Our favorites places to Eat, Drink, Play and Stay around Chicago!
Best restaurants Chicago
What to do in Chicago
Best Chicago Museums.
Read MoreBrooklyn
While Brooklyn and Manhattan are separated only by the East River, Brooklyn’s vibe is a world away from the big City. It’s immigrant enclaves have inspired vibrancy and diversity, while millennials and families who call it home have found solace in its open green spaces, farmer’s markets and welcoming spirit. Come play with the cool kids.
EAT
Celestine Mediterranean restaurant on the water in Dumbo.
Doughnut Plant Tasty donuts in Prospect Heights.
Emily Beloved restaurant serving amazing wood-fired pizzas and burgers in Clinton Hill.
Grimaldi’s This landmark serves some of the best pizza in the Five Boroughs. Stand in line at the Brooklyn Bridge location for a slice or two.
Smorgasburg One of the largest, open-air food markets in the country.
Vinegar Hill House Rustic, cozy restaurant in Dumbo with a back garden. Great for weekend brunch.
Westville Locally sourced ingredients. Locations in Manhattan and Brooklyn, but we like the Dumbo spot.
DRINK
Brooklyn Brewery Book a Saturday or Sunday tour the morning of.
Brooklyn Roasting Company This roastery has a few locations with great ambiance.
Donna Chic cocktail bar in Williamsburg with romantic candle-lit tables and DJs.
Insa Korean barbecue and karaoke bar with private rooms in Gowanus.
Radegast Hall & Biergarten Large, indoor beer hall in Williamsburg with live music and an Oktoberfest vibe.
Spritzenhaus33 Relaxed beer hall in Greenpoint with communal tables, outdoor seating and good food.
PLAY
Brighton Beach Nicknamed Little Odessa and Little Russia for its enclave of Russian speaking immigrants. Eastern Europe Jews began immigrating here in the 1930’s, followed by a wave of Soviet Union immigrants in the 1970’s. Today Brighton is one of our favorite areas in Brooklyn and much less crowded in the summer than its northern cousin Rockaway Beach, and southern sister Coney Island. Head here for a relaxing day at the beach followed by Russian beers, perogies and borscht soup.
Brooklyn Flea A sprawling market known for its myriad of treasures. Open on Saturdays and Sundays in varying indoor and outdoor locations.
Brooklyn Bridge While touristy, the walk across this 19th century landmark should not to be missed.
Brooklyn Bridge Park Excellent views of Manhattan’s FiDi. In the summer movies are shown against the city backdrop on the lawn. Book in advance.
Norbu Contemporary jewellery boutique on Bedford Avenue in Williamsburg,
Prospect Park Peaceful haven with a zoo, botanical garden, and winding paths.
STAY
Our favorite neighborhoods to stay in are Williamsburg, Brooklyn Heights and Park Slope. If you want to be close to the City with nightlife and restaurants, choose Williamsburg, though you will pay a pretty penny. If money isn’t an issue, check out The Hoxton. We loved this hotel for location, comfort, and vibe. Be sure to enjoy the rooftop terrace wtih views overlooking Manhattan and the bay.
Brooklyn Heights and Prospect Park might give you more bang for your AirBnb buck.
LOCATIONS NEARBY
New York City
The City That Never Sleeps evokes all the senses: bright lights, metallic smells from the subway tracks, blaring horns, people jostling along the sidewalk and a diverse food scene thanks to the thousands immigrants calling NYC home. While there are tens of thousands incredible restaurants, bars and places in NYC, those below are just a few favorites.
From JFK airport take the AirTram to Howard Beach or Jamaica to then take the subway to Manhattan. From Howard Beach, take the A train toward Brooklyn and Downtown. From Jamaica, the E will take you to Midtown. From Newark airport, take a direct New Jersey transit train from the airport to Pennsylvania Station.
If you plan to spend at least a weekend in NYC, visit the 911 Tribute Museum and Memorial. While an emotional experience, this Museum is incredibly well done.
We’ve broken out our suggestions below by Downtown (anything below 14th Street) and Uptown (anything at 14th Street and above). In our humble opinion, Downtown has a better nightlife scene overall.
DOWNTOWN
EAT
Adrienne’s Pizza Bar Delicious square-shaped pizzas on Stone Street in the Financial District (FiDi).
Bleeker Street Pizza The best pizza in the city (we think). Pop into their tiny West Village location to grab a slice and takeaway or order delivery.
BondSt. High-end Japanese restaurant in Noho.
Cuba Restaurant and rum bar in Greenwich ViIlage.
Jeepney Filipino food in the East Village.
Jing Fong Enormous Cantonese dim sum restaurant in Chinatown with plates served from push-carts.
Kiki’s Amazing and affordable Greek food in Chinatown. No bookings.
Louie and Chan Italian restaurant in the Lower East Side (LES) with an Asian-inspired cocktail bar in the basement.
The Meatball Shop An NYC institution with locations across the city.
The Odeon French-American bistro in Tribeca. Great for brunch and celeb-spotting.
Pig and Khao Trendy Southeast Asian restaurant in LES.
Red Farm Trendy dim sum in the West Village. The pastrami egg-rolls are a must.
Sauce Cozy, family-style Italian in LES.
Tacqueria St. Marks Place Cheap and good by NYC standards. It gets noisy on the weekends and is on a fun street in the East Village.
Two Hands Australian restaurant in Tribeca with a great wine list and attractive serving staff!
Yuerba Buena Pricey but delicious Latin Food and cocktails.
DRINK
Antler Beer & Wine Dispensary Chill bar in LES. Good for groups.
Blind Tiger Alehouse Craft beer pub in the West Village.
Bonnie Vee Hip cocktail bar and garden in Nolita.
The Dead Rabbit Funky cocktail bar in FiDi.
Decibel Sake speakeasy in East Village.
Hill & Dale Trendy gastropub with a DJ and dancing in the back.
The Flower Shop 70’s style basement bar in LES.
Fools Gold Craft beers on tap in LES.
Happy Bones Sweet, tiny cafe in LES run by Kiwi friends.
Jeremy’s Ale House Dive bar in Seaport popular with locals and firefighters.
McSorley’s Old Ale House 1854 beer saloon in the East Village.
Meow Parlour Cat cafe in the LES that makes great coffee. All of the cats are available for adoption.
The Spotted Pig Posh pub in the West Village.
PLAY
Battery Park Walk around the oldest and southern-most tip of the island of Manhattan.
Comedy Cellar A West Village institution where many of the greats started out and still swing by for late-night gigs.
Staten Island Ferry This is a free way to take a cruise with views of the Statue of Liberty.
Tenement Museum Step back into the 19th and 20th centuries to experience life as an immigrant in New York’s LES.
Wall Street Check out the New York Stock Exchange and statues of the Charging Bull and Fearless Girl.
STAY
For those on a budget, the West Village’s historic Jane Hotel offers rooms that maximize space and shared, communal bathrooms. The Holiday Inn Financial District is another option.
UPTOWN
EAT
Chelsea Market Urban food market next to The High Line. Our favorite stalls are Los Tacos No. 1, Num Pang, the Lobster Place and Doughnuttery. There are often sample sales happening here too.
Eataly It’s touristy but a fun way to spend an hour. Locations in Flatiron and the World Trade Center.
Jacob’s Pickles Southern American in the Upper West Side (UWS). Great for brunch.
Levain Bakery The BEST chocolate cookies in the entire world. This UWS shop sells cookies the size of fists.
Red Rooster Famous Harlem restaurant revered for its Southern-inspiring cooking and jazz brunches.
DRINK
Boat Basin Cafe Great spot in UWS to sit outside as the sun falls across the Hudson.
PLAY
Broadway shows Grab same-day discounted tickets from the TKTS South Street Seaport location.
Central Park Pack a picnic and relax in Sheep’s Field.
The Cooper Hewitt Smithsonian Design Museum Design museum on the Upper East Side.
Dizzy’s Jazz Club World renowned jazz music at Lincoln Center.
The High Line Former raised railway that is now a west side park spanning from 14th Street to Hudson Yard.
The Metropolitan Museum of Art (The MET)
The Museum of Modern Art (MoMA)
Museum of Natural History Stately gem on the UWS.
STAY
If you are on business and based in Midtown, or budget is not an issue, we recommend the Iberostar 70 Park Avenue or The Redbury Hotel.
For a more local, relaxed experience, stay in an Airbnb in a fun neighborhood. Lindsay’s brother and sister-in-law host this brownstone penthouse apartment in Harlem, just two blocks from the 125th Street station.
LOCATIONS NEARBY
Washington, DC
America’s capital is much more than the politics that fuel it. DC’s wide avenues, parks and green spaces, and free national museums and memorials make it especially deserving of a weekend (or week!) away.
Spring and fall are lovely in DC, while the summer is sweltering. The spring is spectacular when the cherry blossom trees are in bloom along the River Basin and Jefferson Memorial.
If staying for a few days, purchase a SmarTrip card to use the Metro and bus system. Metro fares are discounted with the card.
Nearly all of the Smithsonian Museums are free!
EAT
Ben’s Chili Bowl A historic spot serving up late night chili and hot dogs. Obama is a fan!
Bistrot du Coin The best mussels and fries in Dupont.
Lapis Chic and cozy Afghan bistro in Adams Morgan.
Matchbox Home-grown, fancy pizza chain. Try the mini burgers.
Old Ebbitt Grill Steps from the White House, this restaurant is a DC institution and known for its oysters
Perry’s Book the Sunday drag brunch.
Rasika Delicious Indian food with locations in West End and Penn Quarter.
Sakuramen Ramen Bar Tiny spot in Adams Morgan.
Thai X-ing Traditional Thai food in a charming row house on Florida Avenue.
Zorba’s Cafe Casual Greek restaurant in Dupont Circle.
DRINK
American Ice Company Trendy, industrial style bar on V Street.
The Blaguard Local dive in Adams Morgan that is one of the best pubs in the world.
Brixton Three-story British style pub with a roof deck.
Marvin Good music and dancing on U Street.
Masa 14 Asian-Latin fusion restaurant with a hip roof deck bar.
Nellie’s Sports Bar Late night fun.
PLAY
Botanic Garden Smithsonian greenhouse next to the Capital.
Capital Crescent Trail Walk or bike this 11 mile trail along the historic C & O Canal.
Capital Building and White House Tours Book through your local congressional office.
Crumbs & Whiskers Adorable cat cafe in Georgetown. All of the cats are rescues.
Eastern Market Local produce, meat and art in Capital Hill.
Georgetown Internationally known for it’s University (and cupcakes!), spend time walking the cobble-stoned streets of this charming, historic neighborhood.
Holocaust Memorial Museum A national, free museum where visitors can learn about genocide, the Holocaust and remember its victims. A very moving experience.
Meridian HIll Park A terraced, urban park with statues and fountains.
The National Mall Tour the different memorials here and do not miss the Washington Monument, Lincoln Memorial and Jefferson Memorial.
Nationals Park Catch a home baseball game at the Nationals’ stadium near Navy Yard.
National Museum of Natural History The jewel of the Smithsonian museum network. The Hope Diamond is on display!
National Portrait Gallery Smithsonian in the Penn Quarter.
Newseum Interactive, seven-story museum promoting freedom of speech and the American First Amendment. It takes visitors through the evolution of communication. This museum is private and not part of the Smithsonian network.
Rock Creek Park Hike or bike through this park running through the heart of the capital.
STAY
DC is relatively small and there are many good neighborhoods. To be close to food, shopping and nightlife, look for a hotel in Georgetown, Dupont or Penn Quarter (though it will come at a cost).
For a more authentic, local experience, we recommend staying at an Airbnb in Adams Morgan or Capital Hill. Adams Morgan is a diverse, bohemian area while Capital Hill is close to the National Mall and museums.
LOCATIONS NEARBY
Kauai
The smallest and oldest Hawaiian island, Kauai is also the most laid back and rural. Called the Garden Island, it rains nearly every day and is covered in lush rain forests. Head here for quiet beaches and rugged landscapes away from the maddening crowd.
Kauai is remote and the beaches and trails are a distance from each other. Rent a car for your visit to the island.
EAT
Foodland Princeville Get groceries before heading to your rental in Princeville or Hanalei Bay.
Pono Market This small, humble market on the Kuhio Highway in Kapaa has incredibly fresh poké.
Tiki Iniki Tiki-style bar and grill in Princeville with Hawaiian food and fun cocktails.
DRINK
Tahiti Nui Polynesian dive bar and restaurant in Hanalei. Go for happy hour or dinner.
PLAY
Anahola Beach Quiet, locals’ beach on the northeastern face of the island.
Hanalei Bay This natural bay is stunning. Spend an afternoon at the beach and then walk south a few blocks into Hanalei town for happy hour.
Queen’s Bath This natural tide pool in Princeville is beautiful, but can be a treacherous hike and dangerous. Admire the pool versus swimming in it, as this spot has been responsible for dozens of deaths.
Kapaa Town Quiet town on the eastern shore with a handful of shops and restaurants. Visit the the Wailua and Opaekaa falls, both just off the road.
Kalalau Trail Starting from Ha’ena State Park, this 11 mile trail is not for the faint of heart. While difficult, the hike rewards with stunning views of the NaPali coast and is the only way to access its lookouts and hidden beaches, including the beautiful Hanakāpī‘ai Beach.
Kayak Wailua Take a guided kayak tour through the rain forest and down the Wailua River.
Kealia Beach Long beach north of Kaapa Town.
NaPali coastline Kauai’s ancient, jagged coastline is eerily surreal… and familiar (it was featured in Jurassic Park). To appreciate it’s magnificence, take a catamaran day cruise and snorkel trip with Captain Andy’s.
The Sleeping Giant Another hiking trail. However, the Sleeping Giant himself is best viewed from a distance.
Waimea Canyon The “Grand Canyon of the Pacific” is seriously awe-inspiring. Admire the red canyon walls and waterfalls from one of the look-outs, hike through the Waimea Canyon State Park, or take a helicopter tour through the canyon.
STAY
Rent a house or condo in Hanalei or Princeville depending on the size of your group. Both are near world class beaches, restaurants and nightlife.
