Grand Central has always been and will always be my nexus into the city. Besides being a beautiful building, with its own charm and design. It’s host to several “secret” hideouts - remnants of a different era.

Lunch - Grand Central Oyster Bar: Deep in the belly of Grand Central is the Grand Central Oyster Bar, wrapped in subway tile, almost unchanged since they opened in 1913. As a New Englander, I can’t go very long without oysters, clams and seafood, and this place always hits the spot. Plus, this place is always my signal that I’m back in NYC.

After lunch cocktails - The Campbell: This was once a private apartment built in 1923 in the style of a 13th century Florentine Palace. It was eventually turned into a bar hidden within Grand Central. Up until 2019 they had a very strict dress code, but it’s been relaxed in recent years - but you’d still want to look sharp.

Afternoon Stroll - Grand Central Market: Besides trains and hidden restaurants, Grand Central also has a European style market with a dozen or so local vendors selling local products/food. From crafts and art, to tea/coffee and fresh produce.

Accommodations - Make your way uptown (Taxi, Uber, Lyft, Revel, or number 6 train) to your hotel.

Dinner - Elio’s: Elio’s is a family-run, old school Italian restaurant that has been operating in the neighborhood for decades. If you read the Google Reviews of Elio's, almost every review says something along the lines of “this was my first time here, yet I felt like family”. That’s the level of service you’ll find throughout the Upper East Side. Servers will be in impeccable uniforms and executing top-notch service that feels warm and inviting, without sacrificing the quality of the service. Elio’s is cozy, usually packed with regulars and serves up some of the best classic Italian dishes you’ll find in the city.

Nightcap - Bemelmans Bar at The Carlyle: I could write an entire book on just the Carlyle, but Bemelmans is an institution in NYC. The bar walls and lamps were hand-painted by Ludwig Bemelmans (who created the Madeline books and cartoons) and depict 1930s Central Park. They are legendary for martinis but have recently expanded to cocktails as well. They have live jazz/cabaret nightly and are consistently packed with sharply-dressed locals, celebrities and sophisticated travelers.

Since our hotel recommendations all include breakfast, and are often the top spots for breakfast/brunch, we’ll skip covering that meal.

Shopping and Museums

Stepping out in the morning, you’ll notice that it’s fairly quiet. The tree-lined streets aren’t packed and the streets are far from the gridlock and constant honking of Midtown. Walking down Madison, you’ll find higher end shopping like Hermès, Ralph Lauren’s flagship store (with Ralph’s coffee if you need a pick-me-up), The Ludlow, Five Story, Bergdorf Goodman, Chanel and brands of that ilk. You will also find small cafés on every corner, with outdoor seating (weather permitting).

In addition to the shopping, there are several world-class museums here. The big names like Guggenheim and Metropolitan Museum of Art, along with more niche museums like The Frick Collection (my favorite), the Waterfall Mansion and Gallery and the Cooper Hewitt.

Afternoon Tea - The Palm Court at The Plaza: Whether you’re staying at The Plaza or elsewhere, the Palm Court is a sight to be seen, and the perfect place for afternoon tea. The opulent setting, under a glass dome, has been serving afternoon tea since 1907. Besides Afternoon Tea, they have all-day dining, if you need something more substantial.

Dinner - 2 Options: After you burn off the tea, scone and petits fours, you’ll probably be looking for a nice meal to cap the day.

Fine Dining - Le Bernardin: If you’ve loaded up on new clothes and want to go out looking sharp and experience fine dining, this is your spot. This is one of only 13 restaurants in the US with 3 Michelin Stars. This seafood forward restaurant is elegant. They have several tasting menus, and wine pairings, that will all provide an elevated experience.

Casual Cocktails and Bites - NR: NR is a Meiji-style restaurant, which was the period when Japan first opened up to the world after WWII. They serve a fusion of Japanese food, Chinese food and Western cocktails to showcase all the major influences on Japanese culture in the modern period. Expect delicious mixology experiments, some flaming/smoking cocktails, alongside ramen, curries and small bites.

Nightcap - Melody’s Piano Bar: Transport yourself to 1940s Miami at Melody’s. It’s a dark palm-lined bar, with live jazz and an inventive cocktail menu.

Today’s the perfect day to revisit some of the shops and/or museums you missed yesterday or maybe those shoes you tried on yesterday are calling your name. Either way, you now have the daunting task of wrapping up your visit to the Upper East Side.

Upscale Brunch Option - Sant Ambroeus: This is a mainstay on the Upper East Side, and a frequent haunt of celebrities and politicians alike. Think sophisticated vibe, but with pretty relaxed and casual brunch service, all with an Italian spin.

Jewish Deli Brunch - 2nd Ave Deli: It’s not a trip to NYC without stopping by a Jewish Deli. This is old school Jewish Deli classics, but with some input from the new generation, including a cocktail bar on the 2nd floor!

Burger Option - JG Mellon: This is one of the most iconic restaurants on the Upper East Side and maybe all of NYC. It’s been open for 50 years or so, and specializes in burgers, fries and chili. Expect long waits and dining alongside the who’s who of NYC.

Wildcard Option - Breakfast at Tiffany’s: This isn’t the Upper East Side, but it’s worth a mention. Recently opened at Tiffany’s flagship store on 5th Ave; they are offering an afternoon tea service. The room and ambience are designed by the team at Tiffany’s, with Daniel Boulud’s team handling the food side of things. You end up with an elegant brunch or afternoon tea experience, on the 6th floor of Tiffany’s recently remodeled store.

Afternoon Stroll: Central Park has the distinction of being one of the first parks in the country, and it stretches out over 840 acres, right in the middle of one of the busiest urban centers in the world. Central Park has so much to offer in all seasons:

• Hiking the Ramble - Bird watchers and nature lovers will walk these trails and forget their time in the city, as it feels more like the Adirondacks.

• Walking the Mall - There are rows of American Elms, leading to a beautiful fountain.

• Rowing on the lake - You can rent a rowboat for a row around the lake and take in the scenery. If you don’t feel like rowing, they have gondola tours as well.

• Belvedere Castle - The castle was recently renovated and makes for a stunning backdrop for photos. It also features a 3,000-year-old Egyption Obelisk, called Cleopatra’s Needle.

• Ice Skating - Of course, if it’s winter, you can find ice skating at several points in the park.

From here, you can make your way back to the airport or train station, and hopefully have seen a different side of New York and have some great locations for the next time you visit and want to escape the bustle of Midtown.