While Boston is a thoroughly modern city, during your visit you’ll often feel as if you’ve stepped back in time. So much of the city remains unchanged — the gaslit and cobblestone streets of Beacon Hill, the narrow alleyways of the North End, the ducks waddling at your feet in the Public Garden — its romantic side is just below the surface. You’ll find it not only in the obvious places, but also in fleeting moments as you open the time capsule of Boston.
The quintessential “walking city,” Boston provides unlimited opportunities for wandering hand-in-hand with your sweetie. Add a romantic dinner for two with a spectacular view or a ride on a swan boat and you’re well on your way to a Boston vacation teeming with romance.
Amazing Freebies Worth Pursuing
Picnics in the Public Garden; dancing cheek to cheek at a concert at the Hatch Shell; crossing the Charles River to Cambridge via footbridge; window shopping on Newbury Street.
Home Away From Home
The intimate Beacon Hill Hotel (12 guestrooms plus a suite) is as romantic and charming as the neighborhood for which it’s named. Located on the corner of Charles and Chestnut Streets, this neighborhood gem is conveniently located near the Boston Common and Public Garden. Its most outstanding feature is the private roof deck, perfect for sipping champagne before turning in for the night.
Formerly known as the Jurys Boston Hotel, the Back Bay Hotel has a great location and posh digs in the former Boston police headquarters. There’s a two-story glass waterfall and illuminated glass staircase in the lobby, and guestrooms feature pillow-top beds, Frette linens and duvet covers, nightly turndown, and 24-hour in-room dining.
The 60-room Fifteen Beacon Hotel is a boutique property perched atop Beacon Hill, within walking distance of many of Boston’s top attractions. Every room has a gas fireplace, and most have canopy or four-poster beds.
On your first day in Boston, head for Back Bay, the home of the Boston Public Garden (adjacent to the less impressive but historically significant Boston Common, the oldest public park in the U.S.). The centerpiece of the perfectly manicured lawns and flowerbeds of the Public Garden is the lagoon that houses the Swan Boats. Enjoy a peaceful 15-minute ride on the swan-shaped paddleboats.
When you’re ready to leave the tranquility of the Public Garden behind, exit at Arlington Street and make your way to the near end of Boston’s most fashionable shopping and people-watching promenade: Newbury Street. The streets that run across Newbury Street are alphabetically arranged starting with Arlington, then Berkeley, Clarendon, Dartmouth, Exeter, Fairfield, Gloucester and Hereford. As you stroll, you’ll pass Chanel, Burberry, Armani and a variety of high- to mid-range clothing stores, shoe stores and art galleries. Check out Calypso (114 Newbury Street) for funky, high-end beach attire.
If your feet need a rest, stop for a light lunch at Ciao Bella, on the corner of Newbury and Fairfield. Enjoy the Italian fare and sip your wine slowly — the much-coveted patio tables are prime real estate for the best people watching in all of Boston.
After your afternoon of shopping, head back to your hotel to exchange your walking shoes for dressy ones — you’re off to dinner at Top of the Hub. Located on the 52nd floor of the Prudential Tower, the restaurant offers some of the best views in Boston. The elegant decor, top-notch service and live jazz playing in the background are sure to set the tone for the remainder of your night. If you’re in the mood for something less formal, head back to Newbury Street and a restaurant called Tapeo. Sit outside on the patio or inside the dimly lit, tile-walled dining room and share a pitcher of to-die-for sangria and tapas.
Beacon Hill is Boston’s most romantic and most photographed neighborhood. It’s adjacent to downtown and Back Bay, and situated on a series of narrow, hilly streets overlooking Boston Common. This one-square-mile neighborhood’s streets are lined with brick rowhouses, and the scenery includes perpetually burning gaslights, window boxes, hidden gardens and the homes of the city’s wealthiest residents. The jewel in the crown of Beacon Hill is Acorn Street, a cobblestone passageway said to be the most photographed street in America.
At the top of the Hill, you’ll find the gold-domed Massachusetts State House, where free tours are offered daily (schedule in advance). If you are a fan of the television show “Cheers,” make sure you stop in at the Bull & Finch Pub on Beacon Street — it’s the neighborhood bar that was the inspiration for the famously popular television comedy.
For lunch, Beacon Hill offers a few options along Charles Street like The Upper Crust (upscale and creative pizza) and Artu (Italian with emphasis on roasted meats and vegetables). If you’re in the mood for something a little different, head over to Chinatown for dim sum. Once you pass under the Chinese gates, the streets are bustling with activity and lined with restaurants. One of our favorites is Chau Chow City at 83 Essex Street. If you don’t know what to order, just pick what looks good to you off the constantly circling carts and the waitress will keep tabs on what you get.
After lunch, make your way to the Park Street “T” stop at the corner of Park and Tremont near the Boston Common (if you dined in Beacon Hill) or the Boylston Street stop at the corner of Boylston and Tremont (if you dined in Chinatown). Take the Green Line E-train to the Museum stop and walk two blocks to the Isabella Stewart Gardner Museum. Isabella Stewart Gardner’s collection contains more than 2,500 objects including paintings, sculpture, furniture, textiles, drawings, ceramics and photographs. Treasures from ancient Rome, Medieval Europe, Renaissance Italy, Asia, and 19th-century France and America span three floors, all overlooking a stunning garden courtyard. Is your name Isabella? If so, you’ll get to view the museum collection for free. Otherwise, you’ll pay an admission fee at the door.
If you have time, pay a visit to Isabella Stewart Gardner’s most famous neighbor, the Museum of Fine Arts. Otherwise, get back on the Green Line, take it to the Massachusetts Avenue stop and head to Casa Romero for dinner. Tucked away in an alley off Gloucester Street (between Newbury and Commonwealth), this upscale Mexican restaurant’s interior is as warm and inviting as a family home in Mexico, and the romantic patio out back is a hidden gem. Try the passion fruit margarita to start the evening off right.
This is the day to check out two neighborhoods that couldn’t be more different — the South End and the North End. Start your day walking the streets of stylish South End, which boasts the largest collection of Victorian bowfront rowhouses in the country. This neighborhood is constantly changing; what was once low-income housing gave way to a hip and trendy neighborhood and is even evolving again, attracting affluent families with young children. As a result, the South End is an eclectic mix of both people and places.
Take the Orange Line from the Back Bay/South End Station to the Haymarket stop, and you’re just steps from what many consider the country’s most authentic and vibrant Italian neighborhood. The whole place smells like an old-world grandmother’s cramped apartment on Christmas Eve, a tribute to the scores of excellent Italian restaurants that line the narrow streets.
There are two main streets in the North End: Hanover Street and Salem Street. Start with a stroll up Salem Street, lined with specialty grocery stores and restaurants galore. Keep your ears open for the residents speaking (and sometimes shouting) in Italian. At Prince Street, turn right and head up to Hanover Street. On Prince and Hanover, pick up the Freedom Trail (the red bricks imbedded in the concrete sidewalk) and follow it through the North End to historic attractions such as the Paul Revere House and the picturesque North Square. Keep following the trail to St. Stephen’s Church (401 Hanover Street), which is is the last standing church in Boston designed by Charles Bulfinch, and the Old North Church where in the steeple, lanterns were hung to warn Paul Revere how the British were coming — one if by land, two if by sea.
When the scents wafting from the restaurants become too tantalizing, grab lunch at Regina Pizzeria, which is regularly featured on lists of Boston’s best pizza joints. Then, try to resist the temptation of all the pastry shops and cafes on your way to join the North End Market Tour. You’ll not only experience a sense of the neighborhood’s history and Italian roots from a North End native, but you’ll also get to sample treats from the Italian grocery stores and pastry shops all the while, learning how to recognize the ingredients that go into authentic Italian cooking.
After your tour, follow the Freedom Trail in one of two directions from the North End — take it toward the waterfront and over the bridge to historic Charlestown or take it the opposite way to Faneuil Hall and Quincy Market. Whatever you choose, make sure to follow it back to the North End into North Square for dinner at Mamma Maria. This brick townhouse is known for showcasing New England ingredients in its Northern Italian-inspired dishes. The five dining rooms and city views give visitors the feeling they are sharing an intimate dinner in an exquisite Boston home.
After dinner, stroll down Hanover Street to Modern Pastry Shop for a sweet treat and a cappuccino; it’s less crowded than and just as good as famous Mike’s Pastry just up the street.
–written by Genevieve S. Brown; updated by Chris Gray Faust
We hand-pick everything we recommend and select items through testing and reviews. Some products are sent to us free of charge with no incentive to offer a favorable review. We offer our unbiased opinions and do not accept compensation to review products. All items are in stock and prices are accurate at the time of publication. If you buy something through our links, we may earn a commission.
Top Fares From
Today's Top Travel Deals
Brought to you by ShermansTravel
Globus Tours to Greece, Ireland, France...
Avoya Travelvacation $499+
The Caribbean: Luxe, All-Inclusive Sandals Resorts...
Avoya Travelhotel $489+
Azamara Cruises Around the World w/Free...
Avoya Travelcruise $629+