Curator’s statement
Boston is known for its history and architecture, distinctive neighborhoods, food and sports. This itinerary hits each of those categories, all within walking distance, set in the Back Bay neighborhood for the true local experience. If you are lucky, you may experience a true Boston winter with a snowfall in the city!
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Day 1: Arrive in Boston
Start the weekend right with a flight late on a Thursday to allow you to experience the nighttime beauty of Boston before the rest of the jampacked weekend.
Begin the night with dinner reservations at Lolita Back Bay. Lolita is a vibrant Mexican restaurant that offers a lively atmosphere with fun cocktails and modern Mexican dishes.
Walk over to View Boston for the 360-observation deck. Light-night tickets are offered at a discounted rate to view the stunning skyline at night.
End the night with drinks at Blind Duck. Blind Duck is a vintage-inspired speakeasy located in Raffles Hotel with creative cocktails and a seasonally changing menu.
Day 2: Explore Boston's Neighborhoods
Begin the day at Trident Booksellers & Cafe, and independent bookstore that gives you the opportunity to browse books, enjoy local coffee and savor some amazing dishes.
Head over to Memory Shop (230 Newberry Street), a unique Korean photobooth-inspired storefront complete with multiple props and background options. Perfect opportunity to create phototrips of memories that you will cherish forever.
Next, walk around Beacon Hill, a neighborhood known for its cobblestone streets, historic buildings and upscale boutiques. Beacon Hill is a window-shopping dream come true!
Make sure you visit the Charles River Esplanade, for gorgeous views of the city and the frozen river in the winter.
Make dinner reservations at Contessa Boston. Contessa is an upscale Italian-American restaurant with rooftop views and a chic atmosphere.
Watch a Celtics basketball game at TD Garden. A high-energy game with passionate fans is an amazing experience in the historic arena.
We decided to keep the night going at Memoire Boston, a nightclub located inside Encore Boston Harbor. There is also a casino that one can visit at this location.
Day 3: Ice skating at Common Frog Pond
Begin the day at Tatte Bakery & Cafe, known for artisanal pastries, freshly brewed coffee and Mediterranean-inspired dishes. Tattee is a perfect breakfast or quick-bite spot.
Enjoy lunch at Black Seed Halal Grill, right next to the park. You can’t go wrong with shawarma loaded fries, kebabs and amazing burgers.
Boston Common is a historic park with beautiful scenery in the heart of the city. Ice skating Common Frog Pond is outdoor and picturesque during the winter.
Dinner at Yvonne’s, an upscale restaurant and lounge with a cuisine full of global influences in a vintage-inspired place.
Drinks at The Street Bar is located in the Newberry hotel with local beers, craft cocktails and delicious bites.
Day 4: Visit Copley Square and Depart
Coffee at Blank Street Coffee, a chain with a minimalist vibe and the most perfect coffee drinks and pastries.
Lunch at Luke’s Lobster Back Bay, an authentic seafood restaurant known for their lobster rolls along with clam chowder and shrimp rolls.
Copley Square with a visit to the Boston Public Library and Trinity Church. Copley Square is a historic space with landmarks like the Boston Public Library and Trinity Church. The library is known for its architecture and vast book collections, while the church is known for its Romanesque Revival design.
Head back home after a winter weekend full of memories.
Need to know
Airport travel tip! The Logan Express Back Bay bus will bring you into the Back Bay area from the airport at no cost! When you are heading back at the end of your weekend, you can purchase a $3 ticket for the bus that arrives every 30 minutes. You also receive a pass to skip the line at TSA. It is the best Boston public transportation hack!
Travel Advisor
Sasha Brandenberger
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For more inspiration and insider recommendations, visit our Boston page.