If you’re juggling a corporate schedule with limited PTO, weekend trips become your little slice of freedom. And honestly, Boston, Massachusetts is one of the best places for a quick getaway. Whether you’re based in the US, dealing with limited PTO, living that unlimited PTO life (lucky you), or even visiting from abroad, Boston is such an easy city to explore with its walkable streets, historic sites, simple transportation, and endless food spots.

When I first traveled to Boston, I was still in my Corporate era and desperately needed a break from staring at KPIs all day lol. So if you’re craving a short escape too, keep reading — I’m sharing my full weekend Boston itinerary so you can steal it for your own trip!

Day 1 (Explore Boston):

For your first full day, this is the perfect time to get to know Boston. One of the things I love most about the city is how walkable it is, with easy access to public transportation, making it simple to explore top attractions without needing a car.

1. Fuel Up Before Exploring the City at Caffè Nero

Before exploring Boston, it’s a great idea to start your day with breakfast. One cafe I loved for its quick service, convenient locations, and variety of menu options is Caffè Nero, a European inspired coffeehouse known for its handcrafted drinks and freshly made food. I ordered an iced matcha latte along with a warm sandwich pictured above. I forgot to note the exact sandwich at the time, but it was filling and the perfect fuel for a full day of walking around the city.

• Price Range: $ to $$
• Opening Hours:
  • Monday to Friday from 6:30 a.m. to 9 p.m.
  • Saturday from 7 a.m. to 9 p.m.
  • Sunday from 7 a.m. to 8 p.m.

Here’s the map to Caffè Nero:

2. Your First Attraction: Boston Public Library (Central Library)

The Boston Public Library’s Central Library is one of the most beautiful libraries I’ve been to, known for its grand historic architecture and peaceful courtyard. It’s the perfect first attraction to explore.

• Ticket Cost: Free general admission to the main library building
• Average Visit Time: 45 minutes – 1 hour
• Opening Hours:
  • Monday to Thursday from 9 a.m. to 8 p.m.
  • Friday and Saturday from 9 a.m. to 5 p.m.
  • Sunday from 11 a.m. to 5 p.m.
  • Hours may vary or the library may be closed on holidays, so be sure to check before visiting.

Here’s the map to Boston Public Library (Central Library):

3. Head Over to the Harvard Art Museums

If you enjoy museums, Boston won’t disappoint. The Harvard Art Museums are a great place to visit, particularly if you’re interested in seeing the Harvard University campus.

• Ticket Cost: Free general admission
• Average Visit Time: 1.5 – 2 hours
• Opening Hours:
  • Tuesday to Sunday from 10 a.m. to 5 p.m.
  • Closed on Mondays, major holidays, and select dates. Hours may vary, so it’s best to check ahead before visiting.

Here’s the map to Harvard Art Museums:

4. Stop by Bova’s Bakery for Sweet Treats

After some sightseeing, stop by Bova’s Bakery, a classic North End bakery that’s open 24 hours and known for its wide selection of Italian pastries. I got their well known cannolis, and they did not disappoint!

• Price Range: $
• Opening Hours: Open 24 hours

Here’s the map to Bova’s Bakery:

5. Take an Evening Stroll Through Boston Common Park

Boston Common is the oldest public park in the U.S., right in the heart of the city. It’s the perfect spot for an evening stroll, with scenic paths that are especially beautiful as the sun goes down.

• Ticket Cost: Free general admission
• Average Visit Time: 30 minutes – 1 hour
• Opening Hours:
  • Daily from 6:30 a.m. to 11 p.m.
  • Pedestrian access is available 24 hours a day.

Here’s the map to Boston Common:

6. Eat Dinner at French Quarter

Time for dinner! If you’re looking for a New Orleans inspired spot with bold flavors and classic cocktails, then go for French Quarter. It’s a fun place to unwind after a full day of exploring the city and enjoy a hearty dinner with drinks.

• Price Range: $$
• Opening Hours:
  • Monday to Wednesday from 5 p.m. to 9 p.m.
  • Thursday from 5 p.m. to 10 p.m.
  • Friday to Saturday from 11:30 a.m. to 11 p.m.
  • Sunday from 11:30 a.m. to 8 p.m.

Here’s the map to French Quarter:

Day 2 (Day Trip from Boston):

On your second and final day in Boston, spend the first half of the day exploring a nearby city (I visited Salem), then use the rest of the day back in Boston.

1. Have Breakfast at The Paramount

The Paramount is a popular Boston spot known for its atmosphere and breakfast and brunch options. I ordered the Mediterranean omelet, and it was delicious!

• Price Range: $$
• Opening Hours:
  • Breakfast, brunch, and lunch daily from 8 a.m. to 4 p.m.
  • Dinner daily from 4:30 p.m. to 9 p.m.

Here’s the map to The Paramount:

2. Visit Salem, Massachusetts

If you love Halloween or anything spooky (just like me), Salem is definitely a city to visit, especially during the fall season. There are countless things to do, from visiting the Salem Witch Museum and shopping along Essex Street Pedestrian Mall to getting a psychic reading and more. I had such a fun time exploring the city.

Salem is easily accessible by public transportation, Uber, or car, and the trip typically takes about 30 minutes to 1 hour depending on traffic and your mode of transportation.

Here’s a map with multiple routes to get to Salem from Boston:

3. Head Back to Boston and Relax at the Charles River Esplanade

Once you’re back in Boston, spend some time walking through the Charles River Esplanade to wind down and take in the views on your last day in the city.

• Ticket Cost: Free general admission
• Average Visit Time: 30 minutes – 1 hour
• Opening Hours:
  • Daily from dawn to dusk, with the exception of walk-through traffic and permitted events.

Here’s the map to Charles River Esplanade:

4. End Your Trip with Dinner at Back Deck

You can probably guess this already, but Boston has many yummy food options. There are endless places to try, and if you’re in the mood for a casual spot with classic American comfort food and a relaxed pub style atmosphere, try Back Deck. I ate their Mexicali burger, and it was a great way to wrap up the day.

• Price Range: $$
• Opening Hours:
  • Monday to Wednesday from 11:30 a.m. to 9 p.m.
  • Thursday and Friday from 11:30 a.m. to 10 p.m.
  • Saturday from 11:30 a.m. to 10 p.m.
  • Sunday from 11:30 a.m. to 8 p.m.

Here’s the map to Back Deck: