Best results for Anna Maria FL

Explore Sarasota's historic neighborhoods and cultural landmarks on a 90-minute air-conditioned trolley ride.

Solve a circus-themed murder mystery on a rolling trolley with interactive fun and complimentary drinks.

Sing 70s & 80s hits on a trolley with a bar stop at 99 Bottles

Paddle Jim Neville Marine Preserve to water-only Midnight Pass Beach

Explore calm Turtle Beach waterways at your own pace with quality kayaks or paddleboards

Watch the sun dip below the Gulf while cruising past celebrity homes

Snorkel historic ruins and visit three picturesque islands on a flexible 5-hour private charter.

Explore historic Egmont Key, snorkel the ruins, and watch for dolphins on a 4-hour cruise

Cruise Madeira Beach waterways and look for dolphins near John’s Pass

Join a shared 2-hour cruise on South West Florida waters with BYO drinks and coolers provided

Enjoy flexible 2–8 hour rentals to get on the water

Watch vibrant Gulf Coast colors unfold while you relax on a comfortable pontoon at dusk.

Book your own private tiki boat near John’s Pass for 2, 3, or 4 hours

Cruise to Shell Key Island and Egmont Key for shelling, snorkeling, and dolphin spotting

Cruise Madeira Beach for 2 hours on a tiki boat at sunset

Rent an adult bike and ride Gulf Blvd. for 4 hours to 7 days

Rent a paddle board in Madeira Beach for 2–8 hours

Get out on the water with flexible 2–8 hour kayak rentals

Get on the water with flexible 2–8 hour paddle board rentals

Ride a 13-mile historic railroad excursion in open-air or air-conditioned cars.

Visit the gift shop and model railroad display in Parrish

Take the controls of a locomotive for an hour

Bypass traffic and enjoy a Siesta Key sunset with convenient e-bike drop-off and pickup

Stretch, unwind, and rejuvenate—right in the comfort of your vacation rental.