After working in Boston for two summers during college, and finally moving here last fall, I have had the chance to discover many of the amazing things this historic city has to offer. While Boston is a history buff’s paradise, it provides all its visitors an unforgettable experience that includes unique shops and restaurants, delicious food, old-world architecture and breathtaking water views. 

Boston is a fantastic place to visit for a weekend as it is one of the most walkable cities in the country – you can easily hit the best spots around town in two days. The city is also divided into a handful of neighborhoods, each with its own unique charm and activities for you to experience. So if you ever find yourself in Boston, here is my weekend itinerary:

DAY 1: FRIDAY EVENING
  1. Arrive
  2. Dinner at Antico Forno or Bacco ⇢ *Note: Many establishments in the North End are cash only – Antico Forno and Bacco both accept card.
  3. Dessert at Modern Pastry on Hanover St ⇢ Local tip: There is a bar downstairs that serves cannolis and cocktails – Modern is famous for its espresso martinis!  •  While Mike’s Pastry is more popular and well-know by tourists, Modern Pastry is the local favorite because the cannolis are filled to order.
  4. Walk off meal by visiting the Old North Church on Salem St and Paul Revere’s House in North Square (both in the North End neighborhood)
  5. Late night option: Walk along the cobblestone-covered Marshall St to Union St and pick among the many bar/restaurant options ⇢ Local tip: My favorite is Bell In Hand which is named America’s Oldest Tavern.

DAY 2: SATURDAY
  1. Breakfast/brunch at Joe’s on the Waterfront
  2. Duck Boat Tour from Aquarium — this is a great way to see the whole city of Boston and takes you on the Charles River for panoramic city views. ⇢ You can get tickets here! I strongly recommend booking at least one day in advance. 
  3. Explore the booths at Quincy Market in Faneuil Hall
  4. Break
  5. Dinner at Lolita Fort Point or Committee  •  Lolita has another location in the Back Bay but this will not be walking distance to the roof decks below. 
  6. Drinks at Envoy Roof Deck or Yotel’s Deck 12 in the Seaport  •  These rooftop bars have great views of the city and are walking distance from both Lolita Fort Point and Committee. ⇢ *Book dinner and roof deck reservations at least 1-2 weeks in advance as these places are very popular!
DAY 3: SUNDAY
  1. Grab some coffee and walk along the Charles River Esplanade toward Back Bay
  2. Brunch at Stephanie’s on Newbury St
  3. Walk along Newbury St and explore the shops
  4. Stroll down the Comm Ave Mall toward the Public Garden and Boston Common
  5. Window shop on Charles St and explore the Beacon Hill neighborhood  •  Take a picture at Acorn St, the most photographed street in the country with its original cobblestone!
  6. Break
  7. Dinner at the Grotto in Beacon Hill or Citrus & Salt in Back Bay ⇢ Local tip: While the Grotto might not seem like much from the outside, the food and atmosphere inside make it a must-do experience. 
  8. Drinks at Cheers – the bar that inspired the TV show
Boston MA 02116 Public Garden Washington Statue
Boston MA 02116 Public Garden
Boston MA 02116 George Robert White Memorial Public Garden
Boston MA 02108 Chestnut Street