US Sailing Certified Course Provider · Since 1974

The compass course, at sea since 1974.

A keelboat sailing school on the Chesapeake — four US Sailing certifications, five teaching boats, four USCG-licensed instructors, and a fifty-year habit of turning landlubbers into bareboat skippers.

52 yr
On the bay
4
US Sailing courses
5
Teaching boats
2,140
Skippers certified
US SailingCertified Course Provider
USCGLicensed instructors, 4 of 4
ASACross-credit honored
NauticEdLogbook integration
RYAEquivalency on file
Four certifications

From the dock to bareboat charter, in four courses.

Each course follows the US Sailing curriculum to the letter, ends in a written and on-water exam, and credentials a graduate against an internationally recognized standard.
Basic keelboat
Level i
No experience required

Basic Keelboat.

US Sailing 101 — three days · 24 hours

The foundation course. Tack, jibe, heave-to, dock under sail, and crew a keelboat under twenty-six feet in light to moderate wind. Most students leave with their first certification in hand.

3 days
F · Sa · Su
24 hr
Water + class
1 : 4
Instr. ratio
$795All inclusive
Enroll
Coastal cruising
Level ii
Prereq · Basic Keelboat

Coastal Cruising.

US Sailing 103 — five days · 40 hours

Captain a cruising auxiliary up to thirty-five feet on coastal waters. Provisioning, anchoring overnight, fuel and water management, weather, and reefing under load.

5 days
M – F live-aboard
40 hr
Underway
1 : 3
Instr. ratio
$1,795Provisioned
Enroll
Bareboat
Level iii
Prereq · Coastal Cruising

Bareboat Charter.

US Sailing 104 — six days · 48 hours

The certification charter companies require. Multi-day passage, refueling at sea, electrical systems, the dinghy, the head, and the small-systems failures that make a charter trip a charter trip.

6 days
Live-aboard
48 hr
Underway
1 : 3
Instr. ratio
$2,495Provisioned
Enroll
Coastal navigation
Level iv
Classroom · taken with iii

Coastal Navigation.

US Sailing 105 — three weekends · 28 hours

Paper-chart and electronic-chart navigation, dead-reckoning, set and drift, tide and current calculation, the handheld bearing compass. Pure classroom, evenings + Saturday mornings.

3 wkd
Sat · Sun a.m.
28 hr
Classroom
1 : 8
Instr. ratio
$595Books incl.
Enroll
The teaching fleet

Five boats, kept in Bristol order.

A boat is a curriculum. Our keelboats range from the J/22 — sized for first-day stoke and quick learning — to a forty-foot sloop ready for the bareboat exam and a real overnight passage.
Sloop

"Trade Wind"

Beneteau 40 · 1996 · Bareboat boat

The bareboat trainer. Forty feet, two cabins, a working galley, a real holding tank, a real cantankerous diesel.

J22

"Bramble"

J/22 · 1989 · Basic boat
J24

"Sou'wester"

J/24 · 1992 · Basic+ boat
Cruiser

"Halyard"

Catalina 30 · 1988 · Coastal boat
Cutter

"Cape Lookout"

Pacific Seacraft 34 · 2002 · Coastal+
Tour the whole fleet
Four instructors

USCG-licensed, US Sailing certified, seasoned.

Every instructor on staff holds an active USCG Master license, a US Sailing instructor cert, and has logged more than ten thousand sea miles.
Captain

Captain James Whitlock

Head Instructor · Founder
USCG 100-Ton Master US Sailing Lvl 3 34,000 sea miles Trans-Atlantic, 2x
Captain

Captain Eleanor Dawes

Coastal Cruising · Bareboat
USCG 50-Ton Master US Sailing Lvl 3 22,000 sea miles BVI charter capt., 8 yr
Captain

Captain Mateo Reyes

Basic Keelboat · Youth
USCG 25-Ton Master US Sailing Lvl 2 11,500 sea miles Junior coach, 6 yr
Captain

Captain Sarah Linwood

Navigation · Private Charter
USCG 100-Ton Master US Sailing Lvl 3 26,000 sea miles Race-comm. retired, 18 yr
Read each captain's CV
Spring & summer 2026

Book your Basic Keelboat — two seats remain in May.

Class sizes are capped at four to keep the instructor ratio low. The May, June and July weekends fill first; the panel at right shows availability across the next twelve weeks. Bareboat seats book six months in advance.

Basic Keelboat — open seats

Next twelve weeks
May 2–4
Capt. Reyes · "Bramble"
2 seats
May 16–18
Capt. Whitlock · "Sou'wester"
Full
May 30–Jun 1
Capt. Reyes · "Bramble"
3 seats
Jun 13–15
Capt. Dawes · "Sou'wester"
1 seat
Jun 27–29
Capt. Whitlock · "Bramble"
4 seats
Jul 11–13
Capt. Reyes · "Bramble"
3 seats
Reserve a seat
Ages 8–15

The Junior Sailing Camp.

Six week-long summer sessions. Optimist for the youngest, 420 for the older — swim test required, sunburn included. Half-day morning camps and full-day camps both available.

Read the program
By the day

Private charter & instruction.

Got your own boat and want a captain for the day? Family sail experience? Half-day corporate? Captain Linwood books private days year-round, your boat or one of ours.

Book a private day