The Two Day Guide to Greater Boston

Historical Sites

1. My personal favorite part of the Freedom Trail is strolling through Boston Common on a sunny day throughout all four seasons.

2. Take a quick tour through the Old State House, which also has an entrance to the T. You'll also find the cobblestone circle in remembrance of the Boston Massacre just outside.

3. Visit the Granary Burying Ground where you can find the final resting place for Samuel Adams and John Hancock.

4. See the shoreline from the John F. Kennedy Presidential Library and Museum. Located near the UMass Boston campus - you'll be able to learn about the Kennedy family's life in politics and their ties to Boston.

For the Sports Fans

1. I recently took my first tour of Fenway Park with out-of-town family members. The tours run every day, rain or shine. We happened to go on a rainy day and we all had a fantastic time. Tour guides are knowledgeable about more than just the park - but share behind-the-scenes information about the early days of professional baseball and the biggest rivalry in baseball. This activity is perfect for any sports enthusiast from around the world. There are multiple T stops within walking distance depending on where you are coming from and going to.

2. Attend a game at the TD Garden! Whether you're a hockey or basketball fan - there's almost always a game happening between October to May. When selecting tickets - I highly recommend the Loge level seats, which are the most comfortable in any sporting venue I've ever been to. It's convenient to have North Station right under the arena, which makes traveling via the T or Commuter Rail very accessible.

For Holiday Enthusiasts

1. Visit Salem, MA! It’s the perfect stop to find your favorite spooky moments year round as the site of the Salem witch trials. Like Boston, there are many historical sites you can visit, such as graveyards and historic homes. My suggestion is to skip the Salem Witch Museum and instead plan to visit during an outdoor market on a weekend at the Salem Common.

2. Look at one of the many tour options with themes like Ghost City or Bewitched. Halloween is obviously a very popular time in Salem, but there’s so much to do at all times of the year.

3. Check out the various markets throughout the year - my suggestion is Snowport in the Seaport during the winter holiday season. It's an outdoor market with lots of local businesses and food vendors available to enjoy.

1. Bostonia Public House, which offers great weekend brunch options (including a raw bar) and Bloody Marys that are out of this world.

2. The newly opened Margaritaville near Faneuil Hall allows you to get a little taste of summer beach vibes year-round.

3. You are going to love the North End for its Italian bakeries with some of the best cannoli you’ve ever tasted! Go for the win by doing a cannoli taste test featuring the big three bakeries - Mike's Pastry, Modern Pastry & Bova's Bakery.

4. Rochambeau, near the Prudential Center, offers a daily brunch menu with fantastic cocktails that will light up your day. I was a fan of the French Toast during my most recent visit.

5. Check out one of the many restaurants at Eataly inside of the Prudential Center. Terra uses a wood-burning grill to offer unique tastes, while La Pizza & La Pasta is your standard Italian fare.

6. Visit the town of Wakefield and check out the Public Kitchen. The best menu item is the Short Rib & Mozz Stick Grilled Cheese - trust me, it’s as good as it sounds. They also carry a wide variety of local brews and have a great, laid-back atmosphere.

7. In Salem - you'll love the Mexican fare option at Howling Wolf Taqueria. I'm a big fan of their burritos, but you can't go wrong at Howling Wolf.

8. You can't leave New England without having seafood, and for that, I recommend Sea Level Oyster Bar in Salem. The location is fairly small - but does an outstanding job of bringing the classics to you in unique offerings. We really loved the crab cakes as a starter.