16 days in Florida Itinerary

16 days in Florida Itinerary

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Route & dates

16 days in Florida Itinerary

Start: San Diego
Fly + Drive:  9​h 15​min
1
Jacksonville
— 1 night
Drive:  3​h
2
Homosassa
— 2 nights
Drive:  1​h 45​min
3
St. Petersburg
— 2 nights
Drive:  2​h 45​min
4
Naples
— 2 nights
Drive:  2​h
5
Cutler Bay
— 3 nights
car:  3​h 30​min
6
Key West
— 1 night
Drive:  4​h 30​min
7
Boca Raton
— 1 night
Drive:  3​h 45​min
8
Daytona Beach
— 2 nights
Drive:  1​h 45​min
9
Jacksonville
— 1 night
Drive + Fly:  9​h
End: San Diego

1
night
Jacksonville

Jacksonville
The sprawling city of Jacksonville is not only Florida's most populous city, but also the largest city by land area in the continental United States.
For photos, maps, more things to do, and more tourist information, you can read our Jacksonville travel route planner .

San Diego to Jacksonville is an approximately 9.5-hour combination of flight and car. You can also do a combination of flight and bus; or drive. The time zone difference moving from Pacific Standard Time (PST) to Eastern Standard Time (EST) is 3 hours. When traveling from San Diego in May, plan for a bit warmer days in Jacksonville, with highs around 85°F, while nights are about the same with lows around 62°F. You will have some time to spend on the 11th (Mon) before leaving for Homosassa.

Things to do in Jacksonville

Outdoors Tours Parks

2
nights
Homosassa

Homosassa is a census-designated place (CDP) in Citrus County, Florida, United States. Start off your visit on the 11th (Mon): explore the activities along Homosassa River and then appreciate the history behind Old Homosassa Veteran's Memorial. Keep things going the next day: identify plant and animal life at Alpaca Magic USA, immerse yourself in nature at Ellie Schiller Homosassa Springs Wildlife State Park, and then discover the deep blue sea with a scuba or snorkeling tour.

To see traveler tips, where to stay, reviews, and other tourist information, you can read our Homosassa online itinerary planner .

Drive from Jacksonville to Homosassa in 3 hours. Alternatively, you can do a combination of train and bus; or take a bus. In May, daily temperatures in Homosassa can reach 85°F, while at night they dip to 62°F. On the 13th (Wed), you'll have the morning to explore before heading off to St. Petersburg.

Things to do in Homosassa

Wildlife Parks Nature

Side Trip

Ellie Schiller Homosassa Springs Wildlife State Park
Highlights from your plan
Scuba & Snorkeling
Homosassa River ©
Homosassa River

2
nights
St. Petersburg

St. Petersburg ©
Located on a peninsula between Tampa Bay and the Gulf of Mexico, St.
Keep things going the next day: kick back and relax at Clearwater Beach.

To find other places to visit, more things to do, reviews, and other tourist information, read St. Petersburg trip planner .

Getting from Homosassa to St. Petersburg by car takes about 2 hours. Other options: take a bus. Traveling from Homosassa in May, you can expect nighttime temperatures to be somewhat warmer in St. Petersburg, with lows of 73°F. Cap off your sightseeing on the 15th (Fri) early enough to go by car to Naples.

Things to do in St. Petersburg

Parks Outdoors Beaches

Side Trip

Clearwater Beach
Highlights from your plan
Clearwater Beach ©
Clearwater Beach
The Dali Museum ©
The Dali Museum

2
nights
Naples

Naples ©
Naples is a city in Collier County, Florida, United States. On your second day here, admire the natural beauty at Naples Botanical Garden.

To find ratings, more things to do, reviews, and other tourist information, read our Naples trip maker site .

You can drive from St. Petersburg to Naples in 3 hours. Another option is to take a bus. In May, daily temperatures in Naples can reach 88°F, while at night they dip to 70°F. Wrap up your sightseeing by early afternoon on the 17th (Sun) to allow enough time to travel to Cutler Bay.

Things to do in Naples

Parks
Highlights from your plan
Naples Botanical Garden ©
Naples Botanical Garden

3
nights
Cutler Bay

Cutler Bay ©
Cutler Bay is an incorporated town in Miami-Dade County, Florida established in 2005, with a population of approximately 44,700 as of 2016.The borders were established as running from SW 184th Street (Eureka Dr) east of US 1 to the coast, and north of Black Point Marina, at. Your day-by-day itinerary now includes Airboat In Everglades as well as Everglades Nature Tours. Explore the numerous day-trip ideas around Cutler Bay: Everglades National Park (Osceola panthers & Buttonwood Canal) and Miccosukee Indian Village (in Tamiami). Next up on the itinerary: experience rural life at Burr's Berry Farm, steep yourself in history at Cauley Square Historic Village, admire the natural beauty at Pinecrest Gardens, and stroll around Deering Point.

To find photos, more things to do, traveler tips, and more tourist information, use the Cutler Bay itinerary planner .

Traveling by car from Naples to Cutler Bay takes 2.5 hours. In May, daily temperatures in Cutler Bay can reach 85°F, while at night they dip to 72°F. Wrap up your sightseeing on the 20th (Wed) early enough to travel to Key West.

Things to do in Cutler Bay

Outdoors Tours Wildlife

Side Trips

Miami, Pinecrest, Palmetto Bay, Everglades National Park, Goulds
Highlights from your plan
Osceola panthers ©
Osceola panthers
Everglades Nature Tours ©
Everglades Nature Tours
Buttonwood Canal ©
Buttonwood Canal

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.
To find maps, other places to visit, reviews, and other tourist information, read our Key West day trip planning website .

Use the Route module to find suitable travel options from Cutler Bay to Key West. Expect a daytime high around 85°F in May, and nighttime lows around 77°F. Finish up your sightseeing early on the 21st (Thu) so you can travel to Boca Raton.

Things to do in Key West

Museums
Highlights from your plan
The Ernest Hemingway Home and Museum ©

1
night
Boca Raton

Boca Raton ©
A paradise of palm trees and resorts, Boca Raton was once a hub of technological advancement.
To see photos, where to stay, reviews, and other tourist information, you can read our Boca Raton trip planning website .

Traveling by flight from Key West to Boca Raton takes 4 hours. Alternatively, you can do a combination of flight and train; or drive. In May, plan for daily highs up to 85°F, and evening lows to 73°F. Finish your sightseeing early on the 22nd (Fri) so you can drive to Daytona Beach.

Things to do in Boca Raton

Shopping Wildlife Parks
Highlights from your plan
Mizner Park ©
Mizner Park
Gumbo Limbo Nature Center ©
Gumbo Limbo Nature Center

2
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.
Keep things going the next day: walk around Canaveral National Seashore, learn about all things military at Veterans Museum & Education Center, and then contemplate the long history of Stetson Mansion.

To see reviews, maps, more things to do, and tourist information, go to the Daytona Beach road trip planning website .

You can drive from Boca Raton to Daytona Beach in 4 hours. Alternatively, you can do a combination of flight and shuttle; or do a combination of train, flight, and shuttle. Traveling from Boca Raton in May, expect a bit cooler with lows of 66°F in Daytona Beach. Cap off your sightseeing on the 24th (Sun) early enough to go by car to Jacksonville.

Things to do in Daytona Beach

Parks Historic Sites Wildlife

Side Trips

Ponce de Leon Inlet Lighthouse & Museum, Canaveral National Seashore, Stetson Mansion
Highlights from your plan
Stetson Mansion ©
Stetson Mansion
Canaveral National Seashore ©
Canaveral National Seashore
Beach at Daytona Beach ©
Beach at Daytona Beach

1
night
Jacksonville

Jacksonville
For where to stay, other places to visit, more things to do, and other tourist information, use the Jacksonville online driving holiday planner .

Traveling by car from Daytona Beach to Jacksonville takes 2 hours. Alternatively, you can take a bus; or take a train. On the 25th (Mon), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Jacksonville

Outdoors Tours Parks

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