Explore Boston

Boston and NYC in 3 Days: An Itinerary

You have 72 hours to complete a mission of exploring the best of these two East Coast urban centers. Go!

A tale of two rival cities: Boston and New York, both historic, both cosmopolitan, yet each with an identity entirely its own. On the U.S.' East Coast, a mere 214 miles separates them, and it's not hard to get to know both in a short span of time.

Ready? Let's go.

Days 1-2: Boston

Many travelers liken Boston to cities in Europe rather than to its compatriots in America, and there's truth in this. With its rich home-turf history and its array of quaint architecture, haphazard streets, cobblestones and brick, Boston is quintessentially Dickensian. It's also a small, big city when compared to the far-reaching spreads of other metropolitan centers like New York, Chicago or Los Angeles. Bostonians themselves run the gamut from working class to blue-blooded, smarter-than-smart to die-hard fanatic of sports, art, early American history—you name it.   

Start with a hearty breakfast at The Paramount in Beacon Hill. It's been around for 17 years and is a favorite among locals for its fluffy Belgian waffles topped with fresh fruit and its omelets with Cajun-style home fries.

Before leaving the neighborhood, stroll Charles Street and pop in at any boutiques that pique your interest. Gift stores, like Black Ink, Flat of the Hill and Blackstone's, are abundant, but also find antiques, children's clothing, women's interests and gourmet edibles. From Charles, follow Chestnut Street to West Cedar, and then onto Acorn Street, one of the city's most quaint and iconically "colonial." It's a great spot for a photo opp.

Acorn Street is one of Boston's most picturesque streets
Acorn Street is one of Boston's most picturesque streets (©Paul Gelsobello)

Next up: Boston's two State Houses, most straightforwardly named the Old State House and the State House.

First stop is the newer of the two. At the State House—think, 'shiny gold dome'—visitors can take a free weekday tour through the Commonwealth's municipal seat, an activity that isn't pervasively known to travelers or, even, locals. See loads of art, the Senate and House chambers, and maybe run into the Governor.

About a 10-minute walk away, the Old State House served as the seat of British government during Colonial times. Not to mention the Boston Massacre happened right out front. In 1779 and 1780, John Adams and the Constitutional Convention drafted the Commonwealth's original Constitution here, a document that would go on to serve as the example to follow for those creating the Constitution of the United States of America. Today, the building is part of the Freedom Trail and hosts an interesting and informative program where visitors assume the identities of real 18th-century Bostonians and learn history through new eyes.

Get your tourist fix in at lunch at Union Oyster House, established in 1826. It's one of the oldest still-operating restaurants in the country. You must sit at the bar and order fresh local oysters shucked right in front of you. Daniel Webster used to, nearly every day. Other hits include broiled scrod and old-fashioned fish cakes.

Travel across town for an afternoon visit to the Isabella Stewart Gardner Museum, located in the Fenway. This small, salon-style museum is the antithesis of institutions like the Museum of Fine Arts Boston and the Metropolitan Museum of Art. Its eponymous founder and wealthy Bostonian loved art and traveled the world during the mid-19th century amassing a 2,500-piece collection of furniture, sculpture and work by masters, among them Michelangelo, Rembrandt, Botticelli and Degas. She built her home around her private collection, arranging it in highly decorated, room-sized galleries. Early visitors would have stumbled across artists at work, as did those in 1903, when Gardner allowed John Singer Sargent to use the Gothic Room as his studio. Personal and welcoming, spend a few minutes finding your zen in the original wing's garden courtyard; it's one of the most serene and inspiring indoor spots in the city.

Isabella Gardner's prized museum and home
Isabella Gardner's prized museum and home (©Steve Dunwell)

Check in at the Omni Parker House on School Street in Downtown Crossing. This absolute stunner celebrates its 160th anniversary in 2015 and can be tied to dozens of famous characters, from Ho Chi Minh who worked in its kitchen, to Charles Dickens who was a habitual guest of the hotel's third floor. The Parker House is one of Boston's most magnificent places to stay, and hospitality has always been a priority here, especially for founder Harvey Parker. Speaking of whom... He reportedly still walks its halls from time to time to make sure things are running smoothly. Haunting aside, the Parker House is famous for its rolls and as the birthplace of Boston cream pie. Its location in the heart of downtown and steps from the MBTA's Park Street Station means most parts of the city are easily within reach.

After a brief respite, it's time for dinner at Scampo in the West End. Lydia Shire's Italian restaurant holes up on the ground floor of the Liberty Hotel, or as longtime locals identify it, the former Charles Street Jail. Thankfully, today it is prisoner free. Scampo offers an interesting mix of sophistication and impishness and an outstanding menu from the aforementioned chef-owner. Shire's hearty comfort food features uncommon flourish. See: classic Dover sole served aside fried-to-crunchy fish bones you're meant to nibble. Then there's the mozzarella bar, where four varieties of the cheese pair with heirloom tomatoes, or prosciutto and carimañola fritters, or king crab. Weekend evenings feature special meals like suckling pig al forno or a traditional Italian-American Sunday supper. Mmm.

Yvonne's, a fresh face on legendary local restaurant Locke-Ober
Yvonne's, a fresh face on legendary local restaurant Locke-Ober (©Eric Levin)

Until 2012, Locke-Ober held the title as Boston's most legendary grande dame of old-school fine restaurants. Only this year did the historic dining room reopen under new ownership and a new name, Yvonne's, although even this (the title of a nude Frederick Childe Hassam painting that once hung inside) is tied to its history. Step inside this dark, den-like place for a cocktail, like the whiskey-laced Ward 8 (did you know this drink originated at Locke-Ober in 1898?), or, if you dare, a big bowl of Boston Rum Punch.

Sleep tight. You've got a big day ahead.

Days 2-3: New York City

Around 7:30 am, grab a coffee (smooth and nutty La Colombe out of Philadelphia) and an authentic French ham and cheese croissant from Cafe Madeleine in the South End. Eat it as you walk through a quiet corner of the historic neighborhood (West Newton, Greenwich, and St. Botolph being streets of interest) and Southwest Corridor Park. Then walk toward the Prudential Center, along Belvidere Street, where you'll catch a ride to New York City aboard the LimoLiner bus.

LimoLiner is quick and cost effective way to travel between Boston and New York, plus there's wifi, a meal, a movie and beverage service—all complimentary. Or, you can splurge on speedy Amtrak Acela service, which departs Boston's South Station and Back Bay Station and deposits riders in the heart of Manhattan at Penn Station. Or, you can take a number of daily flights from Logan International Airport to JFK or LaGuardia.

LimoLiner drops you off in the vicinity of Radio City Music Hall, an iconic stop around the holidays for its Rockettes.

But we are skipping that and Times Square on this trip, since sitting in traffic getting to and from the area will eat up hours of your time. 

Frank Sinatra wasn’t lying when he sang, “If I can make it there, I can make it anywhere.” New York is faster, tougher and louder than almost anywhere else and is considered a center of fashion, commerce and culture. On any given day at any given hour, Manhattan streets are jammed with locals and visitors alike, honking horns and people shouting the soundtrack. For the unaccustomed, New York can be overwhelming, but it's also got the "best" of nearly everything.

New York City skyline
"If I can make it there, I can make it anywhere." (©dibrova/Shutterstock)

First stop: the Tenement Museum on the Lower East Side. This Orchard Street museum opened about two years ago by two women who bought the building in a deep state of disrepair. No one had lived or done business in it for over 53 years. In turns, the museum served as a German beer hall, a kosher butcher shop and a discount lingerie store, and is now an example of the neighborhood's extensive immigrant history. Visitors can only explore the museum by tour, but really it's the best way to learn. Tour guides walk and talk through the oral histories of the shop life, varied immigrant groups and more.

Have a late lunch a couple doors down at Dudley's, a tiny corner bar. Service is friendly, and the food is excellent. The brown rice bowl, with a soft cooked egg, avocado and pumpkin seeds, is hearty but not too filling, since you're going to eat dinner later. It's definitely a place you'd imagine for New York a la cocktails at 3:30 on a Tuesday afternoon. If you're not ready to start boozing, try one of Dudley's delicious house-made sodas.

Head over to National September 11 Memorial & Museum, a necessary stop, if you haven't been here before. For anyone who lived through the attack or watched it unfold on television, this experience brings memories and emotions flooding back. The museum sits atop the original site of the two World Trade Center buildings and much of its remnants can be viewed inside, including box columns from the South Tower and the Vesey Street stairs, which survivors used to escape. One section of the museum recreates the moments of the attack as if live, showing footage from NBC News and the Today Show, playing distress calls and recordings, showing sequenced images. There are actual plane fragments and fire engines on display, as well as the iconic cross from Ground Zero. Visit on a Tuesday and get in free, but get tickets online in advance on any day.

Inside the National September 11 Museum in New York City
Inside the National September 11 Museum in New York City (©Leigh Harrington)

Comfort food is in order for dinner. The Meatball Shop serves a half-dozen different types of meatballs—and as one would expect with the word "balls" makes a play on its gimmick all over the menu. Diners mix and match: pick your protein, your sauce and your serving style (with a side, as a slider, on a hero, or smashed on a brioche). FYI: the veggie balls with pesto and provolone, smashed, makes for an outstanding meal. Atmosphere is loud and busy, and tables are a hot commodity. Single diners can probably find a seat at the bar.

Since you're on the Upper West Side anyway, stay at Hotel Belleclaire (of course, you'll have made reservations in advance). Part of the Triumph Group, the 100-year-old hotel has charming bones fixed with all the elegant, modern flourishes the Upper West Side requires. Traverse the winding maze of hallway to find your room decked out with wood floors, plush bedding, C.O. Bigelow soaps and shampoo, views of the Hudson. The Bellclaire's location near Broadway and Amsterdam Avenue offers easy access to a plethora of restaurants and is nestled neatly between Central Park and the Hudson River Greenway.

Breakfast can be at your whim and preference. Here are three varied options within four walking minutes of the hotel: Fly-under-the-radar Café Noi on Amsterdam Ave has excellent barista-made coffee drinks and a healthy Kosher menu of items including sweet potato waffles with fruit and nuts or the Noi Breakfast of eggs, Israeli salad and juice. A must try are the burekas. A large Americano, a bowl of oatmeal and a hefty muffins costs about $12.

If you're feeling fancy and French, try the hotel's-own Mille-feuille patisserie. Selections run the gamut from authentique éclairs to pain aux raisins. A Kusmi chamomile tea and two financiers runs you $8.

Get a coffee and a bagel at Zabar's for only $3!
Get a coffee and a bagel at Zabar's for only $3! (©Leigh Harrington)

And, for a quintessential New York experience, head to Zabar's on Broadway. This cafe and grocery has been around since 1934. At first glance, it seems no-frills, but, in fact, quality and attention to detail is what has earned Zabar's its legacy. For $3, get a seriously dense bagel with cream cheese and house-roasted coffee; then nab a spot next to customers from all walks of life at the communal table that takes up the majority of the space in the corner cafe. Did we mention the chocolate doughnut is made with Valrhona chocolate? After, spend some time browsing cheese, caviar, even kitchen tools, at the adjacent market.

Next, take a 90-minute walking tour led by Streetwise New York—which, by the way, is free for guests staying at any Triumph hotels—and get a feel for the Upper West Side neighborhood. Take in gorgeous and varied architecture like the opulent Ansonia Apartments, where Babe Ruth once lived and seals performed in the lobby fountain, to the 72nd Street Station that was once a farmhouse and still resembles one. Pass by the Dakota Apartment building and the spot where John Lennon was killed and then see the Strawberry Fields memorial at Central Park, which honors the Beatle. 

A memorial to late Beatles frontman John Lennon in the Strawberry Fields section of Central Park
A memorial to late Beatles frontman John Lennon in the Strawberry Fields section of Central Park (©Leigh Harrington)

Grab a quick lunch at Gray's Papaya, open 24 hours and famous for its hot dogs and papaya drink. Its first iteration on the Lower East Side known as Papaya King (no longer open) was a place to get tropical drinks, but since the neighborhood was largely German in the 1930s, sausages were added to the menu and became a huge hit. Today, the two elements meld nicely, and you can get two dogs with sauerkraut and a papaya juice for $6. Don't expect to sit though. Wolf 'em down in 5 standing at the counter or take them to go.

Gray's Papaya is legendary for its hot dogs and papaya drink
Gray's Papaya is legendary for its hot dogs and papaya drink (©Leigh Harrington)

Walk off the last 36 hours' serious calorie intake with a 20-block stroll down Broadway into the heart of Midtown. Sights along the way include the expansive Lincoln Center, Time Warner Center at Columbus Circle (where you can break for a sit), the Ed Sullivan Theater where The Late Show with Stephen Colbert is filmed, and the Broadway Theatre, before it runs straight into Times Square.

And there you have it: the great cities of Boston and New York in under three days.