Sailing Sarasota, Longboat Key & Anna Maria IslandCall or text 941-896-6400
Kathleen D catamaran under sail

Six distinct ways to sail

Find your
perfect passage.

Two hours for the dolphins. Four for the sandbar. Six when the whole day belongs to you.

Kathleen D catamaran under sail

Compare the fleet of experiences

Time is the first decision.

Public sails depart from Sarasota. Private departures and minimums vary by location; the booking path shows current availability.

Dolphin Watch

The signature sail

Dolphin Watch

A stable, spacious catamaran gives families an easy vantage point for watching the Gulf’s wild dolphins and learning about the marine life around them.

Duration2 Hours
FormatPublic + private
Base rateSee live calendar
  • Morning and afternoon options
  • Family-friendly format
  • Captain-led wildlife context

Taxes, convenience fees, larger-party terms and sailing minimums may apply. Confirm the live total and availability when booking.

See details & live dates
True Sail

More wind. More water.

True Sail

For guests who want more than a quick cruise: an extended true-sailing experience with time to settle into the rhythm of the Gulf and look for dolphins.

Duration3 Hours
FormatPublic + private
Base ratePublic $143 / Private from $699
  • Extended time under sail
  • Dolphin-watch component
  • Morning and afternoon options

Taxes, convenience fees, larger-party terms and sailing minimums may apply. Confirm the live total and availability when booking.

See details & live dates
Big Pass Adventure

Half-day adventure

Big Pass Adventure

Sail, swim and kayak around Big Sarasota Pass, Longboat Pass or New Pass, with the day shaped by conditions on the water.

Duration4 Hours
FormatPublic + private
Base ratePublic $193 / Private from $910
  • Lunch included
  • Kayaks and water equipment
  • Sandbar and swimming time

Taxes, convenience fees, larger-party terms and sailing minimums may apply. Confirm the live total and availability when booking.

See details & live dates
Sunset Sail

Golden-hour favorite

Sunset Sail

Depart before sunset and watch the Gulf Coast shift from daylight to color from the open deck of a sailing catamaran.

Duration2 Hours
FormatPublic + private
Base ratePublic $99 / Private from $556
  • Timed around sunset
  • Public sails from Sarasota
  • Private options by location

Taxes, convenience fees, larger-party terms and sailing minimums may apply. Confirm the live total and availability when booking.

See details & live dates

Once-a-month twilight

Sunset / Moonrise Sail

A limited private charter planned around the rare overlap of a Gulf sunset and the rising moon over the Sarasota skyline.

Duration3 Hours
FormatPrivate only
Base ratePrivate from $699
  • Private catamaran
  • One additional hour
  • Call for monthly availability

Taxes, convenience fees, larger-party terms and sailing minimums may apply. Confirm the live total and availability when booking.

See details & live dates
Anna Maria Island Adventure

A day built around you

Anna Maria Island Adventure

A customizable group escape with time for Egmont Key, Shell Key, swimming, kayaking, beachcombing and a long exhale on the sand.

Duration6 Hours
FormatCustom private trip
Base rateCall to customize
  • Minimum group of six
  • Swimming and kayaking
  • Custom route and pace

Taxes, convenience fees, larger-party terms and sailing minimums may apply. Confirm the live total and availability when booking.

See details & live dates

Good to know

Bring the day you want.

Picnics & drinks

Pack a picnic and bring your preferred beer, wine or champagne. Hard liquor is not permitted.

Wildlife stays wild

Dolphins are frequent companions, never scheduled performers. Every sighting is a real Gulf moment.

Weather leads

Routes and timing follow safe conditions. The captain makes the final call when weather changes.

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