Sailing in Holmes Beach, FL

Private catamaran sailing with space to swim, paddle, and unwind

Watch the Gulf sunset aboard a traditional schooner

Private daytime sail with dinghy access for island exploring

Private 2-hour sunset sail with downtown St. Petersburg views

Sail Tampa Bay at golden hour aboard a 40-foot luxury catamaran

Sail Boca Ciega Bay on a private schooner with drinks and a restroom aboard

Private evening sailing with sunset views across Tampa Bay

Relax on a 3-hour sail with a U.S. Coast Guard–licensed captain from downtown St. Pete

Sail for 8 hours and choose Egmont Key, Anna Maria, or Shell Key

Private, wind-driven sailing aboard a 48-foot Jeanneau yacht

Sail Boca Ciega Bay and the Gulf while watching for dolphins

Start the day aboard a classic yacht with optional sailing instruction

Private sailing with spacious lounges, swim access, and Sarasota Bay views

Sail to Shell Key for swimming, snorkeling, and shelling

Sail Tampa Bay aboard a private 48-foot Jeanneau yacht

Private 2-hour sunset sail with bay views and dolphin spotting

Sail into golden hour with four spacious places to gather aboard

Classic schooner sailing with open-deck Gulf views

Private evening sailing with sunset views on Boca Ciega Bay and the Gulf of Mexico