38 days in Florida Itinerary

38 days in Florida Itinerary

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Route & dates

38 days in Florida Itinerary

Start: Moline
Fly + Drive:  7​h
1
Santa Rosa Beach
— 4 nights
Drive:  4​h 45​min
2
Clearwater
— 1 night
Drive:  2​h
3
Orlando
— 6 nights
Drive:  2​h
4
St. Augustine
— 5 nights
Drive + Fly:  4​h 45​min
5
Miami Beach
— 4 nights
Drive:  1​h 30​min
6
Key Largo
— 3 nights
Drive:  45​min
7
Islamorada
— 3 nights
Drive:  45​min
8
Marathon
— 4 nights
bus:  1​h 15​min
9
Key West
— 6 nights
Fly:  7​h 15​min
End: Moline

4
nights
Santa Rosa Beach

Santa Rosa Beach ©
Museum-lovers will appreciate Modus Photography and Fusion Art Glass Gallery. You'll visit kid-friendly attractions like Santa Rosa Beach and Henderson Beach State Park.

For photos, reviews, traveler tips, and other tourist information, refer to the Santa Rosa Beach trip itinerary website .

Moline to Santa Rosa Beach is an approximately 7-hour flight. You can also drive. Plan for a bit warmer nights when traveling from Moline in June since evenings lows in Santa Rosa Beach dip to 76°F. Finish up your sightseeing early on the 14th (Fri) so you can travel to Clearwater.

Things to do in Santa Rosa Beach

Parks Outdoors Beaches

Side Trips

Destin, Seaside, Grand Boulevard at Sandestin, Eden Gardens State Park
Highlights from your plan
Eden Gardens State Park ©
Eden Gardens State Park
Blue Mountain Beach ©
Blue Mountain Beach
Henderson Beach State Park ©
Henderson Beach State Park

1
night
Clearwater

Clearwater ©
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.
Kick off your visit on the 15th (Sat): take an in-depth tour of Pinellas County Heritage Village, shop like a local with Graphi-ko Gallery, then take in the exciting artwork at Morean Art Center, then shop like a local with Duncan McClellan Gallery, and finally get interesting insight from Tours. On the 16th (Sun), you'll have a packed day of sightseeing: take in the spiritual surroundings of St. Nicholas Greek Orthodox Cathedral, look for gifts at Miss Merrie's Sweets and Treats, then contemplate the long history of Philippe Park, and finally tour the pleasant surroundings at Clearwater Beach.

To find other places to visit, where to stay, maps, and other tourist information, go to the Clearwater itinerary planner .

Do a combination of bus and flight from Santa Rosa Beach to Clearwater in 5 hours. Alternatively, you can fly; or drive. The time zone difference when traveling from Santa Rosa Beach to Clearwater is 1 hour. Expect a daytime high around 90°F in June, and nighttime lows around 75°F. Finish your sightseeing early on the 16th (Sun) to allow enough time to drive to Orlando.

Things to do in Clearwater

Outdoors Parks Museums

Side Trips

St. Petersburg, Tarpon Springs, Pinellas County Heritage Village, Philippe Park, Parasailing & Paragliding
Highlights from your plan
Duncan McClellan Gallery ©
Duncan McClellan Gallery
Clearwater Beach ©
Clearwater Beach
Parasailing & Paragliding

6
nights
Orlando

Orlando ©
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.
Kids will appreciate attractions like Discovery Cove and Universal Orlando Resort. Have a day of magic on the 18th (Tue) at Walt Disney World Resort. Pack the 20th (Thu) with family-friendly diversions at Universal's Islands of Adventure. Next up on the itinerary: find something for the whole family at SeaWorld Orlando, discover the magic at Magic Kingdom Park, laugh and play at Happily Ever After Fireworks, and look for gifts at The LEGO Store Downtown Disney.

For reviews, traveler tips, maps, and tourist information, read our Orlando day trip app .

Traveling by car from Clearwater to Orlando takes 2 hours. Alternatively, you can take a bus; or take a bus. June in Orlando sees daily highs of 91°F and lows of 73°F at night. Finish up your sightseeing early on the 22nd (Sat) so you can go by car to St. Augustine.

Things to do in Orlando

Theme Parks Outdoors Parks
Highlights from your plan
Universal Orlando Resort ©
Universal Orlando Resort
Walt Disney World Resort ©
Walt Disney World Resort
Discovery Cove ©
Discovery Cove

5
nights
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. Family-friendly places like Andy Romano Beachfront Park and Frank Butler County Park West will thrill your kids. Museum-lovers will appreciate St. Augustine Lighthouse & Maritime Museum, Inc. and St. Photios Greek Orthodox National Shrine. You'll find plenty of places to visit near St. Augustine: St. Brendan Catholic Church (in Ormond Beach) and Bulow Plantation Ruins Historic State Park (in Bunnell). Spend the 27th (Thu) exploring nature at Fort Matanzas National Monument. Next up on the itinerary: tour the pleasant surroundings at St. Augustine Beach, take in the architecture and atmosphere at Cathedral Basilica of St. Augustine, admire the striking features of Old Jail, and brush up on your knowledge of spirits at St. Augustine Distillery.

To see where to stay, more things to do, reviews, and other tourist information, you can read our St. Augustine journey website .

Getting from Orlando to St. Augustine by car takes about 2 hours. Other options: take a bus. In June, daytime highs in St. Augustine are 88°F, while nighttime lows are 73°F. Wrap up your sightseeing on the 27th (Thu) early enough to travel to Miami Beach.

Things to do in St. Augustine

Historic Sites Parks Outdoors

Side Trips

Ormond Beach, Crescent Beach Public Beach
Highlights from your plan
St. Augustine Beach ©
St. Augustine Beach
Cathedral Basilica of St. Augustine ©

4
nights
Miami Beach

Miami Beach ©
Separated by water from the neighboring city of Miami, Miami Beach sits on a barrier island between Biscayne Bay and the Atlantic Ocean.
Lincoln Road and Art Deco Tours will appeal to history buffs. Do your shopping at Aventura Mall and Dolphin Mall. Go for a jaunt from Miami Beach to Sunrise to see Sawgrass Mills about 48 minutes away. There's lots more to do: appreciate the extensive heritage of Art Deco Historic District, tour the pleasant surroundings at South Beach, buy something for everyone on your list at Bayside Marketplace, and make a trip to Collins Avenue.

To find maps, reviews, other places to visit, and more tourist information, go to the Miami Beach visit website .

Traveling by combination of car and flight from St. Augustine to Miami Beach takes 5 hours. Alternatively, you can drive; or take a bus. In June, daytime highs in Miami Beach are 89°F, while nighttime lows are 77°F. Wrap up your sightseeing on the 1st (Mon) to allow time to drive to Key Largo.

Things to do in Miami Beach

Shopping Neighborhoods Historic Sites

Side Trips

Miami, Aventura Mall, Village of Merrick Park, Sawgrass Mills
Highlights from your plan
Lincoln Road ©
Lincoln Road
South Beach ©
South Beach
Art Deco Historic District ©
Art Deco Historic District

3
nights
Key Largo

Key Largo ©
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.
Coral Castle and Saint Justin Martyr Catholic Church will appeal to history buffs. Head to Shell World Florida Keys and Sandal Factory Outletfor plenty of shopping. Step out of Key Largo to go to Everglades National Park and see Anhinga Trail, which is approximately 48 minutes away. There's much more to do: admire nature's wide array of creatures at Island Dolphin Care, explore and take pictures at Spiegel Grove, identify plant and animal life at Florida Keys Wild Bird Rehabilitation Center, and take in the architecture and atmosphere at Key Largo Baptist Church.

For ratings, photos, traveler tips, and tourist information, read Key Largo trip itinerary builder tool .

You can drive from Miami Beach to Key Largo in 1.5 hours. Alternatively, you can take a bus. In July, daytime highs in Key Largo are 89°F, while nighttime lows are 76°F. Wrap up your sightseeing on the 4th (Thu) to allow time to drive to Islamorada.

Things to do in Key Largo

Wildlife Parks Outdoors

Side Trips

Coral Castle, Anhinga Trail
Highlights from your plan
Island Dolphin Care ©
Island Dolphin Care
Dolphins Plus Marine Mammal Responder ©

3
nights
Islamorada

Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
Head to Lobster Trap Art Gallery and Michelle Nicole Lowe Art Galleryfor plenty of shopping. Attractions like Fishing Charters & Tours and Anne's Beach make great kid-friendly stops. There's still lots to do: contemplate the long history of Indian Key State Historic Site, get a taste of the local shopping with The Rain Barrel Artisan Village, get engrossed in the history at History of Diving Museum, and take in the exciting artwork at Gallery Morada.

For photos, ratings, where to stay, and other tourist information, you can read our Islamorada road trip site .

Traveling by car from Key Largo to Islamorada takes an hour. Alternatively, you can do a combination of taxi and bus. In July, daily temperatures in Islamorada can reach 92°F, while at night they dip to 81°F. Cap off your sightseeing on the 7th (Sun) early enough to go by car to Marathon.

Things to do in Islamorada

Outdoors Museums Tours
Highlights from your plan
Fishing Charters & Tours
Anne's Beach ©
Anne's Beach
Old Road Gallery ©
Old Road Gallery

4
nights
Marathon

Marathon ©
A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
Relax by the water at Bahia Honda State Park and Sombrero Beach. You'll visit kid-friendly attractions like National Key Deer Refuge and Sunset Park Beach. And it doesn't end there: take in the architecture and atmosphere at San Pablo Catholic Church, look for gifts at Christina's Consignment Boutique, look for all kinds of wild species at The Turtle Hospital, and get answers to all your questions at Pigeon Key Foundation.

Take the guesswork out of planning a Marathon vacation by using our trip itinerary maker.

Traveling by car from Islamorada to Marathon takes an hour. Alternatively, you can take a bus. In July, plan for daily highs up to 92°F, and evening lows to 81°F. Finish up your sightseeing early on the 11th (Thu) so you can catcht the bus to Key West.

Things to do in Marathon

Parks Wildlife Outdoors

Side Trips

Big Pine Key, Sunset Park Beach
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
National Key Deer Refuge ©
National Key Deer Refuge
Sombrero Beach ©
Sombrero Beach

6
nights
Key West

Key West ©
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.
Bring the kids along to Fort Zachary Taylor and Mel Fisher Maritime Heritage Museum. You'll explore and learn at The Ernest Hemingway Home and Museum and Truman Little White House. There's lots more to do: get a taste of the local shopping with Alan S. Maltz Gallery, take in panoramic vistas at Key West Shipwreck Treasure Museum, look for gifts at Rodriguez Cigar Factory, and stroll the grounds of Key West Cemetery.

For other places to visit, more things to do, maps, and tourist information, read our Key West trip itinerary planner .

Traveling by bus from Marathon to Key West takes 1.5 hours. Alternatively, you can drive. In July, daily temperatures in Key West can reach 89°F, while at night they dip to 81°F. Finish your sightseeing early on the 17th (Wed) so you can travel back home.

Things to do in Key West

Historic Sites Museums Outdoors
Highlights from your plan
The Ernest Hemingway Home and Museum ©
Truman Little White House ©
Truman Little White House

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