36 days in Florida Itinerary

36 days in Florida Itinerary

Created using Inspirock Florida trip itinerary planner

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Route & dates

36 days in Florida Itinerary

Start: Boston
+2
Fly + foot + bus:  7​h 30​min
1
Crystal River
— 2 nights
Drive:  2​h 45​min
2
St. Augustine
— 5 nights
bus:  1​h 15​min
3
Daytona Beach
— 3 nights
shuttle + Fly:  4​h 45​min
4
Key West
— 5 nights
bus:  1​h 15​min
5
Marathon
— 4 nights
Drive:  1​h 30​min
6
Key Largo
— 4 nights
Drive:  2​h 45​min
7
Marco Island
— 4 nights
Drive:  1​h 15​min
8
Fort Myers Beach
— 3 nights
Drive:  30​min
9
Sanibel Island
— 5 nights
Fly:  5​h 45​min
End: Boston

2
nights
Crystal River

The jewel of Florida's Nature Coast, Crystal River spreads around spring-fed Kings Bay, known for maintaining a constant 22 C (72 F) temperature all year long.
Keep things going the next day: find your balance on the water with some of the best stand-up paddleboarding in the area and then take a memorable tour with Tours.

To see reviews, where to stay, and more tourist information, you can read our Crystal River trip planning site .

Boston to Crystal River is an approximately 7.5-hour combination of bus and flight. You can also drive; or take a bus. In February, Crystal River is warmer than Boston - with highs of 72°F and lows of 49°F. Cap off your sightseeing on the 26th (Tue) early enough to go by car to St. Augustine.

Things to do in Crystal River

Wildlife Parks Tours

Side Trips

Alpaca Magic USA, Ellie Schiller Homosassa Springs Wildlife State Park
Highlights from your plan
Scuba & Snorkeling
Three Sisters Springs ©
Three Sisters Springs
Alpaca Magic USA ©
Alpaca Magic USA

5
nights
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. Satisfy your inner culture vulture at Fort Matanzas National Monument and St. Augustine Pirate & Treasure Museum. Your inner history buff will appreciate Cathedral Basilica of St. Augustine and Old Jail. Go for a jaunt from St. Augustine to Jacksonville Beach to see Jacksonville Beach about 50 minutes away. The adventure continues: look for all kinds of wild species at St. Augustine Alligator Farm Zoological Park, take a stroll through Old City, do a tasting at San Sebastian Winery, and kick back and relax at St. Augustine Beach.

To find ratings and more tourist information, read our St. Augustine trip planning tool .

Drive from Crystal River to St. Augustine in 3 hours. Alternatively, you can take a bus. In February, daily temperatures in St. Augustine can reach 68°F, while at night they dip to 51°F. Cap off your sightseeing on the 3rd (Sun) early enough to go by car to Daytona Beach.

Things to do in St. Augustine

Parks Historic Sites Nature

Side Trip

Jacksonville Beach
Highlights from your plan
Lightner Museum ©
Lightner Museum
Fort Matanzas National Monument ©
Fort Matanzas National Monument
Cathedral Basilica of St. Augustine ©

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.
Step out of the city life by going to Merritt Island National Wildlife Refuge and New Smyrna Town Beach. We've included these beaches for you: Ormond Beach and Beach at Daytona Beach. Explore the numerous day-trip ideas around Daytona Beach: Blue Spring State Park (in Orange City) and Stetson Mansion (in DeLand). The adventure continues: visit a coastal fixture at Ponce de Leon Inlet Lighthouse & Museum, pause for some serene contemplation at St. Brendan Catholic Church, and take in nature's colorful creations at Dunlawton Sugar Mill Gardens.

For ratings, other places to visit, traveler tips, and more tourist information, read our Daytona Beach trip maker website .

Traveling by car from St. Augustine to Daytona Beach takes 1.5 hours. Alternatively, you can take a bus. Expect a daytime high around 76°F in March, and nighttime lows around 54°F. Finish your sightseeing early on the 6th (Wed) so you can travel to Key West.

Things to do in Daytona Beach

Parks Beaches Outdoors

Side Trips

Ormond Beach, Blue Spring State Park, Dunlawton Sugar Mill Gardens, Stetson Mansion, New Smyrna Town Beach
Highlights from your plan
Ormond Beach ©
Ormond Beach

5
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 Garden Club are in your itinerary. Mel Fisher Maritime Heritage Museum and Florida Keys Eco-Discovery Center will appeal to museum buffs. Spend the 7th (Thu) exploring nature at Dry Tortugas National Park. And it doesn't end there: see some colorful creatures with a scuba or snorkeling tour, see majestic marine mammals with a dolphin and whale watching tour, stroll the grounds of Key West Cemetery, and learn about all things military at U.S. Coast Guard Cutter Ingham Maritime Museum.

To see maps, ratings, photos, and tourist information, read our Key West vacation planner.

You can do a combination of shuttle and flight from Daytona Beach to Key West in 5 hours. Other options are to fly; or drive. Traveling from Daytona Beach in March, plan for somewhat warmer nights in Key West, with lows around 69°F. Finish up your sightseeing early on the 11th (Mon) so you can catcht the bus to Marathon.

Things to do in Key West

Tours Outdoors Wildlife
Highlights from your plan
Dolphin & Whale Watching
Scuba & Snorkeling

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.
You'll enjoy a bit of beach vacationing at Sombrero Beach and Sunset Park Beach. Explore hidden gems such as Fishing Charters & Tours and Crane Point Museum & Nature Center. There's much more to do: identify plant and animal life at Dolphin Research Center, stroll through Calusa Beach, snap pictures at Seven Mile Bridge, and immerse yourself in nature at Bahia Honda State Park.

To see traveler tips, ratings, photos, and more tourist information, read our Marathon day trip app .

You can take a bus from Key West to Marathon in 1.5 hours. Another option is to drive. In March, plan for daily highs up to 81°F, and evening lows to 69°F. Finish your sightseeing early on the 15th (Fri) to allow enough time to drive to Key Largo.

Things to do in Marathon

Parks Outdoors Wildlife

Side Trips

Big Pine Key, Sunset Park Beach
Highlights from your plan
Sombrero Beach ©
Sombrero Beach
Dolphin Research Center ©
Dolphin Research Center
Fishing Charters & Tours

4
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.
Take a break from the city and head to Florida Keys Wild Bird Rehabilitation Center and A Lil' Tail Charters. Discover out-of-the-way places like Molasses Reef and Contagious Charters. You'll find plenty of places to visit near Key Largo: Islamorada (Robbie's of Islamorada & History of Diving Museum), Everglades National Park (Shark Valley & Anhinga Trail) and Art Deco Historic District (in Miami Beach).

For where to stay, traveler tips, reviews, and other tourist information, read Key Largo trip itinerary app .

Traveling by car from Marathon to Key Largo takes 1.5 hours. Alternatively, you can take a bus; or do a combination of bus and taxi. Traveling from Marathon in March, Key Largo is slightly colder at night with lows of 63°F. Cap off your sightseeing on the 19th (Tue) early enough to go by car to Marco Island.

Things to do in Key Largo

Outdoors Wildlife Parks

Side Trips

Islamorada, Everglades National Park, Art Deco Historic District
Highlights from your plan
Shark Valley ©
Shark Valley
Anhinga Trail ©
Anhinga Trail
Molasses Reef ©
Molasses Reef

4
nights
Marco Island

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. Visit Lowdermilk Beach and Tigertail Beach for some beach relaxation. Step out of the city life by going to Dolphin & Whale Watching and Parasailing & Paragliding. You'll find plenty of places to visit near Marco Island: Speed Boats Tours (in Everglades City) and Audubon Corkscrew Swamp Sanctuary (in Naples). There's much more to do: kick back and relax at South Marco Beach, explore the activities along Capri Paddlecraft Park, take in nature's colorful creations at Naples Botanical Garden, and get a new perspective on things with Boat Tours & Water Sports.

To see ratings, reviews, photos, and more tourist information, use the Marco Island trip itinerary site .

You can drive from Key Largo to Marco Island in 3 hours. Alternatively, you can do a combination of bus and ferry. In March, daytime highs in Marco Island are 80°F, while nighttime lows are 61°F. Wrap up your sightseeing on the 23rd (Sat) early enough to drive to Fort Myers Beach.

Things to do in Marco Island

Outdoors Parks Tours

Side Trips

Naples, Speed Boats Tours
Highlights from your plan
South Marco Beach ©
South Marco Beach
Dolphin & Whale Watching
Speed Boats Tours

3
nights
Fort Myers Beach

Fort Myers Beach is a town located on Estero Island in Lee County, Florida, United States. Your cultural itinerary includes sights like Edison Park and Edison & Ford Winter Estates. Get outdoors at Barefoot Beach Preserve and Dolphin & Whale Watching. Step out of Fort Myers Beach to go to Immokalee and see Ten Thousand Islands National Wildlife Refuge, which is approximately 1h 10 min away. There's more to do: admire the majestic nature at Lovers Key State Park and stroll through Fort Myers Beach.

Planning Fort Myers Beach trip won't be overwheling when you use's Insprock itinerary maker.

Traveling by car from Marco Island to Fort Myers Beach takes 1.5 hours. Alternatively, you can do a combination of taxi and bus. In March, plan for daily highs up to 81°F, and evening lows to 59°F. Finish your sightseeing early on the 26th (Tue) to allow enough time to drive to Sanibel Island.

Things to do in Fort Myers Beach

Parks Wildlife Outdoors

Side Trips

Fort Myers, Barefoot Beach Preserve, Ten Thousand Islands National Wildlife Refuge
Highlights from your plan
Dolphin & Whale Watching
Barefoot Beach Preserve ©
Barefoot Beach Preserve
Lovers Key State Park ©
Lovers Key State Park

5
nights
Sanibel Island

Sanibel Island ©
Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.
Discover out-of-the-way places like Captiva Beach and Sanibel Island Lighthouse. Museum-lovers will get to explore The Bailey-Matthews National Shell Museum and Tower Gallery. Next up on the itinerary: kick back and relax at Bowman's Beach, don't miss a visit to St. Isabel Catholic Church, identify plant and animal life at Pond Apple Park, and admire the natural beauty at In The Garden.

For ratings, where to stay, traveler tips, and more tourist information, you can read our Sanibel Island trip maker app .

Sanibel Island is very close to Fort Myers Beach. In March in Sanibel Island, expect temperatures between 81°F during the day and 59°F at night. Finish up your sightseeing early on the 31st (Sun) so you can travel back home.

Things to do in Sanibel Island

Parks Outdoors Beaches

Side Trip

Captiva Beach
Highlights from your plan
Captiva Beach ©
Captiva Beach
Bowman's Beach ©
Bowman's Beach
Blind Pass Beach Park ©
Blind Pass Beach Park

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