13 Exciting Weekend Escapes from New York City
This blog is for busy professionals in New York City looking for a break, a reset, or even to escape– all through weekend escapes.
Living in New York City comes with its own set of unique challenges—fast-paced days, demanding jobs, and constant hustle. Sometimes, the best thing you can do is escape for a weekend. I know it’s not easy to squeeze in time for travel, but with these weekend escapes, you can make it happen without sacrificing too much PTO. (If you need PTO tips, I got you!)
Whether you’re looking for adventure, relaxation, or a mix of both, here are the 13 best weekend escapes from New York City tailored for busy professionals.
Bermuda (Various Towns)
Just a two-hour flight from NYC, Bermuda is perfect for a weekend escape from the city. Think pink sand beaches, crystal-clear water, and charming pastel-colored towns. You’ll even get the chance to explore more of what makes Bermuda famous… the stories about the Bermuda Triangle! They have great museums and more to learn, but you can also just go and relax at your own pace.
Pro Tip: Rent a scooter to explore the island at your own pace. You can probably get through a few of the towns with a beautiful view along the way.
Toronto, Canada
In case you wanted to leave the city without leaving a bustling area, Toronto is the perfect vacation. It’s a super short flight out of the country, and you can still be in a place that has tons to do all of the time. Even though it’s another city with high rises, it has some beautiful views on the water and picturesque activities.
Explore the iconic CN Tower, discover the Distillery District, or take a day trip to Niagara Falls.
Pro Tip: The PATH, Toronto’s underground city, is perfect for exploring in cooler months.
Miami, Florida
Miami is great for a variety of things– food, relaxation, partying, and more! It offers a perfect mix of whatever you’re looking for. Spend your days lounging on South Beach, getting on the water, exploring the Art Deco District, or dining at some of the hottest restaurants. Plus, it’s a super short flight from the city!
If you’re going to party, definitely hit promoters up in advance. I personally think that the Miami party scene is harder to get into than Vegas so do your research beforehand. We didn’t want to deal with it so we bought tickets when we were there, but I think you can get in depending on who your promoter is.
When I was in Miami, I went on a speedboat, went to some pool parties, and had some amazing food. I highly recommend trying a bunch of different things to fit as much as you can while you’re there! Getting a combination of things makes it a really fun escape from New York City.
Pro Tip: Stay in Brickell for trendy vibes and easy access to everything. I stayed in South Beach and it took a while to get to all the different places.
Montreal, Canada
Even though it’s in Canada, Montreal’s European charm makes it an ideal escape. Stroll through Old Montreal, indulge in poutine, and check out the city’s vibrant art scene. It’s a great weekend escape from NYC without having to bear the 6+ hour flight to Europe!
Pro Tip: Brush up on some basic French phrases—they’ll go a long way with locals.
Washington, D.C.
A quick train ride from NYC, Washington, D.C., is ideal for history buffs and partiers alike.
You can spend your weekend exploring the Smithsonian museums, the National Mall, and some of the city’s excellent dining options.
On the other hand, you could spend it going to the infamous bottomless brunches! There’s a good starter list here.
When I went, I actually tried out some unique experiences. I took a stroll in the Georgetown waterfront park, did a fun escape room, and even went to a SoFar Sounds show. They have those in cities around the world if you want to try them out! It was a great balance of things to do to keep it exciting– I highly recommend.
If you do some of those unique activities and also fit a bottomless brunch in, I think you’ll find it to be the perfect weekend escape from NYC.
Pro Tip: Check out a rooftop bar for views of the Capitol at sunset.
Chicago, Illinois
While it can be tough to visit during the winter, Chicago is absolutely gorgeous during the summer. There are amazing river views, awesome restaurants, and unique activities.
If you can, try to make your way to the lake and walk along the water for some beautiful summer views.
When I went, I stayed near Millennium Park– which was great because that’s where the bean is! It’s also super central to most things in the city. That area is near the water, close to a bunch of restaurants, and more.
Things to try while there: architecture boat tour (sounds weird but I promise it’s cool) and deep dish pizza.
While Chicago is a lot like New York City, it’s the perfect weekend escape from the city for busy professionals who want a change of pace because of the beautiful architecture, fun activities, and more.
Pro Tip: Go for St. Patrick’s day weekend. It’s absolutely insane. They dye the river bright green and the city is absolutely buzzing with people and excitement– something to add to your bucket list for sure. I’ve never seen anything like it.
Nashville, Tennessee
Known for its live music and Southern hospitality, Nashville is a great place to unwind and have fun. Catch live performances on ‘Broadway’, indulge in hot chicken, and explore the vibrant neighborhoods.
Believe it or not, it’s also a huge party town. It’s coined “NashVegas” because of the main strip in downtown lighting up at night. I’ve also heard that the beer trolley’s are a must do! Grab your friends and hop on for a fun adventure through the city.
If you do nothing else, be sure to explore the music scene since that’s the highlight of town!
Pro Tip: Make reservations for rooftop bars in advance to enjoy the best views of the city.
Austin, Texas
With its laid-back vibe, live music, and incredible food scene, Austin is a top-notch weekend escape from New York City. It’s a pretty unique place because even though it’s in Texas, there’s a gorgeous lake and unique downtown. Regardless, it embodies the southern vibes while providing a unique perspective.
Check out Barton Springs, paddleboard on Lady Bird Lake, and don’t miss the tacos!
Pro Tip: Pack for warm weather—it’s hot nearly year-round!
New Orleans, Louisiana
For a weekend full of soul, head to New Orleans. From jazz music and beignets to ghost tours and steamboat rides, the city has endless charm. There’s tons of things to do and it’s one of the most unique cities in America.
You’ll see that people really act like a family around here, making the community super tight. It’s probably one of the most opposite cities you can find to NYC, but I think that’s what makes it such a perfect weekend escape!
Pro Tip: Visit Frenchmen Street for live music that’s less touristy than Bourbon Street.
Montego Bay, Jamaica
For a tropical escape, Montego Bay is a quick flight from NYC. Luckily, the Caribbean and other beautiful island nations are relatively close to the city, so it makes for a great weekend (or longer) escape. Relax on pristine beaches, try jerk chicken, and enjoy the laid-back island vibe!
Pro Tip: Stay at an all-inclusive resort for maximum relaxation.
Nassau, Bahamas
Nassau is another Caribbean gem that’s easily reachable from NYC. Spend your days snorkeling, visiting the famous Atlantis resort, or soaking up the sun on the white sandy beaches. It’s another great place to unplug in nature– a perfect weekend escape from New York City.
Pro Tip: Try conch salad for a true Bahamian experience.
San Juan, Puerto Rico
Puerto Rico is a great country to visit for a ton of reasons– but for Americans, it’s a great place because it’s a U.S. territory! Yet, it has its own unique culture and feels like an entirely different place when you visit.
San Juan is ideal for history and beach lovers. Visit Old San Juan’s colorful streets, relax on Isla Verde Beach, and savor local cuisine like mofongo.
Pro Tip: Explore Old San Juan in the evening when it’s less crowded, and the historic streets are beautifully lit. Grab a drink at La Factoria, a multi-room bar featured on the World’s 50 Best Bars list, and enjoy live salsa music for an authentic Puerto Rican nightlife experience!
St. Thomas, U.S. Virgin Islands
This is another great U.S. territory to explore, again with its own unique culture and vibes. It definitely runs on island time, but is a great hybrid between a typical island culture and American culture.
Escape to St. Thomas for a mix of adventure and relaxation. Spend your weekend snorkeling, shopping in Charlotte Amalie, or hiking to stunning viewpoints.
Pro Tip: Plan for a sunset sail—it’s a magical experience.
Punta Cana, Dominican Republic
With its turquoise waters and luxury resorts, Punta Cana is a fantastic tropical retreat. Spend your weekend lounging on the beach, trying water sports, or indulging in spa treatments. I’d recommend keeping this one for special occasions because the DR is such a unique place!
Pro Tip: Choose a resort with a private beach to avoid the crowds.
Conclusion
Taking time for yourself is essential, especially in the city that never sleeps. These weekend escapes from New York City offer the perfect opportunities to recharge, explore, and return to your busy life refreshed and inspired.
For more tips on maximizing your travel time and budget, check out my blog on travel hacks for busy professionals.
