A Long Weekend In Boston
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
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,
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.
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.
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.
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.
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.
Your next stops for the afternoon are to the cutest, but also perhaps one of the busiest areas and streets of Boston. Even though it's popular due to the cobblestone streets and shopping so it can get quite busy, its definitely worth a stop on your tour!
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.
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.
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.
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.
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!
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!
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).
If you want to try the scene before choosing a restaurant, consider a north-end food tour. This will allow you to taste popular eats from some of the local hot spots and get more recommendations for popular restaurants.
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.
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!).
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.
A Long Weekend In Boston
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
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,
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.
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.
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.
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.
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.
Your next stops for the afternoon are to the cutest, but also perhaps one of the busiest areas and streets of Boston. Even though it's popular due to the cobblestone streets and shopping so it can get quite busy, its definitely worth a stop on your tour!
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.
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.
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.
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.
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!
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!
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).
If you want to try the scene before choosing a restaurant, consider a north-end food tour. This will allow you to taste popular eats from some of the local hot spots and get more recommendations for popular restaurants.
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.
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!).
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.