With all there is to do and see in Boston, it is tough to condense everything into a weekend trip, but when you are fighting with limited PTO, weekend trips are the sweet spot that allow you to travel and explore more often.
To maximize your PTO, take a long weekend to allow for enough time to travel to and from Boston as well as have time to explore. This will only cost you one PTO day but allow for a memorable trip. Now for anyone who is not a Dunkin fan, sorry, but in Boston this is where you need to go for your coffee fix. Coming in second behind New York, with 1,042 Dunkin locations, you cannot walk more than 2 blocks in Boston without running into another Dunkin, and for good reason. As a lifelong Dunkin fan (yes, I know the ratio is never consistent, I love it!) I was in paradise. When we landed in Boston, our first stop was for our daily fix of coffee and a bagel at a Dunkin in Southie.
How to Explore Boston Efficiently
If you enjoy learning about the history of early America, the Old Town Trolley Tours is perfect for you. Especially with a group of good friends, this trolley tour has all the vibes of a middle school field trip with the convenience of stopping at 18 locations around the city to explore at your own pace. At just under $50 per person, this 7-hour hop-on-hop-off tour is extremely reasonable when compared to the cost of other modes of transportation to get to all locations.
Since one day can be quite advantageous to make all 18 stops while taking the time to explore, Old Town Trolley also has a two-day tour option for $79 per person, which will allow you to spend more time at each stop. If you are wanting to stop at each location and you have more than a weekend to explore the city, this is going to be the best option for you as it allows for the most time to stop at each location and is the most cost-effective option.
Boston is known for its American history, but with that history comes many cultures sharing their ways of life and cuisine as well. The only way to truly experience the city is to walk, eat, and learn your way through the past and the present to soak up all the culture Boston has in store.
Best Stops on the Old Town Trolley Tour
If you are really looking to soak up the culture of Boston, you must go to a bar or two as Bostonians are known for their Irish pubs and bars. If great dive bars and sports are what you are looking for, stop by The Bleacher Bar under the outfield of Fenway Park (half mile walk from stop 8). This bar, with its garage door that opens up into Fenway is great for getting to see the field, but best when the Boston Red Sox are playing. (Fun fact, did you know that sox is just a different way to spell socks? Neat, right?!)
Also, located off of Stop 7 on the Old Town Trolley Tour is the Cheers bar. This bar is the inspiration of the iconic bar owned by Sam Malone in the NBC show Cheers that ran from 1982 to 1993. If you are a fan of the show, I would stop by and grab a drink but get there early or prepare for a bit of a wait as it is definitely a popular spot. During your wait, you can head upstairs to see a mockup of the bar set.
Relaxed Evening in Boston
If you are looking for a laid-back evening to relax and catch up with your friends or just a romantic light fare dinner with your significant other, Gray’s Hall is the place. Located in Southie, this wine bar has wine from regions all over the globe with options for whole bottles to share or by the glass. The intimate ambiance of Gray’s is perfect for conversation to catch up with close friends or for a solo evening to read and enjoy a glass of wine at the cute wooden bar top counters that wrap around half of the quaint restaurant. If you are visiting with your significant other and looking for a place where you can enjoy each other’s company, Gray’s also has cozy plush booths perfect for the cuddled-up couple.
Despite me love of wine, I am not a sommelier, but the extensive list of wines from locations all over the world had different wine and grape varietals I have never even heard of. The wines are categorized by type and the servers are incredibly knowledgeable and willing to help you make a decision if you are new to wine or see too many good options to pick from. Since I went with a group of friends, we decided to each pick a different glass so we could try a few different wines without stumbling out of the bar drunk.
For any bar, the most important thing is the snacks…if you can’t drink without something to munch on, you are in luck. The food at Gray’s Hall is phenomenal. The small bites include a creative variety of foods with diverse flavors uniquely integrated together. The grilled carrots accompanied by tahini hummus drizzled in harissa maple and sprinkled with za’atar cashew were our favorite. The creaminess of the hummus complemented the crunch of the carrots and cashew. The sweetness from the maple cut through the bite of the tahini, making this an absolute must-try when you visit.
Tips to Enjoy Boston Cuisine
Now if you are in Boston, yeah you may be there for the history, but the food is what you should be visiting Boston for. As someone who has grown up both in the northeast and the southeast of the US, I can tell you that nothing brings a group of people together the way Italian food does, and American Italian is no exception. In the North End of Boston, is the largest population of Italians in the greater Boston area, so that is where you want to head for that delicious tomato sauce and pastries you crave.
When you think of an old Italian bakery in the northeast United State, Bova’s is exactly that. Refrigeration cabinets full of fresh pastries, cakes, tiramisus, and more. When you walk in the small door at the corner of Salem and Prince St you are welcomed by the smell of fresh baked deserts as you make your way into the narrow shop to examine all of your choices. You step up to the counter, order a selection of their finest looking pastries, and pay. You are handed a white bag full of your treasures and can head on your way to Charter Street where you can grab a seat at Paul Revere Park, savor your desserts, and take in the view of the Paul Revere Statue.
Instead, for us, we were planning on going to The Barking Crab for dinner in Seaport as it came highly recommended from friends and locals, but to be honest, after picking up pastries at Bova’s, we went to find somewhere to sit and enjoy the pastries and ended up in the bar of an Italian restaurant called Monica’s Trattoria. Well, as you can guess, a few espresso martinis later and we just decided to go to La Familia Giorgio’s Italian restaurant which was a quick one block walk away since Monica’s Trattoria was fully booked.
Really, Boston is not one of those places you have to plan out before you go to enjoy your visit. Since the majority of the city is walkable or bike-able and there is something around every corner, I suggest you pick out your top one or two things to do and let adventure lead you from there.
If you are looking for a step-by-step guide to Boston, follow my itinerary below to ensure you experience a taste of the culture that Boston has in store during your short visit here.
A Long Weekend in Boston – Itinerary
Friday:
- Arrive in Boston mid-afternoon
- Check into hotel
- Light dinner and some wine at Gray’s Hall
- Explore Southie
Saturday:
- Walk to pick up coffee at Dunkin
- The walk will allow you to explore the area a bit while sipping.
- Brunch at the Lincoln Tavern & Restaurant
- This is a must-visit on Saturdays for adventurous foodies. The chef has a menu that is available that day only to try out new unique bites and provide your feedback so the chef can decide if it is worthy of a permanent spot on the menu. While there, I tried the Lengua taco and the duck confit eggs benedict which were rich but incredible.
- Hop on to the Old Town Trolley Tour.
- Stop by the Samuel Adams Brewery for great beer and a quick bite.
- Hop off at stop 8 and walk about half a mile to reach Fenway Park.
- Stop into Bleacher’s Bar for a drink and a glimpse of Fenway from the outfield.
- Finish at Stop 2 in Historic North End for dinner, drinks and dessert.
- Start at Monica’s Trattoria and pop into the bar for a pistachio martini or a Peroni to whet your appetite.
- For dinner, walk about a block to La Familia Giorgio’s for some classic Italian American Cuisine and hospitality.
- Venture back to the hotel to get some rest for the next day.
Sunday:
- Grab coffee at Dunkin of course!
- Make your way over to Beacon Hill to see the historic cobblestone streets lines with cute boutique shops great for picking up a moment to remember your travels by.
- Head to North End to pick up some Italian American pastries at Bova’s Bakery after perusing the shops in Beacon Hill.
- Finish your trip at Paul Revere Park to enjoy your pastries and see the Paul Revere Statue.
- Go back to the hotel to check out and make your way back home.
