14 days in Florida Itinerary

14 days in Florida Itinerary

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Route & dates

14 days in Florida Itinerary

Start: Tampa
Drive:  2​h 45​min
1
Sanibel Island
— 1 night
Drive:  1​h 15​min
2
Naples
— 2 nights
Drive:  30​min
3
Marco Island
— 2 nights
ferry:  2​h 30​min
4
Key West
— 3 nights
bus:  1​h 15​min
5
Marathon
— 2 nights
Drive:  45​min
6
Islamorada
— 2 nights
+2
shuttle + Fly + Drive:  5​h 30​min
7
St. Augustine
— 1 day
Drive:  3​h 30​min
End: Tampa

1
night
Sanibel Island

Sanibel Island ©
Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.
Kick off your visit on the 22nd (Fri): enjoy the sand and surf at Captiva Beach and then kick back and relax at Bowman's Beach. Here are some ideas for day two: identify plant and animal life at Pond Apple Park, then shop like a local with Tower Gallery, then examine the collection at The Bailey-Matthews National Shell Museum, and finally see what you can catch with a fishing tour.

To find maps, traveler tips, and more tourist information, you can read our Sanibel Island online holiday builder .

Tampa to Sanibel Island is an approximately 3-hour car ride. You can also take a bus. In February, daytime highs in Sanibel Island are 79°F, while nighttime lows are 58°F. Wrap up your sightseeing on the 23rd (Sat) early enough to drive to Naples.

Things to do in Sanibel Island

Outdoors Parks Beaches

Side Trip

Captiva Island
Highlights from your plan
Captiva Beach ©
Captiva Beach
Fishing Charters & Tours

2
nights
Naples

Naples is a city in Collier County, Florida, United States. Start off your visit on the 24th (Sun): identify plant and animal life at Audubon Corkscrew Swamp Sanctuary and then see majestic marine mammals with a dolphin and whale watching tour. On the next day, admire the masterpieces at Naples Art Association, don't miss a visit to Fifth Avenue South, and then see what you can catch with a fishing tour.

To see maps, more things to do, where to stay, and more tourist information, read Naples trip itinerary builder tool .

Traveling by car from Sanibel Island to Naples takes 1.5 hours. In February, daytime highs in Naples are 78°F, while nighttime lows are 60°F. Wrap up your sightseeing on the 25th (Mon) early enough to drive to Marco Island.

Things to do in Naples

Wildlife Outdoors Tours

Side Trip

Dolphin & Whale Watching
Highlights from your plan
Fishing Charters & Tours
Dolphin & Whale Watching
Corkscrew Swamp ©
Corkscrew Swamp

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. On the 26th (Tue), race across the water with a speed boat tour and then see what you can catch with a fishing tour. Get ready for a full day of sightseeing on the 27th (Wed): browse the eclectic array of goods at Marco Island Farmers Market-Wednesday- Mid November to Mid April, then take a tour by water with Boat Tours & Water Sports, and then get some thrills out on the water with a waterskiing or jet-skiing adventure.

For traveler tips, where to stay, reviews, and more tourist information, use the Marco Island trip builder tool .

Marco Island is very close to Naples. In February in Marco Island, expect temperatures between 77°F during the day and 59°F at night. Wrap up your sightseeing on the 27th (Wed) to allow time to ride a ferry to Key West.

Things to do in Marco Island

Outdoors Tours Wildlife

Side Trip

Speed Boats Tours
Highlights from your plan
Fishing Charters & Tours
Dolphin & Whale Watching
Waterskiing & Jetskiing

3
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.
Popular historic sites such as Key West Lighthouse and Keeper's Quarters Museum and Key West Cemetery are in your itinerary. Visiting Key West Butterfly & Nature Conservatory and Dolphin & Whale Watching will get you outdoors. Spend the 28th (Thu) exploring nature at Dry Tortugas National Park. There's still lots to do: examine the collection at The Ernest Hemingway Home and Museum and look for all kinds of wild species at Wildlife Areas.

To see photos, more things to do, and other tourist information, refer to the Key West trip planner .

Traveling by ferry from Marco Island to Key West takes 2.5 hours. Alternatively, you can drive. Traveling from Marco Island in February, Key West is somewhat warmer at night with lows of 68°F. Finish your sightseeing early on the 2nd (Sat) so you can take a bus to Marathon.

Things to do in Key West

Wildlife Outdoors Tours
Highlights from your plan
The Ernest Hemingway Home and Museum ©
Dolphin & Whale Watching
Scuba & Snorkeling

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.
On the 3rd (Sun), kick back and relax at Sombrero Beach, then look for all kinds of wild species at The Turtle Hospital, and then enjoy the sand and surf at Bahia Honda State Park. Get ready for a full day of sightseeing on the 4th (Mon): look for all kinds of wild species at Dolphin Research Center, pause for some serene contemplation at San Pablo Catholic Church, and then take a memorable tour with Tours.

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

Traveling by bus from Key West to Marathon takes 1.5 hours. Alternatively, you can drive. In March, daytime highs in Marathon are 81°F, while nighttime lows are 69°F. Finish your sightseeing early on the 4th (Mon) to allow enough time to drive to Islamorada.

Things to do in Marathon

Parks Outdoors Wildlife

Side Trip

Bahia Honda State Park
Highlights from your plan
Dolphin Research Center ©
Dolphin Research Center
Bahia Honda State Park ©
Bahia Honda State Park
The Turtle Hospital ©
The Turtle Hospital

2
nights
Islamorada

Islamorada ©
Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
Kick off your visit on the 5th (Tue): stop by Bella Sol Fragrance Bar and Gifts, take in the exciting artwork at Old Road Gallery, then look for all kinds of wild species at Florida Keys Wild Bird Rehabilitation Center, then take in the exciting artwork at Michelle Nicole Lowe Art Gallery, and finally take a tour by water with Boat Tours & Water Sports. Keep things going the next day: head outdoors with Contagious Charters, then discover the deep blue sea with a scuba or snorkeling tour, and then sample the tasty concoctions at Islamorada Beer Company Brewery and Tasting Room.

To see traveler tips, photos, where to stay, and other tourist information, you can read our Islamorada trip planner .

You can drive from Marathon to Islamorada in an hour. Another option is to take a bus. In March, daytime highs in Islamorada are 81°F, while nighttime lows are 69°F. Finish your sightseeing early on the 6th (Wed) so you can travel to St. Augustine.

Things to do in Islamorada

Outdoors Wildlife Tours

Side Trip

Florida Keys Wild Bird Rehabilitation Center
Highlights from your plan
Scuba & Snorkeling
Fishing Charters & Tours

1
day
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. Kick off your visit on the 7th (Thu): see the interesting displays at The Lightner Museum, look for all kinds of wild species at St. Augustine Alligator Farm Zoological Park, and then enjoy the sand and surf at St. Augustine Beach.

To find other places to visit, ratings, maps, and other tourist information, go to the St. Augustine road trip planning website .

Traveling by combination of shuttle, flight, and car from Islamorada to St. Augustine takes 5.5 hours. Alternatively, you can drive; or do a combination of shuttle, flight, and bus. Traveling from Islamorada in March, things will get slightly colder in St. Augustine: highs are around 71°F and lows about 54°F. Wrap up your sightseeing on the 7th (Thu) to allow time to drive back home.

Things to do in St. Augustine

Parks Outdoors Wildlife
Highlights from your plan
Lightner Museum ©
Lightner Museum
St. Augustine Beach ©
St. Augustine Beach

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