Great Loop Update: Portsmouth → Annapolis → Cape May

The journey continues aboard the Pair of Jokers, even if the Wi‑Fi hasn’t always kept up with us. Several marinas along the way offered “internet” that felt more like a polite suggestion than an actual service — but that’s part of the adventure.

Upgrades for Life Afloat

The boat is running beautifully, and we’ve added a few new tools to make the trip even smoother:

• A new Garmin chartplotter, so we can plan full routes instead of hopping waypoint to waypoint
• A remote control for the autopilot, which means we don’t have to climb down from the elevated seat we built for better visibility (and no short‑people jokes today)

These small improvements make long days on the water a lot easier.

Portsmouth, VA — Big Navy on Display

Our stop in Portsmouth gave us a front‑row seat to some serious naval engineering. We watched an aircraft carrier being worked on and maneuvered by tugs — an impressive sight from the water and a reminder of the scale of the fleet.

Annapolis — A Visit to the Naval Academy

We spent several days exploring the United States Naval Academy, and it was a highlight of the trip.

Lejeune Hall

The first building we toured was named after Marine General John Lejeune. Inside is the Academy’s pool and, more importantly, the Wrestling Room, a space filled with history, discipline, and tradition.

The Chapel & John Paul Jones Crypt

The Naval Academy Chapel is breathtaking — soaring architecture, stained glass, and a sense of reverence throughout. Below it lies the crypt of John Paul Jones, beautifully preserved and presented with honor.

Good Food in Annapolis

We enjoyed two excellent meals at O’Brien’s Oyster Bar & Seafood, run by a former Navy Corpsman who knows how to take care of people.

We also visited Chick & Ruth’s Deli. Breakfast was great, but we passed on the famous 6‑pound milkshake — maybe on the return trip.

Under the Chesapeake Bay Bridge

Cruising under the Chesapeake Bay Bridge is a completely different experience from seeing it on land. From the water, the scale and engineering are even more impressive.

Next Up: Cape May & Atlantic City

With the Bay behind us, we’re turning north toward Cape May and Atlantic City. New waters, new towns, and more stories ahead.