Shared Day Sailing Charter

Starting at $179 pp

Description Let us make your vacation complete with a 2 hour small group aboard a cozy sailboat. Enjoy the breathtaking view, feel the wind in your hair and the ocean breeze on your skin as you take in St Augustine landmarks like the Castillo de San Marco, the Bridge of Lions, and the St Augustine Lighthouse. ...

St Augustine
Boat Rental, Boat Tour, Dinner Boat, Dolphin, Eco Tour, Food Tour, Rentals, Sailing, Transportation, Water Activities, Wine
St Augustine Sailing
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Shared Sunset Sailing Charter

Starting at $179 pp

Description Make it a night to remember with a 2 hour small group sunset sail and enjoy the breathtaking view. Feel the wind in your hair and the ocean breeze caress your skin as you take in St Augustine landmarks like the Castillo de San Marco, the Bridge of Lions, and the St Augustine Lighthouse. Let ...

St Augustine
Boat Rental, Boat Tour, Catamaran, Dinner Boat, Dolphin, Eco Tour, Food Tour, Rentals, Sailing, Water Activities, Wine
St Augustine Sailing
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Private Day Sail Along Historic Bayfront

Starting at $595.00

Description We invite you to sit back, relax and enjoy the beautiful view and wildlife as we slip away from the dock and sail down the Tolomato River.  Make sure to look for dolphins as we approach Porpoise Point as we often see a lot of wildlife in this area.  As we continue our sail down the Matanzas ...

St Augustine
Private Tours
Boat Rental, Boat Tour, Catamaran, Dinner Boat, Dolphin, Food Tour, Rentals, Sailing, Sports, Water Activities, Wildlife, Wine
St Augustine Sailing
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Private Sunset Sail Along Historic Bayfront

Starting at $595.00

Description Make it a night to remember with a 2 hour sunset sail aboard a luxury yacht and enjoy the breathtaking view of historic St Augustine bayfront. Feel the wind in your hair and the ocean breeze caress your skin as you take in St Augustine landmarks like the Castillo de San Marco, the Bridge ...

St Augustine
Private Tours
Boat Rental, Boat Tour, Catamaran, Dinner Boat, Dolphin, Eco Tour, Food Tour, Rentals, Sailing, Sports, Water Activities, Wine
St Augustine Sailing
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Shared Brunch Sail Experience

Starting at $229 pp

Rate $229 per person Description Whether you’re celebrating a school break, special family time, or just looking for an adventure on the water, come on aboard!  Kick back and enjoy a delectable brunch while taking in the sun and sea with a unique vantage point of St. Augustine on board our luxury ...

St Augustine
Private Tours
Boat Rental, Boat Tour, Catamaran, Dinner Boat, Dolphin, Drinks, Food, Food Tour, Rentals, Sailing, Transport, Wine
St Augustine Sailing
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Private Luxury Brunch Sail - Family Style

Starting at $1,500 for up to 4

Rate $1,500 up to 4 guests $149 per person for guest 5 - 10 Description Whether you’re celebrating a school break, special family time, or just looking for a fun adventure on the water - come on aboard!  Kick back and enjoy a delectable brunch while taking in the sun and sea with a unique vantage ...

St Augustine
Private Tours
Boat Rental, Boat Tour, Catamaran, Dinner Boat, Dolphin, Eco Tour, Food Tour, Rentals, Sailing, Sports, Water Activities, Wildlife, Wine
St Augustine Sailing
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Shared - Sunset Dinner Cruise

Starting at $549 pp

Experience the most unique dinner setting that our Ancient City has to offer aboard our luxury sailing yacht. You and your guests will have a reserved front-row seat on the water to view the St Augustine bayfront as the sun dips behind the city. This 3 – Hour Charter Experience will include a fabulous ...

St Augustine
3
Private Tours
Boat Rental, Boat Tour, Catamaran, Dinner Boat, Dolphin, Drinks, Food, Food Tour, Photography Tour, Rentals, Sailing, Transport, Water Activities
St Augustine Sailing
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Private Sunset Dinner Cruise

Starting at $1,995 for 2

Experience the most unique dinner setting that our Ancient City has to offer aboard our luxury sailing yacht. You and your guests will have a reserved front-row seat on the water to view the St Augustine bayfront as the sun dips behind the city. This 3 – Hour Charter Experience will include a fabulous ...

St Augustine
2
Private Tours
Boat Rental, Boat Tour, Catamaran, Dinner Boat, Dolphin, Rentals, Sailing, Water Activities, Wildlife, Wine
St Augustine Sailing
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Sunset Tasting Cruise

Starting at $349 pp

Set sail on a luxurious 2-hour Sunset Tasting Cruise with St. Augustine Sailing, where gourmet cuisine and fine wines meet breathtaking coastal views. This exclusive experience includes a sommelier-curated wine flight paired with seasonally inspired appetizers, all served as the sun sets over the water. ...

St Augustine
2 - Hours
Private Tours
Boat Rental, Boat Tour, Catamaran, Dinner Boat, Dolphin, Food Tour, Rentals, Sailing, Sports, Water Activities, Wildlife, Wine
St Augustine Sailing
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Dolphin Delight & Nature's Wonders

Starting at $179 pp

Imagine gliding silently through the sparkling waters off the coast of St. Augustine, the sails full and the sun warm on your face. Around you, dolphins leap and play alongside the hull, their sleek forms slicing through the water as if welcoming you to their home. Overhead, pelicans dive and ospreys ...

St Augustine
2 Hours
Private Tours
Boat Rental, Boat Tour, Catamaran, Dinner Boat, Dolphin, Eco Tour, Food Tour, Photography Tour, Sailing, Water Activities, Wildlife, Wine
St Augustine Sailing
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Shared Nights of Lights Tour

75 Minutes - Starting at $129 per person

Description Experience the most unique setting that our Ancient City has to offer aboard a luxury sailing yacht. As the City of St Augustine lights up the night -you and your guests will be on the water and watching the dazzling lights. To enhance your sailing experience we offer a variety of beer, wine, ...

St Augustine
Sailing
St Augustine Sailing
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Nights of Lights - Twinkle Package

75 Min Cruise - Starting at $595

Experience St. Augustine’s famous Nights of Lights from one of the most unique and unforgettable settings the Ancient City has to offer—aboard a luxury sailing yacht! Step aboard and leave the crowds behind as you enjoy a magical 75-minute cruise on the water. As the sun sets and St. Augustine comes ...

St Augustine
75 minutes
Sailing
St Augustine Sailing
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Nights of Lights - Sparkle Package

2 Hr Cruise - Starting at $795

Description Experience the most unique setting that our Ancient City has to offer aboard a luxury sailing yacht. As the City of St Augustine lights up the night you and your guests will be on the water watching the dazzling lights. Your private cruise will include: - A perfect pairing of sweet and savory ...

St Augustine
Private Tours
Sailing
St Augustine Sailing
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Nights of Lights - Glitter Package

Dinner Cruise - Starting at $549 per person plus tip and gratuity

Description Experience the most unique setting that our Ancient City has to offer aboard a private luxury sailing yacht. As the sun begins to set and the city of St Augustine lights up the night - you and your guests will have a reserved front row seat on the water and watch the dazzling lights come ...

St Augustine
Private Tours
Sailing
St Augustine Sailing
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Crew Membership

Description Are you an aspiring sailor looking to gain more experience and knowledge? Look no further than our Crew Membership Program, a unique opportunity for individuals seeking to enhance their sailing skills while enjoying the thrill of the open water. With this membership, you'll have the ...

St Augustine
Sailing
St Augustine Sailing
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Crew Sails

Starting at $275 pp

Sail Times: As a Crew Member, sailors can join our weekly Crew Sails every Sunday (10AM - 1:00PM or 1:00PM -4:00PM) - twice a month. Here are a few things to keep in mind about the crew program: During the sail, you will have either a USCG Captain or an ASA Sailing Instructor aboard to provide instruction ...

St Augustine
Sailing
St Augustine Sailing
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Intro To Sailing

Maximum of 6 people

Rates Person - $199+ Minimum of 2 guests to depart Duration 2 Hours (9AM /11AM /1PM / 3PM) Description If you've ever wanted to give sailing a try, but didn't know where to start, this is the opportunity you've been looking for.  With just a minimum of two people, we can introduce you ...

St Augustine
Boat Rental, Catamaran, Sailing, Water Activities, Workshop
St Augustine Sailing
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ASA 101 - Basic Keelboat Sailing

Starting at $1,095 | Two Day Course

Rates • Person - $1,095 Duration Two Day Course - Runs 9am to 5pm on consecutive days. About This two day course is the perfect introduction to sailing, or a good refresher if your docksiders are a bit dusty. Able to skipper a sloop-rigged keelboat of approximately 20 to 27 feet in length by day in ...

St Augustine
Boat Rental, Lesson, Sailing, Sports, Water Activities, Workshop
St Augustine Sailing
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ASA 102 - Basic Keelboat Sailing

Starting at $1,095 | Two Day Course

Rates • Person - $1,095 Duration Two Day Course - Runs 9am to 5pm on consecutive days. About This two day course is the perfect introduction to sailing, or a good refresher if your docksiders are a bit dusty. Able to skipper a sloop-rigged keelboat of approximately 20 to 27 feet in length by day in ...

St Augustine
St Augustine Sailing
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ASA 103 - Basic Coastal Cruising

Starting at $1,095 | Two Day Course

Rates • Person - $1,095 Duration Two Day Course - Runs 9am to 5pm on consecutive days. PREREQUISITES: ASA 101 About This two day course expands on the Basic Keelboat class, with an emphasis on safety and seamanship while piloting an auxiliary-powered catamaran in fair to moderate conditions in and ...

St Augustine
Sailing
St Augustine Sailing
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