A Boston Weekend of Historic Taverns, Art & Brunch

Start at J.J. Donovan’s Tavern for a relaxed pint near Faneuil Hall, then head into Province Street for The Hub Pub. Both keep historic downtown Boston compact on foot. Friday night crowds fill the rooms early, so check bar hours and seat availability before setting out.

Spend the afternoon taking in the palazzo courtyard and Venetian galleries at Isabella Stewart Gardner Museum (open Saturday 10:00–17:00, $25 adult admission; official policy requires booking timed entry tickets in advance, and same-day walk-up entry cannot be guaranteed), then shift to Back Bay for drinks at the copper bar at OAK Long Bar + Kitchen. Reconfirm bar table reservations in advance.

Pick up cannoli and pastries at North End Bakery inside Quincy Market at Faneuil Hall Marketplace (not the North End neighborhood; opens Sunday at 11:00 AM), then take the MBTA Red Line or a short rideshare across to South Boston for brunch at Lincoln Tavern & Restaurant (open 09:00–15:00 for brunch). If you want to beat the brunch rush, reverse the order: dine at Lincoln right when doors open at 09:00, then head over to Quincy Market at 11:00 for pastries to go.

Rain or freezing cold: Spend extended hours inside the heated galleries of the Gardner Museum and trade street walks for warm tavern booths downtown.

Crowds: Reverse Sunday plans by arriving at Lincoln Tavern right at its 09:00 AM opening to secure a table, then heading to North End Bakery inside Quincy Market once it opens at 11:00 AM, or opt for an earlier draft at J.J. Donovan's before peak evening rush.

Tighter budget: Stick to affordable draft pints and tavern fare at The Hub Pub rather than high-end cocktails, and make grab-and-go pastries from North End Bakery your casual meal.