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Want to sleep in Boston’s very first skyscraper? Originally constructed in 1893, the 15-story Ames Building was, for many years, the tallest building in the city. Renowned architect David Rockwell helped reconceive the building as the high-end Ames Hotel in 2009, preserving much of the original detailing. Many celebrities have since stayed in the luxury hotel, that’s now part of the Hilton Curio Collection, a collection of unique hotels steeped in history.

The rooms at the Ames feel more like opulent city apartments, with modernist furniture and eclectic details like feather chandeliers and gold-sequined pillows. The property’s historic roots are reflected in the 13-foot ceilings and Romanesque, floor-to-ceiling arched windows. Other classic elements include decorative marble fireplaces and oak wood floors. Centrally located in downtown Boston, the Ames provides easy foot access to many of the city’s best-known attractions.

The Freedom Trail is the artery connecting most of Boston’s key Revolutionary War sites, from Boston Common to the USS Constitution—16 stops in all. Besides providing you with some history, following the red stripe around town also delivers an easy self-guided tour of the heart of Boston, including the lively North End and Charlestown. The Common, Old North Church, the Paul Revere House, and the site of the Boston Massacre are obvious and obligatory stops, but the trail also leads to three legendary cemeteries, the 1718 Old Corner Bookstore (now a Chipotle restaurant, of all things), the 1713 Old State House, and the unmissable Bunker Hill Monument, whose cornerstone was laid by Lafayette to mark the 50th anniversary of the bloody battle between British troops and patriot militias in June 1775.

Borrow a bike and get down by the Charles River to explore this popular linear park, which runs along the river through the Back Bay and the Beacon Hill neighborhood (albeit separated from both by the Storrow Drive expressway). A paved, 18-mile multiuse path popular with cyclists, runners, and in-line skaters helps connect the Esplanade to the parklands of Boston’s Emerald Necklace and provides easy access to landmarks like the Hatch Memorial Shell (the summer stage for the Boston Pops and other performers) and Harvard Bridge (aka the Smoot Bridge). The landmark Community Boating boathouse has kayaks, stand-up paddleboards, and sailboats for rent when you want to get out on the river.

This stunning white-sand stretch, just a five-minute drive east of Port Antonio, is the only beach in Jamaica with waves high enough to surf. Boston Bay is also one of the few remaining public strands on the island. It continues to attract more locals than tourists and as such is nearly vendor-free. You can watch kids splashing about on their boards, or you can rent your own for a Surfing 101 lesson. Be forewarned: As at many beaches, sometimes the waves are flat, but you can console yourself with a short stroll down the beach to the famous Boston Bay jerk chicken stands.

One of the first things I like to find when visiting a new destination is a place to take a good walk. Winding through the city’s waterfront neighborhoods, the design of the HarborWalk allows the public to connect with the cleaned and restored Boston Harbor. The section in South Boston and Fort Point Channel takes you along some of the city’s best views of sparkling high rises, as well as plenty of good restaurants to stop in. Take time to people watch and grab a bite. Their interactive map shows the visitor just where they can connect to it.

If you love art in all its many forms, the Museum of Fine Arts (MFA) in Boston is a ‘must-see’ destination. They have a great collection of Impressionism and Asian art works, from Monet and Van Gogh, to Chinese furniture and Japanese paintings, as well as the Egyptian collections. In addition, their newly opened west wing contains many stunning pieces of American art. Besides the arts, there is a cafe, a restaurant, gift shops of course, and a mini cinema for special shows. To get there: The MFA has its own subway stop called, what else, the MFA. If you drive, there are parking garage options as well. You can easily spend half a day here—or more!

Sure, Faneuil Hall and Quincy Market make up the most touristy part of Boston, complete with street performers, a light show, and the obligatory Yankee Candle store and Cheers restaurant; we nonetheless defy you to stay away. This part of the Boston waterfront has thrived on commerce since colonial times: Faneuil Hall was crowded with merchant’s shops as early as 1743, and the larger Quincy Market was added in 1824 to provide more space (it also was the site of speeches by Samuel Adams and other early patriot leaders). If you’re looking for a Red Sox hat or a “Boston Strong” T-shirt, you’ll find it here.

Jewelry designer Michele Mercado’s showroom and work space in Boston‘s historic South End is filled with metal treasures. Her award winning designs feature 100% recycled Harmony Metals and she is a big champion of up cycling clients old pieces into new designs that will fit with their lifestyle. The timeless styles are minimal, clean and modern. Also on display is a unique grouping of handcrafted pieces of fellow jewelry artists. During my visit the hammered wall compositions of clouage artist Robert Kobayashi were incredibly detailed and meticulously constructed out of old metal.

From the first “woof” of welcome from the resident Canine Ambassador, guests feel a part of this storied hotel’s century-plus history. Located in the Back Bay, not far from Beacon Hill, Newberry Street, and the Freedom Trail, the landmarked Fairmont Copley Plaza houses 383 comfortable guest rooms, each featuring modern-elegant decor as well as signature pillow top mattresses, 46-inch TVs, and coffee makers. Snag a room on the Fairmont Gold concierge floor for extras like private check-in, complimentary Wi-Fi, and use of a snack-stocked lounge.

Sweeping views of the city can be enjoyed from the 3,000-square-foot rooftop gym (which is lined with floor-to-ceiling windows) and the sophisticated event spaces (which, decorated with chandeliers and ornate furnishings, are a top pick of Boston brides). The hotel’s convenient location makes it easy to sample the city’s great eats, but you’ll do well if you stay in, too, thanks to the handcrafted cocktails and farm-to-table dishes served at the on-site OAK Long Bar + Kitchen.

Walking through the narrow streets of Boston‘s North End might have you thinking about a delicious Italian meal. Take the time, however to explore the area on Hanover Street where the surrounding brick buildings suddenly give way to a park where Paul Revere stands guard. Commemorating his ride to warn the colonists of the impending British Invasion, the statue stands in front of a small park leading to the famous Old North Church. The setting is a perfect spot to relive the beginning of the American Revolution, and after exploring, leaves you in a location filled to the brim with restaurants and cafes to recharge before moving on.

A waterfront icon in the spirit of Sydney’s Opera House, the South Boston home of the Institute of Contemporary Art showcases the work of artists like Shepard Fairey, Tara Donovan, and Nan Goldin wrapped in glass and steel and bathed in copious natural light. With gallery and performance spaces boldly thrust above the Seaport District waterfront, the ICA also presents an ongoing calendar of dance, theater, film, and live music; come on Thursday night and admission and guided tours are free. You can drink in the views along with a Harpoon draft or a glass of chardonnay at the Water Cafe—it’s in the lobby, so you don’t need to pay for entrance to the museum to visit.

Positioned right on the historic Freedom Trail in downtown Boston, this discreet 19-story hotel caters to guests who appreciate both classic architecture and of-the-moment amenities. The building initially became a hotel in 2002; in 2006 the Kimpton chain took over the property and added its personalized boutique touch.

Though the lobby is all dark woods and polished marble floors, the rooms are chic and urbane, with high-back seating, and skyline views. The hotel’s Cloud Nine Suite and Inspired Suites offer guests space to spread out with separate living and dining areas, as well as enviable high-tech extras, including the Cloud Nine Suite’s state-of-the-art iris scanning security system. Kimpton properties also take pride in their pet-friendliness: complimentary dog beds await all four-legged visitors, and pet sitting, grooming, walking, and even massage services can be booked through the concierge.

Guests congregate in the lobby each evening for complimentary wine, and the general manager hosts morning runs twice a week. The central location also means visitors can easily immerse themselves in the city’s shopping, dining, and nightlife scenes.

The beauty of running a seafood restaurant that’s not located near the sea is that there’s no regional bias—and Current takes full advantage of this. Chef Alan Brines is able to draw inspiration from seafood meccas such as San Francisco, Boston, New Orleans, Seattle, and others. Located just east of downtown, the simple single-story brick building has been refurbished with a modern feel and can be rented out for private events. Current also hosts special events from time to time, including wine pairings from notable American winemakers.

Boston boasts some of the best beaches around, many within easy reach. Singing Beach can be reached by MBTA and others within an hours drive are well worth the effort. Some are calm, with lake like water and other will have waves for surfers. Whatever you’re looking for, the many choices of sand and shoreline with easy access to the ocean are one of the many things you’ll love about the city.

The hippest kid on the block has risen from the most unlikely of origins: the Fenway Motor Hotel, a run-down mid-century relic that once housed all manner of misbehaving musicians. Today the hotel feels more like an of-the-moment Los Angeles enclave, with mid-century furnishings, floor-to-ceiling Mondrian stained-glass windows, and upscale bathrooms. Local music and pop-culture memorabilia decorate the rooms and foyers, from framed Boston Phoenix covers (the city’s now-defunct alt-weekly) to vintage speakers and ‘70s-era phones.

In keeping with the rock-and-roll theme, both the lobby and the outdoor pool area regularly host live music. Lansdowne Street, home to legendary clubs like House of Blues, is just steps away, and of course no visit to Boston is complete without a stop at next-door Fenway Park (tours of the ballpark are available daily and year-round).