2 hours · Up to 6 guests
Shared Day Sailing Charter
The bayfront by day on a 35-foot yacht.
| Per person | $179 |
|---|
Editorial spotlight · Camachee Cove, St. Augustine
2026 Sunshine Awards nomineeBest Sailing Charter
St Augustine Sailing
Luxury sailing charters on the Matanzas from a fleet of late-model Jeanneau yachts and a Lagoon 40 catamaran, run by a husband-and-wife team who also teach sailing and sell the boats. Shared sails cap at six guests; brunch, tasting and dinner cruises bring a food curator and a sommelier on board.
- Shared day sail
- $179
- Private, up to 6
- from $595
- 5.0
- Reviews
- 774
Editorial spotlight. St Augustine Sailing is a nominee in the 2026 Sunshine Awards. They did not pay for this page and had no say in it. We earn a commission when you book through the links here; your price is the same.
The operation
A family-owned marina business that does more than charters
Owners Rose Ann and Chuck Points run St Augustine Sailing from 3076 Harbor Drive at Camachee Cove, alongside their yacht brokerage, All Points Yacht Sales. Rose Ann cruised the Columbia River as a child, moved to Florida in 1996 and lived aboard a ketch with her children for 13 years; Chuck started sailing at 15. The company is a certified American Sailing Association training facility, and the site says several of its USCG captains began as customers.
The crew page names a full office: Grace as office manager, a staff photographer, a food curator and a sommelier for the culinary sails, and an operations manager, Lance Burkin, who maintains the fleet. The yachts are one to three years old, per the fleet page, and private charters take up to six guests.
“For me, it’s all about the experiences. It’s about the adventure.”
- RP
Owner, captain, instructor
Rose Ann Points
- CP
Owner, captain, instructor
Chuck Points
- LB
Operations manager
Lance Burkin
- G
Office manager
Grace
- AB
Sommelier
Alayna Brewer
- A
Food curator
Amberle
Names and titles as listed on the company’s crew page. Captains named on the page include Chris, Kevin, Dale, Nuri, Dan, Kim, George, Bill, Lauren, Daniel, Scott, Evan, Jeremy and Lisa.
The one to book
Shared Brunch Sail
A sail along the historic bayfront with a plated brunch from the company’s food curator, shared with up to six guests. The private version, family style, takes the whole boat for $1,500.
The dinner cruise runs the same idea at sunset for $549 a person, and the sunset tasting cruise sits between at $349.
| Per person | $229 |
|---|---|
| Private, family style | $1,500 |
Checked against FareHarbor on October 1, 2026.
Check AvailabilityThe boats
Jeanneau yachts and a Lagoon 40
Per the fleet page. Private charters take up to six guests.
Sun Odyssey 349s
- Boats
- Zéphyr, Rendezvous With Destiny, A La Mer
- Length
- 35 ft
Sun Odyssey 380 and 410
- Boats
- Mon Chéri, Enchantée
- Use
- Dinner cruises
Wind Dancer
- Type
- Lagoon 40 catamaran
- Use
- Groups and families
Book it
Sails and cruises
Shared sails are priced per person; private charters per boat for up to six. Checked against FareHarbor on October 1, 2026.
2 hours · Up to 6 guests
Shared Sunset Sailing Charter
The same route at golden hour.
| Per person | $179 |
|---|
Evening · Adults
Sunset Tasting Cruise
Small plates and a sommelier’s pairings at sunset.
| Per person | $349 |
|---|
Evening · Shared
Shared Sunset Dinner Cruise
A plated dinner under sail aboard Mon Chéri.
| Per person | $549 |
|---|
2 hours · Whole boat
Private Day Sail Along Historic Bayfront
A 35-foot yacht for your group of six.
| Per boat | $595 |
|---|
Evening · From Nov 21
Shared Nights of Lights Tour
The holiday lights from the water.
| Per person | $129 |
|---|
Before you go
Know before you go
Departure
3076 Harbor Drive, St. Augustine, at Camachee Cove. Arrive early; the marina is large.
Group size
Six guests on shared and private charters. Larger groups book across boats.
Lessons
ASA 101 through 114 are taught on site; Intro to Sailing is $199.
Pets
The one soft spot in reviews: no pets aboard.
Reviews
What guests say
- 5.0Google774 reviews as of October 1, 2026
- 6GuestsPer boat
- 21–45 ftFleetPer the fleet page
Reviewers name the captains and office staff and praise the boats as immaculate; the only recurring complaint is the no-pets rule.
Questions
Good to know
Where does it leave from?
3076 Harbor Drive at Camachee Cove, St. Augustine.
What does a shared sail cost?
$179 per person for a day or sunset sail. Checked October 1, 2026.
Is food included?
On the brunch, tasting and dinner cruises, yes. Day and sunset sails are scenery only.
Can we take the whole boat?
Yes. Private day and sunset charters are $595 for up to six.
The Ancient City from the water
Shared sails from $179, brunch and dinner under sail, and private yachts for six.
Check Availability