What to do in Boston - a 3 day hybrid itinerary for active travelers
Updated: Nov 9
Boston is a perfect weekend hybrid travel destination. Easily recognized for its contribution to this countries history, its architectural treasures and the many distinct, cobblestoned neighborhoods, this vibrant city is often overlooked for its progressive culture, its many options for outdoor activity, and the many new and upcoming culinary hotspots. Staying active while enjoying all this marvelous food is easy due the many bike paths, esplanades and walking trails that cross and connect each neighborhood. Travelers from all over the country have been coming to this exciting New England city for business, new technology and higher education for years. But now, foodies, wine lovers and active travelers alike are seeing Boston's potential as a hybrid 'weekend escape'. So pack your bags and let’s head to Boston!
Disclaimer - There may be some affiliate links on this page, which means when you click I get a small percentage of the purchase at no extra cost to you. Recommendations come from my own personal experience and/or research. However, my philosophy is ‘you get what you give’. So for every booking or purchase made through these links, Paradox will contribute 20% of the profit to one of the charities highlighted on our site. So not only does this facilitate the continued sharing of great travel tips and recommendations, but your purchase will contribute to something bigger than the both of us. Thank you.
Where to Stay
Luxury abounds in Boston! It’s simply a matter or which neighborhood appeals to you and your style or interest. If you are staying in the Harvard or Cambridge area and are looking for classic elegance with sweeping water views, join the list of the many politicians, celebrities and world leaders who have been welcomed at the Charles Hotel over the last 25 years. But if you are more inclined to luxury and sophistication in the Boston Waterfront or Financial district, you will find ease and chic elegance at the Intercontinental, the W Boston or the Ames Hotel. Are modern and boutique hotels more your style? You won’t go wrong with Kimpton's Nine Zero. But for a one of a kind experience, a stay at the Liberty Boston Hotel is a 'must’. Once the historic Charles Street Jail, this architectural gem has been renovated to tastefully merge historic influence with contemporary design, and has become one of Boston’s premier luxury hotels.
Day 1 - a night on the town
If you are staying near the Waterfront, it’s only a short walk to Legal Harborside for Harbor view cocktails on its four-season rooftop lounge. Then a cab ride over to the Back Bay is recommended for an incredible dry-aged steak at in the plush and club-like atmosphere of Capital Grill. If you are staying near the Saint Charles River at the Liberty Hotel, a drink and some nosh on the patio at the Alibi Lounge is the place to rub elbows with the well-heeled locals. Top the evening with a window-side table at BLU near the Boston Common, for a fresh, seasonal gourmet meal with a city view.
Day 2 - the Freedom trail and Foodie fun
There is so much to see and do in Boston, it’s a challenge to decide where to start. But if the weather is in your favor, how about walking, jogging or cycling the Freedom Trail from the Boston Common to Bunker Hill for a self-guided historical tour of the city. Or you could easily spend a few hours at the New England Aquarium, making sure to stop at Neptune’s Oyster in the North End for a tasty lobster roll lunch! If you are staying near the river, you can spend the afternoon rollerblading, biking or jogging along the 17 miles stretch of the Saint Charles Esplanade. If you are there in the Summer, the Hatch Shell hosts many outdoor concerts, including the annual 4th of July Extravaganza featuring the Boston Pops. And of course, there is always Fenway Park if you are a baseball fan. But if your travels bring you to Boston in the Winter, grab your partner, don some skates and take a few turns on the ice at the Frog Pond in the Boston Common.
You’ve worked up an appetite from your daytime adventures, so a cocktail in the sultry lounge of City Bar, followed by some South American style tapas and tequila in the vibrant atmosphere of Ticos will satisfy nicely. But if you are truly looking for that international neighborhood experience, nothing beats the array of Italian delights in Boston’s North End. In this vibrant scene full of restaurants, salumerias, cafes and mouth-watering pastry shops like Mike's (get a cannoli!), you can easily immerse yourself in the sounds and smells of Euro-American village life, right in the heart of the city.
Day 3 – Brunch and Newbury Street shopping
As your weekend draws to and end, start your day with a intoxicating flavors of an organic french breakfast on the patio of Miel Brasserie Provencale or grab a croissant at Patisserie before heading out to do some shopping on Newbury Street! This popular stretch of Boston is filled with swanky, upscale shops, cafes and opulent brownstones, and will have you checking your bags at airport slightly fuller than when you arrived.