29 days in Florida Itinerary

29 days in Florida Itinerary

Created using Inspirock Florida trip planner

Plan created by another user. Make it yours
1
Siesta Key
— 2 nights
2
Key West
— 4 nights
3
Marathon
— 4 nights
4
Clearwater
— 3 nights
5
Fort Walton Beach
— 5 nights
6
St. Augustine
— 3 nights
7
Merritt Island
— 1 night
8
Orlando
— 6 nights

S M T W T F S
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2
nights
Siesta Key

Siesta Key draws most of its visitors with soft, white-quartz sand beaches and translucent ocean water.
On the 2nd (Fri), kick back and relax at Siesta Beach, kick back and relax at Siesta Key Beach, then enjoy the sand and surf at Crescent Beach, then relax and rejuvenate at some of the top local wellness centers, and finally kick back and relax at Stump Pass Beach State Park. Get ready for a full day of sightseeing on the 3rd (Sat): enjoy the sand and surf at Turtle Beach, glide peacefully along the water with some of the best stand-up paddleboarding in the area, and then get up close and personal with brilliant marine life at Mote Marine Laboratory & Aquarium.

To find ratings, traveler tips, reviews, and other tourist information, refer to the Siesta Key day trip website.

Ocala to Siesta Key is an approximately 3-hour car ride. You can also drive; or do a combination of bus and taxi. Traveling from Ocala in October, you can expect nighttime temperatures to be a bit warmer in Siesta Key, with lows of 68°F. Wrap up your sightseeing on the 3rd (Sat) early enough to travel to Key West.

Things to do in Siesta Key

Outdoors · Parks · Beaches · Adventure

Side Trips

Highlights from your plan
Stand-Up Paddleboarding
Siesta Beach ©
Siesta Beach
Crescent Beach ©
Crescent Beach

4
nights
Key West

Key West ©

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 The Ernest Hemingway Home and Museum and Scuba & Snorkeling will thrill your kids. Next up on the itinerary: identify plant and animal life at Key West Butterfly & Nature Conservatory, don't miss a visit to Duval Street, stroll the grounds of Key West Cemetery, and stroll through Fort Zachary Taylor.

To see ratings, traveler tips, maps, and more tourist information, read our Key West trip itinerary builder website.

Do a combination of bus and flight from Siesta Key to Key West in 7 hours. Alternatively, you can fly; or drive; or do a combination of bus, taxi, and ferry. Traveling from Siesta Key in October, you can expect nighttime temperatures to be somewhat warmer in Key West, with lows of 77°F. Wrap up your sightseeing on the 7th (Wed) to allow time to drive to Marathon.

Things to do in Key West

Museums · Parks · Historic Sites · Tours
Highlights from your plan
Air Adventures Helicopter Tours ©
Air Adventures Helicopter Tours
Fort Zachary Taylor ©
Fort Zachary Taylor
Key West Butterfly & Nature Conservatory ©
Key West Butterfly & Nature Conservatory

4
nights
Marathon

Marathon ©

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 Sunset Park Beach. Kids will appreciate attractions like Theater of the Sea and Sombrero Beach. Venture out of the city with trips to Island Dolphin Care (in Key Largo), Island Flow Yoga (in Islamorada) and Florida Keys Wild Bird Rehabilitation Center (in Tavernier). There's lots more to do: look for all kinds of wild species at National Key Deer Refuge, examine the collection at Crane Point Museum & Nature Center, relax in the rural setting at Grimal Grove, and view the masterpieces at Shady Palm Art Gallery & Photography.

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. Another option is to 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

Highlights from your plan
Island Dolphin Care ©
Island Dolphin Care
Bahia Honda State Park ©
Bahia Honda State Park
Sombrero Beach ©
Sombrero Beach

3
nights
Clearwater

Clearwater ©

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 Madeira Beach for some beach relaxation. You'll visit kid-friendly attractions like Busch Gardens Tampa Bay and Treasure Island Beach. Venture out of the city with trips to St. Pete Beach (Two Friend's Closet & Saint Pete Beach) and Tampa (Sunshine Skyway Bridge & The Florida Aquarium). Next up on the itinerary: get up close and personal with brilliant marine life at Clearwater Marine Aquarium, admire the majestic nature at Honeymoon Island State Park, get interesting insight from Tours, 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 7 hours. Alternatively, you can fly; 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 travel to Fort Walton Beach.

Things to do in Clearwater

Parks · Outdoors · Beaches · Theme Parks

Side Trips

Highlights from your plan
Clearwater Beach ©
Clearwater Beach
Busch Gardens Tampa Bay ©
Busch Gardens Tampa Bay
Saint Pete Beach ©
Saint Pete Beach

5
nights
Fort Walton Beach

Fort Walton Beach ©
Fort Walton Beach is a city in southern Okaloosa County, Florida, United States. Relax by the water at Navarre Beach and Panama City Beach. Bring the kids along to Gulf Islands National Seashore and Okaloosa Island. Get out of town with these interesting Fort Walton Beach side-trips: Santa Rosa Beach (in Santa Rosa Beach), Gail Walsh Massage & Skincare Co. (in Gulf Breeze) and Panama City Beach (St. Andrews State Park & Abc Fine Wine And Spirits). There's lots more to do: tour the pleasant surroundings at Pensacola Beach, learn about all things military at Air Force Armament Museum, kick back and relax at Henderson Beach State Park, and step off the mainland to explore Gulf Islands.

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 6.5 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 drive to St. Augustine.

Things to do in Fort Walton Beach

Outdoors · Parks · Beaches · Nature

Side Trips

Highlights from your plan
National Naval Aviation Museum ©
National Naval Aviation Museum
Navarre Beach ©
Navarre Beach
Gulf Islands National Seashore ©
Gulf Islands National Seashore

3
nights
St. Augustine

St. Augustine ©
St. Kids will enjoy Andy Romano Beachfront Park and Ormond Beach. We've included these beaches for you: St. Augustine Beach and Jacksonville Beach. There's still lots to do: look for all kinds of wild species at St. Augustine Wild Reserve, immerse yourself in nature at Anastasia State Park, gain insight at Flagler College, and go on a hair-raising tour with a ghost and vampire tour.

To see traveler tips, reviews, other places to visit, and other tourist information, use the St. Augustine trip itinerary planner.

You can drive from Fort Walton Beach to St. Augustine in 6.5 hours. Alternatively, you can drive; or fly; or take a bus. Traveling from Fort Walton Beach to St. Augustine, you'll lose 1 hour due to the time zone difference. Traveling from Fort Walton Beach in October, expect a bit warmer with lows of 67°F in St. Augustine. Wrap up your sightseeing on the 22nd (Thu) to allow time to drive to Merritt Island.

Things to do in St. Augustine

Parks · Beaches · Outdoors · Museums

Side Trips

Highlights from your plan
St. Augustine Wild Reserve ©
St. Augustine Wild Reserve
St. Augustine Beach ©
St. Augustine Beach
Ormond Beach ©
Ormond Beach

1
night
Merritt Island

Merritt Island ©
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.

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

Museums · Childrens Museums · Outdoors · Beaches

Side Trip

Highlights from your plan
Space Shuttle Atlantis ©
Space Shuttle Atlantis
NASA Kennedy Space Center Visitor Complex ©
NASA Kennedy Space Center Visitor Complex
Jetty Park ©
Jetty Park

6
nights
Orlando

Orlando ©

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 Universal Orlando Resort and Walt Disney World 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 25th (Sun) at Magic Kingdom Park. Next up on the itinerary: try out the rides at Discovery Cove, look for gifts at M&M'S World Orlando, get in on the family fun at SeaWorld, and discover the magic at Avatar Flight of Passage.

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

Traveling by car from Merritt Island to Orlando takes 1.5 hours. Alternatively, you can take a shuttle. In October in Orlando, expect temperatures between 85°F during the day and 69°F at night. Wrap up your sightseeing on the 29th (Thu) early enough to drive back home.

Things to do in Orlando

Theme Parks · Outdoors · Beaches · Parks

Side Trip

Highlights from your plan
Walt Disney World Resort ©
Walt Disney World Resort
Universal Orlando Resort ©
Universal Orlando Resort
Universal's Islands of Adventure ©
Universal's Islands of Adventure

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