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A Weekend in Downtown Manhattan: The Perfect Two-Day Itinerary

by | Jul 11, 2022

With so much to offer, narrowing down your weekend in Downtown Manhattan with the perfect itinerary is no easy task. An endless number of top-rated restaurants and bars, a diverse range of fascinating and eclectic neighborhoods to explore, and plenty of waterfront paths, iconic art installations, and world-class shopping await. 

Using our local neighborhood real estate experts, we’ve curated a guide that shares the best things to do. In this list, you won’t find the typical touristy mainstays such as the Statue of Liberty, but rather a more curated selection of landmarks and restaurants that more closely represent a local’s weekend in NYC. Dive in to learn more about our recommendations for where to stay, eat, and shop for a weekend in Downtown Manhattan. 

NYC Neighborhoods To Stay In: 

The location of your accommodation will dictate your entire weekend, therefore choosing the right neighborhood for your interests is important. Below, we’ve broken down our favorite hotels across three neighborhoods with very different vibes.


For a weekend filled with the trendiest new restaurants and bars and eclectic boutique shopping, look no further than Tribeca. Home to charming, wide, Belgian block streets and some of the most expensive real estate in Manhattan, Tribeca is a slice of chic calm amidst the concrete jungle. 

Hotel Recommendation: 

The Roxy:  This mid-century modern, art deco-designed hotel offers impeccable service in style. When you stay at The Roxy, not only are you checking into a boutique hotel with fashionable rooms, you are also gaining access to their underground jazz club, independent-film cinema, and famous Sunday brunch




Calling all art connoisseurs: Chelsea is the place to be for those looking to dive into New York’s independent art gallery scene with gusto. It is also home to plenty of nightlife spanning trendy clubs, intimate speakeasies, and local dive bars. Home to Chelsea Market, Little Island Pier, and the High Line, Chelsea makes it easy to explore some of NYC’s top attractions. 

Hotel Recommendation: 

The High Line Hotel: Set in a converted 1865 redbrick seminary (the same place where ‘Twas the Night Before Christmas was penned), the High Line Hotel offers a distinctly unique atmosphere from your typical accommodation. Rooms are vintage-designed with wood floors, antique one-of-a-kind pieces, and exude romantic, gothic vibes. The serene, Parisian-inspired garden courtyard serves several delicious variations of classic frozen cocktails. Frozen Negroni, anyone?  


South Street Seaport


If you’re seeking a laid-back weekend, away from the typical Manhattan hustle and bustle, the South Street Seaport is a great option. Nestled at the intersection of Fulton Street and the East River, adjacent to the iconic Financial District and Wall Street, the Seaport features gorgeous waterfront views of the Brooklyn Bridge, streets paved with Belgian block, and is home to some of the oldest real estate in all of Manhattan. 

Hotel Recommendation: 

The Beekman: Steps away from the Seaport, located in the Financial District lies the Beekman Hotel. Set in a beautifully restored 19th century landmark building, this luxury, vintage-styled Thompson group hotel oozes charm. The ornately designed lobby bar – which makes a mean cocktail – rises up to reveal an intricate 9-story atrium, and the hotel restaurant, Temple Court, is a Tom Colicchio-backed venture that serves up some of the finest food in all of Manhattan. 


Where To Eat:  

For a city filled with delicious restaurants (and new ones popping up every day), narrowing down your eating agenda in NYC is not simple. Below, we’ve broken down a handful of our favorite recommendations according to meal time. 


Sadelles seafood

Photo credit: Major Food Group Instagram

Sadelle’s: Backed by the same restaurant group that owns Carbone and Dirty French, Sadelle’s is a classic brunch spot in the heart of SoHo serving freshly baked doughy NY bagels, smoked fish, sticky buns, egg dishes, caviar, and more. Come for a classic NYC bagel and stay for the gorgeous vintage-style decor and people-watching. 


Balthazar: A Manhattan mainstay for classic French bistro fare, Balthazar has been operating in the heart of SoHo since 1975. Although they excel at martinis, seafood towers, and steak frites, their brunch is a sleeper hit. Order the fresh pastries and a foamy cappuccino and watch the world go by. 

Clinton st baking company

Photo credit: Clinton St. Baking Company Instagram

Clinton St. Baking Company: If you’re craving something sweet, head to Clinton St. Baking Company, located in Manhattan’s Lower East Side, for what is often described as the city’s best pancakes. This classic American restaurant with Mom & Pop roots has been serving up chocolate-chip-filled pancakes since 2001. If you’re not a pancake lover, their menu has several other delicious dishes, like latke eggs benedict and smoked salmon scramble, with nearly all ingredients – be it jam, biscuits, or habanero hot sauce – made on-site. 



Frenchette duck frites

Photo credit: Goldbelly

Frenchette: Tucked away on a quiet side street in Tribeca lies this elegant, contemporary French bistro serving the best duck frites in the city. Helmed by veteran chefs and the winner of the James Beard Award for best new restaurant in 2019, Frenchette is our go-to place for a long, relaxed lunch accompanied by excellent food and natural wines. 

Chelsea Market: Situated in the former Nabisco factory where the Oreo cookie was invented, this cosmopolitan food and shopping hall is an iconic landmark in Chelsea. With a huge range of food stalls and cuisines to explore, there is something for even the pickiest eater. If we had to cull it down, here’s where we’d visit: Los Tacos No. 1 for no-frills, tasty, Mexican street tacos, Miznon for fresh-ingredient Mediterranean street food, and Chinese hand-pulled noodles from Very Fresh Noodles. (Pro tip: don’t forget to save room for dessert with fresh, piping hot doughnuts from Doughnuttery).  


pull apart bread

Photo Credit: Crown Shy Instagram

Crown Shy: Located on the ground floor of 70 Pine – the exquisite art-deco skyscraper in the Financial District – lies Crown Shy, a contemporary, fine dining restaurant that earned a Michelin star within a mere six months of opening. Indulge in the inventive New American dishes – you can’t go wrong – but don’t forget an order of the gruyère fritters and the slightly sticky, always delicious pull-apart bread loaf. 

Estela dish

Photo credit: Estela Instagram

Estela: A classic NYC restaurant with stunning, brilliant food that never disappoints? Meet Estela. A Michelin-starred restaurant helmed by Uruguayan-born chef Ignacio Mattos (owner of Cafe Altro Paradiso, Flora Bar, and Lodi) who fuses Spanish, Italian, and Middle Eastern flavors into bites of pure art. On your table should be at least one order of the delicate, umami-ridden ricotta dumplings. Presented beneath an artistic layer of pecorino sardo swimming in a mushroom broth, it’s a bite to be remembered.

Photo credit: Don Angie Instagram

West Village Italian: While not the name of a single restaurant, the West Village boasts far too many exquisite, delicious, and groundbreaking Italian restaurants to narrow it down to one. You can’t go wrong with any of the following: Via Carota, I Sodi, Don Angie, or L’Artusi. Each famous for a different dish in its own right, these restaurants embody the ethos of good, clean, hearty Italian food in a cozy, intimate setting. Try to secure your reservation in advance or arrive early to ensure a table. 


What To Do: 

Art & Museums

The Whitney Museum of American Art: There’s no doubt that the MET is one of New York’s largest and most comprehensive museums, so if you haven’t been there yet, we highly recommend planning a visit. However, if you are looking for a new museum experience, the Whitney is a wonderful option. Devoted to the promotion of American art, the museum arguably holds the finest collection of 20th Century American art in the world. If your visit happens to time up with the Whitney Biennial, a once-every-two-years hallmark exhibition that features artist work created over the preceding two years, we highly recommend a visit. 

Art gallery

Art Galleries: New York is home to a plethora of art galleries spanning artists, genres, and mediums. The main neighborhoods with galleries in Downtown Manhattan are Chelsea and the Lower East Side. To choose the art gallery crawl that’s most interesting to you, download the app See Saw to view the latest exhibitions and map out your “art crawl.”  If you’d rather wing it, here are the streets to browse in each neighborhood: 

Chelsea: Zig-zag your way between 10th and 11th Avenues from 20th to 28th Street. Recommended stops: David Zwirner, Metro Pictures, Dia Chelsea, Gagosian, and C24.

Lower East Side: Between the borders of Bowery and Henry Street walk along Eldridge, Orchard, and Ludlow Street. Recommended stops: SHIN Gallery, Rachel Uffner, Bureau, PERROTIN, and Richard Taittinger.



Home to a mix of New York’s most luxurious stores and also lesser-known international and local brands, SoHo is one of the most famous and iconic shopping destinations in the world. While 5th Avenue is home to well-known name-brand stores, the western side streets (Wooster, Greene, and Mercer, between West Houston and Broome) house the more interesting boutique brands. Here are some stores we recommend visiting: 

Books: McNally Jackson, an independent bookstore on Prince Street that hosts a range of in-person literary events each month. 

Home Goods: MacKenzie-Childs, a bright and colorful home goods store selling everything from furniture to candlesticks. (This is an excellent store to shop for housewarming gifts.)

Jewelry: Âme, an up-and-coming NY brand selling fine jewelry using lab-grown diamonds. 

Bags: Deco Jewels, situated on an unassuming SoHo side street, this store is a museum of purses made in the 1950s. Each bag is essentially a sculptural work of art. (Note: this store is not on Google Maps but is located on the Western side of Thompson Street between Prince Street and West Houston). 

Oddities: Evolution Store, a landmark shop since 1993, this store houses everything from skulls and skeletons to posters and home decor. It’s well worth a visit simply for the experience! 



High Line: While it’s no secret, the High Line remains one of New York’s best walking tours. What used to be a railroad that transported millions of tons of meat, dairy, and produce from 1934 to the mid-1960s, is now a 1.45 mile, elevated greenway featuring larger-than-life sculptures, 500+ species of plants and trees, food & drink stands, and beautiful city views. Pro tip: start at the northern end of the High Line and make your way south, ending with a bite at Chelsea Market and a stroll through Little Island.

West Side Waterfront: Well worth a stroll, the west side waterfront boasts scenic waterfront views, grassy piers to relax and people-watch, and space to run, bike, or simply sprawl out. With large piers along the boardwalk offering anything from mini-putt to cocktails, there is something for everyone. 

Pier 55 / Little Island: Opened in 2021, this 2.4 acre public park was the passion project of Barry Diller and Diane von Furstenberg who donated $260M to have it built. Designed by Heatherwick Studio and showcasing views of Southern Manhattan, the Statue of Liberty, and New Jersey, the park also has food carts and an open-air amphitheater with performances from dancers, comedians, and musicians. No reservations are necessary before 12 PM every day or all day Monday through Thursday, otherwise timed entry reservations are required at no cost.

Pier 26 & City Vineyard: Nestled at the end of Pier 26, City Vineyard has a sprawling amount of outdoor patio space plus a rooftop to grab a glass of wine and watch the sunset. If you are looking for a fun way to exercise and bask in the sun, there is free kayaking on the Hudson located right at Pier 26. 

Pier 25: Play on the outdoor mini-golf course and then head to Grand Banks, a restaurant on the historic wooden schooner, Sherman Zwicker, for some oysters and chilled white wine. 


Whether you are kayaking along the Hudson, strolling the streets of SoHo, or browsing art galleries in the Lower East Side, a weekend in Downtown Manhattan is to be enjoyed and remembered. If you’re looking to extend your stay in New York City with a permanent address, start by browsing available properties on Triplemint.com and connect with us for expert guidance at 1.866.371.6468 or hello@theagencyre.com.

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