Make it the Best on the Water

Sailboat Charter for Engagement

This charter is a truly special way to make a lifelong memory for you and your beloved. 

We take care of everything so all you need to do is focus on popping the big question as the sun sets over the sea. There is no doubt this moment will be imprinted in your hearts forever.

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So you’ve decided to pop the magic question, “Will you marry me?”

Speak those 4 words at the perfect time aboard the Sailfish as the sun sets.

Swept away from all distractions you will both be fully present to create a memory that will be sure to last a lifetime.

Your crew goes above and beyond to make sure all those special touches are a priority and your expectations are exceeded . 

Book with Stuart Sailing to make this day like no other for you and your love, with the most romantic, original proposal!

Book a Sailboat Charter

Per Hour

This includes our crew prepping for you! We have all the romantic touches for your special proposal!
$250hourly
Book Hourly

Full Day

Soak in the most memorable way to pop the big question to the one your love! All you need to do is remember the ring!
$1,5006 hour
Book Full Day

Overnight

This is a truly special excursion for 2! We help you plan your surprise getaway and perfect proposal!
$2200nightly
Book Getaway

Clients Say

Ah-maz-ing, we had the best week! We had no idea how beyond perfect it would all be! The crew made it beyond our imagination!

Edie Watts

Edie Watts

The beauty of this company is its customization, this is not a cookie cutter experience.

Savitri Hook

Savitri Hook

Truly a life changing trip! I went on a Keys spearfish charter on the Sailboat. Erinn and Captain Matty made it the trip of a lifetime! Amazing food and well organized vessel! youtube.com/c/CaptainJackSpearo

Captain Jack Spearo

Captain Jack Spearo

I must say we enjoyed my daughters 17th birthday with 2 of the most respectable people. Captain Mattey and Skipper Erinn showed us mad love, I highly recommend them!

Stacey Stallworth

Stacey Stallworth

Our Crew

Skipper Erinn Hennessy
Skipper Erinn Hennessy
First Mate / Hostess
Erinn Hennessy 561-801-0080 ErinnLovesHealth.com
Captain Paul “Popeye” Jones

Paul has been sailing since 1979.  He owned a series of larger sailboats in the states and then owned a Moorings/Beneteau 432 charter boat based in Tortola British Virgin Islands for 8 years in the 1990’s. He traded time on it…

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