Sailing Sarasota, Longboat Key & Anna Maria IslandCall or text 941-896-6400
Kathleen D catamaran approaching the Sarasota bridge

Sarasota · Longboat Key · Anna Maria Island

Three departures.
One Gulf.

Choose the place that fits your plans, then choose how long you want the water to yourself.

Kathleen D catamaran approaching the Sarasota bridge
Sarasota & Siesta Key

Public + private sails

Sarasota & Siesta Key

The home base for public departures and private charters, with quick access to Sarasota Bay and Big Sarasota Pass.

2 Marina Plaza · Dock E, Slip 20 · Sarasota, FL 34236

  • Public Dolphin Watch, True Sail, Big Pass and Sunset options
  • Downtown departure at Marina Plaza
  • Private sails available
See departures & live dates
Longboat Key

Private online · public by request

Longboat Key

A quieter mid-key departure for private sails, with shared public sails available by request.

4134 Gulf of Mexico Drive · docks behind Harbour Square

  • Private sails can be booked online
  • Public sails are arranged by inquiry
  • Complimentary parking and bottled water
See departures & live dates
Anna Maria Island

Custom six-hour adventures

Anna Maria Island

Longer, custom outings departing from Holmes Beach, with room for Egmont Key, swimming, kayaking and time ashore.

Holmes Beach Boat Ramp

  • Designed for groups of six or more
  • Custom activity mix and itinerary
  • Departure from Holmes Beach Boat Ramp
Call, text or email to plan

West Florida, by water

From skyline to sandbar.

Sarasota Bay, Longboat Pass and the island keys each offer a different rhythm. The team will match the route to your departure, trip length and conditions.

Sarasota BayLongboat KeyAnna Maria Island

Recognition & community

Proud of thecompany we keep.

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Tripadvisor recognition

Tripadvisor Travelers’ Choice recognition 2023Tripadvisor Travelers’ Choice recognition 2024Tripadvisor Travelers’ Choice recognition 2025

Local tourism partners