A Long Weekend In Boston

A Long Weekend In Boston

Twenty Five Days a Year
Spend the weekend in Boston! This beautiful city has so much to offer. Stroll beautiful areas, eat amazing food, take some great tours, and learn some history (in whichever order you want). This itinerary covers four days worth of activities and includes suggestions on where to eat, stay, tour, and visit in Boston.
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What To Know

Arrive on Friday and leave on Monday - the perfect amount of time to explore Boston and it's highlights. We visited for a long weekend and Boston exceeded all of our expectations. I am not usually a city girl, but Boston has a piece of my heart - its SO clean, has the best food, and there's so much to do and see. 

Where To Stay

Kimpton Marlowe Hotel
@twentyfivedaysayear
We stayed at this hotel and loved it! They had a wine happy hour every day - what's not to love about that. There was also parking in the underground and it was right across from the Charles River where we spent our mornings on a walk or a jog - SO beautiful. Plus it was in easy walking distance to everything we really thought it was the perfect place to stay!
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Boston Harbor Hotel
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This hotel is stunning and located by the water. Its located centrally within walking distance to everything you will want to see in Boston. Another great option of where to stay in downtown Boston!
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The Lenox Hotel
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This hotel is located in the back Bay Area so in a GREAT location with close proximity and walking distance to everything and public transportation. This hotel is highly rated for a reason and staying here means you're closer to everything you came to Boston to see!
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Best Time To Visit

Year-round! We visited in Spring which is usually my least favourite season but the weather was stunning and the trees were starting to blossom (cherry blossom season is a great time to visit). Visit in the summer for the great weather and outdoor activities, the fall for the stunning foliage the east coast offers, or the winter for a snow--dusted city. You really can't lose! 

How To Get Around

We highly recommend having your own vehicle to be able to get in and out of the city (and depending on where you're coming from you may have drove into Boston aswell). However, Boston is an extremely walkable city with good public transportation and taxi / Ubers available so it is not at all necessary. Day tours also exist for a reason so no car is no problem!

Getting around Boston is best by foot anyways - I think one day we walked over 40,000 steps. Bringing comfortable walking shoes is a must. However if you don't want to walk in between all the stops, taking a hop-on hop-off bus on day two will take you to most of the sight seeing spots on your own time. 

Day One

Afternoon

Depending on what time you arrive will determine how much time you have to explore on day one! You'll likely want to check in to your hotel first thing to get settled in and relax a bit before heading out in the evening.

If you arrive early start your day off with a tour (there are a few sprinkled in this four day itinerary so pick one that works for you.

This tour is a whale watching tour which is a great idea ESPECIALLY if you'e visiting from somewhere that's not near water. Best time to try and spot whales is March - November. This tour below offers guaranteed whale sightings or a free voucher for another cruise. 

Also consider checking out the local teams for sports games, the red sox website is linked below, but also check out the Boston Celtics, the Boston Bruins, or the New England Patriots for their schedules! American sports are an experience worth doing. 

Evening

You could start the evening off with a fun group tour involving history and drinks which is a great way to kick off vacation mode but also start by seeing the city! You'll enjoy beer or cider at three of Bostons best spots and learn about the city on your way.

For dinner you'll head over the Charlestown one of the cutest neighbourhoods in Boston! Here you will find history, restaurants, shops, and a great area to walk around. We walked around in the evening and felt like we were in a movie scene with the brick buildings, cobblestone streets, and cozy restaurants to peak into, 

Bunker Hill Monument
@twentyfivedaysayear
Located in Charleston, if you're a history buff this is a great place to visit. Be sure to check opening hours to make sure you can access it. This monument is in place as one of the locations of a major battle during the American Revolutionary War - but don't take my word for it (as I am NOT a history expert) - visit for yourself to learn more.
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USS Constitution Museum
@twentyfivedaysayear
At the end of Bostons Freedom Trail is this museum and is located in the Charleston Navy Yard. Another great spot to learn more about history. Again, be sure to check the opening hours to have access!
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Monument Charlestown Restaurant & Tavern
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This little restaurant is a neighbourhood favourite and likely to be one of yours too! With gastropub cocktails, brews, and food all-day, there's something for everyone. We had one of their burgers, a salad (they have FANTASTIC!!! salads), and a few of their drinks and immediately knew that if all Boston food was on par with this, we were in for a good long weekend.
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Day Two

Morning

We actually opted for Dunkin' Donuts in the morning (as we don't have this where we live), but if you're from America already this likely isn't going to cut it for you so here's another local favourite.

Blackbird Doughnuts Beacon Hill
@twentyfivedaysayear
What is more American that starting your day with great coffee and donuts? This spot has a menu full of creative and delicious donuts - pair this with a coffee and you can't go wrong.
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If you're anything like us you'll be walking thousands of steps today (unless you decide to do the hop on hop off tour and save your legs). Whenever you decide to kick off your day, head over to the Harvard campus area to see this legendary campus and historic buildings. 

You can either walk around the campus or opt for a tour to learn more about the history of Harvard and the ins of the iconic campus. 

Harvard University
@twentyfivedaysayear
This famous university has a stunning campus worth strolling around. See the buildings, dorms, and sports arenas. It is pretty impressive!
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If you're into sports be sure to check Harvard sports schedules to see if there's a game during your visit - it can be a fun way to immerse yourself in the local atmospheres!

Afternoon

After walking around the campus head over to the Harvard Square for lunch.

Harvard Square
@twentyfivedaysayear
The Harvard Square is a great place to visit before / after your Harvard visit for coffee, food, or shopping. It has a great atmosphere!
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Felipe's Taqueria
@twentyfivedaysayear
We came here after our Harvard tour for some great Mexican food - the lines was out the door which is usually a great indication of the food! We got the burrito bowls and loved them.
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The afternoon will be spent walking the cutest areas of Boston!

On your way back from the Harvard area cross the bridge and head back down to the port area. Your first stop on the way back will be the Fenway Park.

Fenway Park
@twentyfivedaysayear
Fenway park is an iconic landmark in Boston where the Red Sox play. Take a tour or just walk in the area where restaurants and bars come to life.
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We only decided to walk around the Fenway park area but got to experience the iconic Fenway Park vibes, the street lined with bars and restaurants, and the Boston ambiance. If you're a big baseball fan or want to learn more, take a tour of Fenway park to get the best views from outside and inside. 

But also be sure to check the MLB schedule to see if they are actually playing a game during your visit as that's the ultimate experience here. 

Back Bay
@twentyfivedaysayear
A popular area for good reason. The cobblestone streets lined with brick buildings around every corner just scream Boston to those visiting. It was such a stunning area.
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Newbury Street
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This street is lined with places to shop, eat, and meander. Its a must visit in the area!
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Levain Bakery – Back Bay, Boston
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These cookies were honestly unbelievable - I am obsessed. They didn't look like much but the reputation is outstanding for a reason! We ordered four different kinds but the OG chocolate chip ones were still warm from the oven and were the winner.
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Another great way to see the city is probably one of the most unique tours we have ever done - the Boston Duck Boat tour. This was the best way to see some of the parts of Boston we didn't make it to yet to scout out locations for the next day. This tour is in an amphibious WW2 vehicle so you'll drive around the city first before heading into the water to see the city from a completely different view - from the Charles River. The tour guides have super-power knowledge of the city so you're bound to learn something about the amazing sights on your trip. 

Evening

Before heading for dinner (or after if you're not a late dinner person) head for a sunset cruise. Boston has some really amazing sunsets however it's sometimes hard to see with all the sky scrapers in the way! A sunset cruise will help get you out onto the open water to see the sunset from a great viewpoint with a drink in hand.

The Barking Crab
@twentyfivedaysayear
This is one of the most popular spots for seafood in Boston. We ordered the lobster rolls with some great drinks and WOW. We sat in the main restaurant (in the summer they have a patio area as well) and it felt like a rustic fishing shack - a great ambiance to match the meal. We highly recommend this restaurant!
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Day Three 

Morning

This morning you'll wake up, grab a coffee, and head out to see the exterior parts of the Boston area - including historic areas such as Salem. Your day very much depends on what type of transportation you are using. If you're taking a car, head down the coast towards Salem. If you're visiting during the summer or feel like a beach stroll to start your morning hit up this beach which isn't too far from town. 

Revere Beach
@twentyfivedaysayear
This beach isn't too far from Boston and is found on the coast lined with beautiful houses and great views. A great place to kick off any day.
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If you don't have a car, consider a ferry to Salem. You'll avoid traffic AND get stunning views of the coast on your way there. 

Salem
@twentyfivedaysayear
This city is known for the infamous witch trials and has a lot of history to come with it! But what I love is the atmosphere here - it has the same cobblestone streets and brick buildings that Boston has with a smaller town feel and less crowds (however, I imagine during fall / halloween time frame this may be a different story!).
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To learn more about Salem (if you want to experience more than just strolling the area), consider taking a tour to learn about the interesting history of the town.

If you have a car, consider driving your way up the coast to see more of Bostons outer areas. The drive was amazing seeing the different beaches, fishing towns, cute neighbourhoods, and amazing houses along the way. 

Manchester-by-the-Sea
@twentyfivedaysayear
We just drove through here on our morning road trip, but if you're looking for the coastal New England feel this town is worth a visit. We visited because of this and also the movie named after this town - the small fisherman town vibe is really alive! I wish we had more time to spend here.
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We drove all the way up to the coast of Rockport and back down the peninsula through Annisquam to return to Salem and really enjoyed the drive. Cute houses and windy roads in nature - I can only imagine this place in full bloom during fall.

Afternoon

We returned to Salem and stopped at this spot for lunch for some more seafood - when on the east coast!

Turner's Seafood Grill & Market
@twentyfivedaysayear
This spot was a great place for lunch in Salem. The menu and drinks were amazing, and it's located in a cute neighbourhood with a fantastic ambiance. We ordered some seafood and wine which was another great way to spend a day in the Boston area after exploring Salem.
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We only took the morning to tour the area, so we had the whole afternoon to explore parts of Boston we missed and saw on our Boston Duck Tour that we needed to see more of!

Beacon Hill
@twentyfivedaysayear
Beacon Hill is a neighbourhood known for it's charm. You can't visit Boston without seeing this neighbourhood - it's almost the essence of what you would expect from Boston (if you've looked up any pictures before coming, its likely from this neighbourhood). You'll find stunning houses, cobblestone streets, and great restaurants.
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Acorn Street
@twentyfivedaysayear
If you're here for the photos, Acorn street is the iconic photo most people take in Boston. A charming cobblestone street in the middle of Bostons brick buildings with the iconic American flag.
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Boston Common
@twentyfivedaysayear
This public garden is the perfect place to have an afternoon hang out or walk. It is usually relatively busy but in the middle of a busy area so there's lots to do around (bars, shops, etc). You'll also have some great photo spots with Boston sky scrapers in the background of duck filled ponds.
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Evening

Tonight is all about insane food. I highly recommend you book your north-end restaurant in advance as these restaurants are in high-demand (for good reason). 

Carmelina's
@twentyfivedaysayear
One of our favourite restaurants in the world. You really must come here if you're in the mood for Italian (which you need to be when visiting Boston, they have some of the best Italian restaurants). We ordered the chicken parm and carbonara and we still dream of it.
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Mike's Pastry
@twentyfivedaysayear
Cannolis are super popular in this area and this is one of the places to get these highly sought after desserts. They have SO many pastries available as well but the ones most talked about are there many many many flavours of cannolis.
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Day Four

Morning

Wake up and finish your time in Boston with another walk along the river. You've likely already been here but it was one of my favourite things to do in Boston. I could only imagine living in a big city and having such easy access to one of the best walking and running routes with views over the city. 

Charles River Esplanade
@twentyfivedaysayear
Walk along the Charles River with stunning views over the city - the best way to see it. This goes on FOREVER giving you all the views you could need.
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Afternoon

If you're not from American you should definitely hit up a few local spots with the BEST snacks and fun items. You could also do this on day two whilst you're in the area of Fenway Park but you'd have to lug your bags around after (and you may have a few!).

Target
@twentyfivedaysayear
I love target for their American snacks they have SUCH a good selection. They also always have such a large selection of cute clothes and aesthetic accessories. Anytime I visit the US I make a point to visit target.
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Trader Joe's
@twentyfivedaysayear
Trader Joe's has the BEST snacks with new ones always in the rotation. This is another place I always try to hit up as I really love so many things in store they have so much to discover!
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Discover Boston!

We loved Boston and hope you do too - the ambiance, restaurants, shops, and views make it such a special city! If you want to see more about Boston or our travels, see more on our blog or feel free to email us at twentyfivedaysayear@gmail.com to hear more from you. 

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ABOUT THE AUTHOR
Twenty Five Days a Year
With a full time job, there are twenty five days a year I want to FILL with travelling and have been doing so every year. We love to research, plan, and travel to new destinations around the world as much as possible. We travel at least twice per year and quite a bit for work, and love to share our favourite places along the way with everyone who wants it!
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