Discovering Boston: A Weekend Escape with History, Charm, and Culinary Delights
Boston is an amazing city where history meets modern charm and culinary delights await at every turn. Whether you’re planning a quick getaway or dreaming of your next city escape, Boston offers a perfect blend of experiences to satisfy every traveler’s wanderlust.
This was a really quick trip for me – about 36 hours in Boston – so I knew I needed to have a good plan. I ended up with the only full day there completely packed and planned down to the route we would be walking! Here’s how the day went, with addresses and our map!
Where to Stay in Boston
Our journey began with a stay at the Envision Hotel Boston, a budget-friendly gem just 20 minutes from downtown. Boston is known for its steep accommodation prices, but Envision Hotel provides a reasonable option without compromising on comfort and convenience.
Exploring Boston’s Historic Treasures
9:00 AM – Breakfast at Mike’s Pastry (300 Hanover St, Boston, MA 02113)
Mike’s Pastry welcomed us with a delightful array of cupcakes and cannolis. The carrot cake cupcake, generously topped with icing, set the perfect tone for our day ahead. Mike’s Pastry is a must-visit for anyone with a sweet tooth, offering a variety of traditional Italian pastries.
9:30 AM – Freedom Trail (Free)
The Freedom Trail is 2.5 miles of historic landmarks through the heart of downtown Boston. It is a free route that includes the site of the Boston Massacre, Faneuil Hall, The USS Constitution, Bunker Hill, and Paul Revere’s House (to name a few). The trail, marked by red bricks, offered a captivating journey through Boston’s revolutionary past. Walking the Freedom Trail is like stepping back in time.
We joined the trail at Paul Revere House, looped to Old North Church and Copp’s Hill Burying Ground before making a stop for lunch. We then continued on the trail at Faneuil Hall and followed along the path to Boston Common near the Public Garden. With our stops for lunch and enjoying the history at each site, it took us about 5 hours to reach the Public Garden.
11:00 AM – Pit Stop for Lunch at Regina Pizzeria (11 1/2 Thacher St, Boston, MA 02113)
Renowned for its authentic pizzas, I was told you have to go to Regina Pizzeria on Thacher St, and it did not disappoint! We ordered the margarita pizza and it was definitely a great pizza! The sauce had rich flavor and the cheese looked like a commercial when you pulled a slice with strings of cheese dancing like icicles! The original Regina Pizzeria, established in 1926, serves up classic New York-style pizza with a perfect blend of crust, sauce, and cheese that has been perfected.
2:30 PM – Boston Public Garden (Free)
Alrighty y’all, this was a highlight of the trip for me! The weather was so mild we just sat on a bench and chatted while enjoying people watching and the rustle of autumn leaves with the soft tunes of an elderly musician playing in the background. Nestled amidst the city bustle, the Boston Public Garden provided a serene interlude.The Public Garden, America’s first botanical garden, offers a picturesque setting with its beautifully maintained landscapes and swan boats.
3:30 PM – Cheers Bar (84 Beacon St, Boston, MA 02108)
Famous for its association with the TV show, Cheers Bar on Beacon St exuded nostalgia. Though bustling, we briefly soaked in its ambiance. The bar retains much of its original charm, making it a popular destination for fans wanting to relive the magic of the beloved sitcom.
5:30 PM – Prudential Tower/Top of the Hub (800 Boylston St, Boston, MA 02199)
The highlight of our evening was the Top of the Hub located in Prudential Tower. Amidst a breathtaking sunset, we indulged in exquisite cocktails and panoramic views, a romantic crescendo to our Boston adventure!
The Prudential Tower offers unparalleled views of the Boston skyline, and Top of the Hub provides an elegant setting to enjoy a drink while taking in the cityscape. Unfortunately, this is now closed, but was replaced with The Cloud Terrace – a viewing deck.
7:30 PM – Dinner at Legal Sea Foods (100 Huntington Avenue, Copley Pl, Boston, MA 02116)
A visit to Boston isn’t complete without savoring its seafood. Legal Sea Foods treated us to a delectable platter of fish, calamari, crab, and fries. Known for its fresh and high-quality seafood, Legal Sea Foods has been a Boston institution since 1950, offering everything from clam chowder to lobster rolls.
9:45 PM – The Wilbur (246 Tremont, Boston, MA 02116)
To cap off our evening, we attended a comedy show at The Wilbur. The theater’s charm and beauty made for a lovely closing act to our Bostonian adventure! There are quite reasonably priced tickets for most shows. The Wilbur Theatre hosts a different show nearly every night including performances from stand-up comedy to live music.
Departure and Reflections
As we bid adieu to Boston and returned home, the city left an unforgettable mark. Its historical richness, culinary diversity, and vibrant culture offered captivating experiences. Whether wandering through its storied streets or savoring its delicious foods, Boston proved a city of endless discovery.
Boston beckons travelers to explore its every nook and cranny! From the iconic Freedom Trail to the serene Boston Public Garden, each moment invites you to embrace the city’s unique essence. Whether planning a quick weekend getaway or a more leisurely exploration, Boston promises experiences that captivate the soul and inspire new adventures.
Check back soon to uncover more destinations and delve into the heart of travel and exploration. Until then, wander wisely and embrace the journey!
