The Ultimate Guide to Boston

Welcome to Boston! This vibrant city holds a special place in our hearts as our former hometown. Whether you’re a foodie, a history buff, an art lover, or a sports fan, Boston has something for everyone. One of its greatest perks? The downtown area is incredibly walkable, making it easy to explore. In this guide, we’re sharing our favorite activities, restaurants, bars, and hotels to help make planning your trip to Boston easy!

Do:

• Stroll through the cobblestone streets of Beacon Hill, and be sure to stop by the most photographed street, Acorn Street
• Have a picnic in Boston Public Garden
• Walk along the Historic Freedom Trail
• Explore Faneuil Hall Marketplace, and check out the nearby Old State House
• Take in the beauty of the Isabella Stewart Gardner Museum (and catch the Netflix documentary about the heist here before you go!)
• Visit Museum of Fine Arts
• Visit the original building of Boston Public Library
• Shop Newbury Street
• Catch a sports game (there are so many options — Bruins, Celtics, Red Sox, professional women’s sports, and all the college sports)
• Family friendly options: New England Aquarium & Boston Museum of Science
• Grab cocktails and race your friends at the F1 Arcade Boston

Eat:

• Contessa (Italian + Brunch, Back Bay)
• Krasi (Greek, Bay Bay)
• Mamma Maria (Italian, North End)
• Capri (Italian, South End – this one is NEW and still on our bucket list!)
• 1928 Beacon Hill (American, Beacon Hill)
• Chickadee (Mediterranean, Seaport)
• Mariel (Cuban, Financial District — FYI this has a clubbier vibe)
• Lolita (Mexican, Back Bay and Fort Point)
• Terra (Italian, inside Eataly, Back Bay)
• Sonsie (Brunch, Back Bay)
• Mooo…. (Steakhouse, Beacon Hill)
• Tatte (quick breakfast, multiple locations)
• Union Square Donuts (multiple locations)
• Mike’s Pastry (pastries, North End)
• Modern Pastry (pastries, North End)

Drink

• Long Bar at Raffles (Back Bay)
• Blind Duck at Raffles (speakeasy, Back Bay)
• Drink (Seaport)
• Coquette (Seaport)
• Wip Shop and Shore Leave (Financial District)
• Trillium Brewery (Seaport)
• Farmacia (still on bucket list)
• Hecate (Back Bay speakeasy, still on bucket list)
• Parla (North End, still on bucket list)
• The Amalfi Patio at Porto (Back Bay, still on bucket list)
• Bubble Bath Boston (Back Bay, NEW and on bucket list!)

Stay:

• The Newbury (Back Bay)
• Four Seasons Hotel Boston (Back Bay, still on bucket list)
• The Langham, Boston (Financial District, still on bucket list)
• Raffles (Back Bay, still on bucket list)
• XV Beacon (Beacon Hill)
• Hotel Commonwealth (Kenmore Square, near Fenway and BU)
• Liberty Hotel (Beacon Hill, close to North End)
• Seaport Hotel (Seaport)
• The Dagny (Financial District, steps from Faneuil Hall)
• Boston Harbor Hotel (waterfront, between Faneuil Hall and Seaport)
• The Whitney Hotel (Beacon Hill, still on bucket list)
• Intercontinental Hotel (Financial District)

Thank you for visiting our site! We may make commission off affiliate links (at no further cost to you), but we would never recommend a place we don’t genuinely want to recommend.

– Kasey & Karen