The DL – Boston in the Fall: Historical with a sense of culture, charm, and good food, fall in Boston is a must. A mixture of crisp leaves and windy air, surrounded by water views, cozy restaurants, and streets filled with “Boston smarts” this is a perfect way to spend a fall weekend.
Don’t Expect: To drive, parking is expensive and difficult. Predictable weather, it changes very quickly so be prepared for all types.
What to Expect: History and lots of it. Lots of walking, transportation options include the usual uber/lyft or public transit, which you use the Charlie card or T Pass. There are lots of college-aged and young adults all over, it is very clean for a large city, lots of Dunkin Donuts, when it’s windy and cold, it’s very windy and cold due to the way the city is set up by the water.
Friday:
Get to the hotel and drop off your stuff then head to lunch. We went to Boston Sail Loft and got their famous clam chowder, portions are big and delicious here!
Afternoon Options:
- Harbor walk if not too cold – we checked this out since it was right next to Boston Sail, you can type in Pilot House Park, then walk to Faneuil Hall and pass Christopher Columbus waterfront park.
- For a view of the city check out The Marriott Custom House roof – at 3 McKinley Square. They can be iffy about nonhotel guests going on the observation deck so up to you on how you get up there!
Visit Downtown:
- Faneuil Hall and Quincy Market
- Boston Public Market – 100, Hanover Street, Boston (W – Sun: 8 – 8 PM)
- Haymarket – located along Blackstone Street between Hanover Street and North Street (Fri – Sat: 6 AM – 7 PM)
- Financial District
- Post office square, federal reserve bank of Boston
- Rose Fitzgerald greenway park
- Head back to your hotel to spruce up for the night or walk (or uber) the short .5 mile walk to seaport district!
Evening:
Seaport – this was probably one of our favorite spots in Boston, very up and coming area.
- Grab a drink at the always busy Trillium brewery
- Eat a late-night dinner at Empire
- Then grab a nightcap at Envoy – lookout rooftop, they had heated igloos on the roof and warm cocktails which was amazing for the cold night we were there
Saturday: Cambridge!
- 9 – Breakfast: Tatte – 1288 Massachusetts Ave – breakfast – Oprah’s choice – 25 bakeries to visit in the world
- 10-12:30 – Tour Harvard Yard/Harvard Square – You can do a guided tour or we followed one by the Harvard Information Center, 1350 Mass Ave, Arcade Level, Cambridge
- Tip: Grab a cannoli at Mikes Pastry here the other location always has a wait 5 times this location.
- 12:30-1:30 Lunch
- Boston Burger Co (like black tap) – Flat patties in Cambridge
- Russel House Tavern – Cambridge
- Or one of the walk in spots around the campus, we found a local greek place and it was great
- 2-4:30 – Head over to back bay to do some shopping on Newbary
- Evening: Improv Asylum – either the Happy hour show or normal show: we chose the happy hour show because we had dinner plans later. It was really fun and you can grab a drink and enjoy the show, note this is an interactive improv show and for a more mature audience.
- Dinner: Little Italy – La Famiglia Giorgio
- LARGE PORTIONS and LONG WAITS but worth it
- Dessert: Modern Pastry
Sunday
Brunch: Frenchie (Don’t have time for sit down get a Union square donut in Boston public market known for the pb and j) – This is a lovely little quaint french restaurant with a glass enclosed garden room, would recommend for both food and atomsphere.
Afternoon:
- Freedom trail guided walking tour – we paid for a tour here and it was worth it just to be able to learn the history and not have to pay attention to navigating the whole time, you meet at Boston Common Visitor Center.
Snack/Lunch – Regina Pizzeria, the lines are going to be long just know that in advance.
North End/West End – Check out anything left on your bucketlist over here like the Old North Church, Paul Revere House, TD Garden
Beacon Hill/Back Bay:
- Walking tour of beacon hill
- Cheers Site on Beacon Street
- Parent Trap Home
- Acorn street – popular photography spot on cobbled streets (see picture below on the right)
Evening:
- Waterfront – Charles River Esplanade. A lovely path is beyond charming with its amazing views of the city, quaint parks, and in the fall, amazing foliage. Grab a cup of coffee and head over for a morning stroll
- Boston Common/Boston Public Garden – the oldest park in the USA
- Dinner: Neptunes – GET HERE EARLY, it’s very small but delicious hot lobster roll
- After Dinner – Beehive, Carries Cocktail Nation, Wallys for Jazz music (hole in the wall, VERY local, will want to uber)
Monday:
- Check out of the hotel but have them hold luggage
- Fenway park tour
- Check out bleacher bar – 82A Lansdowne St.
- Landsdowne street (caskn flagon, lansdowne pub, loretta’s)
1:00 -2:30 Lunch: Sonsie or Lolita
2:30-3: Boston Public Library or any other touristy spot you didn’t get to by your hotel
3 – Get luggage and head to the airport
Extra time:
- Walkthrough the Theatre district – catch a show if you have time
- TD Garden – go to a game or concert
- Day trip to Marthas Vineyard
Overall Food Options:
- Breakfast
-
- Union square donuts – get pb and jelly (in boston public market)
- Tatte
- Brunch – Juliet
- Jugos
- Mike and Patty’s – sandwiches
- Frenchie Boston – Brunch
- Lunch
-
- Island creek oyster
- Boston Sail Loft
- Yankee Lobster Co (seaport district)
- Lukes lobster
- Lolita Mexican
- Boston Burger Co
- Regina Pizza
- Ciao pizza
- Sonsie
- Dinner
-
- LaFamigliaa Georgio
- Coppa
- Pomedoro
- Kava neo taverna
- Barking Crab
- James Hook ad Co
- Island creek oyster
- Rowe 34
- Eastern standard
- Neptunes
- Desserts
-
- Boston cream pie: The Omni Parker House
- Flour Bakery: try the homemade Oreos and cornmeal lime cookies
- Modern Pastry: cannolis – bring some cash since they don’t accept credit cards.
- Mike’s Pastry – cannolis
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