Boston, Massachusetts is one of the oldest cities in the United States, and yet it was such a modern, bustling metropolis that we forgot that it was first settled in the 1600s. The city was absolutely teeming with energy!
To have the “new” built around the “old” is the absolute essence of this city. How it’s reinvented itself to stay relevant. How it maintains its history, it’s traditions. We fell in love and can’t wait to go back!
History of Boston
Boston was initially inhabited by Native Americans, until the 1600s when the English first explored this area. In particular, it was during the expedition of Captain John Smith in 1614 that this region became known as “New England” and the first English settlers (the Pilgrims) arrived. Shortly after, in the 1630s, Puritans also made their way to Boston region (fleeing religious persecution) and over time, the City paid a key role in earning the United States its independence from England. (You may be familiar with such individuals as Ben Franklin, John Hancock, and Sam Adams. They all called the greater-Boston area home!) Fast forward a bit to the late 1700s, when the colonists rebelled against England for “taxation without representation.” One of the better known events during this time was the Boston Tea Party, where colonists dumped almost 45 tons of tea into the Boston Harbor!
Boston also played a key part during the Revolutionary War, where battles such as Lexington, Concord, and Bunker Hill happened. Paul Revere’s famous night ride was through the streets of Boston, as was where the Declaration of Independence was first read out loud! Pretty cool history if you ask us!
Airports: The primary airport is Boston Logan (airport code BOS). For an alternative, we’ve also flown into Providence, RI’s TF Green Airport (airport code PVD) and driven up to Boston. If you go with the latter, be sure to avoid rush hour!
Car Rental: You don’t need to rent a car if you plan on staying in the city, but you will need a car if you want to explore the cities around Boston or take a trip out to Cape Cod. We rented a car for the tail end of our trip (when we were driving out of the city) and found it cheaper to pick up the car outside of Boston Logan airport.
Where to Stay
However you look at it, Boston is an expensive city. We visited after Labor Day and found that most hotel rooms rented at around $200-300/night within City limits, and AirBnB’s in that radius weren’t too much more affordable. However, what you pay for in terms of central location, means that it’s less that you pay for in terms of either an Uber/Lyft ride or a rental car. Keep this in mind as you decide where to stay!
Where to Eat
Boston has so much amazing food to offer! We planned our day around smaller meals so that we could EAT as much as we could in this incredible city!
Lunch: We enjoyed our taco sampler (aka each of us ordering different kinds of tacos) at Anna’s Taqueria. Brandon also ate a classic lobster roll at James Hook & Co. And I enjoyed sampling my way through Boston’s Quincy Market/Faneuil Hall. Finnally, bring some cash to grab a square of pizza (and arancini) at Galleria Umberto!
Dinner: You have to eat at Carmelina’s in the North End. Make sure you have reservations (ask for a window table), and be sure to mention if you are celebrating something special (they offer a complementary glass of wine). We ordered the caprese risotto which was fantastic as was all of their pasta offerings. Or, if you’re craving pizza, stop by Ciao!
Sweets: An absolute must-do while in Boston is the Boston Crème Pie at Omni Parker (where it was first created and served!) We also stopped by Mike’s Pastry for a cannoli, and were underwhelmed. If you have any other suggestions for cannoli’s - please let us know!
Lastly, also check out this guide from one of the bloggers I follow, who is based out of Boston!
What to Do
There is so much to do in Boston that you can spend a few days here, but at the same time, Boston is so compact that you can fit it all in one jam-packed day.
Fenway Park: B is a huge baseball fan, so we had to stop by Fenway Park during our visit. For the full experience, consider taking a tour of the park or plan your visit around a game!
Freedom Trail: The Freedom Trail is a walking path that traverses most of town and captures most of the incredible history. This is an absolute must-do while in town, and all you need are a pair of great sneakers and a quick history at each stop.
Old State House: Technically, this is part of the Freedom Trail but if you don’t have the chance to walk the whole trail, make sure you stop by the Old State House! This is where the Constitution was first read out to the Colonists and is truly humbling to experience!
Beacon Hill: voted one of the cutest neighborhoods in America by Thrillist, it came highly recommended to us. Honestly, we say skip it unless you plan on doing a photo shoot here. It is literally a cobble-stoned, residential neighborhood. Acorn Street is the most popular here, but there are a lot of tourists just taking pictures.
Boston Commons / Boston Public Garden: America’s oldest park and first botanical garden. It’s almost as if the whole city lives here! It was very lively and filled with squirrels (who are not afraid of humans at all). If you have extra time, you can take swan boats around the lake!
Boston Public Library: this public resource holds approximately 19 million volumes, making it the second-largest in the United States, only behind the Library of Congress. The reading room here is *famous* on Instagram/Pinterest for good reason. But we found it a little awkward trying to take a picture as people studied here!
Boston Marathon Finish Line: B is a big runner, so we had to stop by the finish line right outside the library! What a fun way to cap off our full day of sightseeing ♡
We hope you found this itinerary helpful for your trip! Leave us a comment if you have any questions or contact us if we can help you plan your trip!
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