27 days in Florida Itinerary

27 days in Florida Itinerary

Created using Inspirock Florida visit planner

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Route & dates

27 days in Florida Itinerary

Start: Boston
Fly:  6​h 30​min
1
Key West
— 1 night
bus:  1​h 15​min
2
Marathon
— 2 nights
Drive:  4​h
3
Marco Island
— 2 nights
Drive:  1​h 45​min
4
Sanibel Island
— 2 nights
Drive:  2​h
5
Sarasota
— 2 nights
Drive:  1​h 15​min
6
Tampa
— 2 nights
Drive:  3​h 30​min
7
St. Augustine
— 2 nights
Drive:  2​h
8
Orlando
— 4 nights
Drive:  45​min
9
Saint Cloud
— 3 nights
Fly + taxi:  5​h 15​min
10
Pensacola Beach
— 3 nights
Drive + Fly:  5​h 15​min
11
Daytona Beach
— 3 nights
shuttle + Fly:  6​h 30​min
End: Boston

1
night
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.
On the 22nd (Fri), examine the collection at The Ernest Hemingway Home and Museum, identify plant and animal life at Key West Butterfly & Nature Conservatory, then observe the fascinating underwater world at Florida Keys Eco-Discovery Center, then brush up on your military savvy at U.S. Coast Guard Cutter Ingham Maritime Museum, and finally go for a walk through Key West Garden Club. Get ready for a full day of sightseeing on the next day: examine the collection at Mel Fisher Maritime Heritage Museum, then get engrossed in the history at Key West Firehouse Museum, and then take in the architecture and atmosphere at Saint Mary Star of the Sea.

For ratings, reviews, maps, and more tourist information, use the Key West driving holiday planner .

Boston to Key West is an approximately 6.5-hour flight. You can also do a combination of bus and flight; or drive. Expect warmer temperatures when traveling from Boston in November; daily highs in Key West reach 81°F and lows reach 73°F. Cap off your sightseeing on the 23rd (Sat) early enough to catcht the bus to Marathon.

Things to do in Key West

Museums Parks Historic Sites
Highlights from your plan
Florida Keys Eco-Discovery Center ©
Florida Keys Eco-Discovery Center
Mel Fisher Maritime Heritage Museum ©

2
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.
Kick off your visit on the 24th (Sun): explore the gorgeous colors at Sombrero Reef, enjoy the sand and surf at Sombrero Beach, then look for all kinds of wild species at Crane Point Museum & Nature Center, and finally snap pictures at Old Seven Mile Bridge. Get ready for a full day of sightseeing on the 25th (Mon): enjoy the sand and surf at Bahia Honda State Park, then identify plant and animal life at Dolphin Research Center, and then get a taste of the local shopping with Shady Palm Art Gallery & Photography.

For ratings, where to stay, maps, and tourist information, read Marathon online road trip planner .

Traveling by bus from Key West to Marathon takes 1.5 hours. Alternatively, you can drive. In November, daily temperatures in Marathon can reach 82°F, while at night they dip to 72°F. Finish your sightseeing early on the 25th (Mon) to allow enough time to drive to Marco Island.

Things to do in Marathon

Parks Wildlife Beaches

Side Trip

Bahia Honda State Park
Highlights from your plan
Crane Point Museum & Nature Center ©
Dolphin Research Center ©
Dolphin Research Center
Bahia Honda State Park ©
Bahia Honda State Park

2
nights
Marco Island

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. Kick off your visit on the 26th (Tue): get a dose of the wild on a nature and wildlife tour, then head off the coast to Cape Romano, and then kick back and relax at Keewaydin Island. Here are some ideas for day two: get up close to creatures of the deep with a dolphin and whale watching tour, then walk around Mackle Park, and then have some family-friendly fun at Marco Golf and Garden.

To find other places to visit, maps, more things to do, and more tourist information, read our Marco Island travel route planning tool .

Traveling by car from Marathon to Marco Island takes 4 hours. Alternatively, you can do a combination of bus and ferry; or do a combination of bus and flight. Traveling from Marathon in November, you can expect nighttime temperatures to be a bit cooler in Marco Island, with lows of 64°F. Finish your sightseeing early on the 27th (Wed) to allow enough time to drive to Sanibel Island.

Things to do in Marco Island

Outdoors Parks Wildlife
Highlights from your plan
Dolphin & Whale Watching
Keewaydin Island ©
Keewaydin Island
Frank E. Mackle Park ©
Frank E. Mackle Park

2
nights
Sanibel Island

Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.
Start off your visit on the 28th (Thu): contemplate in the serene atmosphere at Captiva Chapel By-The-Sea, then see what you can catch with a fishing tour, then get outside with Whitney's Bait and Tackle, and finally let the kids burn off some steam at Sanibel Community Playground. On the 29th (Fri), you'll have a packed day of sightseeing: enjoy the sand and surf at Captiva Beach, stroll through Bowman's Beach, and then kick back and relax at Little Hickory Beach Park.

To find traveler tips, other places to visit, maps, and tourist information, use the Sanibel Island trip website .

You can drive from Marco Island to Sanibel Island in 2 hours. In November, daytime highs in Sanibel Island are 82°F, while nighttime lows are 63°F. Wrap up your sightseeing on the 29th (Fri) early enough to drive to Sarasota.

Things to do in Sanibel Island

Outdoors Parks Beaches

Side Trips

Captiva Island, Little Hickory Beach Park
Highlights from your plan
Fishing Charters & Tours
Captiva Beach ©
Captiva Beach
Bowman's Beach ©
Bowman's Beach

2
nights
Sarasota

Sarasota ©
Sarasota is a city in Sarasota County on the southwestern coast of the U.S. On the 30th (Sat), enjoy the sand and surf at North Jetty Beach, tour the pleasant surroundings at Coquina Beach, and then get up close and personal with brilliant marine life at Mote Marine Laboratory and Aquarium. Get ready for a full day of sightseeing on the next day: get up close to creatures of the deep with a dolphin and whale watching tour, admire the majestic nature at Ted Sperling Park, then kick back and relax at South Lido Park, and finally stroll around Payne Park.

Use Inspirock's suggestions to plan your Sarasota trip and find the best activities and attractions for your vacation.

Getting from Sanibel Island to Sarasota by car takes about 2 hours. Other options: take a bus. In November in Sarasota, expect temperatures between 80°F during the day and 62°F at night. Finish your sightseeing early on the 1st (Sun) so you can drive to Tampa.

Things to do in Sarasota

Parks Outdoors Beaches

Side Trips

Coquina Beach, Dolphin & Whale Watching, North Jetty Beach
Highlights from your plan
Payne Park ©
Payne Park
Mote Marine Laboratory and Aquarium ©
Dolphin & Whale Watching

2
nights
Tampa

Tampa ©
Tampa ranks among the country's most livable cities, attracting newcomers with its growing economy and status as a major port on the Gulf of Mexico.
Kick off your visit on the 2nd (Mon): find something for the whole family at Busch Gardens Tampa Bay and then walk around Lettuce Lake Regional Park. Get ready for a full day of sightseeing on the next day: explore the engaging exhibits at Glazer Children's Museum, then learn about wildlife with up-close encounters at Big Cat Rescue, and then enjoy the sand and surf at Treasure Island Beach.

To see traveler tips, where to stay, photos, and tourist information, use the Tampa holiday app .

You can drive from Sarasota to Tampa in 1.5 hours. Alternatively, you can take a bus. In December, plan for daily highs up to 78°F, and evening lows to 61°F. Finish up your sightseeing early on the 3rd (Tue) so you can go by car to St. Augustine.

Things to do in Tampa

Parks Theme Parks Beaches

Side Trip

Treasure Island Beach
Highlights from your plan
Big Cat Rescue ©
Big Cat Rescue
Busch Gardens Tampa Bay ©
Busch Gardens Tampa Bay
Glazer Children's Museum ©
Glazer Children's Museum

2
nights
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. On the 4th (Wed), kick back and relax at Crescent Beach Public Beach, have some family-friendly fun at Fiesta Falls Miniature Golf, take an in-depth tour of Medieval Torture Museum, then brush up on your knowledge of spirits at St. Augustine Distillery, and finally get engrossed in the history at Old Florida Museum. Get ready for a full day of sightseeing on the next day: tour the pleasant surroundings at Atlantic Beach, then tour the pleasant surroundings at Jacksonville Beach, and then kick back and relax at Vilano Beach.

To find where to stay, other places to visit, reviews, and more tourist information, read St. Augustine trip planner .

Traveling by car from Tampa to St. Augustine takes 3.5 hours. Alternatively, you can take a bus. Traveling from Tampa in December, things will get a bit cooler in St. Augustine: highs are around 70°F and lows about 55°F. Finish your sightseeing early on the 5th (Thu) so you can drive to Orlando.

Things to do in St. Augustine

Beaches Outdoors Parks

Side Trips

Jacksonville Beach, Crescent Beach Public Beach, Atlantic Beach
Highlights from your plan
Vilano Beach ©
Vilano Beach
Jacksonville Beach ©
Jacksonville Beach
Fiesta Falls Miniature Golf ©
Fiesta Falls Miniature Golf

4
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.
Eschew the tourist crowds and head to Avatar Flight of Passage and Tree of Life. There's more to do: make an unforgettable trip to Pandora – The World of Avatar.

For ratings, traveler tips, and tourist information, use the Orlando trip website .

Drive from St. Augustine to Orlando in 2 hours. Alternatively, you can take a bus. Traveling from St. Augustine in December, expect nights in Orlando to be about the same, around 59°F, while days are a bit warmer, around 77°F. Wrap up your sightseeing by early afternoon on the 9th (Mon) to allow enough time to drive to Saint Cloud.

Things to do in Orlando

Theme Parks
Highlights from your plan
Avatar Flight of Passage ©
Avatar Flight of Passage
Tree of Life ©
Tree of Life
Pandora – The World of Avatar ©
Pandora – The World of Avatar

3
nights
Saint Cloud

Saint Cloud ©
St. You've now added Wild Willy's Airboat Tours to your itinerary. On the 10th (Tue), kick back and relax at Dan Tarell Memorial Point, get a new perspective on things with Wild Willy's Airboat Tours, and then tee off at Royal St Cloud Golf Links. On your second day here, experience rural life at LaPorte Farms and then see what you can catch with a fishing tour.

To see where to stay, reviews, more things to do, and tourist information, go to the Saint Cloud driving holiday site .

Getting from Orlando to Saint Cloud by car takes about an hour. Other options: do a combination of train and taxi; or do a combination of bus and taxi. December in Saint Cloud sees daily highs of 78°F and lows of 57°F at night. On the 12th (Thu), wrap the sightseeing up by early afternoon so you can travel to Pensacola Beach.

Things to do in Saint Cloud

Outdoors Wildlife Tours

Side Trip

LaPorte Farms
Highlights from your plan
Wild Willy's Airboat Tours ©
Wild Willy's Airboat Tours
Reptile World Serpentarium ©
Reptile World Serpentarium
LaPorte Farms ©
LaPorte Farms

3
nights
Pensacola Beach

Pensacola Beach ©
Pensacola Beach is an unincorporated community located on Santa Rosa Island, a barrier island, in Escambia County, Florida, United States. Your day-by-day itinerary now includes Pensacola Beach. You'll visit kid-friendly attractions like Gulf Islands National Seashore and Fishing Charters & Tours. You'll explore the less-touristy side of things at Emerald Coast Zoo and Fort Pickens Area. Step out of Pensacola Beach to go to Fort Walton Beach and see Garnier Post Office, which is approximately 56 minutes away. Next up on the itinerary: look for gifts at Innerlight Surf Shop, brush up on your knowledge of spirits at Rollins Distillery, and walk around Destin Dog Park.

For maps, more things to do, traveler tips, and other tourist information, read our Pensacola Beach sightseeing planner .

You can do a combination of flight and taxi from Saint Cloud to Pensacola Beach in 5.5 hours. Other options are to fly; or drive. The time zone changes from Eastern Standard Time (EST) to Central Standard Time (CST), which is usually a -1 hour difference. Traveling from Saint Cloud in December, things will get slightly colder in Pensacola Beach: highs are around 67°F and lows about 50°F. Finish up your sightseeing early on the 15th (Sun) so you can travel to Daytona Beach.

Things to do in Pensacola Beach

Outdoors Parks Beaches

Side Trips

Fort Walton Beach, Rollins Distillery, Destin Dog Park, Emerald Coast Zoo
Highlights from your plan
Pensacola Beach ©
Pensacola Beach
Gulf Islands National Seashore ©
Gulf Islands National Seashore
Emerald Coast Zoo ©
Emerald Coast Zoo

3
nights
Daytona Beach

Daytona Beach ©
The iconic seaside destination of Daytona Beach once supported sugar mill plantations, but now entertains up to 8 million visitors a year.
You've now added Beach at Daytona Beach to your itinerary. On the 16th (Mon), don't miss a visit to Ritchey Plaza, kick back and relax at Beach at Daytona Beach, then pause for some serene contemplation at Our Lady of Lourdes Catholic Church, and finally contemplate the long history of Mary Bethune Home. Get ready for a full day of sightseeing on the 17th (Tue): join the crowd at Daytona International Speedway, examine the collection at MOAS - Museum of Arts and Sciences, then learn about all things military at Veterans Museum & Education Center, and finally join the crowd at Richard Petty Driving Experience.

To find maps, traveler tips, and tourist information, use the Daytona Beach trip builder .

You can do a combination of car and flight from Pensacola Beach to Daytona Beach in 5.5 hours. Other options are to do a combination of taxi and flight; or drive. Due to the time zone difference, you'll lose 1 hour traveling from Pensacola Beach to Daytona Beach. Plan for somewhat warmer temperatures traveling from Pensacola Beach in December, with highs in Daytona Beach at 75°F and lows at 57°F. Wrap up your sightseeing by early afternoon on the 18th (Wed) to allow time for travel back home.

Things to do in Daytona Beach

Historic Sites Parks Beaches

Side Trips

Dunlawton Sugar Mill Gardens, Andy Romano Beachfront Park
Highlights from your plan
Mary Bethune Home ©
Mary Bethune Home
Beach at Daytona Beach ©
Beach at Daytona Beach
Daytona International Speedway ©
Daytona International Speedway

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