Things To Do
Fenway Park
Bernie took Jenn to many Redsox baseball games when they first started dating. They would cruise over to Fenway Park on Bernie's Honda Shadow and always managed to get prime parking. They also love popping into Bleacher Bar when they are in the area. https://bleacherbarboston.com Situated beneath the bleachers of Fenway Park, the Bleacher Bar has a huge garage window that looks directly into the stadium! Though they never caught a foul ball at a game together, one could argue that not only did he step up to the plate, he clearly scored his career ending grand slam! ;)
Freedom Trail
One of the best free outdoor activities to do in Boston! Bernie may or may not be able to suggest a few local watering holes along the way. ;)
Duck Boat Tour
The duck boats are a must! Though Jenn and Bernie both agree they are very "touristy", they're still so much fun! The duck boat is the only tour that goes on both land and water with great views of the city! The location listed departs from the Museum of Science.
Boston Public Market
The Boston Market is an indoor, year-round marketplace featuring 35 New England artisans and food producers housed under one roof. You'll find fresh produce, seafood, baked goods, crafts and prepared meals. All food is in season, locally sourced right here in New England. You can find Jenn's favorite George Howell coffee here, as well as overnight oats from Mother Juice and donuts from Union Square Donuts!
North End
Artu Restaurant is an absolute staple for a traditional Italian meal! http://artuboston.com Although, you can't go wrong with any of the restaurants in the North End (think little Italy). While you're there, walk down Hanover and up Salem. Great people watching! You'll find Boston's best espresso martini at Bricco on Hanover Street https://bricco.com and the best Italian pastries at Mike's (not Modern!) https://www.mikespastry.com.
Boston Common and Public Garden
September is one of the best months to visit Boston. Its absolutely beautiful! The Boston Common, established 1634, is one of the oldest public spaces in the nation. The adjacent Boston Public Garden (first public botanical garden in America) is a more manicured garden space which was established in 1837 on marshland that was filled in. Separated by Charles Street, the Garden and the Common are open air and free to walk through and take in the sites of the city. Accessible via the Freedom Trail, Jenn and Bernie recommend relaxing alongside the swan boats in the lagoon, colorful and unusual flowers, fountains and monuments along the way.
Harborwalk
One of Jenn and Bernie's favorite walks along Boston's shoreline. The Harborwalk connects Boston’s waterfront neighborhoods to Boston Harbor and each other. The path stretches from the Neponset River in lower Dorchester to Constitution Beach in East Boston via Charlestown, the North End, Downtown, Seaport, South Boston and Dorchester.
Isabella Stewart Gardner Museum
Jenn's favorite museum! Its captivating courtyard and beautiful artwork are a must see! There's also a crazy theft story from 1990 when 13 works of art were stolen in the single largest property theft in the world. The empty frames are still hanging on the wall! Thirty years later and there is still a $10 million reward for info leading to recovery of the artwork!
New England Aquarium
The Aquarium - Bernie's favorite museum! Located right on the water in Central Wharf, you'll find all of the sea animals and whale watches you could ever imagine! If you make it, be sure to say hi to Myrtle the sea turtle. She's lived at the Aquarium since 1970, is more than 90 years old and weighs over 500 pounds!
George Howell Coffee
Ok hands down the best pour over coffee in Boston. You will find George inside the Boston Public Market near Haymarket on the orange line or at their stand alone shop in Downtown Crossing also off the orange line. If you can't make it to George, then Tatte is a close second! https://tattebakery.com
DONUTS!
Located in the South End and Fenway, you will find Jenn's favorite donut shop, Blackbird. They have an array of fancy donuts, traditional donuts and Jenn's favorite donut cake! A very close second is Kanes near Downtown Crossing off the orange line. https://www.kanesdonuts.com. Or just go to both.
Bostonia Public House
Jenn and Bernie's favorite brunch spot in Boston! Even if you just ate somewhere else, at least stop in for the build your own Bloody Mary bar!
Sam Adams Taproom
Need we say more? Sam Adams is a Boston classic. The Taproom in Faneuil Hall is brand new and a great spot to stop in for a taste. The actual brewery tour is even better as you get to see where its all made. Plan your brewery tour here: https://www.samueladams.com/brewerytours#classic
Lobster Rolls!
You can't leave Boston without getting a lobster roll! Our favorite no fuss spot is Yankee Lobster. Their lobster rolls are huge and delicious! The seafood shack is in the Seaport and they're open Th-Sun for lunch, dinner and takeout.
Union Oyster House
The BEST clam chowder in all of Boston! Plus they give you a hearty portion of homemade cornbread to go along with it! ****Late addition to this, but Bernie also wanted to note how amazing the chowder is at James Hook right on the water as well! :)
Pier 6 and The Reel House
Pier 6 Restaurant, located in Jenn's old Charlestown neighborhood, is one of Jenn and Bernie's favorite spots to view the city skyline. For even more amazing views, hop on the P6 free boat taxi right off the dock for a short ride to their sister restaurant, The Reel House. Fun fact, The Reel House is where Bernie proposed!