How to Spend THE Perfect Day in Boston

It doesn’t matter if you’re in town for a conference or to run the Marathon, there are things in Boston you DO NOT want to miss on your first trip. Since we’ve been to Bean Town a time or two, let us share with you how to spend THE perfect day in Boston.

Preparation is Key

Since you’ve only got a maximum of 18 hours of usable time, make sure you’re ready for the adventure in advance.

Make reservations if the restaurant or activity allows them
Wear comfortable walking shoes
Drop off your bag at your hotel if your room isn’t ready
Check the weather forecast the night before and BE SURE to bring a strong umbrella if rain is called for

Broken umbrella from the Pub Crawl — The end of the umbrella

First Stop – Breakfast at Stephanie’s on Newbury

Stephanie’s on Newbury is ALWAYS busy. Not because it’s a touristy place but because it’s JUST THAT GOOD. Consider making reservations in advance or you can put your name in with the hostess and spend some time perusing the shops on the street. Though some are hilariously expensive, we were able to snag a few deals at Uniqlo and H&M.

PRO TIP: Don’t get too full on breakfast because there are SO MANY great places to eat!

Head Over to the Public Garden and Boston Common

A park with a pond and a park bench with people — Go for a walk in the park

Established in the 1600’s, it’s hard to imagine this beautiful space was once the encampment for the British during the revolutionary war and served as the place for public hangings (Eeek). Now you can paddle a swan boat on the pond or make way for the ducklings!

Bronze statues of a duck with her ducklings following in a row. Each one is wearing bunny ears and an Easter-themed shirt — Getting into the Easter spirit

Visit Paul Revere’s Grave at the Granary Burial Grounds

WARNING: As a history hobbyist and nerd, I couldn’t IMAGINE going to Boston and NOT visiting the sites related to the Revolutionary War. So, if history isn’t really your thing…this may not be the day for you. In that case, you may want to try to visit the Irish pubs in walking distance of the Commons. Keep in mind, if you have a drink at each, you may end up crawling by the end.

Headstone for Paul Revere with a small American Flag in front of it

Walk Through Faneuil Hall and Quincy Market

Large brick building with multiple rows of windows and an arched window on the top. In front is a statue of Samuel Adams. — Mr Adams in front of Faneuil Hall

Built before we became a nation, Faneuil Hall served as a hub for the community and is now one of the top 10 tourist destinations in the US! With 80 vendors occupying the 200,000 square foot space, you’ll find a little something for everyone. I should know! Here’s a pic of the prize I picked up on my way over to the new Sam Adams Taproom.

Craft beer in a Sam Adams tulip glass next to The Beatles nesting dolls - John, Paul, George, Ringo and a treble clef. — Here they are…The Beatles (nesting dolls)!

Have Lunch at James Hook & Company by the Water

Two lobster rolls in tin foil, on top of red and white checked paper — The BEST Lobsta

Woman standing behind a lobster statue that says “James Hook” on its claw. They are in front of a small, wooden building — The BEST Lobsta

This is another restaurant that is ALWAYS busy because it is FANTASTIC! The entire restaurant is in a building about the size of a mobile home. If you get there early enough, you might be able to snag a seat at a table indoors but if not, there are picnic tables by the water. You could TRY to eat and walk but the lobster rolls are SO heavy, you might need two hands to manage it. (And then how would you hold your drink or all the napkins you’ll need??)

Walk the Freedom Trail to Paul Revere’s House and the Old North Church

Bronze sculpture showing the way the street looked in the colonial period with Paul Revere’s house in the background. It’s a brown, wooden building with diamond shaped window panes — Paul Revere’s House

Statue of Paul Revere riding a horse with the old North Church in the back ground. There are a line of trees on either side between the two — Paul Revere’s House

You can walk by Paul Revere’s house on the way to the Old North Church but if you have a little extra time, consider taking the tour. It’s only $6 per adult and gives you a GREAT peek into life during the Colonial period. The Old North Church is open every day until 5pm and is TOTALLY free. Oh and speaking of free…

See the USS Constitution on Your Way to the Bunker Hill Monument

A three mast wooden ship, moored by a dock — The USS Constitution

Street lined with brown stone houses with the Bunker Hill Monument at the end. The monument is a white stone pointed obelisk — The USS Constitution

You’ll walk by Old Ironsides at the Charleston Navy Yard on your way over to the Bunker Hill Monument. The monument to the first battle between the New England armies and the British is open every day until 4:30pm. If walking the 294 steps to the top doesn’t appeal to you, the surrounding grounds have multiple display boards that share the highlights of the battle.

Stop By Mike’s Pastry for a Cannoli

White box tied in string that reads “Mike’s Pastry” next to a cup of coffee — Mike’s pastries to go

Man holding a large cannoli with chocolate chips wrapped in wax paper — Mike’s pastries to go

Hopefully you’ve worked up a little appetite from crossing the Charles River and have room for a famous cannoli from Mike’s Pastry. Keep in mind that they only take cash and that one cannoli is enough of a treat for two (even three) people!

Optional…Hop the Train to Fenway for a Game

Infield at a baseball game from the seats. There are people in the stands and the players are celebrating on the field. — Celebrating at Fenway

If you like baseball and have the time, consider going to Fenway to watch the Sox! It is the oldest ball park in the US and the fans are a hoot! You can often get tickets on StubHub for a pretty low price and you can get CLAM CHOWDER from this guy!

Vendor at Fenway balancing a tray on his head that reads “Clam Chowder” — The Chowder Guy

Have Dinner at the Union Oyster House

Woman and man standing in front of a wooden sign that reads “Union Oyster House”

Bowl of clam chowder on top of a placemat at the Union Oyster House

As the oldest restaurant in the United States, a young Daniel Webster was known to sit at their bar and eat his weight in oysters. Same here, Danny. Same here. Also, in my opinion, this is the best clam chowder in Boston so maybe don’t get it from the guy at Fenway.

Not Optional…Finish the Night at the Green Dragon Tavern

Pint of craft beer on a wooden bar — Have a pint to finish the night

Book about the oldest bars in every state, opened to the section on the Green Dragon Tavern — Have a pint to finish the night

We know you’re tired from all the walking and site seeing and that you’re pretty full from enjoying the best of Boston’s fare. But you’ll kick yourself if you don’t end the night at the oldest bar in the United States. The vibe is cozy. The beer selection is really solid and Paul Revere used to hang out here with his friends. So grab at seat at the bar and toast your perfect day!

If you liked finding out how to spend the perfect day in Boston, consider subscribing for free! We’ll send you the latest right to your mailbox, along with curated content just for you! You can also keep up with us in real time by following us on Instagram at the__travel__oracle.