Stuart Sailing Charters

Sunsets / Dinner Cruises

About Your Guide

Profile photo of Captain Experiences guide Erinn Hennessy

Erinn Hennessy

Independent Guide
Talkative
Laid-back
Instructional
Beginner Oriented
Comfortable
Quality
Captain Erinn has been drawn to the water for as long as she can remember. Nicknamed the family's "little mermaid" as a child, she discovered early on that her true passion wasn't speedboats or racing across the water, but sailing, nature, and the peaceful experience of being carried by the wind.

That passion eventually led her to purchase the sailing company she had loved since 2020, turning a lifelong love of the water into a career focused on creating memorable experiences for others. Today, she personally captains charters ranging from romantic sunset sails and proposals to sandbar adventures and private celebrations.

With more than 10 years of sailing experience, a USCG 100-Ton Master Captain's License, and First Aid and CPR certifications, Captain Erinn brings professionalism and confidence to every trip. She's also known for her attention to detail, helping guests customize their experience to make every outing feel special.

Whether you're celebrating a milestone, exploring the Treasure Coast, or simply enjoying a day on the water, Captain Erinn is passionate about sharing the beauty, relaxation, and adventure that first made...

About Your Guide

Profile photo of Captain Experiences guide Erinn Hennessy

Erinn Hennessy

Independent Guide
Captain Erinn has been drawn to the water for as long as she can remember. Nicknamed the family's "little mermaid" as a child, she discovered early on that her true passion wasn't speedboats or racing across the water, but sailing, nature, and the peaceful experience of being carried by the wind.

That passion eventually led her to purchase the sailing company she had loved since 2020, turning a lifelong love of the water into a career focused on creating memorable experiences for others. Today, she personally captains charters ranging from romantic sunset sails and proposals to sandbar adventures and private celebrations.

With more than 10 years of sailing experience, a USCG 100-Ton Master Captain's License, and First Aid and CPR certifications, Captain Erinn brings professionalism and confidence to every trip. She's also known for her attention to detail, helping guests customize their experience to make every outing feel special.

Whether you're celebrating a milestone, exploring the Treasure Coast, or simply enjoying a day on the water, Captain Erinn is passionate about sharing the beauty, relaxation, and adventure that first made
her fall in love with sailing.
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Rapid Fire Guide Q & A

What’s your favorite movie?
Clue

Rapid Fire Guide Q & A

What’s your favorite movie?
Clue
What’s your drink of choice?
Hemp Smoothie
What was your last halloween costume?
Strawberry shortcake
What do you want for Christmas this year?
Experiences
How did you get started guiding?
Fell into it by accident lol
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Stuart Sailing Charters Trips

Choose a trip to get started
Fishing in Destin
Fishing in Destin
Fishing in Destin

Eco Tour, Boat Cruise, Snorkeling in Stuart

Sailbrations: Coastal Adventures

NEW
42 ft 1 - 12 People From $1,300
Fishing in Destin
Fishing in Destin
Fishing in Destin

Eco Tour, Boat Cruise, Sunset Cruise in Stuart

Romantic Sailing Charters

NEW
42 ft 1 - 12 People From $1,300
Fishing in Destin
Fishing in Destin
Fishing in Destin

Boat Cruise, Dolphin Watching, Sunset Cruise in Stuart

Sunsets / Dinner Cruises

NEW
42 ft 1 - 12 People From $1,300

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Potential Target Species

Color-coded seasonality below is based on .
  • Get it while it's HOT!
  • This species is in play.
  • You might get lucky (as long as things are in-season).
  • Couldn't tell ya! (no data)

Stuart Sailing Charters Photo Gallery

Sunsets / Dinner Cruises
June 4th, 2026
Stuart, Florida
Sunsets / Dinner Cruises
June 4th, 2026
Stuart, Florida
Sailbrations: Coastal Adventures
June 4th, 2026
Stuart, Florida
Romantic Sailing Charters
May 21st, 2026
Stuart, Florida
Romantic Sailing Charters
June 4th, 2026
Stuart, Florida
Sailbrations: Coastal Adventures
May 21st, 2026
Stuart, Florida
Romantic Sailing Charters
June 4th, 2026
Stuart, Florida
Sunsets / Dinner Cruises
June 4th, 2026
Stuart, Florida
Sailbrations: Coastal Adventures
June 4th, 2026
Stuart, Florida
Sailbrations: Coastal Adventures
May 21st, 2026
Stuart, Florida
Romantic Sailing Charters
June 4th, 2026
Stuart, Florida
Sunsets / Dinner Cruises
June 4th, 2026
Stuart, Florida
Sunsets / Dinner Cruises
June 4th, 2026
Stuart, Florida
Romantic Sailing Charters
May 21st, 2026
Stuart, Florida
Sailbrations: Coastal Adventures
June 4th, 2026
Stuart, Florida
Sunsets / Dinner Cruises
May 20th, 2026
Stuart, Florida
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