I'm a Travel Writer, and This Is My Go-to NYC Staycation Itinerary—and the Stylish Outfits to Match

Travel + Leisure

9 hours ago

As much as I love experiencing different cultures and traversing new landscapes, there's something special about exploring your own backyard. Staycations are quickly becoming one of my favorite ways to relax, and I recently spent a week experiencing my own city as a tourist.
I live in NYC, so there's plenty to explore. Throughout my week-long staycation, I visited museums, parks, landmarks, and more, and I gained a greater appreciation for the city along the way. Now, I'm revealing my five go-to staycation itineraries, along with the stylish summer outfits to match. Whether you're visiting NYC or romanticizing your own city, keep reading for elevated outfits to make you feel like a jet-setting traveler, wherever you are.
Whenever I have a few days to kill, I make it a priority to see some of the world's best theater at Broadway and off-Broadway shows. To pass the time before the show, I'd head to Soho for some shopping. Soho has some of the most beautiful buildings (and people) New York has to offer—and near countless shops. On my ideal staycation, I'd partake in quite a bit of retail therapy before heading to the Theater District for an early dinner and a show.
This itinerary calls for a slightly dressier outfit, but comfort is still key. After all, this day entails plenty of walking, standing in lines, and sitting for extended periods. The Prettygarden Skirt Set is ideal, thanks to the stretchy, comfortable fabric. I'd pair it with trendy fisherman sandals, plus an oversized tote to help carry the day's inevitable purchases. This outfit looks elevated enough for one of NYC's most fashionable neighborhoods, but it's breezy and cozy to carry you through the day's activities.
The Met's free date night is one of NYC's best-kept secrets. On Fridays and Saturdays, you can head to The Met for live music, drinks, and world-renowned art. Plus, during the summer, you can grab a drink on the museum's Roof Garden and soak in beautiful views of the city.
I'd recommend dressing up for this event, and I found the perfect outfit at Amazon. The Drop's Dia Midi Tank Dress is simple, elevated, and comfortable enough that you won't be fussing throughout the night. I'd pair it with one of NYC's most popular shoes, slingback heels, and I love this pair that adds an edge to an otherwise classic ensemble. Don't forget to bring a simple handbag and throw a cardigan over your shoulders in case it gets chilly in the exhibits.
Hudson River Park has some of Manhattan's most scenic views. The park stretches four miles of riverfront space, with an extensive walking path and beautiful piers. I love to start at Pier 97 and work my way down, stopping by the Little Island, Pier 45, and more sunny destinations on the way. Once you reach the bottom of Manhattan, you can hop on a ferry to Ellis Island—or just soak up views of Lady Liberty from Battery Park.
To stay comfortable throughout this scenic walk, I always wear a sporty ensemble. The Crz Yoga tennis skirt is perfect for the occasion, with a 'buttery soft' and 'lightweight' fabric. I'd snag the coordinating racerback tank and pair the look with a hands-free belt bag that reviewers call a 'perfect dupe' for pricier bands. Since I rack up thousands of steps on this walking path, I always opt for a pair of comfy walking shoes—and the podiatrist-recommended Brooks Ghost 16s are a stylish and comfortable choice.
The Grand Bazaar is one of my favorite spots to visit on Sunday mornings. This shopping market is filled with clothing, art, antiques, food trucks, and more, and I always find something worth taking home. Afterwards, I'd head a few blocks east to spend some time in the sun at Central Park. Who said you have to go south to catch a tan? While most New Yorkers don't have easy access to a beach, some areas of Central Park are packed with sunbathers in the summer.
I love the Berlook Floral One-piece, because it can easily be camouflaged with a casual outfit, and no one will guess you're wearing a swimsuit. I'd pair it with Chartou's Cotton-linen Drawstring Pants and a breezy button-down. Finish off the look with platform sandals for a market-ready outfit that can easily transition to sunbathing later in the day.
Maybe it's just because I'm a Grey's Anatomy fan, but there's something so magical about ferries. Every time I get to cross into Brooklyn on a ferry, it's a treat—and this itinerary is packed with scenic views, on and off the boat. Hop on the South Brooklyn Route of the NYC ferry and get off at Brooklyn Bridge Park for casual dining options and an unbelievable view of Manhattan's skyline. Afterwards, you can check out Dumbo's beautiful cobblestone streets, flea markets, and art galleries. It's truly one of the most gorgeous parts of the city.
Keep things casual for this day of sightseeing—but be prepared for candid photo opportunities. I'd pair relaxed barrel jeans with a summery eyelet top for a look that's equally comfy and stylish. I'd complete this ensemble with simple black flats that 'can be worn all day without pain or blisters', plus a classic straw tote that looks so summery.
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