The two most popular cities on the East Coast are only within five hours of one another, and they couldn't be more different. From the outside, both New York City and Boston seem as though they'd be similar, at least from a city point of view. The first major difference is in the population: New York City has slightly more than 13 times that of Boston. Therefore, everything from the feeling of walking on each city's streets to the number of lodging options visitors will have will vary greatly.
With that being said, Boston isn't necessarily the better city just because the sidewalks aren't as crowded. Alternatively, New York City isn't necessarily better simply because its large population attributes to many of its entertainment and activity options. In order to take an in-depth dive into which city, New York or Boston, is better for a weekend getaway - or even an extended vacation - everything must be considered.
Walking The Streets
City fans can attest to the fact that one of the greatest parts of visiting any new urban destination is how the city walk feels. The vibe that one gets from hitting the pavement and strolling down the street can vary from city to city and it does greatly from NYC to Boston. In New York City, the stride will be fast-paced and it's best for travelers to determine where they're going before heading out, or have their GPS up so they can track where they're headed in a manner of seconds. In the more crowded areas of Midtown, there really are no places to step off and double-check directions without being in someone's way. However, this fast-paced stride is also exciting and makes one feel as though they're truly a New Yorker.
The nice thing about Boston is that its sidewalks are not inundated with people, even around its most popular hubs. However, this doesn't mean that festivals and events won't procure a New York City-sized crowd. If a slower pace is your thing, then Boston is the better option simply for exploration purposes. However, this also means that walking the streets at night, especially those further from the city center, will be scarcely populated.
Waterfront Activities And Skyline Views
Boston has an undeniably beautiful skyline. The view over the historic seafront is truly a sight to behold, especially around Boston Harbor. Visitors can take the views in from Christopher Columbus Waterfront Park or head across Seaport Blvd. to take in the views from Fan Pier Park and Harborwalk, which are probably less crowded. This also happens to be a foodie hub for seafood among other options, as well as where the Institute of Contemporary Art is located.
New York City's skyline, though, is iconic. There are a plethora of ways to take it in from bridges to harbor cruises and even trams, and there are also multiple places around the city from which to view it. the city is so big and its skyscrapers so tall that even a trip to the top of the Empire State Building will result in that classic view of a lifetime. In terms of cityscapes, New York wins this one, hands-down.
Public Transportation, AKA The Subway Systems
There's plenty to be said about the NYC subway stations. More often than not, the subways will be exactly how they seem - cramped, hot, and fairly dingy. The subway is also more expensive in NYC over Boston, however, NYC is more easily walked and most things are within walking distance if travelers pick the right area for their hotel.
Boston's subways are cleaner and cheaper but it's likely that travelers will rely heavily on this, driving, or a taxi if they're planning to do multiple things around the city. In terms of overall cost, according to Budget Your Trip, the two cities are practically identical in terms of lodging, food, and tours, except when it comes to transportation - NYC is nearly double the cost of what Boston is, so, if you're planning on avoiding walking, Boston is the way to go.
Restaurant And Street Food Options
The prices of restaurants in each are nearly the same so in terms of food costs, they're irrelevant. For legendary seafood, Boston does have the upper hand over NYC thanks to its New England location. Boston also has its own regional cuisine that echoes that of the New England region, so it really comes down to which style a traveler is looking for.
New York City is, without a doubt, a foodie's dream, though. Not only does the city offer iconic options such as NYC pizza, halal, and various street vendor foods, but it also offers some of the best steakhouses in the country and a diverse range of cuisines that can be found anywhere, including Hell's Kitchen. NYC wins the food battle.
Architecture, Nightlife, Shopping, And Entertainment
There are historic options in both cities but Boston does offer more early colonial tours and historic sites. With that being said, Boston is also somewhat of a gateway to surrounding areas such as Salem, Plymouth, Cape Cod, and the like. In terms of nightlife and entertainment, there are several major concert halls that have a constant rotation of major artists, but it's best to check schedules before heading into the city. Entertainment is not in short supply in either city, but Boston's venues are slightly smaller, with a wide array of artistic, musical, and comedic shows.
New York City's history varies based on the area of the city one finds themselves in which can make for an exciting trip. Anything from tenement tours to MoMA should be on the schedule for history buffs, along with the more unusual tours that take travelers underground (metaphorically and literally). However, in terms of major shows and concerts, Broadway, alone, makes NYC the ultimate winner - visitors can find practically anything they're looking for, on any given weekend, in the city, from music to comedy and anything in between. Concerts throughout the city parks in the summer also add to this upper hand.