The SW Experts | Planning the Perfect NYC HoliDate
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Christmas in NYC

Planning the Perfect NYC HoliDate

Planning the Perfect NYC HoliDate


British love visiting Manhattan during the holidays.  From shopping to shows, the savvy Brit can get around easily to hit all the must-do activities. As a rule, a British visitor knows the ins and outs of Manhattan, but there may be a thing or two they can learn.


Be it a first date or a date night before your tenth anniversary, we can’t afford to miss an opportunity for what could be an amazing New York HoliDate!


Turning a NYC Winter Wonderland to a Wonderful HoliDate is actually a very simple thing to accomplish, and the week between Christmas and New Year’s is the perfect time to get into the HoliDating scene.  With so many things to do in New York, and with the backdrop of holiday decorations and excitement, the spirit of the season is the fantastic supporting cast to your romantic date.


Here’s a look at my top ten HoliDate ideas found in my own front yard- New York City:


  • Be on the top of the world with Manhattan at your feet!

    Nothing beats a rooftop bar, especially when it’s heated!  Check out the specialty drinks and the view from the rooftop of the Peninsula Hotel.  Great cocktails, and a view of the Fifth Avenue Snowflake that is unparalleled!


  • Shopping and Skating and Snacks…. Oh My!

    Put the “S” in spectacular when you have a HoliDate at the Bryant Park Bank of America Winter Village.  You and your date can do some fun shopping and take a whirl on the skating rink.  Grabbing a snack at Celsius is the cherry on the sundae of this HoliDate.


  • No time travel needed to visit the best Speakeasy in Manhattan.

    In true speakeasy fashion, Attaboy’s front door has no real signage- just the letters “A” and “B” in sticker form.  Once you walk in, you’re sure to have a mixology experience like no other.  Bespoke cocktails based on flavors you like are just a bartender’s skill away.  A few special Attaboy creations are on the limited menu, and if you go that route I highly recommend trying Penicillin, a mixture of scotch, juiced ginger root honey and lemon.


  • Taking in the holiday themed department store windows is picture perfect!

    Nothing says holiday like seeing the windows of New York department stores.  I suggest meeting your date at Macy’s Broadway entrance, and from there head to Lord and Taylor.  Walk uptown on Fifth Avenue, taking in all the store windows, and make a right after visiting Bergdorf Goodman.  Head East, starting with Barney’s and ending with Bloomingdales.  It’s great cardio, and the walk will give you plenty of time for conversation!


  • Keep warm with something chilly.

    You’re already on the East Side from your Window Walk, so why not enjoy a famous Frozen Hot Chocolate at Serendipity!  Of course, it’s romantic to share, but I always want my date to know the real me…. which is why ordering two is mandatory.


  • Sometimes a couple wants a little naughty play…

    One of the top rated swingers’ clubs in Manhattan is Le Trapeze.  A couples only entry policy is strictly enforced, however couples are allowed to bring a third female if desired.  Alcohol isn’t on the menu, but you may bring a bottle if you like.


  • …And sometimes a couple needs a romantic dinner.

    Look no further than River Café for that romantic hotspot. The food is fantastic, and the views of the Manhattan skyline will melt you almost as much as looking into your date’s eyes.


  • Welcome aboard the Love Boat, 2.0.

    A cruise around Manhattan with that special someone can be a fantastic experience.  From dinner cruises to rides with Carolers, there are many options, including New Year’s Eve!  Check out the website below for the perfect sailing!


  • Hamburgers have never been so hot!

    When I first moved to New York, one of my first dates as a new New Yorker was at Molly’s.  This Third Avenue mainstay makes one of the best burgers in Manhattan, and the fireplace is romantic as all get-out!


  • Some like it hot, and some like it FLAMING!

    Think Coyote Ugly, but replace the cast of hot women with even hotter men.  Flaming Saddles is a mainstay in the Hell’s Kitchen neighborhood of Manhattan.  You’ll see several straight couples brushing shoulders and doing shots with the gay men of NYC.


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Regardless of your home base, you can easily take inspiration from these New York ideas and apply them to your location.  Every city has hot chocolate, all towns have cool burger joints, and ice-skating is pretty universal.  One thing’s for sure… if you take advantage of the fun vibe and the excitement in the air, you’re one step closer to ending 2015 with a bang-up date!