Anniversary Getaway: A Long Weekend in Boston

Accommodation & where to stay

Plan to arrive as early as possible to maximize your first day. For optimal convenience, I recommend staying in Beacon Hill, the Common area, or Back Bay—all offer excellent access to the city's top attractions.

If your room isn't ready upon arrival, the bellhop can hold your luggage, though booking through a preferred hotel partner often secures early check-in privileges.

The Newbury Hotel is my top recommendation in this neighborhood—the location is unbeatable and the service consistently exceptional. If you choose to stay in another spot, I recommend down by the Wharf. It will only add 10 to 15 minutes of walking to get to most places. In this area, we enjoyed The Dagny Hotel for their excellent cafe and concierge team.

Exploring Boston

Begin your exploration at Boston Common and the adjacent Public Garden. If you're visiting in autumn, you're in for a spectacular display of fall foliage. Stroll through the Public Garden to see the famous Swan Boats gliding across the lagoon and the beloved Make Way for Ducklings bronze sculptures. Continue toward the Massachusetts State House, easily spotted by its gleaming golden dome.

Boston Public Gardens

Cross Beacon Street to enter Beacon Hill, one of Boston's most enchanting neighborhoods. Here, narrow cobblestone streets lined with gas lamps, historic brick rowhouses, and charming flower boxes create an atmosphere that feels frozen in time. Be sure to visit Acorn Street—Boston’s most photographed street, and for good reason. Take time to wander through Louisburg Square and explore Charles Street, where you'll find excellent boutique shopping and inviting cafes. From there, it's an easy walk to Newbury Street for upscale shopping and dinner options.

Acorn Street

Cap off your evening at 89 Charles, a sophisticated speakeasy in Beacon Hill featuring Art Deco styling and an intimate ambiance. Their espresso martini is not to be missed.

89 Charles

Contessa & the Charles River

Begin your day at Contessa, perched atop The Newbury Boston with sweeping views of the Boston Public Garden and Back Bay's elegant brownstones. This Art Deco-inspired Italian restaurant delivers on both atmosphere and cuisine—an ideal setting to fuel up for the day ahead.

Contessa at The Newbury Boston

Spend your morning strolling the Charles River Esplanade, then circle back to explore two architectural gems: the Boston Public Library, with its stunning McKim Building, and the magnificent Trinity Church in Copley Square.

The Freedom Trail

As early afternoon arrives, it's time to tackle the Freedom Trail. While you may have already encountered a few historical markers during your morning walk, I highly recommend booking a guided tour for a deeper insight into Boston's revolutionary past. Ye Olde Tavern Tours is my top pick—their knowledgeable guides bring history to life while weaving in visits to historic pubs where you can sample local brews along the route.

Freedom Trail

Your tour will likely conclude near Faneuil Hall Marketplace, perfect for souvenir shopping and people-watching. For an authentic Boston dining experience, head to Union Oyster House for their legendary clam chowder or fresh oysters.

Alternatively, venture into the North End—Boston’s charming Little Italy. Hanover Street boasts countless stellar options, though I consistently recommend Assaggio or Carmelina's for dinner. No visit to the North End is complete without Mike's Pastry—their cannoli selection is extraordinary. Just remember to bring cash!

The Green Dragon Pub

Whale-watching

Dedicate your final morning to an unforgettable marine adventure with a whale-watching tour through City Cruises to Stellwagen Bank National Marine Sanctuary, located at the tip of Cape Cod. The onboard naturalists are exceptionally knowledgeable, circulating throughout the boat to answer questions and provide fascinating insights into the local marine ecosystem. During peak season, you'll likely spot numerous humpback whales feeding in preparation for their southern migration—it’s a truly remarkable experience unique to this region.

A word of caution: the journey out to the sanctuary can be choppy, so if you're prone to seasickness, come prepared with anti-nausea medication.

Whale-watching

Harvard Square

After your time on the water, spend the afternoon exploring Harvard Square—a refreshing change of pace from the city's historic walking tours. The MBTA Red Line from Park Street station (conveniently located at the top of the Common) delivers you directly to Harvard Square in minutes. Start with a latte from Tatte Bakery & Café on Massachusetts Avenue (their tagline “Tatte like Latte” will forever be stuck in my head), then meander through Harvard Yard to admire the campus architecture and seasonal foliage. The Harvard Book Store is perfect for picking up reading material for your flight home.

When hunger strikes, I recommend Hokkaido Ramen Santouka for authentic Japanese comfort food, or Felipe’s Taqueria for exceptional burritos paired with a well-deserved margarita—the perfect way to toast your Boston adventure.

The Harvard Bookstore

• Boston is beautiful any time of the year, but the fall was magical. Spring would be equally as pleasant with the weather and new blooms.

• The city is very compact so it is easily walkable but don’t be afraid to use the “T” (subway) for travel as it is very easy to navigate. Google Maps and the MBTA app helped.

• Pick a Freedom Trail tour of some kind—you won’t regret it!

• Do try all the Boston food classics. Clam chowder, Boston cream pie, Lobster rolls, Boston baked beans, and all the amazing North End Italian food.

• Boston’s cost of living has gone up, and dining prices reflect that. Do yourself a favor and book one of our partner properties to get your breakfast included and/or a F&B credit!

• Boston is also a great place to start for day trips. Great options include Salem, MA, Newport, RI, Portland, ME, and Provincetown, MA.

For more inspiration and insider recommendations, visit our Boston page.