St Augustine Sailing - Date Night - Engagement - Proposal - First Date - Unique date ideas - Northeast Florida date night ideas


Our crew at St. Augustine Sailing is ready to help make the romantic moments in your life even more special with our Sweetheart Packages. The crisp February air is the perfect excuse to snuggle up under a blanket on your private boat for two. With a fleet of luxury sailing crafts and over 150 years of combined experience on the water, St. Augustine Sailing is the premiere sailing experience in the historic city. Whether you’re planning to pop the question or just looking for a unique date night that says “I Love You,” our captains know how to create a memorable experience.

“Seeing others fall in love with the salt air, the yachts, the sails and each other – THAT is Amore for us,” smiles Owner and Captain, Rose Ann Points.

You won’t want to miss our romantic Sweetheart Packages, available from February 1st through February 28th. We offer four different experiences, each designed to set the perfect scene for your date on the water. Choose from “Puppy Love,” “Apple Of My Eye,” “Head Over Heels” or “Sweet Dreams.” All charters include convenient on-site, complimentary parking at Camachee Cove Marina.

St Augustine Sailing - Date Night - Engagement - Proposal - First Date - Unique date ideas - Northeast Florida date night ideas


St Augustine Sailing - Date Night - Engagement - Proposal - First Date - Unique date ideas - Northeast Florida date night ideas

Our Puppy Love package is the perfect way to kick off your romantic evening. Watch the sunset sparkle in each other’s eyes as you sip champagne and enjoy a uniquely-themed, delicious dessert. With our one-hour sail, the timing is perfect for couples to head out on the town and enjoy dinner at one of the many cozy restaurants in St. Augustine. Check out three of our favorites, Kingfish GrillLlama or Collage. The Puppy Love package includes a private one-hour charter for two passengers, a bottle of bubbly and dessert.


Looking for more time out at sea with your special someone? Our Apple Of My Eye package extends your excursion to two hours – you’ll have plenty of time to look for wildlife, take in the sunset or share in the power of the sea by taking the helm! You’ll depart the dock at 4pm and return at 6pm. Your private experience includes a two-hour charter for two passengers, a bottle of champagne and a decadent selection of savory and sweet bites. Finish off the evening with a handcrafted nightcap at Oddbirds Cocktail Lounge or a frosty pint at Meehan’s Irish Pub.

St Augustine Sailing - Date Night - Engagement - Proposal - First Date - Unique date ideas - Northeast Florida date night ideas


St Augustine Sailing - Foodie - Culinary Experiences - Appetizer - Date Night

Say “Head Over Heels” in the most luxurious way imaginable with our indulgent three-hour private charter. You’ll board your very own private sailing yacht for an evening full of adventure. Your captains will have ample time to show you all of St. Augustine’s secrets on the water. Keep a sharp eye out for birds of all feathers, dolphins, rays and more. Your private chef will prepare a gourmet, five-course dinner. You and your love can enjoy your meal on deck with a gorgeous sun-drenched skyline setting the perfect mood. Choose a wine that pairs with dinner or sip on some champagne while you cuddle under your very own couple’s blanket. The Head Over Heels package includes a private three-hour charter for two passengers, a five-course dinner prepared by a private chef, a bottle of wine or champagne and a complimentary couple’s blanket to take home.


Don’t let the fun end with your sail – stay the night. Inquire about our “Sweet Dreams” package and your party can spend the night on one of our comfortable and luxuriously-appointed boats. If a bed on land is more your speed, consider indulging in one of our local bed and breakfasts, such as the Bayfront Marin Innthe Cedar House Inn or the St. Francis Inn. And if brunch is calling your name the next morning, local favorite The Blue Hen has a full breakfast menu, with a limited breakfast menu during lunch hours for late risers. The Roosevelt Room offers an extensive brunch menu with a full selection of cocktails.


Perhaps you want to add a special bottle of something to your Sweetheart Sail. Or maybe you’re looking for something totally different, like a fun girls’ night out or a family day on the water. Reach out to our staff and we can help you build the experience of your dreams! From premium beer and wine packages to overnight sailing trips, our goal is to give you and your party the best sailing excursion possible.


Our fleet will be sailing every day in February, weather permitting, but availability is limited, so be sure to reserve your spot today. You can reserve online here or call our office at 904-829-0648. We can’t wait to set sail with you!