The Ultimate Boston Travel Guide: Best Hotels, Restaurants & Things to Do
- Joanna Shroyer
- Apr 2
- 14 min read
Boston has been a regular destination for us over the years, and our trips often revolve around a Bruins game. Sometimes we are only there for a night or two; other times we enjoy the city for several days. We were most recently there at Christmas to celebrate our anniversary.
I’m going to attempt to pull together highlights from our last few trips along with some Boston must-dos so you can plan an epic trip—whether you’re visiting for a family vacation or a destination date. Be sure to check out my other Boston post for even more information. As always, no part of this post is sponsored and all opinions are my own.
Use links to jump:
Transportation
Seasonal Activities
Transportation
Air. I've told you before we are Delta people. Justin is a million miler and has Diamond status. I think we've flown Delta for every trip into Boston Logan which is the nearest airport to the city. You will find the airport easy to navigate, clean, and well maintained. Once you've gathered your bags, you'll head toward ground transportation.
Boston Logan has a specific area for ride share pick up, and it is fast and efficient. Follow the directions in the airport, take the elevator to the correct floor in the parking garage, and wait for your ride. It is a bit of a walk from baggage claim, so be prepared.
Ground Transportation. We usually uber if we need a car in the city. Uber drivers are readily available, and we only had trouble during Covid. Only one time have we had a vehicle and that is a post for another time.
Mostly we walk. We walk so so many steps when we are in Boston. It is one of the most walkable cities ever. Here I'll add that in all the times I've been to Boston, I have never felt unsafe in the streets. Even if we are walking back from a Bruins game late at night, there has never been a time that I felt like we were in a scary situation. Now, as always, please use common sense. Walking alone after dark or in areas of town that are not well lit is not something you should do. Make smart decisions. Uber is too easy to use in the city.
A note here to say that Boston has a public transit system, and I've heard that it's perfectly acceptable. We've just chosen not to use it. Unlike NYC the traffic here isn't usually as congested, so we find the travel via uber easier than transit.
What to wear
You may notice that my outerwear has changed since my earlier post. We’ve traveled to the Northeast so many times during the winter months that I needed something a bit warmer. I really hate being cold, and this coat ensures that I stay toasty warm.
It’s a Canada Goose coat and definitely an investment, but if you want to never worry about being cold, this will do it. There is a store in Copley Place where I was able to try on several different styles before making my decision.
I don’t wear a hat often; I usually just pull up my hood. However, if I know I’ll be outside for an extended amount of time—like when we visited a Christmas market on our last trip and it was freezing—a hat is required. My favorite (and warmest) is from the Musk Ox Farm in Alaska and is 50/50 qiviut and merino. I also have matching mittens that I wear over my fingered gloves when it’s especially cold.
I usually carry a scarf as well, although it’s often more for fashion than warmth. With this combination of outerwear, under layers don’t seem to matter as much. I usually start to get warm quickly, so lighter tops tend to work best.
I still stand by my previous statement that you need good walking shoes in Boston. Be sure to check the weather and plan accordingly. Waterproof sneakers or boots are a must, especially during the winter months. Whatever you are most comfortable walking in is what you should wear.
grey cabi sweater and green cabi pants black cabi travel set yellow top cabi with cream cabi sweatersweater white cabi top with leggings navy cabi sweater with jeans black and cream striped cabi sweater with cabi denim embroidered cabi sweater with cabi denim cabi trench cabi sweater set
Scroll through to see a compilation of outfits I’ve worn over the years while visiting Boston. What do they all have in common? cabi. The pieces are easy to pack, coordinate, and layer, which makes them perfect for travel—so it’s no surprise many of my outfits revolve around the brand.
Places to stay
Westin Copley Place. I love that this hotel is attached to the shopping area. You can access both Copley Place and the Prudential Center from its walkway, which is incredibly convenient when the weather is cold or rainy.
We also received several perks for staying here, including tickets to View Boston, Trinity Church, and bike rentals. Be sure to grab those tickets to Trinity and View Boston whether you think you are going to use them or not. They have long expiration dates so are easily used another time and are even transferrable. We noticed on our last stay at the Westin that as an alternative to the bike rental we could get a Torn Ranch breakfast box. Seeing as how I’ll never willingly ride a bicycle anywhere, we opted for the breakfast box. This prepackaged snack box contains mixed nuts, dried apricots, and small granola squares. The offerings may change with time, so be sure to check out the check-in sheet to see what benefits you might be entitled to. The Westin also has a Hyperice recovery system available for guests, which we were able to take advantage of. It was so nice to take care of our legs after a full day of walking.
View from the 5th floor corner room view from the 35th floor corner room
The W Boston. This is a very nice hotel with a fantastic location. Would I stay here again? Yes. Will it be my first choice? Probably not.
It does offer perks such as tickets to View Boston, Trinity Church, and a few other attractions. So if those things were on my to-do list and other hotels offering those perks weren’t available, I would consider this a solid option.
fireplace at the Ritz Boston Dessert at the Ritz Boston
The Ritz-Carlton. Ultimate luxury. No kidding.
We stayed here one night and it was exactly what you would expect from the Ritz. After dinner that night, we managed to snag a seat near the fireplace and order dessert. It was the most relaxing and beautiful experience.
I absolutely love turn-down service—it feels like the most luxurious thing ever.
Things to do
Catch a show. We don’t usually make too many plans when we visit Boston. I like it that way. But we do check to see if there is a local show or concert happening while we’re in town.
On one trip we caught Blue Man Group. I won’t say it was the most amazing show I’ve ever seen, but I can say I’ve seen it. This is mostly to encourage you to check the event calendar during your visit—you never know what you might find. Over Christmas we even considered seeing Harry Potter and the Cursed Child.
View Boston. Located in the Prudential Center, we received tickets for this attraction as part of our hotel stay. It was such a cool perk that we decided to take advantage of it. Even if you have to pay for it, I think it’s worth it. The views are fantastic.
We enjoyed the experience so much that we went back on our last visit to see the city after dark. Don’t miss the free photo opportunity. You can take your picture using the camera outside the bar and email the photos to yourself at the end of the tour. You’ll receive five different green-screen images included with your entry.
Another thing I loved is that as you walk around the observation deck, there are displays explaining what you’re looking at and helping orient you to the city.
justin and me kissing in front of the greetings fro Boston sign View Boston at night displays that show you what you are looking at View Boston Look around the city with these
Trinity Church. It took us two trips to actually make this visit happen. The first time we tried to go, the church was unexpectedly closed—even though the website didn’t indicate that—so keep in mind that plans can change.
Tickets were included as a perk from our hotel, so we joined a free 1:00 PM guided tour, and it was fantastic. Taking the guided tour took about an hour. Our guide knew so much about the church and its history. We learned all about the designing and commissioning of the stained glass collections throughout the church as well as got to visit the renovated basement where you can see the enormous granite pillars that hold the church up. Highly recommend. The church is absolutely gorgeous and the stained glass is stunning. The city has been doing upgrades on Copley Square just outside the church for awhile; I am looking forward to seeing the final results.
inside Trinity Church granite footings Trinity Church stained glass Trinity Church Stained glass inside Trinity Church Ceiling in Trinity Church Trinity Church
Isabella Stewart Gardner Museum. Hear me out—it’s an art museum for people who aren’t sure they love art museums. You truly have to see it to believe it. Isabella Gardner's life was fascinating, and she hand placed everything you see in the museum. She even prohibited anything from being moved in her will! She was a mysterious woman, but her art museum is one of a kind.
This was the perfect outing for a cold, rainy day since everything is under one roof. She even built an indoor courtyard garden. The entire place is breathtaking and well worth the visit. It took us about two hours to tour the museum. I was especially impressed by the number of chairs and the enormous tapestries dating back to the 1500s. No joke. Incredible.
Piano Horse sculpture indoor courtyard flora art exhibit old book orchid painting on the ceiling courtyard from above
Massachusetts State House. Be sure to walk by this historical building when exploring Beacon Hill and the Boston Commons.
Boston Commons & Public Gardens. I’ve mentioned visiting these before, but I would be remiss if I didn’t point out that if you’re in Boston during the Christmas season, you should make time to visit after dark.
The main Christmas tree is donated each year by Nova Scotia as a thank-you for help following the Halifax Explosion in 1917. The tree is stunning and rivals the one at Rockefeller Center - without the crowds.
There were also drone shows in the park on Saturday. We saw the early show from View Boston and the late show from our hotel window. Such a cool event. Looking for more seasonal things to do? Jump here.
Commonwealth Avenue Mall. This beautiful park extends from the west side Boston Commons just a block over from Newbury Street. It is peaceful and well worth the walk. Enjoy a stroll down the Mall after dark and see the trees lit up. This residential street leaves you feeling like you've stepped into a movie.
Old State House and the Old South Meeting House. A $15 ticket gains you entrance to both historic buildings.
You’ll walk through the places where the American Revolution began and literally follow in the footsteps of history. I’ve become such a history nerd in my old age that I absolutely loved these stops.
Fun fact: The Declaration of Independence was first read publicly from the balcony of the Old State House.
Inside the Old South Meeting House Old State Meeting House Inside Old State Meeting House Old State House Display inside The balcony where the Declaration of Independence was read
Faneuil Hall. It's shopping, eating, and history, You'll find historic exhibits inside this building.
Bruins Hockey. We always take in a hockey game when we’re in Boston. Justin has a friend who invites us as his guests—so maybe this part is technically sponsored? I kid. While we are given tickets, there are no links here where I receive any compensation.
His friend has club level seats, and we always eat in the Boston Garden Society at TD Garden before and during the game. The club is only available to club-level ticket holders.
Because it was the Christmas season, we were also invited to a private meet-and-greet with Santa, along with complimentary appetizers and hot cocoa.
Whether you spring for club seats or not, attending an NHL game in Boston should definitely be on your list. Turns out, I LOVE hockey—and you might too. Just remember: it’s cold inside the arena, so dress accordingly.
Hot Coco and Bruins cookie Ice Hockey Justin and me with Santa out the window of the Boston Society Club Heading into the Boston Garden Society Sign outside the door TD Garden
Shopping
Newbury Street. Literally anything and everything you could possibly want to shop for lies within a few blocks of Newbury. It’s a charming shopping area with restaurants, cafes, and stores all housed in brownstones. Absolutely lovely. If there is inclement weather, your shopping doesn’t have to be stifled! Just visit -
Copley Place & Prudential Center. While not technically the same location, they are connected by covered walkways which makes this shopping experience weather proof. Copley Place houses the luxury shopping stores such as Louis Vuitton, Tiffany & Co, Gucci, Golden Goose, and others while Prudential Center contains other retailers like Hoka, Lululemon, Dick’s Sporting Goods, Sephora, and others. Mixed into both locations are quick service and sit down restaurants as well as coffee shops. You’ll also find entrances for the Westin and Mandarin Oriental hotels.
Places to eat
Prezza. This one is a repeat—and a personal favorite.
The seafood stew really is that good. Make reservations. There isn’t a thing on the menu that won’t change your life. No city does seafood like Boston.
Select Oyster House. Stop everything and order the seafood tower.
This tiny restaurant is top notch. I only eat raw oysters in the Northeast. There’s just something about them being in the water the day before you eat them. The freshness can’t be beat.
This was my anniversary dinner request and it was perfection. Just note: there are no dessert options here. The last time we ate here, there was just two of us so we ordered from the a la carte menu instead of ordering the entire tower.
Seafood Tower at Select Oyster
Eataly. Part Italian grocery store, part restaurant, this is a spot we visit often. We typically stop in for a quick slice of pizza or gelato, but there are also great sit-down dining options and take-away counters. Even if you’re just wandering through to browse the food and kitchen goods, it’s worth a stop while exploring the Prudential Center.
The quick-service pizza is usually our go-to—Justin loves the soppressata, while I almost always order the white. Right at the front, you’ll also find a pasta bar; the tagliatelle verdi I had on our most recent trip was seriously amazing. I love this spot for its flexibility—you can easily satisfy multiple cravings here, which is especially helpful when traveling with picky eaters.
quick service meal
The Friendly Toast. Amazing menu. Even better vibes.
We’ve eaten here at least twice on different trips. Bonus: iced coffee refills are free, which is always a win in my book. The bacon special was truly delicious and the Rice Rice Baby bowl was filling and tasty.
Maple Bacon Chicken Bowl
Joe’s on Newbury. This family-friendly spot strikes that perfect balance between relaxed and elevated—ideal if you’re dining in the city with kids. The children’s menu keeps things approachable, while the main menu offers plenty of standout options for adults, all at a price point that feels fair for the quality.
We kicked things off with the seafood platter before I ordered the crab-stuffed shrimp for my entrée—rich, flavorful, and perfectly cooked. And the butterscotch bread pudding to finish? Completely worth it. We were dining with one of Justin’s coworkers and his boys, and every plate at the table was cleared, which tells you everything you need to know.
Jade Garden. We hadn’t explored Chinatown much before, but our Uber driver recommended this spot. It ended up being the cheapest meal we had all weekend—and the portions were enormous.
I would eat here again, but I wouldn't order this particular shrimp dish; I wasn't a fan of the sauce. The noodles had great texture and taste that was not helped by the sauce. The No. 1 Tidbits, though, was SO GOOD! I love a crab rangoon and the wings were so crispy.
Jumbo Shrimp with Fried Noodles No. 1 Tidbits
The Street Bar. Located inside The Newbury Boston, this is where Justin booked us for holiday tea. They seated us by the window overlooking the Boston Public Garden, and we enjoyed a beautiful four-course tea service. The tea was delicious, there were enough desserts for four people, and you didn't feel rushed or hurried at all.
If the table next to us hadn’t been so obnoxious, it would have been perfect. Take that as your sign not to be those people.
Of course, you can take in the vibes here anytime not just for tea. The Street Bar is a full service restaurant and Bar.
Also be sure to stop by Tiffany & Co. just across the hall.
The Street Bar Menu
Quincy Market. Situated in the Faneuil Hall Marketplace, Quincy Market combines shopping with a food hall experience. Although I had visited before, I only recently dined there for the first time.
This is a great place to stop if you’re traveling with kids since everyone can find something they like.
Dolce. Hanover Street is packed with incredible restaurants and bakeries, which can feel overwhelming.
We stopped here for tiramisu and loved it. They offer many flavors and also serve cannoli and gelato.
Lindt Chocolate Shop. You know it, you love it. Stop into the storefront on Boylston and fill a bag with their signature truffles—because let’s be honest, you’re going to anyway. I always gravitate toward the dark chocolate varieties, but you really can’t go wrong. Consider this your permission to indulge.
L.A. Burdick Handmade Chocolates. If small-batch, artisan chocolate is more your style, this is a must-visit. Easily one of the most charming chocolate shops in the city, and I may have created a bit of a tradition by stopping in. We picked up their signature chocolate mice and one of the Easter lambs, plus a few extras for the kids to try. While we didn’t sample the hot chocolate, it’s highly recommended. Fair warning—this isn’t inexpensive, but it’s truly some of the best chocolate I’ve ever had.
Blackbird Donuts. I’ve mentioned them before, but they’re worth another shout-out. I grabbed a Boston cream donut (custard-filled is my weakness) and coffee before starting our day.
Tsaocaa Boston. I can’t pronounce it, but I needed caffeine after lunch at Jade Garden. I ordered a brown sugar bubble tea and it was fantastic.
iced coffee outside caffe nero iced coffee and a muffin
Caffe Nero. What’s not to love about great Italian coffee? I fell in love with Caffè Nero in London, so I always enjoy grabbing an iced latte here whenever I see one in Boston.
You can find these all over the city but my most frequented location is in Prudential Center. PRO TIP - Download the app for mobile ordering and your first drink is free; you'll also gift me two ;)
Tatte. A true Boston staple. It’s a great option for brunch or casual dining, though seating can be limited depending on the location.
Choices at Tatte bakery Breakfast sandwiches & coffee Meringue and coffee
Seasonal Activities.
Take a walk. Just look at the Christmas decorations all over the city—they are absolutely worth the walk after dark.
Tree at Boston Public Garden Cartier store front Tree at Faneuil Marketplace Boston Christmas Decorations Gingerbread at The Newbury Hotel The Grand Promenade Boston Christmas Decorations Inside the Liberty Hotel
Holiday Markets. Snowport Holiday Market is the market that Justin and I headed out to one evening. Snowport is a free, outdoor market that sets up at the Seaport during the holiday season. It does have specific operating hours during the week and weekends, so be sure to check the website before you take the trek. There is a huge food truck area that you don't want to miss! I picked up some local Maple syrup, a gorgeous Alpaca hair chicken, as well as a cat hat and pen. There was ALL kinds of things to look at and explore. There was a line to get in, but I felt like it moved pretty fast; remember that there are multiple gates to get in, so if one seems long, walk around to another. The other market we considered was SoWa Winter Festival (SoWa is a Farmer's Market on Sundays from May - November). We didn't end up getting down there, but I'm adding it here because I think it deserves your consideration.
Catch the drone show. You'll want to catch the drone show at the Boston Common, specifically at the corner of Boylston and Charles Streets. We overheard someone mention the drone show when we were at View Boston and were able to catch a bit of the first one there. By the time the second show started, we were back in our hotel room and watched from our window. There isn't really a website or place to go to find out about this, so my suggestion is to Google it if you're planning to be in Boston for the holiday season.
And that wraps up highlights from our last several trips to Boston. From unforgettable Boston restaurants and charming cafés to historic landmarks, Bruins hockey, and beautiful city parks, there are so many amazing things to do in Boston. Whether you’re planning a romantic getaway or a quick weekend trip, I hope this Boston travel guide gives you a few ideas for your own visit.
Have a favorite Boston restaurant, hotel, or hidden gem we should add to our list? Drop it in the comments—I’m always looking for new places to explore next time we visit!
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