NYC Weekend Planning Guide Alice Prin at lunch 1920s

WSH’s NYC Planning Guide: The Extravagant Celebration Weekend

NYC Planning Guide Watercolor-of-Metropolitan-Museum
Watercolor of the Metropolitan Museum

What Kind of Weekend are you celebrating?

Planning the perfect weekend for an extravagant celebration? Maybe it’s your 20th wedding anniversary, a big job promotion, or a 21st birthday party.

This isn’t your everyday weekend, you’ll be splurging for the best. Think charming city views, drinks by master mixologists, delicate desserts, delectable bakeries, snazzy jazz clubs, spa treatments, wineries and celebrity-approved eats.

Cost: $$$$ out of $$$$

Why stay at the Washington Square Hotel?

Our little Greenwich Village hotel takes you back to New York City’s golden age. Our magnificent, original art deco décor makes you feel like you’re going to turn a corner and run into old New York’s social elite.

Our superb location puts in walking distance of so many of NYC’s most popular neighborhoods and attractions.

The European flare keeps things quaint, yet classy. You’ll find rich colors, custom artwork by local artist Rita Paul, and all the modern amenities of the 21st century! Elegance and ease—sounds like a treat, right?

Ways to Spend the Weekend

By all means, take our suggestions and make them your own! Everyone has a different idea of how to have an extravagant celebration at their own pace with their own tastes. Ours just happens to be relaxation, treats, fine wines, views, and good music! 

Resources: The 12 Coolest Ice Cream, Gelato, & Yogurt Parlors in Manhattan, 10 of the Classiest Rooftop Bars in NYC, 17 Breweries & Wineries Native to NYC, 24 of the Most Photogenic Places in New York City, 20 of the Hottest Music and Food Venues in Greenwich Village, 10 of the Best Bakeries in New York City, NYC’s 10 Best Hot Chocolate & Apple Cider Spots


Day 1: Museums, Gorgeous City Views & Exquisite Drinks

After you’ve made your way into the city, checked into your hotel and freshened up we suggest starting off your weekend by going straight for the big city views and mastered drinks.

If it’s still early in the day hop on the West 4 Street subway and make your way up towards The MET. If you’d like to enjoy a walk through Central Park, reference our photogenic places ebook for ideas, then head towards the 81St subway station.


If you’d rather get straight to the museum get off at Madison Ave/E 79 St. Once at The Metropolitan Museum of Art you can choose to admire the art or head straight to The MET Rooftop Garden and Martini Bar. We won’t lie, the drinks at the bar are okay but they are a distant second to the views of Central Park blending into the city.

If you’re feeling like a little snack after your museum visit make your way over to By The Way Bakery where you can find muffins, scones, tea cakes, French bread, their famous Challah, and coffee—all handmade from scratch and in small batches.

Afterward, if you still have plenty of time before sunset, you can walk along Central Park and take in its beauty. Or hop on the subway at 5 Av/East 81 St and make your way towards Bar SixtyFive at the Rainbow Room (subway stop 5 Av/w 49 St).

Bar SixtyFive employs some of the best mixologists in the city, so you can expect a tasty drink to fit even the most discerning palette. It also has some of the best views, especially at sunset when the buildings get a beautiful glow. The views here can set the mood for the rest of your trip.

Make reservations in advance if you’d like to sit and have some light snacks. However, without reservations, you’re still welcome to walk in, order drinks, and stand by the bar or outside area.

On a side note, you’ll also be near the Top of the Rock, which offers three floors of panoramic views. You can always take your pick, or visit both and decide which offers your favorite outlook.

Once you’ve taken in the classic city views and realize you’re in one of the most beautiful cities in the world you can continue to rooftop bar hop (you’ll be near Lovage Rooftop as well as The Skylark, a newer rooftop bar which is quickly becoming a city favorite) and find a bite to eat in Midtown or head to the Rockefeller Center subway station and to our North Square Restaurant for an evening meal.

We suggest our North Square Restaurant not only because the food is tasty and we have a thoughtful wine selection, but you can also make reservations for our Dine ‘n’ Groove Package, which includes dinner, wine, and us seeing you off to one of our favorite jazz clubs in the Village—the Zinc Bar. You can enjoy classic and new jazz music, cocktails, and vintage décor in an intimate setting until 3:30 a.m. at the Zinc Bar.

Washington Square Park

Day 2: Relaxation, Sightseeing & Entertainment

After a full first night, a morning of relaxation is a must. Lucky for you, you don’t even have to leave the hotel to treat yourself to some extra relaxation. Schedule anything from a facial, peel, or massage at the Serenity Suite, located inside the Washington Square Hotel. After your refreshing morning, it’ll be time to explore the city as a new person.

Walk just a few steps and you’ll be in Washington Square Park, home to the iconic Washington Square Arch. This is the second park that makes our list of most photogenic places in the city.

A walk through the park and the surrounding area will begin to give you a real feel for Greenwich Village. We like to keep things a little more relaxed so you can truly take in the culture and history of the area…more like a local.

Walk about a half of a block from the park and you’ll be at the Washington Mews. The Mews, as they’re so fondly called, are like looking at a snippet of NYC’s past—right between the towering skyscrapers of New York City.

Walk another two blocks and you’ll find yourself at the authentic Italian gelato shop, Amorino. A stop here is a must as you can treat yourself to a gelato cone reimagined as a rose (this most definitely makes the already delicious gelato taste even better).

Take your gelato to a spot in our most photogenic places ebook. The Jefferson Market Library was built in 1874. The building itself is picturesque, but there’s also a garden to the side you can walk through that becomes pleasantly lush in the warmer months, making it a happy place to finish up your elegant gelato.

From the Jefferson Market Library, you can hop on the 9th Street PATH and ride up to 23rd Street (or you can walk) and make your way to La Birreria at Eataly. La Birreria is another spot that tops our list of classiest rooftop bars in NYC.

The colorful decorations and sleek Italian themed décor along with the drink options make La Birreria a fun classy oasis. It’s right by another building on our most photogenic places list. From this side you’ll get a unique view of the Flatiron Building up close. With rotating authentic Italian themes (and ingredients), we suggest grabbing a bite to eat or appetizer here as well.

If you’ve got some time you can make your way over to Chelsea Market, another photogenic place on the list, where you’ll also find shops with treats, arts, food and clothing.

If you’re at Chelsea Market you’ll be right by the High Line. Follow the High Line south and you’ll find yourself at the Whitney Museum of American Art, a real favorite for us at Washington Square Hotel. If you’ve got the time, stop in to view some cutting-edge art. The Whitney does a fantastic job of showing art that inspired and was inspired by 1960s Greenwich Village.

At this point, you’re probably thinking about dinner.

We have a couple of restaurant suggestions for that!

From The Whitney you can take the 14 Street/ 8 Ave subway stop to West 4 Street and be relatively close to a couple celebrity classics: Minetta Tavern, Mermaid Oyster Bar, and Babbo.

Of course, you’re always invited to dine at North Square again, but you’re going to be joining us for brunch the next morning.

Where some celebrities like to dine

Celebrities like Jerry Seinfeld and Brook Shields have been noted for dining at Minetta Tavern, while Zach Braff, the actor from the hit TV show Scrubs, is an investor in the Mermaid Oyster Bar. The likes of Betty White and Bryan Cranston (lead in the TV show Breaking Bad) have been known for dining at Babbo, right across the street from our hotel.

Dessert ideas

If you’re in the mood for a special dessert you can walk your way to MarieBelle for some handcrafted chocolates and sweets, as well as a sinfully delicious hot chocolate (and coffee and tea).

Finally, if you have enough energy left you can end your day at City Winery, or skip the full dinner and head straight there for Mediterranean bites and wine. City Winery is an on-site winery and a music venue, that has a variety of musicians lined up in their calendar. Spend your whole evening here or make your way (which we highly suggest) to the Village Vanguard. Village Vanguard is one of the most famous jazz clubs in Greenwich Village. It’s been around since 1935, and is known for its iconic bookings in the 1960’s. They still have amazing jazz acts every night until 12:30 a.m.

Mulberry Street

Day 3: Jazz & Special Goodbye Sweet Treats

You have one last chance to enjoy a lovely jazz performance by joining us at our North Square Restaurant for our Jazz Brunch. You can make reservations for 12:30 p.m. or 2:15 p.m. (plenty of time to have a relaxing morning) and enjoy an array of brunch options along with a live jazz performance.

After brunch, we suggest one last waltz through Washington Square Park before you leave. We feel like our little park is one of the most enjoyable parts of our part of town.

And don’t worry, we can hold your bags for you after you’ve checked out so you can stretch the time you have to enjoy the City to the last minute. If you want to grab a treat-to-go you can make your way to the delicious Dominique Ansel Bakery for a delicate French pastry or to Eileen’s Special Cheesecakes for a slice of classic New York City.

If you make it to Eileen’s you might as well go a little bit further down and take a walk down the beautiful Mulberry Street, another photogenic place, right through the heart of Little Italy.

We pretty much guarantee you’ll leave feeling like you indulged in too many treats, enjoyed too much music, and saw too many beautiful sites. Until the next weekend.


Day 1:  The MET Rooftop Garden and Martini Bar, Central Park, By The Way Bakery, Bar SixtyFive, Top of the Rock, Lovage Rooftop, The Skylark, North Square Restaurant, Zinc Bar

Day 2: Serenity Suite, Washington Square Park, Washington Square Arch, Washington Mews, Amorino, Jefferson Market Library, La Birreria at Eataly, Flatiron Building, Chelsea Market, High Line, Whitney Museum of American Art, Minetta Tavern, Mermaid Oyster Bar, Babbo, MarieBelle, City Winery, Village Vanguard

Day 3: Jazz Brunch at North Square Restaurant, Dominique Ansel Bakery, Eileen’s Special Cheesecakes, Mulberry Street