Best 603 things to do in Holmes Beach, FL

Cruise the islands with shade, coolers, and watersports

Private evening boating with beach views and Skyway Bridge access

Fish or cruise with a 225 HP center console and onboard navigation

Paddle Lido Key, then taste your way through downtown Sarasota

Shop boutiques and enjoy bubbles and light bites in Sarasota’s historic districts

Eat your way through Downtown Sarasota with local history and art

Browse boutiques while exploring John Ringling’s legacy over tastings and sparkling wine

Parasail with an 800 ft line and 14 minutes of flight time

Fly parasailing on a private trip for up to 12, with observer spots if space allows

A custom chef‑curated feast celebrating bold local flavors and dietary wellness—served right in your home or rental

Experience marine life up close on a comfortable pontoon cruise for all ages.

Cruise Sarasota Bay to Big Pass for Gulf sunset views

Rent a 22' Bentley pontoon and cruise Sarasota’s Intracoastal waterways

Rent a 24' Sea Ray SunDeck to explore Sarasota waterways and sandbars

Rent a 21' Chaparral bowrider in Sarasota for up to 10 guests

Cruise Sarasota on a 21 ft Chaparral with Bluetooth stereo and swim ladder

Rent a 23.5 ft Mako center console for cruising or fishing in Sarasota

Charter a 38-foot Sea Ray for 6 hours of Sarasota Bay cruising

Charter a 38-foot Sea Ray for a 4-hour Sarasota Bay cruise

Book a 3- or 4-hour private sunset cruise on a 38-foot Sea Ray

Private sunset cruise on Kai Fin with premium seating and water toys

Fish offshore with a USCG-licensed captain, mate, bait, and standard fuel included

Charter the 50' Memory Maker for 3 hours with four lounge areas

Charter the 54’ Pardo Exit Strategy for 4 hours on Sarasota Bay