Now Booking Snowbird Season — Ask About 6–11 Month Rates 56 Residences Across Longboat Key & Lido Key New for 2025 — Club Estate on Longboat Club Road Now Booking Snowbird Season — Ask About 6–11 Month Rates 56 Residences Across Longboat Key & Lido Key New for 2025 — Club Estate on Longboat Club Road

AREA GUIDE / WATER ACTIVITIES & BOATING

Water Activities & Boating worth the trip

Water Activities & Boating across the Sarasota Gulf Coast — the full regional list, wherever it takes you.

All areasAnna Maria IslandBradentonDowntown SarasotaLido KeyOsprey / NokomisSarasotaSarasota Bay / Multiple Pickup AreasSiesta KeySouth Sarasota / Gulf GateVenice
MOST RECOMMENDED
ALL 28 WATER ACTIVITIES & BOATING
Lido Key

Sarasota Kayak Rentals

Kayak & Paddleboard

Guided kayak tours and rentals exploring Lido Key mangrove tunnels and Sarasota's protected coastal waterways.

FamiliesCouples
Sarasota Bay / Multiple Pickup Areas

Sarasota Paddleboard Company

Kayak & Paddleboard

Full-service SUP and kayak outfitter offering rentals, tours, lessons and deliveries around Lido Key, Longboat Key and Sarasota.

FamiliesBeginners
Sarasota Bay / Multiple Pickup Areas

Happy Paddler

Kayak & Paddleboard

Naturalist-led kayak and paddleboard tours and rentals serving Anna Maria Island, Longboat Key, Lido Key and Sarasota.

FamiliesNature Lovers
Sarasota

NL Boat & Jet Ski Rentals Sarasota

Boat Rentals

Sarasota boat and jet-ski rental company offering self-drive rentals, tours and delivery throughout Sarasota County and nearby barrier islands.

Boat RentalsJet Ski Rentals
South Sarasota / Gulf Gate

Siesta Skis

Jet Ski Rentals

Jet-ski rental and tour operator near Siesta Key offering free-ride rentals, dolphin tours, sunset tours and private excursions.

Jet Ski RidersCouples
Bradenton

Anna Maria Jet Skis

Jet Ski Rentals

Jet-ski rental operator serving the Anna Maria Island area with guided access to designated riding waters around Palma Sola Bay.

Jet Ski RidersAnna Maria Island Visitors
Anna Maria Island

AMI Dolphin Tours

Dolphin & Eco Tours

Holmes Beach tour operator offering dolphin and wildlife cruises plus shelling, snorkeling, pontoon rentals and guided jet-ski adventures.

FamiliesDolphin Watching
Anna Maria Island

Island Boat Tours & Adventures

Dolphin & Eco Tours

Bradenton Beach boat-tour operator offering wildlife eco tours, private charters, snorkeling, shelling, sandbars, Egmont Key trips and sunset cruises.

FamiliesDolphin Watching
Anna Maria Island

Anna Maria Charters

Charter Fishing

Holmes Beach charter operation offering inshore, nearshore, offshore, tarpon and fly fishing plus snorkeling and private boat excursions.

AnglersFamilies
Anna Maria Island

Just Reel Fishing Charters

Charter Fishing

Family-friendly Anna Maria Island fishing charter specializing in inshore and nearshore live-bait trips around Tampa Bay and nearby waters.

FamiliesFirst-Time Anglers
Venice

Venice Boat Rental

Boat Rentals

Venice waterfront outfitter offering pontoon rentals, private sunset cruises, banana-boat rides and kayak paddles from Fisherman's Wharf Marina.

FamiliesPontoon Rentals
Osprey / Nokomis

Venice Reef Charters

Charter Fishing

Nokomis/Venice fishing charter offering Intracoastal, nearshore and offshore trips for families and serious anglers across Sarasota County waters.

AnglersFamilies
Sarasota Bay / Multiple Pickup Areas

Chasing the Sun Charters

Private Charters

Private Sarasota boat charters for sunsets, dolphins, sandbars, swimming, shelling and custom island-hopping adventures with a licensed local captain.

CouplesFamilies
Sarasota Bay / Multiple Pickup Areas

Gulf Water Tours

Private Charters

Custom private boat charters around Sarasota Bay and nearby barrier islands with dolphin watching, sandbar stops, beach exploring and sunset cruising.

FamiliesCouples
Sarasota

Barefoot Tiki Tours

Private Charters

Sarasota tiki-boat operator offering private charters and shared dolphin, sunset and sightseeing cruises for groups of up to 16.

GroupsCelebrations
Bradenton

Florida Fishing Fleet

Charter Fishing

Cortez Fishing Village fleet offering party-boat, split and private inshore, nearshore and offshore fishing trips, including options for larger groups.

AnglersFamilies
Downtown Sarasota

Off the Hook Boating

Boat Rentals

Family-owned Sarasota boat rental company launching from Centennial Park with bowriders, tritoons and center-console boats for exploring Sarasota Bay and nearby barrier islands.

FamiliesGroups
Anna Maria Island

Compass Boat Rentals

Boat Rentals

Locally owned Anna Maria Island boat-rental operator in Holmes Beach offering pontoon, tritoon and deck-boat rentals plus captained sightseeing and wildlife tours.

FamiliesGroups
Sarasota Bay / Multiple Pickup Areas

SRQ Boat Charters

Private Charters

Private Sarasota charter service for up to six guests offering custom sightseeing, sunset, dolphin, dining, beach and marine-life trips with a licensed captain.

CouplesFamilies
Anna Maria Island

Sea Rocket Gulf Coast Parasail

Parasailing

Bradenton Beach watersports operator offering parasailing over Anna Maria Island and the Gulf plus private dolphin, sunset, party-boat and Egmont Key excursions.

FamiliesCouples
Lido Key

Almost Heaven Kayak Adventures

Kayak & Paddleboard

Long-running Sarasota kayak outfitter offering guided eco-tours through Lido-area mangroves plus self-guided kayak rentals and stand-up paddleboard rentals/delivery.

FamiliesCouples