Quick trips can feel limited but if planned well, you can pack quite a bit into two days. On my most recent visit to Boston, I had only two full days to re-explore this city that I love. I’ll be the first to admit, two days hardly seems like enough time. I did manage to visit all my favorite spots plus see a few new ones though. If you only have a few days in Boston for an upcoming trip, this guide is going to be a great friend.

Day 1: The Historical North End & Lots of Fantastic Food
You can’t go to Boston and not spend time in the North End. Several of the Freedom Trail stops are here and some of the best Italian food in Boston. Kick the day off with a cup of java at Thinking Cup and make your way through the cobblestone streets. The North End is where you’ll feel the city’s history the most. From the oldest tavern in the US to the 17th-century buildings, this is one place where you wish the walls could talk.

A few Freedom Trail stops include the Paul Revere House, Old North Church, Faneuil Hall, and Copp’s Hill Burying Ground. Hanover Street will be the main road while exploring the North End but make sure you veer off some of the side roads. Salem Street has a few hidden gems and the Instagram opportunities (since that’s so important these days) are endless.

Enjoy a slice of pizza from one of many places including Umberto’s while taking in some of the best views of the Boston skyline in North End Park. Then make your way to Faneuil Hall Marketplace for some afternoon shopping. Faneuil Hall Marketplace is comprised of Faneuil Hall, Quincy Market, North Market, and South Market. The promenade features cobblestone pedestrian roads plus live music and other entertainment year-round. There were several historical moments in Faneuil Hall Marketplace and it’s long been known as Boston’s central meeting place.

If you’re looking for a place to stay that’s central to the North End, check out The Boxer Boston. It’s also near Beacon Hill, the Back Bay, and the Boston Common. A few other restaurant recommendations in the North End include Neptune’s Oyster Bar (a staple if you can eat shellfish) and La Galleria 33 for incredible Italian.

Day 2: Browsing Newbury Street, Strolling Through the Back Bay, & Seeing the World From Almost 100 Years Ago
I didn’t spend much time in the Back Bay on my previous trip to Boston so I made it a priority this time. It also helped that I stayed a few blocks away from Beacon & Newbury Streets this time around. Newbury Street is famous for its shopping and dining. Eight blocks have everything from designer boutiques to small businesses including coffee, art, retail and more. It’s a bustling street with outdoor cafes and lots of life. I’m not a shopper but I did find a few coffee shops like Caffe Nero and Thinking Cup that were fun to sit and pass some time in.

Boylston Street is another popular spot to explore. A few of the big ones are Copley Square, Trinity Church, and the Boston Public Library. There are lots of other great restaurants and shopping on Boylston including Tatte’s Bakery which is a favorite of mine whenever I visit Boston. Keep walking down Boylston Street to Massachusetts Ave for the Mary Baker Eddy Library where you can visit the Mapparium. This was such a unique experience. A three-story stained-glass globe shows a map of the world form 1935. It’s so interesting to see how things have changed since before World War II and the globe itself is stunning.

Quiche from Tatte’s Bakery on Boylston Street

The Back Bay is also home to Commonwealth Avenue. A “greenway” separates the street with memorials and statues like the Boston Women’s Memorial and a statue of Alexander Hamilton. It’s actually a gorgeous path to walk along with benches in case you’d like to enjoy some outdoor reading. The brownstones up and down Commonwealth are also magnificent and very photogenic.

If you have a little extra time left in your day exploring the Back Bay, venture over to the Boston Common or Beacon Hill neighborhood for a bit. Beacon Hill is probably my favorite part of the city if I had to choose. The famous Acorn Street is in Beacon Hill as well as several great restaurants and the Massachusetts State House. The Boston Common is stunning any time of year and worth getting lost in for a few hours. Every visit I take to Boston, I always make sure I have an hour or so dedicated to walking around and finding a bench to sit and read for a bit.

The Boston Common - these views never get old

Back-Up Day: John F. Kennedy Presidential Library & Museum
On the off chance one of the days during your visit has inclement weather, or in my case, stifling heat, here’s a great option to kill an afternoon indoors. The JFK Library has some of the most gorgeous views of the city’s waterfront which are worth a visit alone. The museum begins with a short film documenting the life of JFK up to the election for the presidency.

The exhibits feature an in-depth look at his presidential campaign and election to the presidency. You'll learn about life with Jackie and the kids and life inside the White House. Dive into the Cuban Missile Crisis, the establishment of the Peace Corps and the space program. There's an exhibit spotlighting Robert Kennedy as Attorney General and a few focused on Jackie Kennedy. A few of her gorgeous dresses worn for special events are on display. Plus, learn about the work she did as First Lady including advocating for the arts, preserving history, and more.

The museum also has special exhibits including the Freedom 7 Space Capsule and Ernest Hemingway Collection. As a literary nerd, I’d be lying if I said that the Hemingway collection wasn’t a part of the reason the JFK Library was on my “must-see” list. There are several other short films you can watch to learn more about different events in history throughout the museum as well. It’s an easy way to spend at least a few hours if you need to escape the rain, or in my case, the heat.