Best 465 things to do in Siesta Key, FL

Sail into golden hour with four spacious places to gather aboard

Cruise Sarasota Bay and relax at anchor aboard a crewed 112-foot Westport

Cruise, swim, and relax aboard a crewed 112-foot Westport yacht

Cruise Sarasota’s intracoastal waterways on a 21' Bennington tritoon for up to 10

Sample Sarasota bites and paired drinks on a guided culinary walk

Customize a 4-hour private cruise with snorkeling, paddleboarding, dolphin watching, and more.

Paddle Lido Key’s mangrove tunnels with a private guide from Ted Sperling Nature Park

Cruise into the Florida sunset with a US Coast Guard licensed captain

Watch Key West's sunset from a private sport yacht

Cruise with up to 13 friends on a spacious pontoon equipped for sandbar hopping

Cruise Anna Maria Island by captained tritoon with room for up to 6

Cruise Palma Sola Bay on horseback and ride through the water

Ride from the beach into the water with one-on-one horse guidance

Enjoy a self-guided paddle adventure with a versatile inflatable board.

Ride the latest 3-seater jet skis and enjoy hassle-free fun on the water.

Design a private day of fishing, snorkeling, and sandbar stops

A private sunset cruise with Gulf views, wildlife searching, and a possible sandbar stop

Customize a private 3–6 hour cruise to Egmont or Passage Key with snorkeling and sightseeing led by experienced captains

Practice yoga on a paddleboard and connect with nature in a tranquil setting.

Explore mangrove tunnels by kayak or paddleboard with experienced guides in Neal Preserve.

Cruise to a local sandbar and swim or snorkel

Cruise the Gulf and back bay to look for dolphins and seasonal manatees

Cruise into the evening and watch the sunset from the water

Set your own course for sandbars, swims, and open-water exploring