Annapolis, Maryland: A Wheelchair Accessible Family Getaway That Exceeded Every Expectation

When I first found out we were heading to Annapolis for a long weekend, I was genuinely excited. I'd only been there once before for a football game and we barely got to experience the town. I remember driving through thinking, man, I want to come back here for a real vacation someday!

As a full-time wheelchair user, planning a trip always comes with a few unknowns. You can research hotels, attractions, and restaurants, but some things you just can't know until you arrive. Will the sidewalks be smooth? Will the curb cuts actually work? Will accessible parking be available? Will a supposedly accessible attraction really be accessible?

After spending four days in Annapolis with my husband Chris, and our daughter Kaylee, I can honestly say this was one of the most accessible destinations we've visited.

Getting there

Our travel day started off surprisingly smoothly. We actually arrived at the airport early, which never seems to happen Since the Hurricanes were in the playoffs, I was really grateful for the Wi-Fi so we could watch the game. We flew right over the stadium when they scored!

We flew into Baltimore, which is about 40 minutes from Annapolis.

The most helpful thing was that our accessible van, which we rented from Mobility Works, was waiting for us in the parking garage. We knew exactly where it would be, thanks to photos that were sent ahead of time. That small detail eliminated so much stress. The hotel was not too far from the airport, check-in was very easy, and we needed to get to bed early for a busy day the next morning!

A hotel that got accessibility right

One of the first pleasant surprises was our hotel room.

We stayed at Crowne Plaza Annapolis, and our room was conveniently located near the elevator, which might sound minor, but a lot of times accessible rooms end up as far away as possible at the very end of the hall. Walking in I was very surprised and excited by the space. The suite had a separate bedroom and living area, which we took full advantage of. My husband likes it freezing and I like it warm, so he took the pullout couch and me and Kaylee took the bedroom. It worked out perfectly.

Even the carpet deserves a mention. Wheelchair users know that some carpet feels like pushing through quicksand. This carpet was easy to navigate and never felt like a struggle.

The bathroom was very accessible. Grab bars on the back and side of the toilet, multiple grab bars in the shower, a pull-down bench that was spacious and sturdy, and a roll-under sink. The only things I would change are that the shampoo and soap were mounted on the opposite end of the shower from the bench. It doesn't bother me because I bring my own stuff, but it's just something to consider. They also had a towel rack under the roll-under sink, but it's completely removable. I'm sure customer service would have moved it if I'd asked.

Exploring downtown Annapolis

The next morning started with a slight setback when we accidentally slept through our alarm and woke up an hour late. Thankfully, downtown Annapolis was not far from our hotel at all so getting there was a breeze.

Our first stop was Miss Shirley's Cafe. It immediately became one of my favorite meals of the trip. I'm a big breakfast girlie, so I got their apple cinnamon French toast and it was honestly some of the best French toast I've ever had. I think I want to go back to Annapolis just for that! The tables were far enough apart that I didn't feel cramped and I could easily roll right up. The bathroom has a large accessible stall and a sink I could roll under. We also got the Kickin' Creole Shrimp Deviled Eggs, which everyone loved. My daughter got the chocolate chip pancakes and I had a pineapple coconut colada served in a mason jar that tasted like a vacation in a glass.

After breakfast, we boarded a Watermark Harbor Cruise and I was blown away by how smoothly everything worked. The dock had multiple ramps and they knew I was coming, so without me even asking, they had the boarding ramp onto the boat ready to go. I could easily roll right on. The views were stunning with so many sailboats on the water, and the weather was perfect. I spent the whole ride on the lower deck with the wind in my face and the sun shining. The only things that weren't accessible were the upper deck and there were no wheelchair accessible bathrooms, but the cruise is only an hour so neither of those was a big deal.

Next was the Banneker-Douglass-Tubman Museum. I rarely feel like I can go into old historical buildings but this one was renovated well enough that I could! They had an elevator to the second floor, a spacious layout in the exhibits, and all the interactive buttons were low enough for me to reach. The only thing I would change is that the third floor isn't wheelchair accessible, but it was a limited exhibit anyway. All the main stuff is on the second floor.

For lunch we headed to Chick & Ruth's Delly, which is like a staple in Annapolis. Don't get discouraged if you see a step at the front entrance. There's an accessible brick ramp around the back. However, this place is extremely tight and busy because everyone wants to go, so maneuvering is a bit of a challenge, but I was able to get up the ramp, pull into my spot at the table and enjoy some fantastic crab cakes and crab dip. My husband got sweet potato fries and I stole all of them.

For dinner we went to Carrol's Creek Cafe. This place is right on the water and it's absolutely beautiful. It has accessible parking near the entrance, ramps connecting different seating areas, and the absolute star of the show: a separate family restroom. I don't think I've ever seen that in a nice restaurant like this. Honestly I don't think I've seen it in any restaurant ever! The food was just as impressive. I had a filet mignon because steak is kind of my thing, my husband tried soft-shell crab for the first time as it's a local delicacy, and we had their award-winning she-crab soup which absolutely lived up to the hype.

The experience i'll never forget

The following morning brought the highlight of the entire trip.

We spent the morning with CRAB (Chesapeake Region Accessible Boating), a nonprofit that offers adaptive sailing experiences for people with disabilities. And it's completely free!

Everything about the facility was designed with accessibility in mind. Wide parking spaces, accessible restrooms, ramps to the docks, and even a Hoyer lift for getting onto the boats. Whenever we try to do fun stuff, Chris always has to physically lift me, so this was such a huge help for both of us. Once aboard they put me in basically a racing car type seat with a full harness so I wouldn't fall over with my limited trunk control, and they have an adaptive extension for the tiller so I could operate the sails on my own. Of course I needed some guidance, but it definitely felt free!

Being on the water has always been a huge part of my life, especially growing up in Virginia Beach. The moment they handed me the tiller was something special. The weather was beautiful, my family was smiling, and for a few moments I felt like my old self again. Not because I forgot my disability existed, but because it simply wasn't the focus. I was just out on the water, sailing.

Lunch at Caliente Grill

After sailing we headed to Caliente Grill for lunch. This place is definitely authentic! The parking was right next to the ramp to get inside, and the waitress pulled a chair out from the table right away so I could roll straight in. I had some tacos and chicken fajitas, my daughter got the chicken quesadilla, but the absolute winner was the cheese dip. It literally had sausage in it and I have never seen that before! We had to get two orders. The bathroom here is very spacious with a large accessible stall and a roll-under sink.

A beach day on the Chesapeake

Later that day we visited Sandy Point State Park and this was another surprise favorite. I am totally a beach girlie, but before this trip I never knew Annapolis had a beach.

One thing every person needs to know: they now do reservations for the beach ahead of time to keep it from getting too overcrowded. It's a new thing, so just make sure to book before you go or you might not get in. Find more information about reserving.

There's lots of accessible parking with paths down to the beach, and a really accessible women's locker room area. If you go to the lifeguard office, you can rent a beach wheelchair for the day for free. And an awesome touch is that the beach wheelchair comes with an umbrella! Due to my injury being high in my spinal cord, I can't regulate my body temperature or sweat, so I can overheat really easily. That umbrella could literally be a lifesaver. The views were absolutely beautiful looking across the water at the Chesapeake Bay Bridge.

Sunset at Yellowfin

That evening we had dinner at Yellowfin Steak and Fish House and this was definitely my favorite food spot of the whole trip. There are windows all around the dining area and is the place to be at sunset. We sat in the corner so we could really see the colors and the sky turned pink and purple. It was just stunning.

We went a little hard on the appetizers and got the Thai shrimp egg rolls, the crabcake egg rolls, and the coconut shrimp. All three were 10 out of 10 in my book. Since I have steak so much, I went with a ribeye and it was so, so good. My husband got the lobster tail dinner.

We left very happy.

A historic city that's actually easy to navigate

On our last full day we went back downtown to explore more and the shopping was so fun! Usually when you go through a town like this, especially a historical one, the roads are really uneven and the curb cuts aren't smooth. Downtown Annapolis is so different from that. At no point did we come across a barrier we couldn't handle. I was even able to take the curb cuts independently, which in a lot of towns is just not possible. The sidewalks were great, the streets were great, and the vast majority of stores were accessible. I could have easily spent the whole day there.

Before heading home

On our final day we squeezed in some activities closer to the airport. First stop was Arundel Mills Mall in Hanover, about 10 minutes from the airport. It is huge! It's an outlet mall so the prices are really good and I probably didn't even see half of it. I could have easily spent the whole day here.

My favorite thing at the mall was The Great Big Game Show, a place where you can compete against your friends and family in a real hosted game show setting. I literally felt like I was on TV. I spun the wheel, rolled some dice, played a bunch of mini games, and me and Kaylee beat Chris! He thought he had it because he's a teacher (haha!) The mall is not cramped at all and there are accessible bathrooms throughout.

Then we went to Live! Casino and Hotel. It was busy because of graduation crowds, so we couldn't see everything, but accessibility was really consistent. Elevators everywhere and ramps wherever there were stairs. We ate at David's inside and had some of the best pull apart bread with rosemary sea salt, parmesan honey butter and truffle essence. One of the best hamburgers I've had too.

Final thoughts

If another wheelchair user asked me whether Annapolis is worth visiting, my answer would be immediate: absolutely!

The biggest mistake we made wasn't choosing the wrong attraction or restaurant. It was not staying longer. There were multiple places where I felt like I could have spent an entire day and I didn't get the full experience by packing it all in. Of course, I still had a blast!

And if there's one experience I would tell every wheelchair user not to miss, it's adaptive sailing with CRAB. Long after the meals, museums, and shopping trips fade from memory, I'll still remember sitting on that sailboat, steering across the water with my family smiling beside me, feeling completely free. For a few perfect moments there were no barriers, no obstacles, and no reminders of what I couldn't do. There was only the water, the wind, and the simple joy of being out there.

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