Parks

Side Trips

Siesta Key

— 2 nights
Siesta Key draws most of its visitors with soft, white-quartz sand beaches and translucent ocean water.
Start off your visit on the 5th (Mon): kick back and relax at Crescent Beach, then stroll around Siesta Beach, then tour the pleasant surroundings at Turtle Beach, and finally kick back and relax at North Jetty Beach. Get ready for a full day of sightseeing on the next day: enjoy the sand and surf at Stump Pass Beach State Park, then relax and rejuvenate at some of the top local wellness centers, then kick back and relax at Coquina Beach, and finally get up close to creatures of the deep with Anna Maria Island Dolphin Tours.

To find other places to visit, photos, reviews, and other tourist information, refer to the Siesta Key online trip maker.

You can drive from Clearwater to Siesta Key in 1.5 hours. Other options are to do a combination of bus and taxi; or take a bus. In October in Siesta Key, expect temperatures between 86°F during the day and 68°F at night. Finish your sightseeing early on the 6th (Tue) so you can fly to Miami Beach.

Things to do in Siesta Key

Outdoors · Parks · Beaches · Wildlife

Side Trips

Miami Beach

— 3 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.
You'll visit kid-friendly attractions like South Beach and Rickenbacker Causeway Beach. You'll get in some beach time at Haulover Beach Park and 12th Street Beach. Venture out of the city with trips to JP Outfitters Inc. (in Hollywood), Wiener Museum of Decorative Arts (WMODA) (in Dania Beach) and Fort Lauderdale Beach (in Fort Lauderdale). There's much more to do: get a tailor-made plan with Art Deco Walks, enjoy some diversion at Lock & Load Miami, test your team's savvy at South Beach Room Escape, and wander the streets of Collins Avenue.

To find ratings, photos, and more tourist information, go to the Miami Beach itinerary planner.

Traveling by flight from Siesta Key to Miami Beach takes 3 hours. Alternatively, you can drive; or take a bus. Traveling from Siesta Key in October, plan for somewhat warmer nights in Miami Beach, with lows around 74°F. Finish up your sightseeing early on the 9th (Fri) so you can go by car to Marathon.

Things to do in Miami Beach

Parks · Outdoors · Beaches · Neighborhoods

Side Trips

Marathon

— 3 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.
Visit Bahia Honda State Park and Sunset Park Beach for some beach relaxation. Attractions like Sombrero Beach and Library Beach Park make great kid-friendly stops. Explore the numerous day-trip ideas around Marathon: Island Flow Yoga (in Islamorada) and Tavernier (Florida Keys Wild Bird Rehabilitation Center & Scooby's Popcorn). Next up on the itinerary: fly like a bird with Z Flight Watersports, stroll through National Key Deer Refuge, view the masterpieces at Shady Palm Art Gallery & Photography, and take in the views from Seven Mile Bridge.

To see other places to visit, where to stay, reviews, and tourist information, read Marathon travel route builder website.

You can drive from Miami Beach to Marathon in 3 hours. Alternatively, you can do a combination of flight and bus; or take a bus. October in Marathon sees daily highs of 87°F and lows of 77°F at night. Finish your sightseeing early on the 12th (Mon) to allow enough time to drive to Key West.

Things to do in Marathon

Parks · Outdoors · Wildlife · Beaches

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.
Kids will appreciate attractions like Fort Zachary Taylor and Scuba & Snorkeling. There's still lots to do: see the interesting displays at The Ernest Hemingway Home and Museum, don't miss a visit to Southernmost Point, take in the exciting artwork at 7 Artists & Friends Gallery, and explore the different monuments and memorials at Key West Cemetery.

Before you visit Key West, use our trip planner to discover what you can do and see there.

Traveling by car from Marathon to Key West takes 1.5 hours. Alternatively, you can take a bus. In October, daytime highs in Key West are 86°F, while nighttime lows are 77°F. Finish up your sightseeing early on the 17th (Sat) so you can catch the flight to Fort Walton Beach.

Things to do in Key West

Historic Sites · Museums · Parks · Outdoors

Fort Walton Beach

— 5 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 Panama City Beach. Kids will enjoy Gulf Islands National Seashore and Okaloosa Island. Get out of town with these interesting Fort Walton Beach side-trips: Pensacola Beach (in Pensacola Beach), Fly The Boat (in Navarre) and National Naval Aviation Museum (in Pensacola). The adventure continues: kick back and relax at Santa Rosa Beach, fly like a bird with Sun Dogs Parasail, contemplate the waterfront views at Destin Harbor, and brush up on your military savvy at Air Force Armament Museum.

Find out how to plan Fort Walton Beach trip without stress by asking Inspirock to help create an itinerary.

You can fly from Key West to Fort Walton Beach in 6.5 hours. Alternatively, you can drive; or do a combination of shuttle and bus. Traveling from Key West to Fort Walton Beach, you'll gain 1 hour due to the time zone difference. In October, Fort Walton Beach is little chillier than Key West - with highs of 80°F and lows of 60°F. Wrap up your sightseeing on the 22nd (Thu) to allow time to fly to St. Augustine.

Things to do in Fort Walton Beach

Outdoors · Parks · Beaches · Nature

Side Trips

St. Augustine

— 2 nights
St. Start off your visit on the 23rd (Fri): kick back and relax at Crescent Beach Public Beach, explore the galleries of St. Augustine Lighthouse & Maritime Museum, Inc., then enjoy the sand and surf at St. Augustine Beach, then see the interesting displays at The Ximenez-Fatio House, and finally don't miss a visit to St. George Street. On the next day, stroll through Ormond Beach, then explore the activities along River to Sea Trail Preserve, then meet the residents at St. Augustine Wild Reserve, and finally tour the pleasant surroundings at Jacksonville Beach.

For reviews, where to stay, photos, and more tourist information, you can read our St. Augustine driving holiday planner.

Traveling by flight from Fort Walton Beach to St. Augustine takes 5.5 hours. Alternatively, you can drive; or take a bus. The time zone changes from Central Standard Time to Eastern Standard Time, which is usually a 1 hour difference. Plan for somewhat warmer nights when traveling from Fort Walton Beach in October since evenings lows in St. Augustine dip to 67°F. Wrap up your sightseeing on the 24th (Sat) early enough to drive to Merritt Island.

Things to do in St. Augustine

Parks · Outdoors · Beaches · Museums

Side Trips

Merritt Island

— 1 night
Start off your visit on the 25th (Sun): don't miss a visit to Sams House at Pine Island Conservation Area, then engage your brain at Space Shuttle Atlantis, then examine the collection at NASA Kennedy Space Center Visitor Complex, and finally head outdoors with Local Lines Guide Service.

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

You can drive from St. Augustine to Merritt Island in 2.5 hours. Alternatively, you can do a combination of bus and car; or do a combination of bus and taxi. Expect a bit warmer evenings in Merritt Island when traveling from St. Augustine in October, with lows around 73°F. Finish your sightseeing early on the 25th (Sun) to allow enough time to drive to Orlando.

Things to do in Merritt Island

Childrens Museums · Museums · Outdoors

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.
Family-friendly places like Universal's Islands of Adventure and Discovery Cove will thrill your kids. Have a day of magic on the 26th (Mon) at Walt Disney World Resort. Next up on the itinerary: find something for the whole family at Universal Orlando Resort, make an unforgettable trip to Disney's Typhoon Lagoon Water Park, stop by M&M'S Store at Disney Springs, and experience rural life at Beck Brothers blueberries U-Pick.

To find traveler tips, more things to do, photos, and other tourist information, read Orlando journey planning site.

Drive from Merritt Island to Orlando in 1.5 hours. Alternatively, you can take a shuttle. October in Orlando sees daily highs of 85°F and lows of 69°F at night. Wrap up your sightseeing on the 31st (Sat) to allow time to travel back home.

Things to do in Orlando

Theme Parks · Shopping · Historic Sites

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.