Lost in Boston

Grab some goodies

On the first day of your four-day Boston itinerary, take in the city sights from your hopefully high hotel floor. If you are staying near Copley Square, all you have to do is walk out the door to find some great restaurants.

You can head over to the Copley Square Mall to do some light window shopping or grab some hotel snacks and drinks, as well as dine over at Eataly and take a peak inside their large Italian Market for lots of goodies. You could also register ahead of time for one of their fresh pasta-making classes for the evening.

Or, if you are in the mood for some local fare, head to Dirty Water Dough Co. It might look like a dive, but they make some tasty late-night pizza perfect for after a long day of travel. But...make sure and ask them why their pizza dough is so good!!

Cobblestones & commons

Start your day walking around Copley Place, located in central Back Bay, starting with the Boston Public Library. Inside you will find unique sections to study, the quietest room I have ever been in and a central courtyard to soak up some sun. There are also a few great places to eat inside, including the The Newsfeed Café, the Courtyard Tea Room and Map Room Tea Lounge. Make sure to reserve your spot for dining if you want a great breakfast or brunch.

Next check out Trinity Church. You can visit this picturesque spot for a tour, for prayer or for sight-seeing. Then find the Boston Marathon Bombing Memorial on Boylston, do some shopping on Newbury Street, stroll along the historic Commonwealth Avenue Mall and head east toward Boston Common. It is a great place to people watch or enjoy a picnic lunch.

Lastly, make sure to walk a bit north to the quaint and quiet neighborhood of Beacon Hill. Acorn Street is a must-see. Getting there around sunset makes for the best photographs! You won't want to miss the magical cobblestoned streets.

Then head a little further east, past the golden-domed Massachusetts State House for dinner at Emmetts Pub & Restaurant. The shepherd's pie is delicious. My other dining recommendations in the area include the famous Cheers Boston for drinks, Tatte Bakery for tasty coffee and pastries, Luke's Lobster for lobster rolls and lobster bisque or the Atlantic Fish Company for their fresh catch of the day.

The Old North

On day two of your four-day Boston itinerary, depending on your location in the city, walk, take the subway or jump in an Uber over to the sea port. Grab some breakfast treats and taste all five of the teas dumped into Boston Harbor at the Boston Tea Party Museum. From there you can start on the Freedom Trail. Walk a few miles up to Faneuil Hall and Quincy Market to take in the numerous shops and food choices.

Head up Atlantic Avenue toward Long Wharf and hop on the Charlestown Ferry for a great view of the city and the USS Constitution to the Bunker Hill area. If you are feeling extra athletic, walk up the 294 stairs to the top of the Bunker Hill monument.

For lunch, take a brief walk down to the historic Warren Tavern, where George Washington used to hang out. Then walk or Uber back toward the North End for some old-world, historic, Italian charm, where you will be back on the Freedom Trail. You can see the Skinny House in Copps Hill, Paul Revere's house, Old North Church and the Clough House, the oldest building in Boston.

Then, pick any Italian restaurant for dinner. Seriously! Just pick one because they are all winners.

For dessert afterward, grab some to-go cannoli's from Mike's Pastry or head to Caffe Vittoria on Hanover Street for a sit down, dine-in, dessert feast.

Other food choices include: Giacomo's, Libertine or Quattro.

Wicked smaht

Start your day off heading toward Cambridge to visit Harvard University, whether by subway or Uber. Get "wicked smaht" by taking a walk around the campus, joining a group tour or visiting the Harvard bookstore for souvenirs. You can also visit the Sunken Garden, the Memorial Church or Winthrop House on Mill Street, where President John F. Kennedy used to be a resident.

There are also a lot of great places to eat anywhere around campus. Bluestone Lane Coffee is great if you need a place to stop and catch your breath or grab a quick bite for lunch.

Then head over to MIT. Walk or bike around campus with one of Boston's Bluebikes and make sure to take in the Great Dome in Killan Court, visit the MIT museum or see the amazing Stata Center building on Vassar Street, with its vast variety of interesting architecture.

Finally, finish the day taking in a baseball game at the historic Fenway Park, home of the Red Sox. Eat a great big hot dog, guzzle down some pints and grab a seat with a great view of the big "Green Monster".

Other places to eat are the Russell House Tavern near Harvard and Sweet Cheeks Q on Boylston for a fun BBQ meal near Fenway.

If you have extra time on your trip, you night want to try:

Taking a Boston Duck Tour

Visiting the Benjamin Franklin Statue

Dining at Legal Seafood's rooftop bar

Seeing the Mapparium at the Mary Baker Eddy Library

Eating at the famous Union Oyster House

Getting a cocktail at The Bell in Hand Tavern

Spending an afternoon at the New England Aquarium