Greetings from Annapolis, Maryland!
After years of dreaming about bringing our boat to the boat show — we’ve done it!
Flashback to this time last year, Michael and I took a weeklong vacation to sail around the Chesapeake Bay on Osprey. We made it as far north as St. Michaels, Maryland, where we had one of the most delicious dinners ever — but that’s a story for later.
On our third-to-last day of that trip, we began our return south to Deltaville, VA. We woke up early and started preparing the boat to get underway — totally normal stuff. We pulled up the anchor and headed down San Domingo Creek to Broad Creek and finally out into the Chesapeake Bay.
As we turned into the Bay, we saw something not so normal (at least to us) — dozens upon dozens of boats heading south in one big herd!
That’s when we remembered it was only a few days after the Annapolis Boat Show — when cruisers unite to network, socialize, and equip their boats before heading south for the winter. What we were witnessing was the mass migration of liveaboard sailors doing the very thing we were dreaming of and preparing for. As we watched, we smiled at each other and said, “That will be us next year!”
Fast forward to this year — our time in Annapolis has been everything we hoped for!
Our First Floatchella
The first leg of our journey to Annapolis started in Solomons, Maryland. We had hunkered down at a marina for a few days to tackle some boat projects and hide out from Hurricane Humberto and Tropical Storm Imelda. In the end, both storms stayed well out to sea!
From Solomons, we enjoyed an eight-hour sail up to the Rhode River, where we planned to meet a few other members of the Young Cruisers’ Association for a good old-fashioned floatchella. Osprey arrived a few days early, so we had plenty of time to enjoy sunrises, sunsets, and even our first TRX workout on the boat.
Saturday was floatchella day — several boats tied up next to one another to enjoy good times and camaraderie. This was our first time rafting up with other sailboats, and while we were a little nervous, it went off without a hitch. We met several other young cruisers, including folks who live aboard full-time and those who enjoy weekend sailing on the Chesapeake Bay.
Upside of a Small Boat
The floatchella broke up Sunday morning, and Osprey began making her way toward Annapolis proper. The Sailboat Show is a popular event with limited space for boats to moor or anchor close to the action. We’d heard that prime spots start filling up in mid-September, so we were a little worried we wouldn’t find one.
For context, most people who live full-time on their sailboats have boats a bit larger than ours — anywhere from 38 to 50 feet. Osprey is 35 feet, so she’s on the smaller side. Living on a smaller sailboat comes with its challenges: less storage space, not much room for hosting guests, and constantly being in one another’s way are just a few.
But the upside? Osprey can fit in places the bigger boats can’t.
Thanks to a helpful tip from a sailor we met in Solomons, we knew about a mooring field right next to the boat show that’s limited to boats 35 feet and under. We crossed our fingers that a mooring ball would still be available.
If sailing is new to you, one of the most nerve-racking parts is navigating tight spaces — and the Annapolis harbor is tight, especially during the busy week leading up to the show. As we arrived, my heart rate started to climb as I took in all the things we’d need to avoid: anchored sailboats, motorboats zipping by, even a string of a dozen sailing dinghies skippered by kids in sailing school!
But fear not — skilled Captain Michael navigated it all with ease, including guiding us through a drawbridge and into the mooring field.
There were several mooring balls available, and we easily picked one out. Michael motored us close, I snagged the line with a boat hook, and we secured Osprey smoothly. It was our first time tying to a mooring ball, and we were both proud of how seamlessly it went!
Prime Directive: Make Friends
People attend the Annapolis Sailboat Show for three main reasons:
Browsing sailboats — either because they’re shopping for one or just love looking at boats
Shopping for boat parts and accessories
Meeting other cruisers — it can be hard to meet people living aboard, so the boat show is part reunion, part networking event
Because we already have a boat (and most of the accessories we need), our primary goal was to meet as many cruisers as possible — and hopefully find some friends to buddy-boat down to the Bahamas.
We met a ton of friendly, adventurous sailors at several meetups, including:
Young Cruisers Association sail on the Schooner Woodwind
Women’s Happy Hour, hosted by 59° North Sailing and Women Who Sail
Totem Raft-Up Dinner for the clients of our sailing coaches/ mentor
Young cruisers at Davis’ Pub s
Enjoying Painkillers with friends and dinner with the Totem Raft Up
Gale Warnings
Fortune favored us the prior week when Humberto and Imelda stayed far out to sea. However, it seemed our streak of avoiding bad weather might not last. A nor’easter was forecast to hit the Mid-Atlantic, including Annapolis, during the last days of our stay.
As all good sailors do, Michael and I kept a close eye on the forecast to prepare for strong winds and rain. The mooring field was well protected, and we trusted Annapolis to have well-secured mooring balls.
While we were busy at the show, Maisie was staying with a local boarder. Since she was still adjusting to life aboard, we decided to extend her stay so she wouldn’t have to experience the storm on the boat.
As the week went on, the forecast mellowed. The actual impact was minor — a bit of gusty wind and a few days of light rain. We took the opportunity to hunker down on Sunday and enjoy some football and rest after a busy weekend.
South for the Winter
With the boat show (and the warm summer temps) behind us, it’s time to turn our attention to our southward voyage for the winter. We’ve got a few things to check off the list before pointing Osprey’s bow down the Intracoastal Waterway:
Install a watermaker — so we can have freshwater at the push of a button
Restock provisions — now that we know what we actually eat and where to store it
Attend a friend’s wedding in Richmond — after weeks of being salty sailors, it’ll be fun to clean up and dress up!
We’ll be at our home marina in Deltaville for the next few weeks — so if you happen to be in the area, let us know!
Cheers!
- Jen, Michael and Maisie
Love reading about your adventures. Keep ‘em comin’, safely of course. 🙂