A Mid Atlantic Staycation To Recharge, Feel Welcome, & Be Yourself

When it comes to a staycation in the Mid Atlantic states, one city that gets overlooked is Annapolis Maryland. Under one hour from Washington, D.C. and about two hours from Philadelphia, Annapolis is an easy journey to make for millions of Americans. 


Why did we choose to look at Annapolis for a staycation? Well, we had never been. I’ve personally just considered the cities of DC and Philadelphia as places I would want to visit, and having visited Baltimore before as a kid and as an adult only seen the Baltimore area from the highway (not a pretty sight), I jumbled Annapolis in with that mess. Why did we choose Annapolis?  We’ve been hearing great things about how simple , comfortable, and welcoming the city is. We also heard that the economics of Annapolis were strong, per capita income was great, the US Naval Academy was there, and maybe we could find a sugar daddy or sugar son. Kidding!  Maybe …

Image from Westin website

Where to Stay – 

We chose to stay at the Westin Annapolis since we love to build up our Marriott Bonvoy account and we know the quality present.  The location was spot on as it was at the edge of the historic down town area, giving us the opportunity to remain out of the action, but be steps away from the sights of one of the most quaint downtowns we have visited in a long time. Not only do we know the quality of Marriott locations and especially the Westin brand, but we also know that the Marriott brand is handling COVID the same way nationwide. No matter where the Marriott lodging is in the nation, no matter the COVID regulations in where everville USA, the Marriott brand is making sure that their locations, staff, restaurants, cleaning procedures are all what needs to be done.  I was very satisfied and felt safe staying at the Westin. 

The biggest alteration, besides 2 max patron limit in an elevator at once, the 6-feet apart from other guests, and making reservations for the indoor pool usage, was the food service. If guests desired food or breakfast or lunch, there was a wonderful and quite varied selection at the food bar in the lobby. The breakfast tacos are still fresh in my mind as being amazing. We as well ate dinner served from the restaurant, but per Marriott best practices, all food was packed as to go orders and were eaten in our rooms or at the bar area.

Where to Eat – 


We actually do not have one specific recommendation to grab some grub, but if you are in Maryland, you had better eat the crabs or they may look at you funny.  When we left the hotel to walk downtown, many restaurant fronts were spaciously filled with patrons. One place that I did try out was the Sailor Oyster Bar for a late night drink with a local (the apps work very well in Annapolis and the quality of men is very nice). It was so nice to meet someone to chat with and learn about the city.  I was informed that there had never really been a solid/dedicated gay bar in town, but many were friendly and some had gay nights.  So the COVID effect didn’t shut any of our establishments down, for there were none.  And maybe why this is why the app usage in Annapolis was so robust and pleasant. 

Going back to the eating options, they were plentiful and so many had great outdoor seating.  We chose to eat inside at the Middleton Tavern for it was a hot day and I wanted a cold beer.  Annapolis actually was trying its hand at helping out restaurants with more outdoor seating with a program called the “Recovery Zone” where major roads like West Street between Cathedral Street and Church Circle were closed to vehicle traffic so restaurants could take over the brick roads to offer al fresco dining. Bravo Annapolis!

One more fun treat was my Peanut Butter – Oreo ice cream from Annapolis Ice Cream Co. Neither additive overpowered the treat.  I think they knew what they were doing as the company was founded by two New England natives who missed the homemade ice cream of their childhood and were surprised that Annapolis lacked a similar product. They built Annapolis Ice Cream Company to capture the rich ice cream history of New England and make it in Annapolis and they are the only ice cream in Annapolis made-on-site daily. I also had to buy a penguin, I mean, come on!

What to Do – 


Well, we had planned on doing more than we did when visiting Annapolis, but COVID did shut down most of the museums we wanted to visit and since cadets/students were back on campus at the Naval Academy, there was no visiting the academy grounds. But walking around town and going into some of the shops was ample entertainment.  Being from New England, walking down its Main Street, Annapolis reminded me of a coastal town in Massachusetts or a Belfast or Camden, Maine, just a little bigger and more men and women in their white uniforms, and there were plenty of those to look at.  

The relationship to the water is everywhere in town without being too in your face. (Image from Westin website)

But one of the big draws to Annapolis is the water, being near it, on it, (not sure about in it or under it). We were fortunate enough to get a spot on a Schooner Woodwind Sailing Cruise. Our boat ride was from 3 to 5 PM, the wind was epic (crew said the best they had all summer), the seating arrangements on the 74-foot schooner made all patrons very comfortable and safe.  The 3-person crew, including the captain, were jovial and helpful. I would go again at a moments notice. We were a party of 2, but they have seating sections for parties of 4 and 6 and serve water, soft drinks, and alcohol on the boat. Not only did we get to see a great amount of the water, we were given a tour of the shoreline, sailed past many cadets on their smaller boats, and even buzzed by the football practice and athletic fields to see some of the cadets earning their tuition with sweat equity. 

Verdict on Annapolis – 

We only have smiles when we think of Annapolis. The visuals and the ease and walkability of downtown go very far in our book. The safety precautions at the Westin and truly at everywhere across the city were reassuring that these people get what we are fighting.  We found the people to be welcoming, warm, intelligent (that goes far, too), and just an overall delight to interact with on all levels. We did see presence of gay life, of LGBTQ presence around town, but that is not always a necessity in my review.  We do not need to see rainbows and unicorns and gyms and bars everywhere to feel that there is a place for LGBTQ people in a community or if the community is safe to live in. Annapolis was dangerously comfortable.  Should we look at job openings, rentals, and cost of living?  We might just be doing that now.


As a frequent traveler along the east coast, Annapolis may just be the Mid Atlantic city I seek out to rest my rump, refresh my mind, and reward my eyes during my next journey through the Delmarva area.

For more information about Annapolis, head over to visitannapolis.org.

And as always, here are some more pictures of our trip!

Rooms art the Westin embraced the coastal theme very subtly with its grey, sand, white and blue color scheme.
Palatial? Can I use that word? Yes, the Westin had a presence on West Street. (Image from Westin website)
I was hungry and forgot to take a picture of my breakfast turkey tacos. There were 3, I swear and they were so good.
I will again visit Sailor Oyster Bar (SOB). the staff treated you better than family and they are flying our colors!
Inside the rustic Sailor Oyster Bar.
I believe Tsunami was one of the bars mentioned that had an LGBT night pre-COVID. Next time I will pop in for a beverage.
Approaching West Street from Church Circle we saw the signs for the Annapolis outdoor eating scene.
… and it seems the people were enjoying the Recovery Zone experience. This was just one of many locations and nights this program was offered across the city.
I was pleasantly surprised to see how big 74-feet was. Yep. I could go sailing on this.
There were some times the boat was at a 30 degree angle or more, but it was thrilling. Masks were worn until we were out of the harbor, but once out on the open water, we could remove them when in our designated seating area.  Sign me up for another ride when I am in town.
Some remnants from the U.S.S. Maine at a park on the shore at the Naval Academy. This Mainer did not know those were here!
Next time a zoom lens to see football practice better at the Naval Academy.
Historic Annapolis (Westin website image)



Leave a Comment