The Planned Path Through Boston

travel, boston, guide

I love Boston. The accents, the attitudes, the history, the atmosphere! It’s big enough to have plenty to offer, but not so big that it’s stressful and overwhelming. You can easily overhear a conversation of someone saying exactly what they think (no sugarcoating here) with an attitude and tone to shock any old southern lady, and the person on the other end just dishes it right on back, and nobody is offended! It’s just the way they communicate. I love it! I went on a fourteen day road trip with my husband to everywhere from Alabama to Maine, and Boston was by far one of my favorite places. So, in honor of my love for this brilliant city I’ve written an easy to follow travel guide to help you along on your journey, and inspire you to plan a trip! (FYI, I am not being paid to recommend any of these places. All opinions stated come from personal experience or extensive research.)


Bed & Breakfast, hotel
Harrington House B&B
  • The Charming Bed & Breakfast: Harrington House B&B- This is a lovely historic home (built in 1885)  located in the small oceanside town of Winthrop right outside of Boston. This is the perfect place to stay if you want a more relaxed small town vibe with a cozy atmosphere. This is where my husband and I stayed when we came to Boston. Everything was decorated nicely, and the breakfast was amazing. We got to eat breakfast with a very friendly and interesting Australian couple. (Rates start at $109; website)
  • The Haunted & Historic: Omni Parker House- Opened in 1855 (but later rebuilt in 1927), it has had such figures as Charles Dickens, John Wilkes Booth, and John F. Kennedy reside in its confines. The third floor is said to be haunted (elevators often go there when no button is pushed), and roamed by the ghost of the hotel’s original owner, Harvey Parker (creeeepy). Despite its supposed haunting, it is a grand and luxurious hotel located right along the Freedom Trail.  It is on the pricier side though, but if you have some money to throw around, go for it. (Check website for rates; website)
  • The Affordable 19th Century Brownstone: Beacon Inn- Located on the popular Beacon Street, this bed and breakfast is within walking distance of Fenway Park, and convenient to public transportation to whisk you away to downtown Boston within minutes. The fact that it is conveniently located, the rates are affordable, and it has beautiful Victorian architecture and rooms,  makes it seem like such a great value! If I go back to Boston I’m definitely checking this place out. (Check website for rates; website)


swan boats, Boston, Public Garden
Swan Boats
  • Swan Boats  These puppies (swans actually) have been in operation since 1877. Hello historical experience! They take you on  a lovely ride through a large pond in Boston’s Public Garden. You will pass by flowing weeping willows, ride under a cute little bridge, and you might see an actual swan or two. ($3.50 admission;
  • Freedom Trail  Why else would you come to Boston, except to see the history of our great nation and founding fathers. Maybe you just really like Cheers, I don’t know, but this is the thing to do if you came for the history . It’s a 2.5 mile long trail packed full of historical sites. Here’s a handy link to an official Freedom Trail map. All you have to do is follow the red line through the city. We started off at Boston Common where the visitor’s center is located. Here are some of the cool sites you will see along the way (check out the Freedom Trail’s website for more detailed descriptions
    • Boston Common- It’s America’s oldest public park, and almost 50 acres in size. It has been used for everything from public hangings of pirates to a campsite for British troops.
    • Granary Burying Ground- Historical figures such as John Hancock, Samuel Adams, and Paul Revere are all buried here.
    • Old South Meeting House- This is where the Boston Tea Party began! ($6 admission)
    • Old State House- Many events important to the American Revolution took place here. They have a velvet red suit on display believed to have been worn by John Hancock, and the Boston Massacre happened right outside! ($10 admission)
    • Paul Revere House ($3.50 admission)
    • Old North Church- where two lanterns were hung to signal the movements of the British due to Paul Revere’s famous midnight run.
  • Walden Pond  For all you literary buffs out there, this is the place where Henry David Thoreau stayed and wrote Walden (owned by Ralph Waldo Emerson!). It is located in Concord, Massachusetts, about 40 minutes from Boston. If you’re not into literature or Henry David Thoreau, well…then it’s just a pretty pond in the middle of the woods. (website)

“I went to the woods because I wished to live deliberately, to front only the essential facts of life, and see if I could not learn what it had to teach, and not, when I came to die, discover that I had not lived.”  -Henry David Thoreau, Walden

  • Harvard University  Established in 1636, it is the oldest college in the United States, and has the largest academic library in the world. A plethora of U.S. presidents are among its alumni, as well as many other notable figures in literature and history. Harvard offers a historical one hour tour that is completely free of charge (score!). If you would prefer something a little more self-guided they also offer a mobile tour for your phone that you can use to guide you through Harvard’s campus. You can visit their website for tour schedules and more information. (website)
  • Boston Public Library  It’s the second largest public library in the United States right behind the Library of Congress. Even if you’re not interested in books it’s a gorgeous building to see. Do a google image search of it, and you will see what I mean. It offers free public tours daily. Here’s a link for more info: Boston Public Library Tours.
  • Fenway Park Home of the Boston Red Sox, this is the oldest ballpark in Major League Baseball (opened in 1912). Whether you’re interested in baseball or not this is the perfect place to have a hotdog, yell for some peanuts, and take part in a classic American experience. Before you attend the game you can take a tour of the park for $18 a pop  (Fenway Park Tours).  (website)


union oyster house

  • Union Oyster House  The oldest restaurant in America, Union Oyster House was opened in 1826, but the building itself was built sometime before 1714. John F. Kennedy frequented the restaurant and even had a favorite booth that you can check out. The interior is seriously cool, and makes you feel like you are in a different era. It is located along the Freedom Trail, so it’s a great place to stop for lunch along the way. (website)
  • Wahlburgers  If you are a fan of the reality TV show Wahlburgers or just a diehard New Kids On The Block fan, then Wahlburgers is only a 40 minute drive away from Boston. The burgers are pretty great too. (website)
  • Faneuil Hall Marketplace  This place has been around since 1742 as a marketplace and meeting hall, with such figures as Samuel Adams giving spirited speeches within. It’s filled with plenty of shops and great restaurants for you to choose from. (website)


  • The Boston Go Card is a great value if you are wanting to go to a lot of places that require an  admission price. Basically you pay a set price and can go to 49 different attractions  in Boston using the card. Some of the places include the Fenway Park Tour, all the stops on the Freedom Trail (plus you can get a tour guide), Swan Boats, the aquarium, and a whole lot more. Also if you get the card you can use the hop-on/off trolley to take you around town and see the sites. If you get a 3-day pass you can get free admission to a Boston Red Sox game. Prices are based on how many days you purchase on the card. A 1-day card costs $54 for an adult, and $37 for a child. (website)
  • If you are planning on doing the Freedom Trail make sure you schedule a full day for it, because there is a lot to see and do.
  • If you would like to track down some good hotel deals Groupon is a great place to look. Here is a link to their Boston hotel deals:

I hope this travel guide has given you at least some help and inspiration. Safe travels mo chairde!