Florida Road Trip: Siesta Key to Key West, 26 Stops

Explore Florida's diverse coastline across 26 iconic destinations spanning 6,214 km, from Siesta Key and Clearwater Beach to Key West and the Florida Keys. This comprehensive route connects major landmarks including Fort De Soto Park, Jupiter Inlet Lighthouse, Fort Lauderdale, and the historic Castillo de San Marcos in St. Augustine, showcasing both natural wetlands and urban attractions.

Distance
6214.8 km
Mode
route
Start
Welcome to Florida
End
South Beach
Stops
26
Video author
travmap
Updated

Stops on this route

  1. Welcome to Florida — The southernmost continental U.S. state renowned for subtropical climate, diverse ecosystems, and year-round tourism attractions spanning beaches to wetlands.
  2. Siesta Key — Barrier island on Florida's southwest coast between Robert's Bay and the Gulf of Mexico, recognized for Siesta Beach as one of the best beaches in the world.
  3. Key West — Southernmost city in the continental United States, located approximately 90 miles from Cuba, historically an important naval base protecting the Florida Straits.
  4. Honeymoon Island State Park — Barrier island formerly known as Hog Island, created in 1921 when a hurricane split the original island, located across St. Joseph Sound from Dunedin.
  5. Fort De Soto Park — A 900-acre barrier island park featuring pristine sandy beaches, historic Civil War fortifications, and abundant wildlife viewing opportunities in the Tampa Bay area.
  6. Jupiter Inlet Lighthouse — Historic lighthouse standing watch over the coast since the 1800s, a famous site in Jupiter with wide beaches shaped by Atlantic currents.
  7. Anna Maria Island — Island situated between the Gulf of Mexico and Sarasota Bay, formerly part of the Safety Harbor culture area inhabited long before European arrival, near Tampa Bay.
  8. Tampa — Gulf Coast city shaped by calm waters of Tampa Bay and Old Tampa Bay, home to the largest port in Florida and historic Fort Brooke founded in the 19th century.
  9. Clearwater Beach — Acclaimed white sand beach officially crowned as one of the 15 best white sand beaches in the world as of 2025.
  10. Florida Keys — Island chain in southern Florida shaped by limestone formation and major sea level changes, including Elliot Key and notable islands with the Florida Reef offshore—the only…
  11. Fernandina Beach — Victorian seaport town on Amelia Island with charming historic downtown architecture, deep-water port access, and championship golf courses along Florida's northeastern coast.
  12. Sunshine Skyway Bridge — Major bridge spanning Tampa Bay, important shipping route connecting to Port Tampa Bay and Port of St. Petersburg.
  13. Marco Island
  14. Biscayne Bay — Shallow lagoon along the South Florida Atlantic coast providing natural storm protection, part of the intracoastal waterway used for travel and trade.
  15. Rickenbacker Causeway
  16. Fisher Island — Exclusive private island retreat near Miami featuring luxury resort amenities, pristine beaches, and world-class dining accessible to resort guests and members only.
  17. Lake Eola Park — Downtown Orlando's scenic urban park with a one-mile walking trail circling a natural lake, offering recreational facilities and downtown city views.
  18. Fort Lauderdale
  19. Castillo de San Marcos National Monument
  20. Virginia Key
  21. Daytona Beach
  22. St. Pete Beach
  23. Fort Myers
  24. Port St. Lucie — Growing Atlantic coast city notable for outstanding recreational fishing, spring training baseball facilities, and expanding waterfront development and amenities.
  25. Seven Mile Bridge — Iconic elevated causeway in the Florida Keys spanning turquoise waters, offering stunning ocean vistas and connecting Mid-Keys islands along the scenic Overseas Highway.
  26. South Beach

Useful for your trip

Tip
Siesta Key's white quartz sand stays cool even on hot days, making it comfortable for walking barefoot.
Transport
Walking is the best way to explore Key West due to its small size (4 miles long, 1 mile wide) and narrow streets.
Timing
Fort De Soto Park is a key stop on the Great Florida Birding Trail, especially during spring and fall migrations.
Tip
Jupiter's coastline juts farther into the ocean than anywhere else in Florida, offering unique coastal views.
Tip
Anna Maria Island has two very different coastlines: the Gulf of Mexico to the west and calm bays to the east.
Timing
Jupiter experiences warm weather most of the year with sunny winters, though summer afternoons often have quick rain showers.
Tip
Fort De Soto Park encompasses 1,136 acres across five separate islands connected by bridges, with over 328 bird species recorded.
Where to stay
Honeymoon Island welcomes over 1 million visitors yearly but remains largely undeveloped with protected dunes, pine forests, and wetlands.
Tip
Key West is only about 90 miles from Cuba and closer to Havana than to Miami by air.

Video on this route

Wonders of Florida | Florida Like You've Never Seen It Before | Travel Video 4K

More routes nearby

Map