3 Days in Boston: A Perfect First Timer’s Guide for A Weekend Getaway

Boston is one of those cities I just always want to go back to. I’ve visited three times and haven’t gotten tired of it yet – and I really don’t think I ever will. It has such a great mix of history, big city, and old time charm, with plenty of attractions worth visiting. Although I could spend forever there, I’ve found that 3 nights and 3 days in Boston is the perfect amount of time for a first trip.

Every year for my birthday I try to take a little tiny trip. Last year it was Chicago. This year I dragged my boyfriend Ryan to Boston for 3 days since he had never been and I was itching to go back. I was exceptionally excited for this trip, because it was the first time I visited Boston outside of winter. The skies were blue and the temperature stayed above 60 degrees the whole time and I was in pure heaven.

Getting to Boston

Getting to Boston is insanely easy coming from New York City. Sure you can look up quick flights to Logan International Airport, but by the time you make it to your hotel, you’ll have eaten up a half a day traveling. I am always looking for ways to optimize my days and nights while on vacation. Leaving out lengthy commutes to and from airports is an easy way to do that.

I decided to book a Megabus for about $40 round trip and I would do it again in a heartbeat. It was an easy Midtown pickup and the bus dropped us off at South Station in Boston. That’s a pretty easy starting point to get to wherever you need to go. If you’re staying Downtown, you might even be able to just walk to your hotel from there.

As much as I usually avoid buses, for really quick trips they make so much sense. Especially when you consider the price. Just getting to the airport and making it through security can add an extra 2 hours to your trip. Plus, a bus is just so much less stressful than dealing with TSA.

Getting Around Boston

Once you get to Boston, you’ll realize how easy it is to just walk everywhere. I would avoid getting a Charlie Card unless you are actually staying outside Boston proper. My 3 day in Boston itinerary below can mostly be done by walking. I did take the train once to Cambridge to visit Harvard Square. You’ll also have to take the train if you’re coming from the airport.

If you do find that you need to use the subway often, a 7 day pass will cost you $22.50. A one way trip on the subway will cost $2.40. Keep in mind the the trains do not run 24 hours. Typically they run until about midnight and late night service can be slow and inconsistent. They can run as late as 1am on weekends. We did use Lyft a few times at night for quick trips when we just didn’t feel like walking.

Day One

I’ve learned over many MANY trips that it pays to take it a little easier on your first day. At least it does for me. A travel day just takes more out of me than I ever expect to. Although I can count on adrenaline and excitement to keep me going easily for the first 24 hours or so, it eventually catches up to me.

How early you get to Boston and get settled will determine how much time you actually have to explore. On our first night, Ryan and I stayed with some friends in Somerville. This was a pretty quick trip from South Station and gave us an opportunity to see the suburbs of Boston, which I hadn’t really experienced before. It also meant that our first day in Boston started around 5:00 in the evening.

Your first night out I suggest checking out one of Boston’s local breweries. Boston has an incredible beer scene with some major breweries and plenty of smaller ones. It’s filled with tap rooms and pop up tasting shops and I suggest putting at least one on your list. We went to the Night Shift Brewery at Lovejoy Wharf which I would highly recommend. If you’re into sour beers, they had one of the best I’ve ever tasted. Oh and try their freshly baked pretzel for a little snack.

Have Dinner at Union Oyster House

I don’t think you should be allowed to leave Boston without having dinner at the oldest restaurant in the country. Union Oyster House is on every Boston to do list, and it should be. It’s a charming old restaurant – the oldest restaurant in the US with continuous service – and lives up to the hype.

Having a reservation is advised. However, we didn’t have a reservation and only waited for about an hour for a party of 4 on a Saturday night. We killed some time at the bar and had a variety of oysters while we waited for our table. The restaurant is adorable and the food is seriously good. I tried my first full lobster dinner here (when in Rome, right?). It’s a truly historic place to eat and I wouldn’t miss it.

Day Two

Day two should start with a trip to Fenway Park. I’m not a big baseball fan but I think it’s pretty cool to see historic sporting venues. I prefer live sports to anything I can watch on TV, and I have a soft spot for giant over priced beers. The very first time I went to Boston I stayed with a friend in Kenmore Square who’s building’s rooftop looked right into Fenway Park. It was an awesome neighborhood to stay in and was cool to be so close to the stadium.

Although Ryan wasn’t interested in seeing the famous baseball stadium, I think it should be added to your Boston itinerary. I’ve never been lucky enough to have the Red Rox in town while I’m there, but I’d definitely squeeze in a game on a future trip. If you’re actually a huge baseball fan, you can look into touring Fenway Park when there’s no game.

Visit the shops on Newbury Street

Talk about your perfectly picturesque shopping street. I have had Newbury Street on my list for a few trips now, but kept missing it. This was the first time I actually made it happen. It honestly doesn’t matter if you’re in the mood to shop or not, I would still stroll through here.

I’m normally disappointed in large shopping districts. They are usually filled with just a bunch of commercially popular shops that you can get anywhere you are in the world. Newbury Street definitely has those, but there are plenty of boutique shops to balance it out. Plus it’s just so pretty.

This is a good spot to grab coffee and lunch. I recommend stoping at Trident Booksellers & Cafe where you can grab a cup of coffee and look for some small souvenirs. If you’re looking for a quick vegetarian bite, By Chloe nearby has some great options.

Boston Tea Party Museum

I am extremely selective in what guided tours I’m actually willing to pay for. I’ve been on quite a few duds during my travels. Not to mention the precious hours wasted with boring guides that taught me nothing I couldn’t have just read on a Wikipedia page in a quarter of the time. So I’m usually pretty weary when parting with my money for a tour.

Ryan and I decided on a whim to actually get tickets for the Boston Tea Party Ships & Museum tour and it was so much fun. Boston is filled with a lot of history and having a guide is so helpful to really soak up all that you can. The actors who put on the tours are extremely entertaining and stay in character the whole time. Sure it can be a little corny, but I happen to like corn a lot.

Day Three

Getting a hotel our second night that was right on the cusp of Beacon Hill was the best thing I could have done. Beacon Hill is just dreamy and getting up really early on my third day in Boston to wander around with my camera was my favorite part of this past trip. I left my hotel around 6 o’clock in the morning because I really wanted to take some pictures of Acorn Street before it was filled with other travelers.

Beacon Hill is lined with Victorian brick houses on steep hills and everywhere you look is breathtaking. It’s a quiet area and early Monday morning is a perfect time to capture photos of the picturesque streets, Boston Commons and the Boston Public Garden. If you want to take photos on Acorn Street, please be respectful that it’s a private road and people actually live in this neighborhood.

I brought my tripod, camera and a hot cup of coffee from my hotel while Ryan slept in and had a lovely morning exploring this area before I made it back to our hotel for breakfast.

Freedom Trail Tour

One of the things I refused to leave without doing on this trip was the Freedom Trail tour. Since my previous two trips to Boston happened in the winter, I couldn’t bring myself to actually do the 90 minute walking tour. But because I was up so early on my last day, I was able to still squeeze in the earliest Freedom Trail tour at 11 am.

If you do just ONE guided tour during your 3 days in Boston, this one should be it. During the mile long walk you go to 11 of the 16 official Freedom Trail sites and get to listen to a historian or actor guide you through essential parts of American history. I prefer walking tours more than anything so this was perfect. I think walking just allows you to see more and lets you stop whenever you want to take in your surroundings.

This is one of the best tours I’ve done while traveling anywhere. The historic sites you’ll visit will most likely be on your to do list anyway and for the $14 ticket you can’t go wrong. Keep in mind if you purchase tickets online you have to print them out before hand. Also, the 11 am one is their most popular tour time and can be really crowded.

Lunch at Regina’s & Dessert at Mike’s Pastry

The Freedom Trail tour will drop you off right in Quincy Market. You could have lunch here, but I recommend using this opportunity to continue north on the Freedom Trail. We headed to the North End and made our way to Regina Pizzeria after we wandered Quincy Market for a bit.

Regina’s is a popular pizzeria that has some of the best pizza in Boston. There’s a few locations throughout the city but rumor has it that the North End is the one to visit. So of course that’s where I had to eat. I know the line here can get really long but we were really lucky to get right in on a Monday around 2:00.

Once you’ve had your pizza in the North End, there’s no reason NOT to go indulge in some dessert at Mike’s Pastry. I mean after all, you’re in the North End already and it’s like RIGHT there. Don’t you want to taste the most famous cannoli in Boston?

Visit Cambridge and Harvard Square

If you’re going to take a train anywhere outside of the city center, I recommend checking out Cambridge. The Harvard campus is old and beautiful and will make you long for an Ivy league college experience of your own. I don’t know why I have such a soft spot for wandering the campus and nearby shops, but I put this on my list every time I’m in Boston.

Going when school is in session is the best experience and makes going to the local bars a little more fun. We ended up having some drinks at Grendel’s right near the campus and I felt right at home there. We took a Lyft back to our hotel which was just about $15 and made it back in time for our dinner reservation.

Dinner in the North End

Some of the greatest Italian restaurants in the country are in Boston. You may not know this, but Italian’s make up the second largest ancestry in Boston, next to Irish. So of course the city is full of delicious Italian food. I can not stress enough the importance of having dinner in the North End. It’s an excellent way to spend your final night in the city.

Side note about Boston. When I traveled there five years ago, I happened to be in the city during St. Patrick’s Day weekend and had no idea what I was in for. I didn’t know that there was such a large Irish population in Boston so I was surprised by the massive celebrating that happened all weekend – including a huge parade in Southie. I guess what I’m saying is if you want to celebrate St. Patrick’s Day in a big way, come to Boston.

Anyway, back to your mandatory Italian dinner. We went to Dolce Vita after doing a little research for the best Italian restaurants in the North End. There are endless to choose from though and I’m sure you can’t go wrong with wherever you choose.

I definitely hit the pillow on the last night of my 3 days in Boston fully exhausted. I considered this trip to be my most successful one so far. Partially because the weather was so great but also because it was my third visit and I knew what to expect. You know what they say, third times a charm.