After successfully sailing most of the way to Annapolis from Middle River, our mission was to grab a mooring ball. The “front forty” field was full the day we arrived, but the next day we were able to score one of the balls that wouldn’t be affected by the boat shows. This was the deciding factor for us to stay through the sailboat show which was still 3 weeks away. We wanted to secure a mooring close to shore since we were unsure of Sophie’s progress from surgery and wanted the shortest dinghy ride possible. Once we snagged a ball, we went into shore to pay up at the Harbor Master’s office and check out the town.

Annapolis, Maryland’s capital city, is absolutely charming with its 18th century brick mansions, historic inns and scenic brick-lined streets with restaurants, pubs and shops. It’s not surprising to me that it has earned such titles as “Prettiest Cities” (Southern Living, “America’s Most Romantic Towns” (Travel + Leisure), and “Most Charming Cities in the USA” (Travel Mag). Aside from these earned titles, it also has a  few nicknames. One of them is “America’s Sailing Capital”, and upon arriving it’s very easy to see why. Literally thousands of sailboats line the water ways through Spa Creek and Back Creek. Hundreds of charter boats and smaller sailboats from the local clubs and schools would pass our boat in the mooring field. Sailing is a big deal here, so. It makes sense why they hold one of the largest sailboat show in the world.

United States Naval Academy

Annapolis is probably most famous as the home to the United States Naval Academy. Its massive campus can be seen upon entering the harbor from the mooring field. Anyone can visit once you present your driver’s license or photo ID. Randy and I chose to explore it by doing a running tour. After googling best places to run in Annapolis, I found a route on MapMyRuns that takes you through the sprawling campus of the Naval Academy. Our first run on the campus was more of a run/walk/stop-to-take-photos, but it was so cool to see such an impressive complex of buildings, sports fields, and training facilities. We decided to make this our running spot the rest of the trip since it was probably our favorite so far since cruising with it’s wide open space, less traffic than city streets and the ability to run along the water around the perimeter of the harbor.

A cruiser-friendly city

One of the things we loved most about Annapolis is the cruiser-friendly dinghy docks. There were 4 docks we used frequently, and according to the harbor master’s website there are 22 total, located where any public street ends at the water. The downtown areas of Annapolis and Eastport are very walkable, so having different dinghy docks located throughout allowed us to explore and provision with ease. We frequently used a dinghy dock in Spa Creek that let us visit the famous The Boatyard Bar Grill and Horizons Brewery in Eastport. One of the dinghy docks located in Back Creek positioned us just one mile from a grocery store. The weeks before the sailboat show, we had great access to the main dock at the harbor where we would take laundry to wash, grab a coffee at the Red Bean or explore the streets to visit the governors mansion or the capital. While there, my cousin from Washington DC and friend came to visit us in Annapolis where we grabbed brunch at the Iron Rooster before dinghying them to Blue Turtle for a tour.

Boat Shows and Logistics

During our second week in Annapolis, we witnessed the logistical phenomenon of the set up of 2 major boat shows. We watched smaller boats pushing in floating docks while workers connected them and turned them into a small floating city. The set up of both shows was amazing to watch. As we dinghied to shore, giant tents were being erected, trucks full of merchandise and goods were being unloaded and large boats waited for their slips to be ready. The power boat show, held one week prior to the sailboat show, doesn’t seem to be quite as large or attended. We were able to get dockage at the dinghy dock easily. The streets and restaurants were definitely more crowded but this was the calm before the storm. The week of the sailboat show, the anchorage in the harbor filled to capacity and there wasn’t a spot to be found at the dinghy dock. We were surprised by the the massive scale of this show and the amount of attendees. Randy and I only attended the show one day which was enough for us. We went earlier in the day for a few hours which was definitely the most trafficked, then went back in the late afternoon (after taking Sophie out) which was a great time to see everything since it was less crowded. 

Sailors and cruisers unite

The amazing thing about the sailboat show was the amount of cruisers who were all in one spot sharing a common interest. We met so many new and amazing people. We even met some “famous” cruisers like the crew of SV Delos. We happened to see them dining at Davis Pub one evening when Sophie caught their attention. We took her over and introduced ourselves and got our photo with them. Randy and I have been watching the Delos crew on Youtube and dreaming for years. These guys are the real deal and inspire so many cruisers to dream big.

While at the show, we also got to catch up with Kirk and Lauren of Sailing Soulianis. They were at the show to greet fans at the Youtube and Highfield tents. Last time we saw them years ago, they spent a month in the slip next to us at Salty Sam’s Marina. They now have an adorable daughter and are starting their next chapter cruising with a trailerable trimaran.

The Annapolis Sailboat Show is the cruising social of the year. We met so many cool folks on shore or in our dinghy. We got to meet folks we only knew on Instagram, like SV Mystic Hearts. We also got to meet up with other owners of CSY sailboats.

CSY Meetup at the Boatyard Bar and Grill

Since I knew of at least 2 other CSY sailboats in the area (Marionette’s Revenge and Surprise), I decided to organize a meetup. I didn’t realize we had other CSY’s in the area until I posted the meetup on the CSY Owners Facebook page. We arranged to meet at the Boatyard Bar and Grill and ended up with about 16 people representing 8 boats ranging in size from 33’, 37’ and 44’. We had such a great time talking cruising and talking boats.

Annapolis and the Sailboat Show was so much fun! We got to see and do so much and meet wonderful folks during the 3 weeks we stayed. We will definitely stop here again during our next trip to the Chesapeake.