A Wheelchair Accessible Boston Getaway for the Holidays

Boston is one of those cities that truly comes alive during the holiday season. Their historic streets glow with festive lights, seasonal music fills grand concert halls, and there is a warmth in the air that makes even the cold New England weather feel magical. I recently spent several days in Boston during the holiday season, and I was pleasantly surprised by how wheelchair accessible the city is, especially when it comes to attractions, dining, and entertainment.

This trip was the perfect mix of festive experiences, culture, incredible food, and thoughtful accessibility. From staying at a luxury waterfront hotel to attending iconic holiday performances and exploring museums and markets, Boston delivered in every way. If you are planning a holiday getaway and use a wheelchair, this itinerary shows just how accessible and memorable Boston can be.

Day 1: Arrive in Boston

Check In to Boston Harbor Hotel

While in Boston, my mom and I stayed at the wonderful Boston Harbor Hotel, and it ended up being an excellent choice. The hotel is in a perfect location near many of the city’s best attractions and restaurants, and being right on the waterfront made the stay even more special during the holidays.

We stayed in an accessible one bedroom suite, room 1017, and I was extremely impressed. The suite was very spacious and thoughtfully laid out. The living room had a couch, TV, desk, mini fridge, and a Nespresso machine, with plenty of room to comfortably navigate my power wheelchair.

The bedroom featured one king sized bed and another TV. The bed was 30 inches tall and had plenty of clearance underneath for a hoyer lift. I also appreciated that the hotel can remove the box frame if needed, which lowers the bed to 19 inches. That kind of flexibility is rare and incredibly helpful for wheelchair users with different transfer needs.

The bathroom was well designed, with a roll in shower, grab bars, a pull under sink, and a shower seat provided. One feature that really stood out was the accessible push button at the door, which made getting in and out of the room effortless. The suite also had great views of the city, which added to the overall experience.

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Between the location, the spacious suite, and the thoughtful accessibility features, the Boston Harbor Hotel truly exceeded my expectations.

Dinner at Legal Sea Foods Harborside

For my first dinner in Boston, I headed to Legal Sea Foods Harborside, a quintessential Boston dining experience with stunning waterfront views. The restaurant is wheelchair accessible, with step free entry and plenty of room to comfortably navigate inside.

I started with the calamari, which was perfectly cooked and full of flavor. I also ordered the crab cake and shrimp entree, and it was excellent. Legal Sea Foods is known for its classic New England seafood, and everything tasted fresh and expertly prepared. This was the perfect way to kick off my Boston holiday getaway.

Day 2: Art, Music, and Holiday Magic

Enjoy Immersive Art at the WNDR Museum

For our first full day in Boston, we kicked things off at the WNDR Museum with my friend Adriana, who is a fellow wheelchair user. We had such a blast exploring all 20 immersive and interactive installations throughout the museum.

A few of the installations required some assistance for Adriana and me as wheelchair users, but many were fully accessible. We took our time exploring the different rooms, soaking in all the colors and sounds, and just enjoying the chance to experience art in such a fun and engaging way. We laughed nonstop and truly had the best time together. It is always great to see Adriana, and experiences like this make our time together even more special.

I also want to give a major shoutout to the museum for having an all gender accessible restroom. That attention to inclusion really stood out. Our Boston adventure was officially off to a great start.

Brunch at Oak Long Bar and Kitchen

After the WNDR Museum, we headed to Oak Long Bar and Kitchen for brunch. Located inside the Fairmont Copley Plaza, this restaurant offered comfort and elegance all in one place and was wheelchair accessible with smooth entry and plenty of space between tables.

Adriana and I decided to split two dishes, and I am so glad we did. The crab cake benedict was rich and flavorful, and the Boston croque sandwich, which included lobster (or should I say “lobstah” as the locals say) was tasty and incredibly satisfying. This brunch felt relaxed yet elevated and was a great way to recharge before an afternoon filled with holiday festivities. 

Oh, and if you pass through the lobby of the Fairmont Copley Plaza hotel on your way to dine, look for their resident canine, Cori. I was excited to meet her and even gave her a quick snack provided by the hotel concierge. 

Listen to the Holiday Pops in Symphony Hall

Later that day, I went to see the Holiday Pops in Boston, and wow, what an incredible show. A full orchestra and choir performed all the Christmas favorites for a full two hours, and it was impossible not to feel festive.

We sat on the floor level in the table seating area and had a perfect view of the stage. Accessibility was great throughout the venue, which made the entire experience even better. Being able to enjoy such a grand and joyful performance without worrying about accessibility barriers meant a lot to me. I also loved that they had a food and drink menu that you can scan with your phone on every table, and the waiters and waitresses will quickly bring your items to your seat. 

If you are looking for something to truly spark that Christmas spirit, the Holiday Pops in Boston absolutely delivers.

Watch Boston’s Holiday Drone Show

After the Holiday Pops, we headed over to Boston Common to watch Boston’s Holiday Drone Show. This show is part of their “Frostival” celebration. Seeing the night sky light up with festive and city themes created by synchronized drones was such a cool experience.

Viewing areas were accessible, and it was exciting to see a modern holiday tradition set against Boston’s historic skyline. Several food trucks were set up to provide food and drink purchases while enjoying the show, making this a great family or date night event. 

Dinner at Nautilus Pier 4

We wrapped up day two with dinner at Nautilus Pier 4, a waterfront restaurant offering creative, shareable small plates. The restaurant is wheelchair accessible, and staff members were attentive in making sure our table placement worked well. The atmosphere was warm and welcoming, and the full bar had all of your favorite drink options. 

I loved the Japanese fried chicken, the Szechuan green beans, and the spoon tuna chips and dip. Everything was flavorful and perfect for sharing, and the harbor views made the evening even better.

Day 3: History, Theater, and Holiday Shopping

Visit the Boston Tea Party Ships and Museum

Day three started with a visit to the Boston Tea Party Ships and Museum, an interactive attraction that brings American history to life. I was impressed by how accessible the experience was overall.

The museum offers step free entry and accessible pathways throughout, and the replica ships are accessible as well. Staff members were trained and ready to assist wheelchair users when needed.

I had such a fun experience being able to watch as visitors were asked to throw crates of faux tea overboard the ship as part of the interactive experience. The combination of live actors and hands on exhibits made the experience both educational and engaging. 

Don’t forget at the end of your tour to stop by Abigail’s Tea Room and enjoy some of their soothing teas and delicious cookies. 

Brunch at The Banks Seafood and Steak

After the museum, we headed to The Banks Seafood and Steak for brunch. This restaurant has a relaxed but refined vibe and is fully wheelchair accessible, making it easy to enjoy without stress. I was also impressed to see a spacious companion care restroom in house. 

I ordered the lobster benedict, which was absolutely incredible and easily one of the best brunch dishes I had in Boston. The seafood was fresh and perfectly prepared.

There was also a live jazz band playing during our Sunday brunch, and fireplaces glowing throughout, which added a really nice touch and made the experience feel extra special.

See a Show at Huntington Theatre

In the afternoon, we attended a show at the Huntington Theatre. This historic venue has made meaningful efforts to improve accessibility, and it came as no surprise to learn that they had actually won a Tony award for Outstanding Regional Theatre.

My experience there was very positive and I was blown away and filled with emotions as I watched the musical, Fun Home. Each actor and actress made me feel as if I was a part of the show and I could feel the momentum as they sang each song. Fun Home is hands down an incredible show and I can’t say enough good things about the actors/actresses who made this come alive. 

My wheelchair accessible seating was located on the left side, and staff members were welcoming and helpful to assist me to find my seat. Being able to enjoy live theater in such a beautiful space was a highlight of the trip.

Shop Till You Drop at SoWa Winter Festival

Next, we explored the SoWa Winter Festival, a festive holiday indoor market filled with local vendors, seasonal treats, and beautiful decorations. The layout was largely wheelchair accessible, with wide aisles and manageable crowds in most areas. 

The entire street level of the market was flat and paved and absolutely filled with more food and gift purchases than you can imagine. Near the back right corner was an elevator to take you to floors 2 and 3. The second floor was complete with live music and a full bar, and level three entailed some fun photo ops! 

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I loved browsing the handmade items and soaking in the holiday atmosphere, and I may have snacked on way too many great items. I found some delicious chocolate covered strawberries, some tasty empanadas and even some incredible hot chocolate. It felt like a true Boston holiday experience.

Dinner at Kaia

Dinner on day three was at Kaia, a fully wheelchair accessible Greek restaurant offering bold and vibrant flavors. Navigating the space was easy and comfortable.

Kaia brought bright coastal modern and reinvented Greek flavors to the table, with every dish impressing me. When dining here, do not miss the zucchini chips with caviar, which were incredibly addictive.

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The Spanish mackerel was beautifully prepared, and the baklava for dessert was the perfect sweet ending to the meal. This restaurant would be the perfect spot for a romantic dinner or a fine dining experience when out on the town. 

Day 4: Views, Museums, and a Perfect Farewell

Take in the Scenery from View Boston

On my final day in Boston, I started with a visit to View Boston, a 360 degree observation deck experience offering panoramic views of the city. The attraction is wheelchair accessible, with elevators and spacious viewing areas. Its entrance can be found inside the Prudential Center, and there are plenty of great shopping options nearby. 

After grabbing tickets and taking an elevator ride to the top, I found there to be some of the most incredible views of Boston on both their indoor and outdoor viewing decks. From here, I could easily see Fenway Park, MIT, Harvard campus, the JFK Presidential Library, and so much more.

I also found it very relaxing that there is a full bar on the level below the observation decks so that you can sip on a drink and still enjoy the gorgeous floor to ceiling window views of the city below. 

Seeing the vast city of Boston decorated for the holidays from above was incredible and gave me a chance to reflect on just how special this trip had been.

Admire Art at the Museum of Fine Arts

Next, we visited the Museum of Fine Arts, one of Boston’s most celebrated cultural institutions. This museum is one of the largest art museums in the United States and houses over 450,000 works. I most enjoyed the extremely tall and breathtaking Chihuly glass sculpture located near the dining area. And I also loved the Monet exhibit and the ancient Egyptian relics, among many others. 

This museum is highly wheelchair accessible, with elevators, ramps, and accessible restrooms throughout. One of the restrooms here offers a full sized adult changing table, but for this particular one you must request the key from a staff member. There are also wheelchairs and walkers in house that can be used on a first-come, first-serve basis. 

I enjoyed exploring a wide range of exhibits, from classical art to contemporary works, all at my own pace. Accessibility here made the experience even more enjoyable and I could’ve easily spent most of the day enthralled in the exhibits. 

See Aquatic Animals at the New England Aquarium

After the MFA, we headed to the New England Aquarium. This attraction is very wheelchair friendly, with elevators and wide pathways that make navigating the space easy. This aquarium features thousands of aquatic animals and I thoroughly enjoyed seeing as much as time allowed. 

The central tank is especially impressive, and seeing the aquatic animals up close was fascinating. I loved that the large penguins display had plenty of lowered glass viewing areas so that I could easily see the cute little penguins in their habitat from my wheelchair.

Another highlight for me was the harbor sea lions with an elevated ramped viewing area and the anaconda which was way bigger than I would care to see.

The aquarium felt festive during the holidays, which added to its charm and you must visit the gift shop so that you can take home a memory before departing for the day. 

Dinner at MIDA Fenway

For my final dinner in Boston, we headed to MIDA Fenway, and it was the perfect way to end the trip. This Italian restaurant is wheelchair accessible and has a cozy, inviting atmosphere.

They are well known for their handmade pastas and fresh seasonal ingredients, as it is truly special. I highly recommend the Gnocchi Cacio E Pepe, which was unforgettable and honestly the best gnocchi I have ever eaten. It was so much lighter than your usual gnocchi, and absolutely melted in my mouth.

You also should order the focaccia bread as a starter. This bread was so delicious, it would be worth driving there just for it alone! They also serve 14 inch pizzas and many other scrumptious dishes. I enjoyed the raspberry gelato for dessert and I honestly believe it was even better than the sweet tasty treats I had earlier this year in Italy. 

Ending the trip with such an incredible meal felt like the perfect send off, and I highly recommend dinner here during your visit. 

Final Thoughts on a Wheelchair Accessible Boston Holiday Getaway

Boston exceeded my expectations as a wheelchair accessible holiday destination, as well as any time of year. From luxury accommodations and incredible dining to historic attractions and festive events, the city offered so much to enjoy. What stood out most was how thoughtfully accessibility was integrated into so many experiences, allowing me to focus on making memories instead of navigating barriers.

If you are looking for a holiday getaway that combines history, culture, great food, and festive charm, wheelchair accessible Boston is a fantastic choice. I left feeling inspired and already planning my return visit.

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