There is nothing sweeter than love, especially in February. Just imagine romantic sailing experiences! There is no better time to celebrate with the one you cherish most.  Whether you are popping the question, looking for a romantic overnight, or something in between, St Augustine Sailing offers the perfect enchanting excursions aboard our private luxury yachts.

With a glass of bubbly in hand, you and your sweetheart will relax on board your private yacht relaxing on the beautiful waterways of the Oldest City.  St Augustine Sailing romantic sailing experiences and Sweetheart Packages include a variety of customizations, and each one can be enhanced with food and beverage additions available for purchase, including beer, wine, canned cocktails and specialty boards.


romantic sailing experiences

Puppy Love

This intimate 1-hour charter includes a bottle of bubbly and six chocolate-covered strawberries.  Starting at $595, snuggle with your loved one under a cozy blanket made for two while you sail along the beautiful waterways together watching the sunset over the landscape.

romantic sailing experiences

Apple of My Eye

This Romantic 2- hour charter includes a bottle of bubbly or bottle ow wine, as well as perfect pairings of sweet and savory bites.  Starting at $795, sail together as the sun begins to set over the cityscape and the sea shimmers around you.

romantic sailing experiences

Head Over Heels

This enchanting 3-hour charter includes an upscale five course dinner for two prepared by a private chef aboard, as well two bottles of house sparkling wine.  Starting at $2,150, wine and dine with your beloved as you soak in the sights along the intracoastal waterway and the Matanzas Bay.

Sweet Dreams

This is a night to remember! Starting at $1,785, this overnight stay is highly customizable and can be added on to enhance any of other Sweetheart Packages or be a stand alone experience.  You and your best mate will experience life aboard while taking in the breathtaking views of historic St Augustine, including landmarks such as the Castillo de San Marco, Bridge of Lions, Great Cross, and St Augustine Lighthouse.  The vessel departs two hours before sunset and returns to the dock just after, where you and your sweety will then have the yacht to yourselves until morning (check out is 10:30 AM).

Come sail away with your sweetheart at St Augustine Sailing, and make memories that will last a lifetime on our romantic sailing experiences

Learn more about our Sweetheart Packages here!

St Augustine Sailing - Sailing Experiences - Sweet Dreams