5 Steps to The Ultimate Upper East Side Experience

Sunday, 7, September, 2014 2 , , , Permalink 3

During this last week in NYC, I had the most perfect, unplanned day on the Upper East Side. I love it when that happens when travelling. Everything just fell into place – I didn’t get the wrong subway or find the shop/restaurant/museum closed or feel like I was rushing around with an itinerary. The day – spent entirely by myself – seemed to just flow, ticking off a lot of must-see / must-do activities without feeling remotely touristy or hectic. So, here is my guide to the ultimate Upper East Side experience:


1. Have a true NYC breakfast


First things first. Start the day with a bagel at the famous Ess-A-Bagel near the corner of Third Ave and 51st Street. Get there early, because there will be a line. I arrived at about 9am (opens at 6am) and waited for 25 minutes. There is a selection of bagels, flavoured cream cheeses and other fillings. I highly recommend the cinnamon bagel with raisin walnut cream cheese (USD$3.75).


2. Shop till you drop


Walk a few blocks uptown to Bloomingdales and see how many Big Brown Bags you can accumulate. Head straight to the Visitor’s Centre on Level 1 and show your ID to get a 10% off voucher (not valid on cosmetics and fragrances unfortunately). If you spend more than $300, you get a free gift (it was an umbrella when I was there – not amazing but practical and free nonetheless). If you’re feeling particularly indulgent, head to Level 4 and make an appointment with a personal shopper. It’s completely complimentary. Your personal shopper will walk the floors with you to pick out the best of the new season and you can try on, pay for and relax in the exclusive fitting rooms on Level 4 (the kind that have Chanel and Valentino fragrances and hand cream for you to use). There’s no pressure at all to buy (but, trust me, you probably will). If you can, try to call beforehand to make an appointment – I was lucky enough to score an afternoon appointment by stopping by in the morning.


3. Be deliberately serendipitous

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When you’ve had enough of shopping, take a short stroll to Serendipity at 225 E 60th Street. This little cafe was made famous by John Cusack and Kate Beckinsale in the movie (Serendipity) and people now cue for a table every day of the week. If you’re travelling solo (like I was), you’ll most likely be able to skip the 1 – 2 hour wait and get seated straight away. You have to order the famous frozen hot chocolate (USD$9.50). It’s difficult to finish on your own, but give it your best shot – you’ll burn it off with all the walking anyway right?


4. Stroll and window shop


Once ranked the most expensive street in the world, Fifth Avenue is the place to find the best of the best. You’ll find upscale boutiques and all the big chains like Zara, Sephora and H&M. It’s definitely worth popping into Tiffany & Co for some window shopping too if nothing else. The vibe on Fifth Avenue is pretty special. I didn’t wander too far down and stayed at the Upper East Side for most of the day.


5. Take in the view

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Finish your day by heading down Fifth Avenue to the corner of 82nd to the Metropolitan Museum of Art – the rooftop that is. Enter the museum and pay what you wish (recommended $12 – $25). When you finally find the elevator (it’s a maze in there!), go to the 5th floor and head straight for the bar – after all, most views are best enjoyed with a drink in hand. I had (and highly recommend) the cucumber, basil and Hendrix cocktail. Enjoy views of the Manhattan skyline and Central Park, rest your weary feet on the astro turf and soak up the atmosphere.


This was my day from about 9am – 6pm on a Saturday in NYC in late August – it’s probably one of those days that if I tried to recreate it, wouldn’t be as perfect. But hopefully you can prove me wrong. The evening ended up being pretty fun too, although not on the Upper East Side. I used Uber to arrive in style at the 230 Fifth Outdoor Rooftop Bar (I don’t think you ever get sick of rooftop views of Manhattan, particularly when the Empire State Building is lit up front and centre). We also checked out Jay Z’s 40/40 club – a sports bar designed to combine “the lavish warmth of a New York City penthouse with the vivacity and glamour of courtside seats at a championship game”. And the music is as good as you’d expect. We finished off the night dancing at Ritz Bar & Lounge – a gay club in Hells Kitchen with 3 different levels of music to dance to. There’s always so much to do in NYC but I feel like I somehow managed to fit in a pretty amazing selection in one Saturday.


With Love


  • Tag Along Travel
    September 8, 2014

    Sounds like a perfectly lovely day. Every trip should include at least one unplanned day to just explore. NYC is perfect for this because there is something intriguing to experience around every corner.

    Thanks for the info on the personal shopper at Bloomingdales. I had no idea it was a free service.

  • Emma
    September 12, 2014

    I had no idea either! We have similar service at David Jones in Australia but I think there is certainly pressure to purchase something. I didn’t feel like that at all at Bloomingdales – it really makes it a shopping “experience” though to have a personal shopper 🙂 I now have a Michael Korrs and a Diane von Ferstenberg dress to thank them for.

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