11. Boston Public Garden

Boston Public Garden

Conveniently adjacent to Boston Common, this beautiful garden is another must-see while visiting downtown. The gorgeous garden is home to many unique plants and a beautiful lake. It’s a beautiful place to take a stroll no matter what time of year your visit falls. When the weather is nice, you can take a relaxing ride along the famous Swan Boats. Movie buffs will be interested to know that several popular movies filmed here.

The lagoon in summer vs. winter. Two drastically different settings, yet both are equally beautiful in their own way.

Lagoon at Boston Public Garden
Winter scene at Boston Public Garden

Movie fans will probably remember this bench, which Robin Williams and Matt Damon sat on during one of Good Will Hunting’s most memorable scenes! Being a big movie buff (esp. of 80’s and 90’s movies), I just had to get my pic!

Good Will Hunting bench in Boston Public Garden

Tip: Plan for a visit each season to experience the gorgeous changing landscapes.

12. North End Neighborhood

Union Oyster House on the North End of Boston
The Union Oyster house has been serving the best seafood in town since 1826!

I recommend a stroll around the city’s historic North End neighborhood. It’s so beautiful with the old architecture and cobblestone streets. A section of the Freedom Trail travels right through this neighborhood, so you don’t have to plan a special trip. One cool thing to do is touring the Paul Revere house. The house was originally built in 1680 and many of the original structures are still standing despite renovations.

The area is also known for being home to some of the best Italian restaurants in the city. If you feel like splurging, check out Giacomo’s, a great local restaurant serving authentic Italian cuisine. I absolutely love their pumpkin tortellini. I’ve been to a lot of Italian restaurants across the US and this is by far my favorite.

Pumpkin Tortellini at Giacomo's in downtown Boston
Pumpkin tortellini
Lobster ravioli at Giacomo's in downtown Boston
Lobster ravioli

Tip: Visit on a weekday for less crowds. A long line often begins to form shortly after opening!

13. Self Guided tours of Plymouth historic sites

Plymouth, Massachusetts waterfront area

Plymouth is an amazing coastal city located just 45 minutes from the city. If you are at all into history, I recommend a daytrip. There is so much to do and see in this historic city, most of which is free.

The Mayflower II replica and Plymouth Rock are the big tourist draws here. These iconic attractions are located along the waterfront at Pilgrim Memorial State Park. However, numerous other historical attractions such as the National Monument to our Forefathers (at 81 foot tall, it stands as the 3rd largest US statue) First Parish Church (built in 1620 it is the oldest running church congregation), and Old Burial Hill (one of the oldest and most picturesque cemeteries in the US) are also worthy of a look while in the vicinity. You can check out my Plymouth guide for more details.

Mayflower replica in Plymouth
Mayflower II replica, built in 957
Plymouth Rock in Massachusetts
Plymouth Rock
Burial Hill in Plymouth, Massachusetts
Take a ghost tour through Burial Hill, est in 1620
National Monument to our Forefathers
The world’s tallest solid granite monument

The fun doesn’t stop at history! Be sure to take a walk along Plymouth’s beautiful waterfront – the scenery is so gorgeous. Summer and fall are my favorite times to walk around. In summer, it’s just so lively with so many different events and the greenery is beautiful. Fall offers cooler temps, beautiful foliage, and an attractive drop in crowds. There are also a few beaches where you can enjoy the scenery and look for seaglass.

Plymouth harbor pic
Fall is a great time weatherwise and crowds are basically non existent
The beautiful Plymouth waterfront
So gorgeous during the summer season!

Tip: If you feel like splurging a bit, consider taking a whale watching cruise. Sightings are guaranteed (we saw many!) or your money back so a good bang-for-your-buck deal in my experience.

14. Myles Standish State Forest

Pretty views at Myles Standish State Forest in Massachusetts

An hour south of Boston, you will come across the largest recreation area in Southeast Massachusetts. At 13,000+ acres, you will never run out of things to do here. This preserve is located pretty close to my apartment so I basically use it for everything – biking, half marathon training, snowshoeing, and leaf peeping. It’s an absolutely gorgeous place to hike with never ending views of beautiful pristine pine forests. A variety of hikes take you past picturesque ponds and reservoirs. I recommend the 3 mile Reservoir loop for first time visitors. Get out your walking shoes or bike (or even skis) and enjoy a natural escape from the city. The drive is more than worth it for the relaxing experience.

Myles Standish in autumn
Myles Standish is a great leaf peeping destination
Cross country skiing at Myles Standish State Forest
The tranquil vibe is perfect for snowshoeing

Tip: Sign up for a guided hike. The First Sunday of every month, The Friends of Myles Standish offer free walking tours.

15. Harvard University Tour

Widener Library at Harvard University - Cambridge, Massachusetts

Tours are offered of the Harvard Yard area of historic Harvard University. If you have the time, I recommend the unique opportunity to learn about the history and academics of this world-class university. The grounds are absolutely gorgeous and this alone makes it worth it in my opinion. Current students will lead you around to some of the best sights including beautiful Widener Library (pictured above), built in the early 1900’s as a memorial to a student who died on the Titanic.

A really unique part of the tour takes you past the John Harvard statue, otherwise known as the “Statue of 3 Lies.” Legend says that if you rub his foot you will have good luck. You may be wondering what is with the strange nickname? We learned why on our tour. First off, the statue is not of John Harvard’s likeness. No one really knows who the statue represents. Second, Harvard did not found the University as stated on the plaque. He was rather a major benefactor. Finally, Harvard was not founded in 1638. It was founded in 1636, which makes it America’s oldest university.

Gorgeous grounds of Harvard
The gorgeous grounds
Harvard Memorial Hall
The Hogwarts like interior of Harvard Memorial Hall

Tip: Plan your tour during the fall season to enjoy incredible architecture surrounded by the vivid colors of the season.