Sailing Sailing Tipsy Gypsy Travels

Living in Maryland – Charming Annapolis & Sailing the Chesapeake Bay

Okay, I didn’t feel right about not writing another post about Maryland. We had such an amazing time there for the entire month of October. Our dock neighbors were great, we hosted amazing visitors from back home, and when we stayed a bit too long, had even greater company at anchor. Our goal was to get to Annapolis by October to enjoy the United States Sailboat Show which we made with a few days to spare. From there, we stuck around Maryland for a few weeks waiting for hurricane season to pass through and to enjoy the Chesapeake Bay. If you’d like to know more about that US Sailboat Show, check out that post here –> Maryland #1. If you’re interested in learning about all the sponsored beverages and delicious cocktail recipes, check out that post here –> Sponsored Cocktails.

Charming Annapolis

We ended up waiting in Annapolis for just over a month. This gave us plenty of time to take care of maintenance, entertain incoming friends and family, and in general relax from traveling for a bit. Our bodies got used to staying still and in the end caused us a bit of delay in getting back into the swing of things. That’s okay though because Annapolis is SUCH AN AMAZING CITY.

The Port Annapolis Marina, where we stayed, was only a 15 minute dinghy ride to Downtown Annapolis. It was a breeze to get there and provided us delicious food and beverage to enjoy anytime we’d like. We’ll go into food/beverage later but first of all let’s talk about this amazing marina. For us, it felt like a resort. Except for when we were docking. See, we tie up bow in. This marina however was our first experience with a stern tie up. We figured it out in the end but people gave us some looks a couple of times wondering if we’d make a mess of things. Nah, we’re good. We’re still learning but we’re not going to cause a scene. Okay, back to the marina. They provide multiple amenities that I would not normally think to have (pool, fitness room, event space, etc). They also have such great service! Everything felt like home while we were there and gave us a nice break from our quick-ish pace.

Alright, now let’s talk food and beverage. There is an abundance of fresh seafood stops, infamous breakfast stops, and basically any type of food you’re craving. It’s all good too! We stopped at quite a few places and enjoyed everything along the way. Here’s a top ten list for your reference! Such a yummy city!

Top 10 Restaurants/Bars in Annapolis

  1. Tsunami – Everything is worthwhile but definitely try the Tuna Lollipops
  2.  Davis’ Pub – Sailor hideaway
  3. Vida Taco & Bar – A la carte tacos and delicious margaritas
  4. Chick & Ruth’s – I’ve been here multiple times but have only ordered the Crab Lump Eggs Benedict. It’s amazing
  5.  Dry 85 – Speakeasy, delicious cocktails
  6.  Fox’s Den – Speakeasy, great food
  7. Reynold’s Tavern – 1747 Pub – A very old place
  8. Federal House – Amazing crab soup!
  9. Middleton Tavern – Breakfast is delish.
  10. Sam’s Waterfront Grille – Tiki bar close to our marina

Another awesome part of visiting Annapolis was the shopping. We didn’t buy much but the shopping is always an ideal time in this sailing city. Our favorite store is Captain’s Club Apparel. They sell FEAT socks that are comfy with cool designs. Other than that, we only window shopped due to all the outfitting we did for our boat at the US Sailboat Show. Plus, we splurged on these motorized scooters –> Genesis Electric Scooters.

Sailing the Chesapeake Bay

We had quite a few visitors while we were held up in Annapolis. It made our stay feel like home but only actually went sailing twice before officially leaving. When we were out sailing, the fresh air made us excited to continue our travels but reminded us of how nice it is to have friends and family alongside our adventures.

This area is a sailing mecca and for good reason. Chesapeake Bay is the nation’s largest estuary with decent coverage from gales and wind for every level of experience. When we did take Tipsy Gypsy out, our wind was sufficient for relaxing day sails. We had forgotten how nice it was to just go sailing and not worry on which direction to go or how many miles to cover. We could always go back to doing day sails but we want to keep traveling. It would be time to leave the Chesapeake Bay and begin our travels down the ICW.

We stayed in Annapolis from September 30th to November 5th. We officially left the Chesapeake Bay November 8th. Our stay was extended due to it’s endless amount of things to do and our love of being social. Thank you so much to all those who made our stay in Annapolis so amazing –> Bill, Brian, Nate, Taylor, Brenda, Tyler, Haley, Colin, Ron, Joy, Kolby, Dave, Luis, and others.

To Annapolis: We’ll see you next October!

Cheers & thanks for reading!


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