Top 5 Weekend Trips from New York City

New York City has the flights to make almost any city in the United States and Canada easily accessible. However some cities are simply too far away for quick weekend trips, so I compiled 5 cities that would be easier to travel to. These cities are simply a suggestion and when put together they show the variety of places one could go to, on a relatively short flight from New York City.

Fun in the Sun

Miami, Florida

Top 5 Weekend Trips from New York - Miami

Hands down the “fun in the sun” city is Miami. The flight is close enough where a weekend trip is doable, and there are many flights from New York direct to Miami. Simply I love Miami because of the carefree attitude and for it being a wild place to have fun. Some people may hate the scene but with lovely beaches, a lively night scene and relatively inexpensive flights from New York City, I can’t see how you could go wrong with a weekend here.

Pros: Usually sunny, great beaches, wild nightlife

Cons: A little far, somewhat expensive hotels

Foreign Traveler

Montréal, Canada

Top 5 Weekend Trips from New York - Montreal

If you’re looking for a totally different country mixed with a different language, it has to be Montréal. There is much to explore in this lovely French-Canadian city and to brush up on your French, if that’s your thing. Most come in summer, by for diehards who love cold, Montréal is your city. The only possible downside is that flights to Canada are typically pricy but this city is worth it for a weekend trip. Also, for the ambitious, Québec City is just a 2 hour drive north. You’ll feel like you’re in France!

Pros: French-speaking, close flight, lots of unique culture

Cons: Expensive flights, expensive hotels

Food Lover

Chicago, Illinois

Top 5 Weekend Trips from New York - Chicago

So you’ve discovered all the food in New York City or you’re just tired and want variety. Come to Chicago, the city that I call home, for a weekend trip. I’m bias but this city does one thing right, the food! Chicago pretty much rivals New York for variety, quality and prestige when it comes to food. There are so many top restaurants in Chicago, that you could literally come for a weekend and just eat your way through the city. Also the flight is pretty short from New York.

Pros: Short flight, beautiful city, Chicago loves food and drinks, historical

Cons: Museums are slightly overpriced, hotels are nearly as expensive as New York

Nature Enthusiast

New Hampshire/Vermont

Top 5 Weekend Trips from New York - New Hampshire Vermont

Maybe you’re looking for a more scenic, restful time and don’t want to fly that far. New Hampshire and Vermont are really great ideas for a nature getaway weekend trip from New York City. Most of these two states are secluded, covered in green and prime for outdoor enthusiasts. Simply driving around these two beautiful states would put anybody at ease. Burlington is a legitimate great scenic city over looking Lake Champlain and New York, while New Hampshire has lovely Mount Washington.

Pros: Beautiful, quiet, green, driving from New York is an option and mostly secluded

Cons: Flights may be pricier

Southern Charm

Savannah, Georgia

Top 5 Weekend Trips from New York - Savannah

Perhaps you want some southern charm in your life or just want to escape the north for a bit. My last pick is Savannah because of its pure beauty, relaxing values and a chance to chill out in warmer weather. The main charms are the huge oak trees that line the city, set among the historic southern style houses. Nearby are local beaches, popular in the summer, and famous Hilton Head in South Carolina. This is a city to relax in and to force yourself to vacation at a slower pace.

Pros: Beautiful charming city, warmer weather, slow pace atmosphere

Cons: Flights are trickier, somewhat touristy




images by: steve, stephen, shawnvoyage

By | 2017-08-23T10:34:36+00:00 December 6th, 2015|


  1. Sapna Parmar May 5, 2017 at 1:10 am - Reply

    Hello Shawn, Wow, you got me excited about New York City! It looks so beautiful. I hope to make it to New York City this or next year, fingers crossed…

    • Shawn May 5, 2017 at 12:47 pm - Reply

      New York City is great! Have fun!

  2. abigail July 27, 2017 at 6:09 am - Reply

    You shared great and this information impressive on my self. About 1 year ago i went there and all attraction visit there. After reading your blog so i wish again go there and again enjoy this place.

    • Shawn August 13, 2017 at 12:17 pm - Reply

      New York is meant to be visit multiple times! Have fun when you go back!