The Perfect Itinerary for One Day in Boston

Sooo, you’re shipping up to Bah-ston, eh?! While we highly recommend spending more than 24 hours in Boston since it’s so full of culture and history, if that is all you have we’re here to help you make the most of it! Our 24-hour Boston itinerary is a great way to see some of the historic sights, savor some of the best food and experience some of the most beautiful scenery. If you have more than just 24 hours in Boston we would love for you to join us for a food tour so you can experience one neighborhood more intimately, but if you’re trying to cram a bunch into one day then here’s how we suggest doing it (PS – there are plenty of coffee shops around to fuel up along the way!).

Hotels: For this itinerary we recommend staying somewhere in the Back Bay neighborhood or the South End (not to be confused with South Boston aka “Southie”) – if you are staying the night that is.

Breakfast at Flour Bakery – Clarendon

Photo Credit: Flour Bakery

If you’re trying to tackle Boston in one day then you need a good, but not too lengthy, breakfast! Flour Bakery + Cafe is a beloved local chain with nine locations that started in 2000. We work with them on our Sweet & Savory South End Tour. At the helm is Joanne Chang, Flour’s co-owner and a James Beard Award-winning pastry chef. From their breakfast sandwiches to their pastries and drinks you can’t go wrong, but one thing you MUST get is a sticky bun. Flour is known for them and they go fast so best to get there as early as you can. You’ll definitely want to get it warmed up to soften up the dark, sticky caramel and toasted pecans on top.

Next…

Boston Public Garden, Beacon Hill & State House

Photo Credit: BOStoday

Photo Credit: coleong/Getty Images

Photo Credit: Secretary of the Commonwealth of Massachusetts 

We recommend taking a walk through the Boston Public Garden to take in the beautiful scenery, especially if you are visiting during a more lush or colorful season. If you have the time, take a ride on the Swan Boats! Boston Common, which is a stop on the Freedom Trail, is connected to the Public Garden but we recommend taking a left on Charles Street into the historic Beacon Hill neighborhood. From there you can continue through the cobblestone streets, enjoying the architecture and popping in and out of little shops (fair warning there are some steep hills). Finally, on your way out of Beacon Hill you can catch a glimpse or pic of the State House, another stop on the Freedom Trail.

Next…

Head to the North End for Lunch

Photo Credit: Cathay Pacific

Boston’s historic North End, which is its own Little Italy, is a great place to explore and have some lunch! The small streets are quaint and there are tons of restaurants to choose from but our most favorite restaurant in the North End and actually, all of Boston is The Daily Catch. There is not a lot of extra elbow room in this rustic establishment but one whiff of what’s coming out of the open kitchen and you will be sold. You can get some of the best pasta and seafood here, which is a great two-for-one in Boston especially if you only have one day. The North End is close to Boston’s Waterfront, where many restaurants get fresh seafood daily. We highly recommend the house-made squid-ink pasta (served right in the sauté pan) and the calamari meatballs. If you order wine, which we suggest, be prepared for it to come in a plastic cup – remember it’s rustic. Trust us, the vibe fits.

Photo Credit: The Daily Catch

Photo Credit: The Daily Catch

Next…

Explore the North End & Stop for a Cannoli

Photo Credit: The Cultural Landscape Foundation

Photo Credit: Best Boston 

Photo Credit: Bova’s Bakery

Once you’ve fueled up, there are some other things you must do in the North End before heading out. If you don’t do this before lunch, be sure to walk by the Paul Revere House and Old North Church – both stops on the Freedom Trail and great photo ops. Then, you MUST get a cannoli! Our favorite comes from Bova’s Bakery but if you can’t ignore all the buzz about Mike’s Pastry or Modern Pastry then get one there. Just GET ONE, or two or three!

Next…

Walk Through Faneuil Hall & Quincy Market

Photo Credit: The Cultural Landscape Foundation

Walk over to the bustling Faneuil Hall and take a peek inside Quincy Market. This area in general is often referred to as “Faneuil Hall” collectively, but technically, the collective name for everything is “Faneuil Hall Marketplace.” Faneuil Hall Marketplace is actually four great places in one location – all set around a cobblestone promenade where all sorts of street performers entertain visitors. There are also lots of shops and restaurants for you to check out. While it’s known as a historic marketplace, Faneuil Hall also provided a platform for the country’s most famous speakers such as Sam Adams and George Washington. On your way out you can also see the Old State House and grab a photo if you’d like as it’s right across the street.

*Here is a great time to pop back over to your hotel if you need to rest or refresh before dinner*

Next…

Dinner at The Elephant Walk in the South End

The South End is PACKED with excellent restaurants representing a unique mix of cultures and cuisines. You really can’t go wrong but with this itinerary we think The Elephant Walk is a great place for dinner. They are also one of our South End tour partners and we love everything about them from the French-Cambodian menu to the fantastic cocktails and hospitality. Some other suggestions for dinner are Bootleg Special, Orinoco, Burro Bar, Bar Mezzana, Coppa and literally anywhere that looks good to you! PS pictured above in order is the Rouleaux, Porc Aux Piments Doux Shishito, and Chocolat Liégeois.

Post-Dinner Drinks at Yvonne’s

Photo Credit: Yvonne’s

Photo Credit: Yvonne’s 

Dark, seductive and elegant – Yvonne’s is a must if you only have one night in Boston – even if it’s just for one drink – and that drink may be set on fire if you order the right one. There are two bar areas – one in the darker, library-inspired lounge area and one in the ornate main dining room with chandeliers strung everywhere.

…or Post-Dinner Drinks at a Fenway bar

Photo Credit: Bleacher Bar

If it’s baseball season and you are a big sports person then it’s definitely worth stopping by the Fenway area, even for just a quick picture or one drink before or after dinner. If there is a game it will be bumpin’ for sure but that’s part of the fun. For one of the most classic bar experiences head to Bleacher Bar, a unique bar beneath Fenway Park’s bleachers with a view of centerfield.

We hope you have a great time visiting Boston!!

Your itinerary, in summary:

1) Breakfast at Flour Bakery – Clarenden

2) Walk through the Boston Public Garden / Beacon Hill / see the State House

3) Lunch in the North End at The Daily Catch

4) Explore the North End / Paul Revere House / Old North Church / pickup a cannoli from Bova’s Bakery

5) Walk through Faneuil Hall / Quincy Market / Old State House

*maybe stop at hotel to rest/refresh*

6) Dinner at The Elephant Walk in the South End (or anywhere!)

7) After dinner drinks at Yvonne’s in Downtown or Bleacher Bar in Fenway

Other things you can do depending on time and your personal preference:

*History: See the Bunker Hill Monument / USS Constitution in Charlestown (stops on the Freedom Trail)

*Art/Culture: Visit the MFA or the Isabella Stewart Gardner Museum

*Shopping: Newbury Street / The Prudential Center / Boston Public Market

*Sports: Fenway Park – Red Sox Game or Tour