Home / The four captains

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. Below — the four captains, in the order they joined the school.

Captain Whitlock
Founder · Head Instructor
1974Joined the school
Captain i.

James Whitlock.

Head Instructor · School Founder
USCG license
100-Ton Master, 47 yr
US Sailing
Level 3 Instructor
Sea miles
34,000 + logged
Bluewater
Trans-Atlantic, 2x
Specialties
Bareboat · Heavy weather
Boats taught
All five in fleet

Captain Jim founded the school in 1974 with a borrowed J/22 and a sign on the dockmaster's office. Fifty-two seasons later, he still teaches the Bareboat course every other month, and still answers the phone before 7 a.m.

"I've watched two thousand students leave this dock as new sailors. The thing they all have in common is — they didn't think they could, and then they could. That's all the job is."

A short sailing CV

  • 1972
    First trans-Atlantic, Newport to Falmouth, as second mate aboard the schooner Ariel.
  • 1974
    Founded the school. First class: three students, one boat, one weekend.
  • 1989
    Acquired Bramble. Logged 1,400 students aboard her since.
  • 1996
    Acquired Trade Wind. Brought her up the coast from Stuart, FL.
  • 2008
    Trans-Atlantic, second time. Solo, 28-day passage.
Captain Dawes
Coastal · Bareboat
2009Joined the school
Captain ii.

Eleanor Dawes.

Coastal Cruising · Bareboat Instructor
USCG license
50-Ton Master, 17 yr
US Sailing
Level 3 Instructor
Sea miles
22,000 + logged
Charter
BVI fleet captain, 8 yr
Specialties
Coastal · Bareboat exam prep
Boats taught
Halyard, Trade Wind, Lookout

Captain Eleanor came to the school by way of eight years working out of Tortola for a major BVI charter fleet. She has run more bareboat hand-overs than any other captain in our state, which is exactly the experience the Bareboat course requires.

"The boat is not the hard part. The walk-through with the charter manager — that is the hard part. I make sure my students have done it twenty times before they ever get to a real one."

A short sailing CV

  • 2001
    Crossed her first Gulf Stream as a deckhand on a delivery skipper's 42-foot ketch.
  • 2005
    Started running BVI charters out of Tortola, mostly Beneteau and Jeanneau hulls.
  • 2009
    Joined the school full-time, brought charter-fleet check-out methodology with her.
  • 2017
    Co-wrote the school's bareboat-prep workbook, now in third edition.
  • 2024
    Trans-Caribbean delivery, BVI to Newport, as captain.
Captain Reyes
Basic Keelboat · Junior
2018Joined the school
Captain iii.

Mateo Reyes.

Basic Keelboat · Junior Camp Director
USCG license
25-Ton Master, 9 yr
US Sailing
Level 2 Instructor
Sea miles
11,500 + logged
Coaching
Junior racing, 6 seasons
Specialties
Basic · Junior camp · Race series
Boats taught
Bramble, Sou'wester, Optis & 420s

Captain Mateo learned to sail in Optis at this school as an eight-year-old, came back to crew for the racing series at sixteen, and is now the captain who runs the entire junior program. The cleanest tack on the water belongs to him.

"I learned to sail on Bramble. Twenty-three years later, I teach on Bramble. The same dock, the same boat, the same lesson."

A short sailing CV

  • 2002
    First lesson at this school, age 8, in an Opti named "Splinter."
  • 2014
    Junior crew aboard Sou'wester for the school's Wednesday race series.
  • 2017
    USCG OUPV, then 25-Ton Master in 2019.
  • 2018
    Joined as a Basic instructor; took over the junior camp in 2020.
  • 2024
    Crewed the Newport-Bermuda race aboard a borrowed J/120.
Captain Linwood
Navigation · Charter
2014Joined the school
Captain iv.

Sarah Linwood.

Navigation · Private Charter Captain
USCG license
100-Ton Master, 22 yr
US Sailing
Level 3 Instructor
Sea miles
26,000 + logged
Race comm.
Retired, 18 yr senior
Specialties
Coastal Nav · Private charter
Boats taught
All five, plus your own boat

Captain Sarah taught celestial navigation in the Navy for ten years, served eighteen seasons on the local race committee, and is the captain we send out on private-charter days when an owner wants someone behind the helm who has seen everything once already.

"Coastal Navigation is the only course on our ladder that lives entirely in the chart room. It is also the course that gets students into the most trouble — and the only one that gets them out."

A short sailing CV

  • 1996
    Commissioned, U.S. Navy, taught celestial navigation at the Academy.
  • 2006
    Took her 100-Ton Master and joined the local race committee.
  • 2014
    Joined the school, redesigned the Coastal Navigation curriculum.
  • 2019
    Took over the private-charter program, teaching by-the-day for owners.
  • 2023
    Crossed the Strait of Belle Isle in fog, hand-bearing only, as a delivery captain.
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