The best things to do in New York: Our Ultimate Guide

Five days in New York is a good amount of time to see the best the city has to offer. It never sleeps after all and so our founder, Darren Burn, shared his top tips for seeing the ultimate in New York.

Friday

Catch an early flight from Heathrow to New York. Arrive at lunchtime and check in to your choice of hotel or apartment. Getting to Manhattan from JFK is simple – take the Air Train to Jamaica and then the Long Island Rail Road (LIRR) to Penn station in the heart of the city and right by Madison Square Garden.

Start your afternoon leisurely by getting your bearings. Head to Times Square to immerse yourself in its shining bright lights. Do this before you do anything else – not only will it really get you into the hustle and bustle of the New York way of life but it’s a good one to tick off early so you don’t need to return!

Head for a casual dinner in Hell’s Kitchen on your first night – we opted for VNYL which had decent food and a cafe feel to it. Not only is it a foodie haven, but there are plenty of cool bars for you to explore. You’ll be tired after the time zone change, but it’s much easier flying west than east and so go with it and stay up late.

Stonewall Inn New York / OutOfOffice.com

Then it’s time to visit New York’s gay bars. Visit Therapy – a lounge bar – for a laid back cocktail. Sometimes it boasts live music and comedians depending which day of the week you go.

After a couple of drinks in Flaming Saddles, head around the corner to dance the night away at the relatively new Industry. It’s good for a dance, it’s not pretentious and there’s a wide selection of drinks. Don’t forget that in NYC they free pour drinks and after that long international flight you’ll likely be ready for bed a little earlier than you bargained!

Saturday

Start early by heading down to the High Line – New York’s disused railroad which has been transformed into a garden and is great to walk along. If you’re feeling energetic then you can jog along it heading south. At the end, you’ll find Bubby’s – renowned for brunch. Many reviewers have raved about it but it has seemed to have lost its edge and the service wasn’t up to NYC’s standards. Perhaps they’ve rested on their laurels a bit. Still, it’s worth a visit.

Stonewall Inn New York / OutOfOffice.com

After brunch, stroll down through Greenwich Village for a look at the iconic Friends’ apartment building on the corner of Grove and Bedford Street. Also visit the iconic Stonewall Inn just a few streets away. Then make your way downtown towards Battery Park. You can either then take the Staten Island ferry over the water to catch a view of the Statue of Liberty, but better still head to Zephyr Statue of Liberty Express which takes you on a boat trip around Manhattan (including under the Brooklyn Bridge) and up close to the Statue of Liberty. There are other options if you want to get off at Liberty Island, but bear in mind you get just a good of a view from the water and don’t have to wait for a return ferry.

In the evening, eat at the Best Rooftop Bars in New York list).

Try the legendary Marie’s Crisis if you want a small dingy bar with piano singalong show tunes and once a month you’ll find a great gay club night in New York called Holy Mountain at Slake which is in Midtown. It’s a multi-level club with a number of different rooms spinning lots of different genres.

Sunday

Start your undoubtedly hungover Sunday by visiting The Park for brunch. Perhaps our favourite brunch spot, this trendy Chelsea hotspot has a terrace and glassed garden.

If planes and war are your cup of tea then visit the New York Public Library before enjoying a coffee just behind it in Bryant Park.

Then it’s time to enjoy some cocktails at Bar 54, a rooftop bar at the top of the Hyatt hotel which offers great views of the Freedom Tower and looking down onto nearby Times Square. Make sure you book here as the terrace has limited space.

Top of the Rock New York

For a top end dinner, it’s a five minute walk around the corner to the Hunt and Fish Club where you’ll find vintage wines served alongside seafood and sumptuous steaks. You probably won’t have room for dessert!

Monday

Brunch at Freedom Tower. Ascend to the 102nd floor of the tallest building in North America and one that is as symbolic as it is awe-inspiring. On a clear day you can see for miles. Have your camera ready!

Come down and pay your respects at Ground Zero where two fountains in the ground mark the floor plan of the Twin Towers.

Then stroll across to the Downtown Manhattan Heliport where you can take a helicopter ride to experience New York from up even higher. Again, usually best to pre-book a New York helicopter tour and something we can help secure at OutOfOffice.com.

After the ride it’s a short walk to Battery Park and the Smithsonian’s National Museum of the American Indian which charts the course of Native American history.

This evening, try dinner at Rosa Mexicano tonight, though if you’re sticking to the daily itinerary then Mondays tend to be fairly quiet!

Tuesday

Central Park New York

Finish your trip to NYC with a visit to Central Park. Have a cheap and cheerful breakfast at the Loeb Boathouse Central Park which has relatively simple but reasonably priced pancakes, croissants and fruit salads. If you have time take a rowing boat on the lake.

For your final afternoon head to Brooklyn. If you’re travelling light walk across the bridge. Realistically though take a cab or the subway. Leave your luggage at one of New York’s many luggage story facilities and spend the afternoon exploring the food and drinks and independent shops around Bedford Street. If you skipped breakfast at Central Park, then opt for a bottomless brunch at William Vale Hotel where the views are worth drinking over!

Brooklyn Bridge New York

Then, take your final journey by cab to JFK for your flight safe in the knowledge you’ve shown New York a good time and let it show you its best bits. Oh and we forgot to even take in a Broadway show! Best come back then, hadn’t we?

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