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Downtown Tampa’s skyline above the Hillsborough River, with a road bridge crossing in the foreground

Best Weekend Getaways From Tampa

Reviewed September 2026

4 min read·Updated Sep 2026
⏱ 3 min read📖 661 words📅 Sep 2026

Tampa sits within a comfortable drive of more variety than most people give it credit for, and the twelve below are ordered by how long it takes to get there. Drive times are for clear roads, so add to them for a Friday evening start.

1. St. Petersburg (about 35 minutes)

The Dali Museum holds the largest collection of his work outside Spain, and the surrounding downtown has become the best walking-and-eating district in the bay area. Sunset at the pier costs nothing.

2. Clearwater Beach (about 40 minutes)

Wide, white and shallow a long way out, which is why families default to it. Pier 60 runs a nightly sunset market. Parking is the whole problem: arrive early or use the Jolley Trolley.

3. Anna Maria Island (about 1 hour)

Old Florida on a barrier island, with a building height limit that has kept the condo towers off and a free trolley running the length of it. Quieter than anywhere else this close to Tampa.

4. Sarasota and Siesta Key (about 1 hour)

Siesta Key’s sand is quartz rather than crushed shell, so it stays cool underfoot. In Sarasota the Ringling estate gives you an art museum, a circus museum and a Venetian Gothic mansion on the bay.

5. Crystal River (about 1 hour 30 minutes)

The only place in the United States where you can legally snorkel with West Indian manatees. They gather in the springs from roughly November to March, which is when to go.

6. Orlando (about 1 hour 30 minutes)

The theme parks are the obvious draw, but Winter Park, the Morse Museum’s Tiffany collection and Leu Gardens make a very different weekend for a fraction of the cost.

7. Cedar Key (about 2 hours)

A fishing village on stilts in the Gulf, with clam farming rather than tourism as the main industry and almost nothing to do, which is the attraction.

8. Fort Myers and Sanibel (about 2 hours 15 minutes)

Sanibel lies east to west, which is why shells pile up on it, and the Ding Darling refuge covers much of the island. Check current conditions before booking: these barrier islands have taken repeated hurricane damage.

9. Naples (about 2 hours 30 minutes)

Expensive and aware of it, with a long pier, calm Gulf water and the Naples Botanical Garden. The Everglades begin immediately to the east.

10. St. Augustine (about 3 hours)

The oldest continuously occupied European settlement in the country, with a Spanish stone fort, a walkable old town and a very good beach a bridge away.

11. Everglades National Park (about 4 hours)

Best reached through the Gulf Coast entrance at Everglades City or the Shark Valley entrance on the Tamiami Trail. Winter is the season: fewer mosquitoes and wildlife concentrated at the water.

12. Miami (about 4 hours)

The long one, and better on the train or a cheap flight. South Beach art deco, the Wynwood murals and Little Havana are the standard three, and all three earn it.

Getting out of Tampa without a car

Thin, and worth checking rather than assuming. Amtrak serves Tampa, but Florida’s long-distance schedules have been unsettled, so look at the live timetable rather than a guide before you plan around a train. Brightline’s proposed Orlando to Tampa extension had no committed funding and no construction start date as of 2026, so do not build a trip around it yet.

Cheap weekend getaways from Tampa by car

  • St. Petersburg: the pier and the waterfront parks are free
  • Anna Maria Island: the island trolley runs free end to end
  • Cedar Key: nothing to do and nothing to pay for, which is the point
  • Clearwater: the beach is free once you have solved the parking

Last-minute weekend getaways from Tampa

  • St. Petersburg, thirty-five minutes and full of beds
  • Anna Maria Island midweek, when the rentals loosen
  • Cedar Key, which is quiet by design
  • Orlando, where the hotel supply is effectively bottomless

If you are deciding on the day, work backwards from the drive rather than the destination: anything under two hours leaves you a genuine Saturday, and anything past four is really a three-day trip wearing a weekend label.

Planning the other long weekend? Memorial Day 2027 falls on Monday 31 May, making Saturday 29 to Monday 31 May a three-day weekend. See the 12 best Memorial Day weekend getaways for 2027.