Friday Dinner Recommendations
Chart House
Chart House Boston is a waterfront restaurant located on historic Long Wharf along Boston Harbor, one of the city's oldest and most significant maritime sites. Today, Chart House preserves that sense of history while offering panoramic harbor views and a refined seafood-focused menu. The building features an original, authentic safe built into the wall, used by Hancock for his shipping business in the 18th century. Takes reservations.
The Daily Catch Waterfront
The Daily Catch Waterfront is a beloved Boston spot known for its rustic Sicilian-style seafood, fresh calamari and handmade pasta served in a casual, waterfront setting. With beautiful harbor views and a lively atmosphere, it's a perfect place for guests to enjoy an authentic, relaxed New England dining experience. Be aware there are multiple locations (we've made the mistake of booking the wrong one!), and the Waterfront location is situated closest to the trolley. Takes reservations.
Union Oyster House
Union Oyster House is one of Boston's oldest continuously operating restaurants, serving classic New England seafood in a historic, wood-paneled setting. It's especially notable for its long-standing ties to American history, including visits from figures like John F. Kennedy, making it both a dining destination and a piece of living history. Takes reservations.
Legal Sea Foods - Long Wharf
Legal Sea Foods Long Wharf is a waterfront Boston staple known for its fresh New England seafood, especially its clam chowder and lobster dishes. Located on Long Wharf, it offers guests classic coastal views and a reliably high-quality, casual dining experience rooted in the city's maritime tradition. There are several locations, so double check that you've selected the Long Wharf location. Takes reservations.
Joe's Waterfront
Joe's Waterfront is a vibrant waterfront restaurant overlooking Boston Harbor, offering a quintessential New England dining experience with fresh seafood and classic coastal flare. It's lively atmosphere and scenic harbor views make it an ideal setting for guests to enjoy a memorable meal in the heart of the city's historic waterfront. Takes reservations.
Quincy Market
Quincy Hall is a modern food hall in Boston that brings together multiple local vendors offering a range of cuisines, from casual bites to chef-driven dishes, along with craft cocktails and communal seating. It's designed as a social, energetic gathering space where groups can sample different foods in one location, similar in spirit to Boston's historic market halls but with a contemporary dining focus. No reservations.
The Green Dragon Tavern
Green Dragon Tavern is one of Boston's most historic taverns, once a gathering place for revolutionaries and often referred to as the "Headquarters of the Revolution." Guests should visit to enjoy its old-world tavern atmosphere while experiencing a piece of living history tied to the city's role in the American Revolution. This is more of a place to grab a pint than to have a meal prior to the trolley ride. No reservations.
Bell in Hand Tavern
Bell in Hand Tavern is America's oldest continuously operating tavern, offering a lively downtown Boston atmosphere with classic pub fare and drinks. Guests should stop in to experience a piece of living history while enjoying a fun, energetic spot that's been welcoming visitors since the 1700s. Similar to the Green Dragon Tavern, this spot is more for the ambiance and a drink before or after the trolley. No reservations.