Second cities: Destinations to add onto a trip to New York City

Nov 23, 2019

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Welcome to TPG’s Second Cities series, where we help you find amazing places that are only a couple of hours away from your original destination. This way you get the most out of your itinerary and visit less-popular or less-frequented destinations that deserve more attention.

New York, New York. Its jagged skyline, busy streets, eccentric residents, grit and luxury have been immortalized in books, film and TV. Times Square, Fifth Avenue, Chinatown, the Statue of Liberty and the Brooklyn Bridge feel familiar, even to those who have never visited. It’s no wonder a trip to the City That Never Sleeps tops nearly every traveler’s destination list.

New York City has so much to offer that it can be overwhelming, so why not give yourself a break from the big city and add on a day trip or overnight stay to check out other great destinations in the area.

Philadelphia, PA 

Philadelphia is a convenient side trip from New York. It’s easy to navigate without renting a car, packed with American colonial history and boasts excellent food and drink. You’ll also find top-notch museums — all without the people-packed sidewalks and noise of NYC.

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Getting there: No need to use your airline miles for this trip. Philly is a quick two-hour bus ride from New York via multiple carriers with departures every 30 to 60 minutes from midtown Manhattan. It’s also easy on Amtrak: Trains depart from Penn Station every 30 minutes or so for the 90-minute trip to Philadelphia’s 30th Street Station (redemptions for tickets on this route start at 1,500 points via the Amtrak Guest Rewards program). Partner programs include Hilton Honors and Wyndham Rewards. Check here for the current exchange rate between programs.

Where to stay: There are several Category 5 Marriott hotels in the city center, including an Autograph Collection, Le Méridien, Aloft and a Westin. However, for the ultimate treat, book into the elegant Ritz-Carlton, Philadelphia, a Category 6 hotel, where you’ll find off-peak redemption rates that start at 40,000 points (standard redemptions are 50,000 points). Housed in a former bank building built in the early 1900s, the hotel’s neoclassical architecture and renovated interiors are gorgeous. The views of the city from the 30th-floor Club Lounge aren’t bad either.

What to see and do: 

Explore the city’s world-class museums. There’s the riverfront Philadelphia Museum of Art with 80 period rooms and a renowned collection; the Mütter Museum with a collection of medical oddities; the Barnes Foundation with roomfuls of French Impressionist works, and the Museum of the American Revolution. Arch Enemy Arts is an independent gallery with an edgy collection of local contemporary art.

Can’t-miss Philadelphia attractions for families

History buffs should start with a saunter through Elfreth’s Alley, the oldest residential street in the country. Several walking tours cover sites ranging from Independence Hall, where the Declaration of Independence was signed, to the building where flag-maker Betsy Ross lived.

For spooky experiences, walk through the former home of macabre writer Edgar Allan Poe at the Edgar Allan Poe National Historic Site, take one of the city’s many ghost tours or tour the dilapidated remains of the Eastern State Penitentiary, an enormous prison that once held mobster Al Capone.

To round out your visit, you must sample the city’s distinctive food and drink. If you’re short on time, downtown Reading Terminal Market is a venerable food hall packed with some of the city’s best vendors. Or head to South Philly for a cheesesteak taste-off between Geno’s Steaks and Pat’s Steaks. Wash them down on a tour of the city’s best drinking neighborhoods, from funky Fishtown to Rittenhouse Square and Midtown Village.

Kingston, NY 

Want to know where the 30-and-40-something New Yorkers are moving? It’s 100 miles north of New York City to Kingston, a small town on the Hudson River and the first capital of New York State. This historic country town now has a noteworthy collection of restaurants, arty boutiques, great vintage stores and hip counterculture growing faster than you can say “bar-and-bookstore hybrid.” It’s all the cool of Brooklyn with more space and charm and less pretense and outrageous cost.

Getting there: Kingston is a two-hour drive from New York City. If renting a car is not on the agenda, jump on the Adirondack Trailways bus. There are also two train options: Amtrak and Metro-North to Poughkeepsie.

Where to stay: Of the two Marriott properties in town, both Category 4 hotels, the Courtyard by Marriott Kingston has a better and more walkable Uptown location, and standard redemption rates that start at 20,000 points. Rooms are basic but comfortable and the hotel has free on-site parking and a bistro serving food and drinks. For those looking to dump some Hilton Honors points, the Hampton Inn Kingston is four miles from downtown and has a standard redemption rate of around 40,000 to 45,000 points per night, depending on your dates of stay.

What to see and do: Kingston doesn’t follow your typical small-town-with-a-Main-Street layout. Instead, there’s Uptown and Downtown, each with is own main drag and vibe.

Uptown Kingston is home to the Stockade National Historic District, full of notable 17th century colonial architecture, like the Old Dutch Church and Senate House Museum, and heaps of history that you can soak in from the beautiful bluestone sidewalks.

Wall Street and Front Street have a quaint vibe and are lined with cute, eclectic boutiques and colorful historic buildings. Retro culture lovers should head to Rhino Records and Rocket Number Nine, where music comes in analog format, or grab a beer and a book at the bookstore-bar hybrid Rough Draft Bar and Books located at the Four Corners intersection (where John and Crown Streets meet). It’s famous as the only place in the country where all four corners house stone buildings that predate the Revolutionary War. Around the corner, another hybrid shop, Outdated, allows customers to sip coffee as they sift through antiques.

Downtown Kingston, also known as the Rondout district, is a walkable neighborhood that runs along the waterfront and swaps out cute and quaint for a historic, industrial maritime vibe. Many of the warehouse buildings in the area are being repurposed into cool shops, restaurants and galleries. After perusing the waterfront and dipping into the shops, hop onto a river cruise or launch a kayak to soak in Kingston from the water.

Kingston also has a lively arts and music scene, so it’s worth checking what’s happening online before you visit. You will also see fliers posted around town — or just arrive on the first Saturday of the month when there’s a citywide art walk of open studios.

Boston, MA 

It would be a pity to bypass New England’s biggest city when it’s so close. Don’t let Boston’s deep historical roots fool you: It’s one of the country’s most progressive cities. A healthy arts scene, strong love of sports, famous educational institutions and its deft balance of history and modernity (there’s no better side-by-side example than the architecture in Copley Square) make it an easy crowd-pleaser. Plus, its proximity to New York makes it an easy side trip.

Getting there: Direct flights from New York (JFK and LGA) to Boston (BOS) clock in at just under 90 minutes — about the time it would take to get from Brooklyn to the Bronx on the subway. American Airlines, JetBlue, and Delta have multiple flights every day from both New York City airports and fares are usually affordable enough that you’ll feel good earning miles instead of spending them.

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Where to stay: Boston’s neighborhoods come with their own personalities. The Back Bay has a central location, beautiful streets and is close to top tourist sites. There the Westin Copley Place, Boston (Category 6) boasts contemporary rooms, high-floor city views and a restaurant and bar, at a standard nightly redemption rate of 50,000 Bonvoy points. For a real treat, upgrade to an Imperial Suite for a chic double living room, a dining room where you could hold a dinner party and a main bedroom with floor-to-ceiling city views and a modern four-poster bed.

6 of the best-value points hotels in Boston

What to see and do: 

Boston’s walkable layout and quick and affordable public transit make it easy to break down your visit into short bursts. For a thorough look at the city’s colonial past, hike the Freedom Trail, a two-and-a-half mile route that hits 16 of the city’s top historic sites as it winds through downtown Boston.

In the North End, you’ll see the cobblestone streets and old wooden homes of Boston’s oldest neighborhood. Look into the Old North Church, where lanterns were hung that triggered Paul Revere’s ride. You can also walk by Revere’s house before sampling the tastes of the neighborhood’s Italian immigrant roots.

8 mistakes every traveler makes in Boston

Boston Harbor has 34 islands, many with outdoor activities and just a quick ferry ride from downtown (seasonally from mid-May to mid-October). Rent a bike or walk the paths of the World’s End peninsula park, where you’re likely to spot butterflies and birds in spring. Explore 19-century Fort Warren on Georges Island. Take in the events on Spectacle Island, from yoga and 5K runs to jazz concerts, clambakes and educational pop-ups.

In Back Bay, enjoy Boston Common, the country’s oldest park. Then stroll through the neighborhood’s cobblestone streets past the beautiful brownstones of Marlborough Street. For a taste of the city through its iconic dishes, check menus around town for Boston cream pie, buttery lobster rolls and New England clam chowder.

Bostonians are well known for their sports fervor, and many sports fans come to the city just to visit renowned venues like Fenway Park and TD Garden. The city’s Ivy League schools are also a draw for tourists who visit next-door Cambridge for a peek at Harvard and MIT.

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