
Sip & Sail
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One hour luxury sailing around St Augustine
Afternoon and sunset sails with wine tasting
Minimum of two guests and maximum twelve
Captain provided for a smooth and safe experience
Experience Luxury Sailing Through The Historic Waterways Of Beautiful St. Augustine On A Private Yacht
Embark on a serene journey through the historic waterways of St. Augustine aboard a luxury sailing yacht designed for comfort and relaxation. This unique maritime experience invites guests to witness the Ancient City from a fresh perspective while enjoying the gentle breeze of the Atlantic coast. Whether you choose a bright morning sail or a golden sunset cruise, the vessel provides an intimate setting for friends to gather and appreciate the stunning coastal scenery.
The sailing adventure is tailored to provide a smooth and enjoyable passage, with the captain navigating the local waters while guests unwind on deck. Morning departures often feature refreshing mimosas, while afternoon and sunset sessions include a curated tasting of three to five seasonal wines. This combination of sightseeing and leisure creates a perfect atmosphere for social connection, allowing participants to escape the bustle of the city and embrace the tranquil rhythm of the open water.
Safety and comfort remain top priorities throughout the voyage, with the yacht accommodating groups of up to twelve guests. Participants are encouraged to wear comfortable, non-marking footwear and clothing suitable for movement on a boat. While the experience focuses on relaxation, the crew ensures that every detail is managed, from boarding procedures to the proper handling of beverages. Guests should arrive early to ensure a prompt departure and a full five hours of nautical enjoyment.
Beyond the scenic views, the experience offers a deep dive into the maritime charm of St. Augustine. By limiting the number of passengers, the tour maintains an exclusive feel that is ideal for special occasions or casual outings with friends. As the yacht glides past historic landmarks and natural habitats, the connection between the passengers and the environment becomes the highlight of the trip, leaving everyone with lasting memories of their time on the water.
Experience Luxury Sailing Through The Historic Waterways Of Beautiful St. Augustine On A Private Yacht
Embark on a serene journey through the historic waterways of St. Augustine aboard a luxury sailing yacht designed for comfort and relaxation. This unique maritime experience invites guests to witness the Ancient City from a fresh perspective while enjoying the gentle breeze of the Atlantic coast. Whether you choose a bright morning sail or a golden sunset cruise, the vessel provides an intimate setting for friends to gather and appreciate the stunning coastal scenery.
The sailing adventure is tailored to provide a smooth and enjoyable passage, with the captain navigating the local waters while guests unwind on deck. Morning departures often feature refreshing mimosas, while afternoon and sunset sessions include a curated tasting of three to five seasonal wines. This combination of sightseeing and leisure creates a perfect atmosphere for social connection, allowing participants to escape the bustle of the city and embrace the tranquil rhythm of the open water.
Safety and comfort remain top priorities throughout the voyage, with the yacht accommodating groups of up to twelve guests. Participants are encouraged to wear comfortable, non-marking footwear and clothing suitable for movement on a boat. While the experience focuses on relaxation, the crew ensures that every detail is managed, from boarding procedures to the proper handling of beverages. Guests should arrive early to ensure a prompt departure and a full five hours of nautical enjoyment.
Beyond the scenic views, the experience offers a deep dive into the maritime charm of St. Augustine. By limiting the number of passengers, the tour maintains an exclusive feel that is ideal for special occasions or casual outings with friends. As the yacht glides past historic landmarks and natural habitats, the connection between the passengers and the environment becomes the highlight of the trip, leaving everyone with lasting memories of their time on the water.
- One hour sailing session
- Captain and crew
- Scenic views and guided sailing experience
- Personal expenses
- Gratuities
$ 179
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This activity is managed by our trusted partner FareHarbor.
Additional taxes and fees may apply — total shown at checkout.
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Activity Provider: St Augustine Sailing
Customer Reviews

We had an amazing time! We've taken sip and sail cruises in Florida and this Michigan sip and sail cruise definitely hit the mark with service and experience. The waitresses were taking orders so you didn't have to crowd the bar for drinks. Drinks came fairly quickly considering the initial high volume of orders to serve everyone on the boat at once. The live music was a great touch! We loved the cruise under the Mackinac Bridge and poising the boat in a perfect place on the water to watch the sunset over the bridge. I highly recommend this cruise.

My husband and I had the best time on the sip n sail cruise! It was the highlight of our trip! The musicians were amazing and the crew was superb!

Ty made our trip it was the best sip and sail cruise I’ve ever been on. It was absolutely amazing he was awesome the music was absolutely incredible it was awesome Emily was the best. Owen was the most attentive and passionate waiter I’ve ever had he not only was from Mackinac island and knew the area but was super nice and great at his job. Overall I would choose this boat over any other option 100/10 times it was amazing and I can’t stress how good Ty was as the captain he was absolutely amazing












