A Weekend Away in Boston

A Weekend Away in Boston: A Stay at The Liberty Hotel & Iconic City Spots

Looking for the perfect weekend getaway in Boston? Whether you're planning a romantic escape, attending a special event, or just craving a bit of historic charm mixed with culinary delights, Boston is packed with things to do—and we found the perfect home base for exploring it all: The Liberty Hotel.

The Liberty Hotel in Boston

Stay: The Liberty Hotel in Boston

Our weekend began with a late Thursday night arrival at The Liberty Hotel, a luxurious and imaginative transformation of the historic Charles Street Jail. Built in 1851, this national historic landmark has been reimagined into one of Boston’s most iconic boutique hotels. With original jail cell doors, wrought-iron accents, and catwalks preserved from its past, every corner tells a story. It’s nestled in the charming Beacon Hill neighborhood, just steps from the Charles River Esplanade.

After checking in, we grabbed a late-night snack and cocktail at The Liberty Bar, the hotel’s chic lobby lounge. Sipping a craft cocktail under the soaring rotunda ceilings with soft lighting glinting off the granite walls? A vibe.

Boston Common & Public Garden

Day 1: A Stroll Through Boston’s Charm

Breakfast: Tatte Bakery & Café

We kicked off Friday with breakfast at Tatte Bakery & Café, just a short walk from our hotel. With airy interiors, pastries that rival Paris, and Mediterranean-inspired egg dishes, it’s no wonder this Boston-born chain has a cult following. (Pro tip: Get the Shakshuka or a pistachio croissant.)

Morning: Boston Common, Public Garden, and West End Museum

Fueled by flaky pastry and strong coffee, we walked through Boston Common, America’s oldest public park, then wandered the winding paths of the Boston Public Garden. The swan boats, the bronze “Make Way for Ducklings” statues, and the weeping willows made for a dreamy morning stroll.

With a little time to spare and a desire to keep exploring, we made a spontaneous stop at the West End Museum—a hidden gem just steps from our hotel. This small but meaningful museum preserves the stories of Boston’s West End, a once-thriving, diverse neighborhood largely displaced by urban renewal in the mid-20th century. It was a fascinating and heartfelt look at a side of Boston’s history that often goes untold.

Beacon Hill Books & Café

Lunch: Beacon Hill Books & Café

For lunch, we visited Beacon Hill Books & Café, a true hidden gem. Tucked inside a gorgeous historic townhouse, this bookshop-meets-café offers light, elegant fare in the most whimsical setting. It’s hard to decide what’s more delightful—the tea service or the curated bookshelves on every floor.

Afternoon: Isabella Stewart Gardner Museum

Later, we explored the Isabella Stewart Gardner Museum, one of Boston’s most beloved cultural landmarks. Housed in a Venetian-style palazzo, this museum feels more like a magical private collection than a traditional gallery. The lush courtyard garden in the center is breathtaking—and if you’re into art history, the unsolved 1990 art heist adds a mysterious twist to your visit.

Isabella Stewart Gardner Museum

Dinner: Row 34

For dinner, we headed to Row 34 in the Fort Point neighborhood—a must for any seafood lover visiting Boston. Known for its fresh oysters, lobster rolls, and warm, industrial-chic interior, it’s a go-to for elevated New England seafood. Don’t skip the brown butter lobster roll or a flight of local craft beer.

Day 2: History, Seafood & Celebration

Original Plan:
We had planned to spend Saturday walking the full length of the Freedom Trail, soaking up Boston’s revolutionary landmarks on foot. But when the weather had other ideas, we shifted gears—and still managed to make the most of a day rich in history, flavor, and celebration.

Breakfast: The Liberty Hotel
We started the day with a relaxed breakfast at The Liberty Hotel, enjoying coffee and pastries while watching the rain fall outside the towering windows of this historic landmark.

Paul Revere House

Morning: Paul Revere House
Since the full trail was off the table, we focused our morning on one of its most iconic stops: the Paul Revere House in the North End. Touring this 17th-century home brought Boston’s revolutionary past to life—and kept us mostly dry in the process.

Lunch: Neptune Oyster
Afterward, we grabbed lunch at Neptune Oyster, one of the city’s most beloved seafood spots. The hot buttered lobster roll was a standout, and the intimate setting made it the perfect spot to linger out of the rain.

Neptune Oyster

Afternoon: JFK Presidential Library
In the afternoon, we headed to the JFK Presidential Library. Set on a quiet stretch of waterfront, the museum’s exhibits gave us a thoughtful glimpse into JFK’s legacy and vision.

Pre-Wedding Pause: Beacon Hill Chocolates + Souvenirs
Before getting ready for the wedding that brought us to Boston in the first place, we stopped in Beacon Hill for a few last treats—chocolates from Beacon Hill Chocolates, two books from Beacon Hill Books & Café, and a plush duckling souvenir from Whitney + Winston for our son.

Beacon Hill Chocolates

Evening: Wedding Festivities
Then it was time to return to The Liberty, get dressed up, and head out for a beautiful night celebrating love, surrounded by Boston’s storied charm.

Sample Weekend Itinerary in Boston

Thursday

• Late arrival at The Liberty Hotel

• Drinks & snacks at The Liberty Bar

Friday

• Breakfast at Tatte Bakery & Café

• Stroll through Boston Common & Public Garden

• Visit the West End Museum

• Lunch at Beacon Hill Books & Café

• Afternoon at Isabella Stewart Gardner Museum

• Dinner at Row 34

Saturday

• Breakfast at Café Bonjour

• Walk the Freedom Trail (or visit Freedom Trail sites if weather is bad)

• Lunch at Neptune Oyster Bar

• JFK Presidential Library

Sunday

• Return home

Final Thoughts

If you’re planning a Boston weekend itinerary packed with culture, food, and a touch of romance, this is it. Between the luxe jail-turned-hotel, dreamy cafés, iconic historic landmarks, and seafood that defines the region, Boston checks all the boxes for a weekend getaway.

A Weekend Away in Boston

Books Set in Boston

Here’s a short, curated list of fiction and nonfiction books for readers interested in Boston—perfect for setting the mood before or after a trip:

📚 Fiction Set in Boston

1. The Boston Girl by Anita Diamant
   A coming-of-age story set in early 20th-century Boston, told through the voice of a Jewish immigrant reflecting on her life.

2. Mystic River by Dennis Lehane
   A gripping psychological thriller set in a working-class Boston neighborhood—dark, atmospheric, and unputdownable.

3. The Secret History of Wonder Woman by Jill Lepore
   While technically nonfiction, this biography/historical narrative delves into Harvard and Boston-area academia and culture—it reads like fiction!

4. Make Way for Ducklings by Robert McCloskey
   A beloved children’s book set in the Boston Public Garden—sweet, nostalgic, and a must for families or nostalgic adults.

5. The Art Forger by B.A. Shapiro
   A fast-paced art thriller inspired by the real-life Isabella Stewart Gardner Museum heist.

📚 Nonfiction About Boston

1. A People’s History of the American Revolution by Ray Raphael
   Focuses on Boston’s crucial role in the Revolution with the voices of everyday people.

2. Common Ground by J. Anthony Lukas
   A Pulitzer Prize-winning account of race, class, and Boston’s busing crisis in the 1970s—deeply researched and powerful.

3. Black Mass by Dick Lehr and Gerard O’Neill
   The true story of Boston gangster Whitey Bulger and the FBI’s most infamous corruption case.