I help everyday people bring more exciting bucket list experiences and fun things to do to everyday life.

I go to Boston frequently and people often ask me: How many days should I spend in Boston? How do I spend a long weekend in Boston? Is 2 days enough in Boston?

In this session of The Everyday Bucket List Podcast, my husband & I discuss a recent Boston weekend trip. We also talk about what Boston is known for. We even include what a 1-2 day itinerary or more could look like based on what we did. Get ideas for restaurants, historical things to do such as a visiting the Boston Tea Party Ships, Fenway and more. 

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Today’s Everyday Bucket List Guest

I’m happy to welcome yours truly and my husband back to the Everyday Bucket List Podcast!

boston weekend trip
You can also listen to my podcast on Apple Podcasts. Here’s my recent episode about How to Plan a Weekend Bucket List Trip to Boston on Apple and Spotify. I’m also on Stitcher and many others.

Karen Cordaway of KarenCordaway.com

What You’ll Learn From Our Weekend Boston Trip

  • Discover what Boston, MA is known for
  • Hear about my 1-2 day Boston itinerary to potentially figure out how to spend a long weekend
  • Get a variety of suggestions for Providence, Rhode Island restaurants
  • Find out where to stay in Boston for a weekend
  • Plus, there’s additional video content to plan your Boston weekend itinerary


Is 2 days enough in Boston?

Two days is enough in Boston if you want to visit a few must-do spots and eat at some delicious restaurants. Though I would personally stay for at least four days, a week can help you more fully take in many of the bucket list attractions.

If you only have a weekend, you can still pack a lot in. I personally like to go back and see something different every time I visit. I also like visiting places where I have to do a lot of walking in shorter spurts.

Where to Stay in Boston for a Weekend

We stayed overnight at the Hyatt in the Seaport District. We absolutely loved it. It has a great view from the room. In addition, you could eat and drink outdoors on their terrace or rooftop deck. Depending on where you want to stay, there are a wide variety of great places to stay in Boston.

Boston Itinerary Day 1

The Barking Crab – Situated right next to the Fort Point Channel, not far from the Boston Tea Party ships, grab a bite to eat and catch a view of the water. Choose from a wide array of seafood and enjoy the casual vibe and nautical decor. Get more details and find out about other casual restaurant in Boston.

The Boston Tea Party Ships – Whether you view it from the sidewalk or you purchase a ticket to have a get up close and personal with “the famous event that changed the course of American history,” it’s something you shouldn’t miss. Tickets are $30 per person. Actors are all dressed up in that time period and someone is physically throwing the tea off of the ship.

boston weekend trip

Jaho – After walking through Chinatown, this is the place where we had Japanese style ice cream. There are multiple locations in Boston, but I wanted to highlight the one we visited. Their site explains, “this location features a Loring Kestrel Roaster, a state of the art slow coffee bar, the full array of our food offerings and baked goods and a wide selection of craft beers, wines and spirits.”

Eataly – This is located on the first level of the Prudential Center. You’re greeted by a cannoli stand right at the entrance to this high quality food market that also contains restaurants inside. No matter if you opt to eat a meal, grab some groceries or both, you won’t be disappointed with the wide array of food to choose from.

Boston Itinerary Day 2

Fenway Park – If you choose to go to a game, block out a big chunk of your day, unless you leave a little early. If you have a vehicle with you, you’ll have to find a place to park. Prices vary depending on how close you are to the stadium. You can also just tour the stadium as a bucket list thing to do.

fenway park

Copley Square – On our way to Fenway, we stopped at Copley Square. Outside of being a beautiful place to sit and relax, the HistoryList.com explains that “Copley Square is one of Boston’s most architecturally significant and instantly recognizable public locations. This urban square is home to Trinity Church, the Boston Public Library, Old South Church and the Hancock Tower, among other important landmarks.” I highly recommend a visit to that area.

What 3 Days in Boston Could Look Like

If you have a long weekend or you’re opting to stay for 3 days in Boston, here are some other things you can do.

Trolley Rides – Get a ticket and take a guided tour around Boston. The drivers will tell you stories, interesting facts and more. From the seaport to Boston Common as well as other historical areas and well known streets, stay comfortable while exploring the city from the trolley. The one we caught allows you to hop on and off to see the sites up close.

Swan Boats – Open from May to Labor Day, take a ride on the Swan Boats in Boston Common. It’s a short, affordable ride that great for all ages. Here’s the blog post I mentioned on the show. It includes information about the Botanical Center including the moon gate and some of the other ideas I mentioned on the show.

Boston bucket list

Duck Boat Tour – If you have a little over an hour and want to check the iconic duck boat tour off of your list, I think this qualifies as a must-do item. Listen to a knowledgeable guide rattle off the historical significance of different landmarks and neighborhoods all while cruising along in a boat on wheels. I don’t know if this was just my guide, but this was a very interesting tour.

After you finish on land, then you you head to the water for the last part of the tour. This was one of my favorite bucket list adventures.

Free Things to Do During a Weekend Trip to Boston

Freedom Trail -Walk along the line marked on the pavement to follow the Freedom Trail. It takes you through “a unique collection of museums, churches, meeting houses, burying grounds, parks, a ship, and historic markers that tell the story of the American Revolution and beyond.” You could also opt for a formal tour or informally walk around to take in the history on your own. Get more details about the Freedom Trail and Little Italy here.

USS Constitution – This is one of the special spots on the Freedom Trail. Visit the museum where two ships are located. Also, take in interactive exhibits and more.

Black Heritage Trail – Walk along the trail in person or take a peek virtually online. Self-guided tour take 60 -90 minutes. So plan your visit, learn about the park or even get involved.

Also, check out:

  • Places to stargaze
  • Little Italy
  • Bunker Hill Monument
  • Boston Common

Bonus Content for Boston Weekend Itinerary

If this isn’t enough to make your decision, I added some additional content with videos so you can catch a glimpse and judge for yourself. So if you’re still wondering, “Is Boston worth a trip?”, here’s my last ditch effort to convince you that yes, Boston is worth a trip.

Firstly, take a peek at the very popular North End restaurants. Get ideas for where to visit and where you can grab dessert. Though the first video was shot during warm weather, these are great places to visit any time of year. Be sure to make a reservation. You may have to try a week in advance at minimum.

@everyday_bucket_list Like & follow. Here are some of the best Italian restaurants in Boston's North End. I'll leave details about gluten friendly & gluten free options I had in the comments. Do you have a fave restaurant in the the North End? Let me know in the comments! 👌🏼 #BostonRestaurant #BostonFoodies #Boston #BostonTiktok #Boston #NorthEnd #Restaurant #Bostonfood #BostonRestaurants #bucketlist #capcut #italianfood #bostonma #bostondateidea #northendboston #italianrestaurant ♬ Standout – Kid Dean

Secondly, this is another video of a bakery. Whether you are heading to Bean Town with friends, family or you’re looking to have a romantic weekend in Boston, MA, check out this bakery.

@everyday_bucket_list Trying to figure out what to do in the North End of Boston? Head to Modern Pastry. Here's my honest review with photos (videos) In this video I discuss the service, atmosphere and baked items. Psst! Let’s also find out if it had one of the best cannolis in Boston. It’s from me, your host of The Everyday Bucket List podcast. Discover a wide variety of some of the best cannolis, cookies, cakes pastries + more. Watch the whole video to the end. They even have gluten-free items (cannoli and whooping pies) Perfect for a date night or place yo go with friends and family. FAQs – Does Boston have a Little Italy area? Yes, Boston has a Little Italy area a.k.a. the North End neighborhood. It is lined with restaurants, bakeries, shops and more. – Is Modern Pastry cash only? Yes, Modern Pastry is cash only, but there a few ATMs close by. There’s one next store. There’s a CVS and another spot that I noticed. – Who owns Modern Pastry Boston? The Picariello Family owns Modern Pastry. See their website for their story & more details. – Modern Pastry North End Hours Sun-Thurs: 7am-10pm Fri-Sat: 7am-12am Check website for most updated details. #boston #bostoncannoli #northend #littleitaly #bostoneats #modernpastryshop #bostontiktok #fyp #thingstofoinboston #exploringboston #tourists #locals #gfeats #gftravel #glutenfreetravel #glutenfree #gf #gftiktok #glutenfreetiktok #podcaster #podcast #glutenfreelife #edblpodcast ♬ 1901 – Instrumental – Phoenix

Lastly, if you want to throw in some more free things to do into the mix when it comes to your Boston weekend itinerary, see if any of these places are open when you visit. Also, check out part 1 of Free Things to Do in Boston here and follow along on Tiktok.

@everyday_bucket_list Like & follow! If you searched for “winter Boston activities”, “Boston winter” or you just need to add to a Boston winter itinerary, you’re in luck. Here are some fun things to do in Boston without spending any money. I've got you covered w/ these amazing free things to do in Boston for 2023 and beyond! They make the perfect day activities. Create a Boston bucket list of some of the best free things to do in Boston. Here's a quick list of simple activities that won't cost you a penny. Get ready for endless fun without breaking the bank! Perfect for couples, friends or to do alone. #bostonbucketlist #freethingstodoinboston #funthingstodoinboston #creatememories #livelifetothefullest #boredombusters #bostontiktok #bostonlover #bostontourist #bostonma #bostonwinter #fyp #capcut #wintertodo #bostonwinter #winterplan #bostonlife ♬ Lisztomania – Phoenix

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