C. RUFUS PENNINGTON, III – TRIAL ATTORNEY, OF COUNSEL AT COKER LAW CLICK HERE FOR MY LAW PRACTICE →
Log of a sailor

Rufus Pennington
upon the sea

Forty years in the courtrooms. Another apprenticeship under sail — coastal passages, blue-water crossings, and the slow education of wind, current, and weather.

30°20′ N, 81°24′ WHome port — Atlantic Beach, FL
EST. 1993Years under sail
OFFSHORE / COASTALPassage type

How this began

Long before closing arguments and appellate briefs, there were small boats and a Florida coastline with beaches and salt creeks. Sailing started as a way to leave work behind for a weekend and became, over four decades, a second education — one measured in hard-earned wisdom and nautical miles rather than verdicts and judgments.

The trips grew into coastal passages, then offshore legs, explorations of the Bahamas, then full ocean crossings — each one a study in patience, preparation, and respect for a sea that does not care about a trial calendar.

The next time someone tells you they have a crazy idea — sailing alone across an ocean, or something just as impractical — don't tell them to wait until they have more money, or time, or a better excuse. Let your first words be, "oh, hell yes." — on solo ocean sailing
Home Waters
Northeast Florida / Atlantic Coast
Longest Passage
3,088 nm, Maine to Portugal, solo
Notable Waters
Bahamas, Caribbean, Gulf of Maine, North Atlantic, the Azores, Europe

The boats

Current vessel — in preparation

Guerrera

TypeClass 40 Akilaria RC3
LOA40'
Built2017
Draft10'
RigSloop, single backstay
MissionSolo, nonstop circumnavigation
Prior vessel — transferred to new stewardship, 2025

Malabar

TypeHinckley Bermuda 40
Built1973
RigYawl
RefitExtensively rebuilt after back-to-back Cat. 5 hurricanes, Caribbean
Notable passageSolo Atlantic crossing, Maine to Portugal, 2025
FateSold, unexpectedly, to a Spaniard

Expedition log

202444°17′N
68°19′W

The First Trial

Malabar left Southwest Harbor, Maine in June 2024, bound for Europe by way of the Azores — a boat freshly refit after back-to-back Category 5 hurricanes in the Caribbean, and a captain who thought he was ready. He wasn't wrong about the boat. Cold Gulf of Maine water, sleep deprivation, and long stretches of whale-watching gave way, once past the Gulf Stream, to a morning when the wheel spun free in his hand. Below, the autopilot ram had sheared from the rudder post and the steering cables had jumped their sprocket — almost certainly a collision with something unseen, half-submerged, in the dark. A jury-rigged fix, talked through by satphone with the Hinckley yard in Maine, held just long enough for three days and nights of hand-steering to the nearest harbor.

Route: Southwest Harbor, ME → Halifax, NS (voyage aborted) · 3 days hand-steered · boat trucked home
202544°17′N, 68°19′W
→ 37°01′N, 8°58′W

Solo, Alone, Across

A year and a full rebuild later — new heater, new autopilot, new steering gear, spares for the spares — Malabar sailed out of Southwest Harbor again, solo, in June 2025. A gale off Cape Sable put her through her paces; sailing on under a double-reefed main and staysail was the better bet over heaving to, though the cross-seas eventually threw her captain headfirst into the stove, breaking his wrist (a fact he wouldn't learn until a Mayo Clinic visit six weeks later). A furling jam, a headsail lost overboard and hauled back aboard, a snapped lifeline, and one more gale before landfall — sixteen days and roughly 2,000 nautical miles out of Maine, the volcano of Pico rose out of the Azores on the horizon, the same sight Joshua Slocum described in 1895. Five days in Horta for repairs, then back out for the final leg to Europe — a last gale off the Portuguese coast, and on July 3rd, anchor down at last off Cabo São Vicente. The next day, Independence Day, he motored up the canal to Lagos under the Stars and Stripes to clear customs.

Route: Southwest Harbor, ME → Horta, Azores → Lagos, Portugal · ~2,900 nm · 16 days to the Azores, solo

Routes sailed

2024 — Aborted passage

Southwest Harbor, ME → turned back short of Halifax, NS

2025 — Solo crossing

Southwest Harbor, ME → Horta, Azores → Lagos, Portugal

The training path for a solo nonstop circumnavigation

Guerrera's proposed programme for a solo, nonstop circumnavigation attempt — commissioning in the Solent, working south and west through long training passages, solo and double-handed.

156Est. sailing days
31,500Est. total nm
9,500Est. solo nm
3Solo passages
2026
August 10–24

Commissioning Solent UK Gosport

The Solent gives good protected water for day sailing

8 days500 nm
August 24–31

Channel/Biscay/N Atlantic

Solid week sailing ending Haslar or Cherbourg

7 days1,500 nm
September 1–15

Haslar or Cherbourg — Rufus Away, Josh at Boat

Maintenance and checking, sailing day or 2 with Cris when they arrive boat

September 16–30

Biscay / N Atlantic

Training — following the weather, short stop Coruna, maybe Azores

14 days3,000 nm
October 1–15

N Atlantic

Training ending up in Madeira or Canarie Islands

15 days3,000 nm
October 16–30

Madeira or Canaries

Rufus away 2 weeks, Josh at boat maintenance/checks

November 1–18

Rufus Solo to Recife Solo

Josh routing, etc. and meet boat Recife

16 days2,500 nm
November 20–30

Recife

Rufus home Thanksgiving, Josh prep boat next leg — etd Recife 29/30 nov

December 1–22

Training Double Recife to Cape Town

Aim to arrive Cape Town ahead of Christmas

24 days4,500 nm
December 22–31

Cape Town

Rufus home, Josh at boat, maintenance and checks and servicing starts

2027
January 1–15

Cape Town

Maintenance and checks, Rufus home, Josh at boat

January 15–31

Cape Town & S Atlantic

Training sailing out of Cape Town

15 days3,000 nm
February 1–15

Cape Town & S Atlantic

Training sailing out of Cape Town

15 days3,000 nm
February 15–28

Cape Town

Rufus home, Josh home, boat Cape Town

March 1–15

Cape Town

Rufus home, Josh home, boat Cape Town

March 15–31

Rufus Solo Cape Town to Recife Solo

Some days final prep Cape Town, Josh routing, etc.

20 days4,000 nm
April 1–7

Rufus Solo Cape Town to Recife

Josh meet boat Recife

April 7–21

Recife

Rufus home, Josh prep boat for next leg

April 22–30

Rufus Solo Recife to Horta Azores Solo

Josh routing, etc.

18 days3,000 nm
May 1–10

Rufus Solo Recife to Horta Azores

Josh routing, etc., joins boat Horta

May 11–18

Azores

Rufus home for a week, Josh prep boat

May 19–31

Double Azores to Caen France

12 days1,500 nm
June

Mini Refit/Prep

Antifoul, new rods, running rigging, any mods found whilst sailing

July

Mini Refit/Prep

Antifoul, new rods, running rigging, any mods found whilst sailing

August 1–15

Re-commissioning Fine-tuning

New sails bent on. Food aboard, etc.

August 15–31

Channel/Biscay

More sailing double Rufus to boat for 15th

2,000 nm
September 1–15

Channel/Biscay

As much sailing as possible

September 15–30

Coruna

Rufus home, Josh prep boat

Sailing days are estimated and factor in work days needed at every stopover for maintenance, checks, and reprovisioning.

Follow the voyage

Day-to-day updates, photos, and video live on Instagram and Facebook — the website gets the long version.