Boston Weekend Itinerary: Solo Edition

Because doing Boston solo should feel anything but lonely.

There’s something uniquely empowering about exploring a city on your own terms—no compromising on where to eat, how long to shop, or when to order that second cocktail. Boston is that kind of city: walkable, charming, energetic, and ideal for a solo reset. I live in Beacon Hill, so yes, I’m biased—but this city has my heart. And it’s even better when you get to romanticize it on your own timeline. I got to learn this city slowly alone in the winter before gaining incredible friends who now join me on my ventures - though I still take some days to do it solo.

Here’s my personal, curated itinerary for the ultimate solo weekend. Think espresso, gallery walks, rooftop drinks, and the kind of energy that reminds you you’re the main character.

Day 1: The Beacon Hill Dream Sequence

The start of your solo weekend

• Morning Stroll through Beacon Hill
  This is where I live—so naturally, I’m obsessed. Start your morning on Charles Street, where everything looks like a movie set. Browse through antique shops, indie boutiques, and small art galleries that feel like secrets.

• Coffee & Bookstore Energy
  Grab a coffee at Tatte (yes, it lives up to the hype) or Bourbon Coffee if you want something low-key. Then head to Beacon Hill Books & Cafe, where you’ll want to move in. I stop here way too often—it’s that cute.

• Midday Reset at The 7’s
  After a dreamy morning, go gritty. Pop into The 7's—a true neighborhood dive bar. Order something simple, sit at the bar, and just exist. It’s the kind of place where no one asks questions and that’s the charm.

• Afternoon Walk through the Commons
  Walk from Beacon Hill to the Boston Public Garden and Boston Common. It’s calm, beautiful, and full of energy without being overwhelming. One of my favorite resets when I need to clear my head.

Day 2: Solo Chic in the City

High energy, high style, no distractions.

• Late Breakfast + Newbury Street Stroll
  Sleep in. Brunch at The Friendly Toast if you want funky, or Buttermilk & Bourbon for something a little more indulgent. Then hit Newbury Street—Boston’s answer to Fifth Ave, with a little less chaos and a lot more charm. You’ll find everything from Luxury stores, Zara to local bookshops, plus a ton of places to stop for a midday drink.

• Luxury Pause at Contessa
  When you're in the mood to feel rich (even if you’re not), Contessa is the move. It’s a rooftop restaurant with velvet booths, marble tables, and the best light for a solo photo or two. I go for the martinis.

• Golden Hour at the Esplanade
  Keep walking all the way to the Charles River Esplanade. If you packed snacks, even better. I’ve sat here with a picnic and a journal plenty of times—it’s quiet, pretty, and makes you feel like you’re exactly where you’re supposed to be.

Day 3: Culture + Cocktails

Your last day = museums, pasta, and vibes.

• Morning Museum Moment
  Choose your vibe:

  • Isabella Stewart Gardner Museum – Romantic, moody, a little mysterious.

  • Museum of Fine Arts – Big, beautiful, and energizing.
    Either way, walk slowly. You don’t have to match anyone’s pace.

• Afternoon in Cambridge
  Cross the river and spend time in Harvard Square. I love browsing Harvard Book Store, grabbing a coffee, and pretending I’m in a collegiate rom-com. It’s laid-back and inspiring in its own way.

• Evening in the North End
  If I’m alone, I always go straight to the bar at Umbria—no reservation needed. Order pasta, a glass of wine, and soak up the energy. Everyone’s loud, the waiters are charming, and it just works.

• Walk it off with a Modern Pastry cannoli. Non-negotiable.

• Final Nightcap in Seaport
  End your weekend with a solo drink in Seaport. I love the bar at Moxies, ReelHouse, or Strega Waterfront—yes, another Strega, it’s that good. No reservations. Just walk in, order something strong, and take in the skyline. You’ll feel like you did something for yourself—and you did.

Bonus (Because Solo = Freedom)

• Walk the Seaport boardwalk — best done at sunset or late morning, depending on your mood.

• Treat yourself — blowout, facial, new book, whatever. You’re in Boston and alone. The OMNI Hotel has a great day spa!

• Don’t overplan — this is your weekend. Skip something. Linger longer. That’s the point and the fun of solo travel.