Guide to a Fall Weekend in Boston

We never learn our lesson here in New Orleans. As soon as October arrives, we begin pulling out our scarves and booties in the hopes that the temp will drop asap. Surprise, surprise, Fall didn’t come nearly soon enough this year. So, we jaunted off to Boston, a place we have heard has REAL FALL YA’LL. It was like a fall dream. We are talking orange, yellow and red leaves falling from the trees, hot coffee, and crisp air.

Day One

Visit Tatte for Breakfast and Coffee. With locations throughout Boston, you will be able to find one near you.

tatte boston
The original location in Brookline

The pastries, breads, avo toast and really everything on the menu are all unbelievable. It doesn’t hurt that every stunning location is more perfect than the next  for the ‘gram. We went twice. 🙃

hazelnut morning bun, pistachio croissant & cappuccino

After breakfast, take a stroll through the Boston Public Garden. It was the first public botanical garden in America and remains one of the most beautiful. You can’t beat the bright colors of the foliage here during the fall. Take all the photos and maybe even a ride in one of the famous swan boats!


Just a short stroll from the gardens, a walk through the Beacon Hill neighborhood is a must. The cobblestone streets, ivy and beautiful brownstone homes make this historic neighborhood the most ‘grammable in all of Boston.


Don’t miss seeking out the picturesque Acorn Street. We didn’t know a street could be so cute. Pop into all of the adorable shops on Charles Street a couple of blocks away after.

acorn street

For a late lunch, it was time for the obligatory New England lobster roll and clam chowder. We thought we’d pop into Neptune Oyster,  but we were hungry and there was a 2.5 hour wait *gasp*. Pro tip: the strategy here is to show up a couple of hours before you actually want to eat, get on the list, and go do something else until they call you. Luckily, we had a back up. We were happy sitting at the bar at Row 34 where the chowder and lobster roll did not disappoint.

After a lobster-roll induced nap, we were on our way to one of Boston’s trendiest spots, Saltie Girl, for happy hour cocktails and New England oysters, located in the Back Bay neighborhood where many of the chicest places are. The small space also comes with a super long wait, but there is standing room if you’re just there for the oysters and cocktails which we were satisfied with. The neighborhood has a young vibe, and lots of great shopping.

salty girl
Not a New Orleans fish bowl!

An Italian dinner in the North End of Boston is another absolute must. A bustling stretch on Hanover Street is filled with so many top notch Italian eateries, it’s hard to chose just one. We opted for Lucca  where we stuffed our faces with some of the most delicious pasta we had ever had. The restaurant has a second location in Back Bay now as well, but we recommend sticking to the original in North End for a more authentic feel.

If you have room and the patience to wait in a very long line, grab a cannoli at Mike’s Pastry followed by a nightcap at Nathalie wine bar.

Day Two

Harvard’s campus which is particularly beautiful in the fall. What, like it’s hard? We headed there in the morning for a coffee and a stroll. If you’re there on a Sunday, brunch at Puritan & Company is a delicious option. They are only open for Sunday brunch so if it’s Saturday, head to Lincoln Tavern in the South End. If you want to be super extra (we know you do), order whatever crazy mash up they have on the menu. Fruity pebble pancakes? Yes, please!

lincoln tavern
Fruity pebble pancakes at Lincoln Tavern

Boston’s Freedom Trail is made up of 16 historical sites that tell the story of the American Revolution. We didn’t do the entire thing, but covered the USS Constitution battleship and Bunker Hill Monument. Newsflash: you will not see the actual U.S. constitution which is what we were searching for on the boat. It’s a boat 😂

USS Constitution
USS Constitution is the oldest commissioned warship afloat

Boston is like super into sports and baseball is their fave so go check out Fenway Park where the Red Sox play! Hello, Babe Ruth is like the one baseball player we could probably name. If you’re really dedicated, you can actually go inside for a game and eat a hot dog or something.

fenway park

America’s oldest restaurant, Union Oyster House, was hands down the most Boston experience we had. We sat at the busy bar, sipped a local beer, and shared steamers and oysters with two locals who had the Boston accents you hear in the movies.

Then, we were off to Lolita for dinner. A few people had recommended this hip tequila bar and restaurant, but we weren’t completely sold on it because who eats Mexican food in Boston? It was so much fun, so extra, so delicious, everything we love. You are greeted with a grapefruit snoball like palette cleanser (tequila optional, we opted for it duh), and bid farewell with a huge cotton candy for the table.

Stumble (literally bc the shots at Lolita are the size of full water glasses) to a dive bar nearby for a nightcap. Then, if you’re like us, it will probably be time to make your way back to the hotel for some zzz’s.

Day Three

We crammed one more breakfast in at Tatte before making our way to the airport. We think we did Boston pretty well. Until next time, Boston. ✌️