A Whisky Lover's Travel Guide to Boston

In this semiquincentennial year, American history is front and center, and few cities lay claim to as much of it as Boston. Ever since the Pilgrims landed at nearby Plymouth Rock in 1620, a long list of important historical events has unfolded here, from the Boston Tea Party and Paul Revere’s ride to the nation’s first public school and city park. Today, it offers visitors a unique blend of New England traditions and living history, along with top-flight whisky venues. And the city’s small geographical footprint makes it even more desirable. Boston Logan Airport is less than three miles from downtown, and Amtrak serves the city’s central train stations. Once you’re here, Boston is compact and mostly walkable.

Day One

Get into the Boston spirit and walk the Freedom Trail, a 2.5-mile path that links 16 key historic sites, including Old North Church, where Paul Revere’s famous “One if by land, two if by sea” lanterns were hung; the Granary Burying Ground, where Revere, Samuel Adams, and John Hancock have their final resting places; and the USS Constitution. The Freedom Trail begins at Boston Common, America’s first public park, founded in 1634, and the adjacent Boston Public Garden, where you can ride the pond in the famed Swan Boats.

Grab lunch (Wednesday to Sunday) at Buttermilk & Bourbon in the heart of the Back Bay, three blocks from the Garden. In addition to the signature buttermilk-fried chicken, specialties include warm honey- glazed biscuits with pimento cheese, New Orleans-style barbecued shrimp, and crawfish arancini, all washed down with whiskey cocktails like the Honey Butter Old Fashioned, made with brown butter-washed private barrel Maker’s Mark, honey, and Angostura bitters. There’s a concise but well-curated whisky list. Highlights include Eagle Rare 10 year old ($16/2 oz.) and the house private barrel Maker’s Mark ($17).

The city’s top waterfront lodging is Boston Harbor Hotel, which has a gorgeous setting on Rowes Wharf, with direct ferries to and from Logan Airport. The location is ideal—a short walk from the North End, Faneuil Hall Marketplace, and the Seaport District. Boston Common is also close, and ferries to Boston Harbor Islands National Park are less than a five-minute stroll. But the main draw for whisky lovers is The Dark Bar (from 4 p.m. daily), one of the best in the city. Inspired by Boston’s Colonial history, the cocktail menu has traditional 17th to 19th century punches, plus historic spin-offs like Fizzes, Sours, and Juleps, including a Whisky Punch made with Macallan 12 year old, lemon juice, Drambuie, and allspice dram. The spirits list has about 120 whiskies, including many rarities: Pappy Van Winkle 23 year old ($745/2 oz.), Macallan 30 year old ($755), and Laphroaig 34 year old Ian Hunter Book 5 ($385). More affordable options are available, even for unusual selections like Ireland’s Dunbrody Bourbon Cask ($19).

But that’s just the start. If you really want to splurge, The Dark Bar is one of the few places in the world where you can try Balvenie 60 year old, distilled in the first year of legendary malt master David Stewart’s tenure, with only 71 bottles ever made. A 1.5-oz. pour runs $12,500. The Dark Bar also offers “The Barrel Tasting Experience,” four 1-oz. pours of its rotating private cask bottlings and a classic Manhattan or Old Fashioned made using your favorite of the flight. This must be pre-booked, but is available Tuesday through Saturday, 5-10 p.m.

If you’re looking for an upscale but more modestly priced hotel, try The Liberty in the popular and walkable Back Bay. It’s an architectural masterpiece converted from an 1851 jail. Touches like cell doors and observation catwalks have been left in place, but instead of cells and a mess hall, there are comfortable guest rooms and one of Boston’s best slates of restaurants and bars. Riding the trend of “experiential travel,” The Liberty has a magic show and frequent lobby activations, with craft artisan stands, local food, wine, and spirits tastings, live music, and other pop-ups. Among the venue’s restaurants is Scampo, an Italian spot with elaborate homemade pastas and signature lobster pizza by celebrity chef Lydia Shire, plus several bars.

For a happy hour snack and libation, hit Vermilion Club in the heart of downtown. It’s a full-service high-end restaurant, but from 3-6 p.m. Monday through Friday, the bar serves discounted New England seafood specialties like clams casino, fried calamari, and even $1 oysters. While 70-plus whiskies are offered, the focus is on cocktails, headlined by the house Manhattan: private cask Knob Creek bourbon, Inniskillin Cabernet Franc ice wine, and house bitters ($18).

Then head to Bully Boy Distillers in an industrial part of the Roxbury neighborhood. Bourbon is its flagship product, and they make three styles: a high-rye (23%) bottled in bond, a high-wheat (30%) straight, and a limited single barrel Experimental Series, along with an American straight whiskey. Tours and tastings are available. Flights of its two permanent bourbons and American whiskey are offered ($13/3 1-oz.), along with both classic and creative cocktails. They always have three rotating barrel-aged seasonal whiskey cocktails. Be prepared to settle in and chat with the passionate staff.

New England is famous for its seafood, and no trip to Boston is complete without sampling dishes like clam chowder, haddock, and shellfish. Head to Seamark Seafood & Cocktails, which also doubles as your evening’s entertainment, as it’s located in Encore Boston Harbor, one of the largest and liveliest casino resorts in the Northeast. You can try your luck at gaming, enjoy DJs and live music, or even the occasional title fight, and then head to dinner.

Not many seafood specialists have the kind of whisky program you’ll find here, with over 100 selections, but don’t overlook the delicious specialty cocktails, like the Mr. Lee Manhattan (Nikka Coffey Grain, Lillet Blanc, and orange bitters) or the B-Town Old Fashioned (Michter’s US*1 straight rye, Bacardi Reserva 8 year old rum, Vermont maple syrup, and chicory pecan bitters). There’s a full raw bar with local oysters and clams, plus a menu of New England classics, including clam chowder, lobster bisque, spicy fried calamari, and baked haddock, along with wagyu steaks for surf & turf.

There are few upscale seafood spots with this much whisky, but even fewer with a hidden speakeasy. Old Wives’ Tale is inside Seamark and has its own list of specialty cocktails, as well as everything on the main menu. Pop in after dinner and try a Japanese spin on a Sazerac with Toki, Okinawan black sugar, Peychaud’s bitters, and absinthe, or an Old Wives’ Tattletale, mixing Glenlivet 12 year old and Ardbeg 10 with wildflower honey and bitters.

Day Two

Tatte Bakery & Café began with a pastry chef selling her creations at the city’s Copley Square Farmers Market. While it has since expanded to Washington, D.C., the small chain remains a local favorite, with locations throughout the city, including Charles Street and High Street near Boston Harbor Hotel. The pastries are delicious, but there is also a full breakfast menu, from oatmeal to shakshuka to breakfast sandwiches.

Take a walk around Faneuil Hall, the pedestrianized historic waterfront area that includes shops, street performers, and Quincy Market, full of local eateries, as well as the immediately adjacent North End, Boston’s “Little Italy.” If you still have an appetite, grab a cannoli at one of the neighborhood’s famous rivals, Mike’s Pastry or Modern Pastry, just down the block from each other on Hanover Street.

Then head to the Seaport District and stop at the Boston Tea Party Ships & Museum, a kitschy but very popular attraction with costumed staff who provide an interactive experience as you relive the Boston Tea Party. You even get to dump tea into the harbor off the 18th-century ship.

The Seaport is a new mixed-use pedestrian area with lots of shops, restaurants, offices, entertainment, and a large collection of outdoor art. It has venues for live music, comedy, pickleball, ice skating, and the first F1 Arcade in the country, using high-tech race simulators. But for whisky lovers—and barbecue fans—the highlight here is The Smoke Shop BBQ by Andy Husbands. The namesake owner is an award-winning pitmaster and author of five cookbooks. Smoke Shop, with six locations in the greater Boston area, is a four-time winner of Boston Magazine’s Best Barbecue award. The food is great, but the whisky list is even better, claiming to have New England’s largest American selection, with around 300 expressions at the Seaport location (the suburban Assembly Row spot has the most, around 430). All locations feature the signature Smoke Shop Old Fashioned using brisket-infused Jim Beam, house-smoked simple syrup, and Angostura and Regan’s orange bitters, served in a smoked glass. The group currently has 14 private casks, though not all are available at every location.

The “Rare & Allocated” section has nearly 100 entries, from Pappy Van Winkle 15 ($100) to oddities such as Legent Yamazaki Cask Finish blend ($60), Blue Run Blue Sizzle and STK 8 year old bourbon ($55), and Lock, Stock & Barrel 13 year old rye ($23). On the regular list there are many at $14 or less, including Castle & Key Small Batch, David Nicholson Reserve, and Basil Hayden Toast bourbons. There is always a $10 Whiskey of the Week, along with monthly whisky dinners.

If you’re not a fan of barbecue or just want more whiskey, a few blocks away is Trillium Fort Point’s taproom, roof deck, and outdoor patio. Trillium is a brewery but also has a distillery, one of the largest in the Northeast, in Canton, 20 miles outside Boston. Here, head distiller Kyle Wortz (formerly of Utah’s High West) uses estate-grown barley and corn from its 170-acre Connecticut farm to produce Wake Robin whiskeys, with several bourbons and ryes and a soon-to-be-released American single malt. You can try all the spirits and beers here at this 500-seat facility. They offer whiskey flights of three 1-oz. pours for $22 and house cocktails like the Blood Orange Bourbon Punch ($15). Nantucket-based Cisco Brewers also operates a seasonal outdoor beer garden in the Seaport, and Island Creek Oysters Raw Bar—a legendary aquaculture farm outside the city, many chefs believe to be the world’s best—has a year-round (weather permitting) outdoor raw bar.

Boston Harbor Distillery sits south of downtown in the Dorchester neighborhood, in an 1859 brick industrial building that once housed the Putnam horseshoe nail factory. Founder Rhonda Kallman was also one of the founders of Boston Beer Company. The tours ($20 and $50)—often personally led by Kallman—start with a lengthy tasting. There is a full cocktail bar and gift shop on-site.

The signature product is Putnam American single malt, aged 3.5 years in wine barrels from Napa’s Silver Oak winery, which is also available as a 4 year old bottled in bond. There are several ryes (straight, cask strength, and red wine barrel finish), as well as a spicy hot pepper and rye concoction called Demon Seed that’s made for cocktails, pre-made bottled Old Fashioneds with Vermont maple syrup, and a line of spirits distilled from seasonal batches of Samuel Adams beer, like an Oktoberfest brewed especially for the distillery.

A fairly new addition to the Boston entertainment scene is acclaimed Australian magician Christopher Wayne’s Saturday (and occasional Friday or Sunday) shows at Boston’s Theater of Magic in the Liberty Hotel. The 90-minute performances, with basic cocktails available, are a fun and different highlight of a Boston visit, with reservations mandatory. Then it’s time for dinner.

Steakhouses and whisky have a deep history together, and the leading independent steakhouse in Boston has long been Grill 23 since its opening more than 40 years ago. Make reservations early, as it books up quickly. The expansive menu ranges from classics like wedge salad, French onion soup, hash browns, steak frites, and prime New York strip to Japanese wagyu and 100-day ultra-dry-aged rib eyes. It has a long whisky list, complete with cocktails and flights, along with the highest possible Wine Spectator Grand Award of Excellence for its encyclopedic list.

There are 15 whisky flights, with prices starting at $25, each with three 1-oz. pours, including brand horizontals (Laphroaig, Glenmorangie, Glenfarclas, Mars, Kujira, Michter’s, and WhistlePig); regions, such as the Far East (Hatozaki Small Batch, Hakushu 12, and Matsui-Shuzo The Kurayoshi 18, $52); and age, (25 year old Bowmore, Macallan, and Balvenie, $269 each), and more.

Then there’s the main list of close to 250, with over 60 bourbons including Van Winkle 12, 15, and 23 ($85, $198, $340/2 oz.) and Michter’s Celebration sour mash, a blend of straight whiskeys from 12 to over 30 years old ($1,205). There are 30 ryes, a smattering of Irish whiskeys, and around 80 scotch single malts, from Glenturret Triple Wood at $12 to Glenfiddich 44 year old 1975 at $905. There are a dozen blended scotches, and an impressive list of nearly 40 Japanese, including eight from Chichibu’s Ichiro’s Malt Card lineup alone. It’s a wonderful grand finale to your Beantown visit, and you won’t leave hungry—or thirsty. But if you do, there’s one more chance: Boston Harbor Distillery has a cocktail lounge, restaurant, and bottle shop at Logan Airport in Terminal E.