Olivia Catherine & Charles Daniel
Recommendations
Dinner Recommendations
Italian: La Padrona, Umbria, and Ciao Roma Steak: Grill 23, and Moooo... Seafood: Ostra, James Hook + Co., and Select Oyster Bar Good Vibes: Lolita, Barcelona, and Mariel Aesthetic picture-op: Contessa, Yvonnes, Terra at Eataly, and Capri
Drink Recommendations
Brewery: Sam Adams Tap Room, Cheeky Monkey, and Night Shift Brewing Cocktail Bar: Oak Long Bar, Marcelino’s, and Extra Dirty Cocktail Club Irish Pub: The Dubliner, Mr. Dooleys, and L Street Tavern (as seen in Good Will Hunting) Sports Bar: Banners, The Harp (Bills bar.. Go Bills!), and The Sporting Club Live Music Bar: Lucky's Lounge, Grace by Nia, and Loretta's Activities Bar: Flight Club, SPIN, and Encore Casino (put $100 on red for me)
Boston Common
Skate at the iconic Frog Pond on Boston Common
Photo-op
Stroll through Beacon Hill and Back Bay to enjoy classic brownstones, gas lamps, and winter lights—don’t miss iconic Acorn Street, Boston’s most photographed spot.
Faneuil Hall Marketplace
Visit Quincy Market for a lively mix of local food, unique shops, and historic charm right in the heart of Boston.
North End
Known as Little Italy, offering authentic restaurants and bakeries, such as Mike's Pastry.
Newbury Street
Stroll Newbury Street for charming brownstones, stylish boutiques, and some of the city’s best cafés and shopping.