Sailing Sarasota, Longboat Key & Anna Maria IslandCall or text 941-896-6400
Sunset Sail with Kathleen D Sailing Catamarans

Two hours · public or private

Sunset Sail
Two Hours

Leave in daylight and watch Sarasota Bay turn gold, coral and violet from the deck of a sailing catamaran.

Sunset Sail with Kathleen D Sailing Catamarans

The experience

The best sunset seat is already moving.

The sail departs before sunset so the evening has time to unfold on the water. From Sarasota, the route aims toward Big Sarasota Pass and the Gulf horizon. From Longboat Key, private sails cross the north end of Sarasota Bay with the sun falling beyond Longboat Key.

  • Approximately two hours
  • Timed around the evening sky
  • Public Sarasota or private Sarasota/Longboat Key

What to expect

A sail with its own point of view.

Sarasota horizon

Sail toward Big Sarasota Pass for a west-facing view over the Gulf of Mexico as daylight gives way to evening.

Longboat perspective

Private Longboat Key departures sail the north end of Sarasota Bay with the sunset settling beyond the key.

An easy occasion

Date night, anniversary, family evening or a quiet gathering with friends—the changing sky does most of the decorating.

Sunset Sail calendars

Choose how you want to take the Sunset Sail.

The experience and duration are already selected. Choose a shared Sarasota sail or reserve the full catamaran from Sarasota or Longboat Key to see the matching live dates.

7–11 guests? Online checkout is capped at six. Send a prefilled inquiry for one Maine Cat.

Want a shared Longboat sail? Public departures are available by request. Ask about this trip from Longboat Key.

Live dates, sailing minimums, taxes, fees and final totals are shown in Kathleen D’s booking calendar.

Before you step aboard

Plan around the sun, not a fixed clock.

Departure time shifts through the year with sunset. Choose the appropriate live calendar for current times and availability, and share any special occasion with the team when reserving.

Live availability

Choose a date

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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