Sailing Sarasota, Longboat Key & Anna Maria IslandCall or text 941-896-6400
Anna Maria Island sailing area

Six-hour custom private adventure

Anna Maria
Island

Give the day enough room for sailing, swimming, kayaking and time ashore around the islands of Tampa Bay and the Gulf.

Anna Maria Island sailing area

A full day on the water

Six hours gives the islands room to unfold.

The Anna Maria Island Adventure is a private, customizable outing for groups of six or more. Instead of rushing through one stop, the longer format leaves time to sail, get in the water and explore places such as Egmont Key or Shell Key when conditions allow.

  • Six-hour private outing
  • Designed for groups of six or more
  • Departs from Holmes Beach Boat Ramp

What makes this departure different

Build the day around the way your group likes to travel.

Egmont Key

Clear water, wildlife and the remains of historic Fort Dade make Egmont Key a memorable possibility for swimming, snorkeling or time ashore.

Shell Key

Calmer water and shell-covered shoreline make Shell Key a natural stop for kayaking, beachcombing, a picnic or an unhurried break on the sand.

Water time

Swim, paddle a kayak or simply stretch out on the beach. The captain will match the activity and route to the day’s conditions.

Plan the six-hour adventure

Start with your group and the kind of day you want.

The departure is already known: Holmes Beach Boat Ramp. Send the group details and preferred day so the team can shape the route and activity mix.

Email the team to planCall or text 941-896-6400

Before the sail

Tell the crew what a good day looks like to you.

Swimming, kayaking, beach time, wildlife and a picnic can all be part of the conversation. The trip departs from Holmes Beach Boat Ramp, and the team will build a realistic route around your group, the weather and the water.

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