39 days in Florida Itinerary

39 days in Florida Itinerary

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Route & dates

39 days in Florida Itinerary

Start: Tallinn
Fly:  9​h 30​min
1
Orlando
— 2 nights
Drive:  2​h
2
St. Augustine
— 3 nights
Drive:  4​h 15​min
3
West Palm Beach
— 2 nights
Drive:  1​h 15​min
4
Miami
— 7 nights
Drive:  2​h 30​min
5
Marathon, Florida Keys
— 3 nights
Bus:  1​h 15​min
6
Key West
— 3 nights
Ferry:  3​h
7
Naples
— 4 nights
Drive:  2​h
8
Sarasota
— 4 nights
Drive:  1​h 30​min
9
Clearwater
— 7 nights
+2
Bus + Foot + Fly:  6​h 15​min
10
Pensacola
— 2 nights
Drive + Fly:  23​h
End: Tallinn

2
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.
Pack the 14th (Thu) with family-friendly diversions at Discovery Cove. Pack the 12th (Tue) with family-friendly diversions at Universal's Islands of Adventure. It doesn't end there: find something for the whole family at SeaWorld and take in nature's colorful creations at Harry P. Leu Gardens.

To plan Orlando vacation without wasting time, ask Inspirock to design an itinerary.

Tallinn, Estonia to Orlando is an approximately 18-hour flight. You can also do a combination of ferry and flight. The time zone changes from Eastern European Time (EET) to Eastern Standard Time (EST), which is usually a -7 hour difference. Traveling from Tallinn in January, things will get much hotter in Orlando: highs are around 25°C and lows about 13°C. Finish your sightseeing early on the 14th (Thu) to allow enough time to drive to St. Augustine.

Things to do in Orlando

Theme Parks Parks Outdoors
Find places to stay Jan 12 — 14:
Highlights from your plan
Universal's Islands of Adventure ©
Universal's Islands of Adventure
SeaWorld ©
SeaWorld
Discovery Cove ©
Discovery Cove

3
nights
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. Step out of St. Augustine with an excursion to Washington Oaks Gardens State Park in Palm Coast--about 38 minutes away. The adventure continues: sample the fine beverages at St. Augustine Distillery, explore the wealth of natural beauty at Fort Matanzas National Monument, immerse yourself in nature at Anastasia State Park, and learn about winemaking at Vino Del Grotto Winery.

To find maps, reviews, more things to do, and more tourist information, refer to the St. Augustine road trip tool .

Getting from Orlando to St. Augustine by car takes about 2 hours. Other options: take a bus. Expect a bit cooler weather when traveling from Orlando in January: highs in St. Augustine hover around 21°C, while lows dip to 11°C. On the 17th (Sun), wrap the sightseeing up by early afternoon so you can drive to West Palm Beach.

Things to do in St. Augustine

Parks Nature Outdoors

Side Trip

Washington Oaks Gardens State Park
Find places to stay Jan 14 — 17:
Highlights from your plan
Washington Oaks Gardens State Park ©
Washington Oaks Gardens State Park
St. Augustine Distillery ©
St. Augustine Distillery
Fort Matanzas National Monument ©
Fort Matanzas National Monument

2
nights
West Palm Beach

West Palm Beach ©
With a warm climate and sandy stretches, it's no surprise that West Palm Beach is a popular vacation spot.
Start off your visit on the 18th (Mon): look for all kinds of wild species at Gumbo Limbo Nature Center, then relax and rejuvenate at Spa Palazzo at Boca Raton Resort & Club, and then stroll around Sugar Sand Park. On the 19th (Tue), you'll have a packed day of sightseeing: admire the masterpieces at Norton Museum of Art, then look for all kinds of wild species at Green Cay Nature Center and Wetlands, and then identify plant and animal life at Wakodahatchee Wetlands.

To see other places to visit, photos, traveler tips, and other tourist information, use the West Palm Beach travel planner.

Traveling by car from St. Augustine to West Palm Beach takes 4.5 hours. Alternatively, you can do a combination of car, flight, and train; or take a bus. In January, West Palm Beach is a bit warmer than St. Augustine - with highs of 28°C and lows of 18°C. Finish your sightseeing early on the 19th (Tue) to allow enough time to drive to Miami.

Things to do in West Palm Beach

Parks Wildlife Spas

Side Trips

Boca Raton, Green Cay Nature Center and Wetlands, Wakodahatchee Wetlands
Find places to stay Jan 17 — 19:
Highlights from your plan
Green Cay Nature Center and Wetlands ©
Wakodahatchee Wetlands ©
Wakodahatchee Wetlands
Norton Museum of Art ©
Norton Museum of Art

7
nights
Miami

Miami ©
Florida’s mecca of fun in the sun, the lively tropical metropolis of Miami is one of the world’s top vacation spots.
Explore the numerous day-trip ideas around Miami: Fort Lauderdale (International Swimming Hall of Fame & Stranahan House), Homestead (Knaus Berry Farm & R.F. Orchids) and Burr's Berry Farm (in Goulds). Next up on the itinerary: enjoy the sand and surf at South Beach, stop by Espanola Way, make a trip to Bayside Marketplace, and steep yourself in history at Barnacle State Historic Site.

Quickly create a custom-made itinerary for Miami using our trip planner.

You can drive from West Palm Beach to Miami in 1.5 hours. Other options are to take a bus; or take a train. In January, daytime highs in Miami are 29°C, while nighttime lows are 20°C. Finish your sightseeing early on the 26th (Tue) so you can drive to Marathon.

Things to do in Miami

Parks Outdoors Zoos & Aquariums

Side Trips

Miami Beach, Coral Gables, Fort Lauderdale, Homestead, Aventura Mall
Find places to stay Jan 19 — 26:
Highlights from your plan
The Kampong ©
The Kampong
South Beach ©
South Beach
Lincoln Road ©
Lincoln Road

3
nights
Marathon, Florida Keys

Marathon ©
A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
Venture out of the city with trips to Islamorada (Theater of the Sea & Robbie's of Islamorada), Florida Keys Wild Bird Rehabilitation Center (in Tavernier) and SpaTerre at Little Palm Island Resort (in Little Torch Key). And it doesn't end there: kick back and relax at Bahia Honda State Park, observe the fascinating underwater world at Florida Keys Aquarium Encounters, look for all kinds of wild species at The Turtle Hospital, and browse the exhibits of Crane Point Museum & Nature Center.

To see more things to do, topicsMoreInfo.option.ratings, other places to visit, and tourist information, use the Marathon trip itinerary app .

You can drive from Miami to Marathon in 2.5 hours. Alternatively, you can take a bus; or do a combination of flight and bus. In January, daily temperatures in Marathon can reach 29°C, while at night they dip to 22°C. Finish your sightseeing early on the 29th (Fri) so you can take a bus to Key West.

Things to do in Marathon

Wildlife Parks Outdoors

Side Trips

Islamorada, Bahia Honda State Park, Florida Keys Wild Bird Rehabilitation Center, SpaTerre at Little Palm Island Resort
Find places to stay Jan 26 — 29:
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
Crane Point Museum & Nature Center ©
Crane Point Museum & Nature Center

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.
Key West is known for wildlife, museums, and adventure. Your plan includes some of its best attractions: examine the collection at The Ernest Hemingway Home and Museum, take in nature's colorful creations at Audubon House & Tropical Gardens, indulge in some personalized pampering at Prana Spa, and make a trip to Mallory Square.

To see maps, more things to do, topicsMoreInfo.option.ratings, and more tourist information, refer to the Key West journey planning website .

Getting from Marathon to Key West by bus takes about 1.5 hours. Other options: drive. In January, daily temperatures in Key West can reach 28°C, while at night they dip to 22°C. Finish your sightseeing early on the 1st (Mon) so you can travel to Naples.

Things to do in Key West

Parks Historic Sites Museums
Find places to stay Jan 29 — Feb 1:
Highlights from your plan
Audubon House & Tropical Gardens ©
Audubon House & Tropical Gardens
The Ernest Hemingway Home and Museum ©

4
nights
Naples

Naples ©
Naples is a city in Collier County, Florida, United States. Explore the numerous day-trip ideas around Naples: Six Mile Cypress Slough Preserve (in Fort Myers) and Estero River Outfitters (in Estero). The adventure continues: relax and rejuvenate at diVINE SPA, immerse yourself in nature at Delnor-Wiggins Pass State Park, take in the waterfront at Naples Pier, and tour the water at your own pace with Park Shore Marina.

To find photos, maps, where to stay, and more tourist information, read Naples journey planner.

Traveling by ferry from Key West to Naples takes 3 hours. Alternatively, you can drive; or take a bus. Expect slightly colder evenings in Naples when traveling from Key West in February, with lows around 18°C. Cap off your sightseeing on the 5th (Fri) early enough to go by car to Sarasota.

Things to do in Naples

Parks Outdoors Transportation

Side Trips

Six Mile Cypress Slough Preserve, Estero River Outfitters
Find places to stay Feb 1 — 5:
Highlights from your plan
Six Mile Cypress Slough Preserve ©
diVINE SPA ©
diVINE SPA
Naples Botanical Garden ©
Naples Botanical Garden

4
nights
Sarasota

Sarasota ©
Sarasota is a city in Sarasota County on the southwestern coast of the U.S. Change things up with these side-trips from Sarasota: Emerson Point Preserve (in Palmetto) and Bradenton (De Soto National Memorial & Thrive Yoga and Fitness). The adventure continues: explore the different monuments and memorials at Sarasota National Cemetery, categoryPhrases.phrase.get_up_close_and_personal_with_brilliant_marine_life_at Mote Marine Laboratory & Aquarium, look for gifts at Le Macaron, and get outside with SUP Sarasota.

To find traveler tips, maps, other places to visit, and tourist information, use the Sarasota trip planner.

Traveling by car from Naples to Sarasota takes 2 hours. Alternatively, you can take a bus. Expect a daytime high around 28°C in February, and nighttime lows around 15°C. Finish your sightseeing early on the 9th (Tue) so you can drive to Clearwater.

Things to do in Sarasota

Parks Outdoors Historic Sites

Side Trips

Bradenton, Emerson Point Preserve, Oscar Scherer State Park, Siesta Beach
Find places to stay Feb 5 — 9:
Highlights from your plan
Sarasota National Cemetery ©
Sarasota National Cemetery
Siesta Beach ©
Siesta Beach
Marie Selby Botanical Gardens ©
Marie Selby Botanical Gardens

7
nights
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.
Explore the numerous day-trip ideas around Clearwater: Tampa (ZooTampa at Lowry Park & Busch Gardens Tampa Bay), Fort De Soto Park (in Tierra Verde) and Saint Pete Beach (in St. Pete Beach). There's lots more to do: explore the world behind art at The Dali Museum, relax and rejuvenate at The Body Electric Yoga Company, trot along with C Ponies Beach Horses, and get outside with Clearwater Paddleboard Company.

To see reviews, more things to do, other places to visit, and more tourist information, you can read our Clearwater trip itinerary planner.

Traveling by car from Sarasota to Clearwater takes 1.5 hours. Alternatively, you can take a bus. In February, plan for daily highs up to 27°C, and evening lows to 16°C. Wrap up your sightseeing on the 16th (Tue) to allow time to travel to Pensacola.

Things to do in Clearwater

Parks Outdoors Beaches

Side Trips

St. Petersburg, Largo, Tampa, John's Pass Village & Boardwalk, Clay and Paper Gallery of Art
Find places to stay Feb 9 — 16:
Highlights from your plan
Saint Pete Beach ©
Saint Pete Beach
Busch Gardens Tampa Bay ©
Busch Gardens Tampa Bay
The Dali Museum ©
The Dali Museum

2
nights
Pensacola

Pensacola ©
Surrounded on three sides by water, Pensacola offers access to white-sand beaches and emerald-green ocean unspoiled by large resorts.
Kick off your visit on the 17th (Wed): enjoy the sand and surf at Pensacola Beach, then steep yourself in history at Fort Pickens Area, then brush up on your military savvy at National Naval Aviation Museum, and finally stop by Joe Patti's Seafood Company. On your second day here, look for all kinds of wild species at Uncle Sandy's Macaw Bird Park, then make a trip to Veterans Memorial Park, and then stop by Crabs.

To see where to stay, maps, more things to do, and more tourist information, refer to the Pensacola online trip planner .

You can do a combination of bus and flight from Clearwater to Pensacola in 6.5 hours. Alternatively, you can drive; or do a combination of bus, flight, and taxi. You'll gain 1 hour traveling from Clearwater to Pensacola due to the time zone difference. Expect a bit cooler temperatures when traveling from Clearwater in February; daily highs in Pensacola reach 23°C and lows reach 11°C. Wrap up your sightseeing on the 18th (Thu) early enough to travel back home.

Things to do in Pensacola

Historic Sites Parks Outdoors

Side Trip

Pensacola Beach
Find places to stay Feb 16 — 18:
Highlights from your plan
National Naval Aviation Museum ©
National Naval Aviation Museum
Fort Pickens Area ©
Fort Pickens Area
Pensacola Beach ©
Pensacola Beach

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