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5 Day New York Itinerary for Gay Couples: First-Timers Guide to NYC

By Joe
5 Day New York Itinerary for Gay Couples: First-Timers Guide to NYC

5 Day New York Itinerary for Gay Couples: First-Timers Guide to NYC

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Table of Contents

Why New York Should Be On Your Radar

The bartender at the Hard Rock rooftop bar handed us our third vodka soda and said, "First time in the city?" We nodded. She smiled. "You're gonna love it. Everyone does."

She wasn't wrong. But here's what surprised us about New York for gay couples: it's not just the nightlife or the Pride flags everywhere (though there are plenty). It's how the city manages to feel both overwhelmingly enormous and somehow intimate at the same time. You'll turn a corner from Fifth Avenue's designer chaos into a quiet SoHo cafe where the barista knows everyone's order. You'll walk through Central Park at sunset and forget you're surrounded by millions of people.

This 5 day New York itinerary covers everything we actually did in summer 2024—the good (Virgin Upper Class, Eagle NYC, Broadway magic), the mistakes (never skip the LIRR, always carry water in July heat), and the honest truth about being a gay couple in America's biggest city. We're not here to give you a list of "must-sees." We're here to tell you what actually happened, what we'd do differently, and whether New York lives up to the hype for LGBTQ+ travellers.

Our Story: First Pride, First Big Apple

I'd been to New York once before—Joe had. Alex hadn't. And the difference in our reactions when we landed at JFK on July 31st, 2024, said everything.

Joe: "Right, let's get moving. We've got five days."

Alex: "Jesus Christ. Look at the size of this place."

The scale of New York hits you immediately. Not in a "wow, beautiful" way, but in a "how does anyone actually live here?" way. The noise, the heat, the sheer volume of humans moving in every direction. Alex was slightly overwhelmed at first. By day two, he loved it. By day five, we were already planning our return.

We flew from London Heathrow on the 8:20am Virgin Atlantic flight—more on that Upper Class experience in a moment—and landed around 11:25am local time. Five nights, one hotel, zero plans to relax. This was our first 5-day New York summer trip, and we wanted to see everything. Which, spoiler alert, is impossible. But we tried.

Here's what we actually managed to fit in: Central Park picnics, Fifth Avenue shopping sprees, the American Museum of Natural History in 35-degree heat, a speed boat tour that left us soaked, Broadway magic, the 9/11 Memorial (heartbreaking), Stonewall (complicated feelings), the Eagle (always reliable), Brooklyn Bridge at sunset, and enough rooftop bar hangovers to last a lifetime.

Did we do it perfectly? No. Did we make mistakes? Absolutely (hello, subway confusion). Would we do it again? Without question. If you're planning your first visit to New York as a gay couple, this guide is everything we wish we'd known before we went.

Flying Virgin Atlantic Upper Class to JFK

We'll do a full review of the Virgin Atlantic Upper Class experience in another post, but here's the short version: it was incredible.

We travelled down to Heathrow the night before to make the most of the Upper Class lounge in the morning. Pro tip: if you're staying in a hotel slightly outside the airport, get off at West Drayton and grab a taxi from there. It's much cheaper than paying the TFL surcharge that applies to stations within the airport itself—we saved about £10 per person doing this.

Virgin's Upper Class Wing is worth mentioning too. Instead of queuing with everyone else, you're dropped off at a private entrance with dedicated security. It's ridiculously smooth and makes you feel like you've already started your holiday before you've even checked in.

The flight itself? Virgin's brand new A330neo didn't disappoint. The new Upper Class seats are spacious, the cabin feels bigger thanks to the new seat doors, and the service was—as always with Virgin—excellent. The food, the wine, the lie-flat bed, the pyjamas. All of it. We landed in New York feeling surprisingly human for people who'd just flown across the Atlantic.

If you're considering splashing out for Upper Class on your trip to New York, we'd say it's worth it. Especially if you're flying early and want to hit the ground running when you arrive.

Getting from JFK to Manhattan (And Our Mistake)

Right. Here's where we messed up.

We knew we needed to get from JFK to Manhattan. What we didn't know—because we didn't research properly—was that the Long Island Rail Road (LIRR) is significantly faster and more comfortable than the subway. Instead, we ended up on a packed subway during rush hour with our luggage, sweating, confused, and regretting every decision we'd made that morning.

Here's what you should actually do:

When you land at JFK, follow the signs for the AirTrain (it's free within the airport). Take the AirTrain to Jamaica Station. From there, buy a ticket for the LIRR to Penn Station or Grand Central (depending on where your hotel is). The total cost is around $15.75—about $8 for the AirTrain and $7.75 for the LIRR during off-peak hours. The journey takes roughly 35 minutes, and you'll arrive in Midtown Manhattan without the stress of navigating multiple subway changes.

We took the subway. It was hot, slow, and involved two changes. Learn from our mistake. Take the LIRR.

💡 TIP: If you're travelling on a weekend, the LIRR costs just $4 per person, making it even better value. Download the MTA app before you arrive to buy tickets and check schedules.

Where to Stay: Hard Rock Hotel Times Square

We stayed at the Hard Rock Hotel near Times Square for all five nights. Yes, it's touristy. Yes, Times Square is loud, crowded, and overwhelming. But for what we wanted—central location, easy access to everything, and a base we could return to without schlepping across the city—it was perfect.

Why We Booked It

We found the hotel through Luxury Escapes, which had a money-back offer running on the Platinum American Express card. Quick mention: the Amex Platinum is expensive (we know), but between the money-back offers, lounge access, dining credits, and travel insurance, we find it pays for itself. We'll do a separate post breaking down the benefits in detail, but if you're a frequent traveller, it's worth looking into.

What We Loved

The hotel itself was lovely. Because we were staying five nights, we got breakfast included, which saved us time and money each morning. We also received daily bar credit, which we used every single evening at the rooftop bar. And that rooftop bar? Beautiful. Great views over Times Square and towards Billionaires' Row, brilliant sunset vibes, and strong drinks. We spent far too much time up there.

The Room

The room was comfortable, modern, and clean. Nothing groundbreaking, but everything you need. Good air conditioning (essential in July), a decent-sized bathroom, and enough space to unpack properly for five days. The location meant we could walk to most things or hop on the subway in minutes.

Worth It? Yes. If you want to be central and you're planning to spend most of your time out exploring, the Hard Rock Hotel is a solid choice.

Book here: Hard Rock Hotel Times Square on Booking.com

🏙️ First Impressions: The Iconic Sights

On our first full day, we did what every first-timer does: we went to see the famous stuff.

Rockefeller Center. Grand Central Terminal. Times Square. All of it. And here's the weird thing about visiting New York when you've grown up watching American TV and films—it genuinely feels like you've been there before. You recognise everything. The yellow cabs, the steam rising from the streets, the billboards, the noise. It's oddly comforting and completely surreal at the same time.

Rockefeller Center

We didn't go up to the Top of the Rock (we'd already booked the rooftop bar for sunset views), but we spent time walking around the plaza. It's massive, impressive, and packed with tourists taking photos. Worth seeing? Absolutely. Worth queueing for an hour in the heat? Probably not unless you really want the view.

Grand Central Terminal

This one surprised us. Grand Central is stunning. The architecture, the light streaming through the windows, the sheer scale of the main concourse. It's one of those places where you stop, look up, and think, "Yeah, okay. I get it now." Spend 20 minutes here. It's free, it's beautiful, and it's a nice break from the chaos outside.

9/11 Memorial

We also visited the 9/11 Memorial, and it's impossible not to be moved by it. The reflecting pools, the names etched around the edges, the silence despite being in the middle of Manhattan. It's beautifully done, deeply sad, and absolutely worth visiting. Take your time here. It's important.

⚠️ MISTAKE: We didn't factor in how emotionally draining the 9/11 Memorial would be. Give yourself time afterwards to process it—don't rush straight into another activity.

🌳 Central Park & The Zoo

Central Park is one of those places that looks small on a map and then you arrive and realise it's absolutely enormous. We spent an entire afternoon wandering through it, and we barely scratched the surface.

Why It's Brilliant

It's green. It's peaceful (in parts). It's a huge advantage for New Yorkers to have all this open space in the middle of such a massive city. We stopped at a cafe for drinks and ice cream, sat on a bench in the sun, and just... existed for a bit. No agenda, no rushing. It was lovely.

The weather was beautiful—mid-30s, clear skies, and just warm enough to justify sitting in the shade with a cold drink. If you're visiting New York in summer, Central Park is essential. Bring water, wear sunscreen, and find a quiet spot away from the crowds.

Central Park Zoo

We also went to the Central Park Zoo ($20 each), and honestly? We loved it. It's small compared to other zoos, but the fact that there's a whole zoo in the middle of a city is wild. The penguin exhibit was the highlight—watching them dive and swim while skyscrapers loom in the background is such a New York moment.

Worth It? Yes, if you've got a few hours to spare and you like animals. No, if you're rushing to fit in ten other things that day.

💡 TIP: Visit Central Park early in the morning or late afternoon to avoid the midday heat. And always, always carry water with you in summer.

🏛️ American Museum of Natural History

The American Museum of Natural History ($25 each) was on our list because, well, it's iconic. We'd seen it in Night at the Museum. We wanted to see the dinosaurs. We wanted to feel like kids again.

Here's what actually happened: we got the entry times mixed up and ended up queueing outside in extremely hot weather for over an hour. By the time we got inside, we were dehydrated, sweaty, and slightly grumpy. Not the museum's fault—entirely our fault for not double-checking the timings.

Once We Got Inside

It was worth it. The dinosaur exhibits are incredible. The scale of some of those skeletons is genuinely mind-blowing. The planetarium is beautiful. The gem collection is dazzling. It's huge, so give yourself at least three hours to explore properly.

What We Learned

Always check entry times. Book your tickets online in advance if you can. And for the love of God, carry water with you. New York in July is no joke, and standing in the sun for an hour without water is a quick way to ruin your afternoon.

Worth It? Absolutely. Just don't mess up the timings like we did.

🛍️ Shopping on Fifth Avenue

Of course we went shopping on Fifth Avenue. We love shopping. Always have. And Fifth Avenue is one of those streets where you feel like you're in a film just by walking down it.

Tiffany & Co.

We both got something from Tiffany. Nothing massive—small pieces we'd been eyeing for a while—but it felt special to buy them in New York. The store itself is beautiful, the staff were lovely, and the whole experience felt exactly as iconic as you'd hope. If you're into jewellery or you want to treat yourself, it's worth a visit.

The Vibe

Fifth Avenue is busy. Really busy. Designer stores, tourists, street performers, everyone moving in ten different directions. It's fun for a few hours, but it's also exhausting. We spent the morning there, grabbed lunch, and then escaped to somewhere quieter (Central Park, if you're wondering).

💡 TIP: Go early in the morning if you want to actually browse without being shoulder-to-shoulder with crowds. And wear comfortable shoes—you'll be walking more than you think.

🌃 Gay Nightlife: Where We Actually Went

Right. Let's talk about New York's gay nightlife, because this is probably one of the main reasons you're reading this guide.

The Eagle NYC

The Eagle never disappoints. Every city has an Eagle, and every Eagle is reliably excellent. We went on Jock Night, which was... exactly what you'd expect. The crowd was friendly, the staff were great, and the vibe was classic leather bar without taking itself too seriously.

One thing to note: it's cash only. We had to find an ATM, which wasn't a huge drama, but worth knowing in advance. Drinks were reasonably priced, music was good, and we stayed far longer than we'd planned.

Worth It? Absolutely. If you're looking for a classic gay bar experience in New York, the Eagle is reliable.

📍 Location: 554 W 28th St, Chelsea

Stonewall Inn

We had to go to Stonewall. It's Stonewall. The birthplace of the modern LGBTQ+ rights movement. We appreciate the history, we understand the significance, and we're grateful for everything that happened there.

That said, we were disappointed. It felt very commercial. A bit tacky, if we're honest. It's clearly set up for tourists now—which is fine, and probably inevitable—but it didn't feel like a place we'd return to for a night out. We had one drink, took a photo, and left.

Worth It? Once, for the history. Not for the vibe.

📍 Location: 53 Christopher St, Greenwich Village

The Greenwich Village Scene

We also explored the other bars around Greenwich Village, and there are loads of options. Julius' is one of the oldest gay bars in New York and has a much more relaxed, neighbourhood feel. The Monster has a piano bar downstairs and a dance floor upstairs. Henrietta Hudson is a great spot for women and queer folks looking for a more inclusive vibe.

The area is very gay-friendly, and you'll feel comfortable walking between venues. Just be prepared for crowds, especially on weekends.

💡 TIP: Download Grindr or Scruff before you arrive to find out where the locals are actually going. Pop-up events and smaller bars often have the best atmosphere.

🎭 Broadway: Aladdin at the New Amsterdam Theatre

You can't go to New York for 5 days and not see something on Broadway. We chose Aladdin at the New Amsterdam Theatre, and it was absolutely brilliant.

The sets, the costumes, the performances—all of it was top-tier. Genie steals the show (obviously), and there were moments where the entire audience was on their feet. It's big, it's bold, it's classic Broadway magic, and it's one of those experiences that reminds you why theatre matters.

How to Book

We booked our tickets a few weeks in advance through the official Broadway website. Prices vary wildly depending on where you sit, but we went for mid-range seats and had a great view. If you're on a budget, look into lottery tickets or rush tickets—many shows offer discounted same-day tickets if you're willing to queue.

Worth It? 100%. Even if you're not usually into musicals, Broadway is an experience. Do it.

💡 TIP: Book at least a week in advance to get decent seats at reasonable prices. And arrive early—the theatre district gets chaotic right before showtime.

🚤 Hudson River Speed Boat Tour

The Hudson River speed boat tour was one of the highlights of the trip. We booked it through Viator, and it was worth every penny.

You see all the main landmarks from the water—the Statue of Liberty, Ellis Island, One World Trade Center, the Brooklyn Bridge—and the boat goes fast. Really fast. We got absolutely soaked, and it was brilliant. The guide was funny, the views were incredible, and it's one of those activities that feels like a proper New York experience without being overly touristy.

What You Need

  • Water. Seriously, bring water. It's hot, you're in the sun, and you'll get dehydrated quickly.
  • A good phone camera. The views are stunning, and you'll want photos.
  • A waterproof bag if you're bringing anything valuable. You will get wet.

Worth It? Absolutely. One of the best things we did all trip.

Book here: Hudson River Speed Boat Tour on Viator

🌉 Brooklyn Bridge & DUMBO

We walked the Brooklyn Bridge on our last full day, and it was the perfect way to end the trip. The views back towards Manhattan are stunning, the bridge itself is iconic, and it's one of those things that feels like a proper New York moment.

DUMBO

After crossing the bridge, we spent time in DUMBO (Down Under the Manhattan Bridge Overpass). It's one of those Instagram-famous spots—everyone's taking photos of the Manhattan Bridge framed by the buildings—but it's also just a really nice neighbourhood to wander around. Cobblestone streets, waterfront views, independent shops, and great cafes.

We grabbed coffee, sat by the water, and just enjoyed the quieter pace after five days of constant movement. If you've got time before your flight, DUMBO is worth a visit.

Worth It? Yes, especially if you're flying home from JFK—it's on the way.

🥐 The High Line & Chelsea

The High Line is one of those New York attractions that's completely free and absolutely worth doing. It's an elevated park built on old railway tracks, and it's beautifully maintained. Great views, interesting art installations, and a lovely way to walk from Chelsea to Hudson Yards without dealing with street-level crowds.

We walked the whole thing, stopped for photos, and then explored Chelsea afterwards. It's one of the more relaxed neighbourhoods in Manhattan—still busy, but not overwhelming—and there are loads of great cafes and shops to explore.

Worth It? Definitely. It's free, it's beautiful, and it's a nice break from the chaos.

📺 Sex and the City Pilgrimage

Being a huge Sex and the City fan, we had to visit Carrie's house and Magnolia Bakery. Both are in the West Village, and both are still pilgrimage sites for fans all these years later.

Carrie's House

It's just a normal brownstone on a residential street, but there are always people taking photos outside. We got our photo, felt slightly ridiculous, and then left. It's fun if you're a fan, but we can't imagine how annoying it must be for the people who actually live on that street.

Magnolia Bakery

The cupcakes are good. The queue is long. The nostalgia is real. We got our cupcakes, sat on a bench nearby, and felt like we were living in a sitcom for five minutes. It's touristy, but it's also fun.

Worth It? If you're a fan, yes. If you're not, skip it.

Is New York Safe for Gay Travellers?

This is one of the most common questions we get asked, so let's address it properly.

New York has strong anti-discrimination laws protecting LGBTQ+ people. Under the NYC Human Rights Law, discrimination based on sexual orientation or gender identity is illegal. The city is overwhelmingly progressive, LGBTQ+ people are visible everywhere, and Pride flags are all over Manhattan.

Our Experience

We felt completely safe the entire time. We held hands in public, we kissed at bars, we were openly affectionate, and we never once felt uncomfortable or unsafe. New York is one of the most LGBTQ+-friendly cities in the world, and it shows.

That said, this is still America. Political tensions exist. We visited in summer 2024, and while we personally felt safe, we were aware that security concerns around Pride events had been raised by officials earlier in the year. It's worth being aware of your surroundings, especially at large LGBTQ+ events or in less central areas.

Neighbourhoods to Know

  • Greenwich Village is the historic heart of LGBTQ+ New York. Stonewall is here, and the area is very queer-friendly.
  • Chelsea has a strong gay scene, with bars, clubs, and a visible LGBTQ+ community.
  • Hell's Kitchen is another LGBTQ+-friendly neighbourhood with great bars and restaurants.

Safety Tips

  • Public transport is safe, even late at night. Stick to well-lit, busy stations.
  • Times Square and Midtown are very safe due to heavy police presence and tourist crowds.
  • Avoid empty streets late at night, especially in outer boroughs you're unfamiliar with.
  • Trust your instincts. If something feels off, leave.

Bottom line: Yes, New York is safe for gay travellers. We felt welcomed, visible, and comfortable everywhere we went.

FAQ: Your New York Questions Answered

Is 5 days enough for New York?

Five days is enough to see the main highlights and get a feel for the city, but you'll leave wanting more. We covered a lot, but we also missed loads. If you can stretch it to a week, do it.

What's the best time to visit New York for gay travellers?

June for Pride is the obvious choice—NYC Pride is one of the biggest in the world. September/October has great weather without the summer crowds. Winter is beautiful but freezing. We went in July/August, which was hot and crowded but still brilliant.

How much should I budget for 5 days in New York?

Accommodation: £150-£300 per night for a decent hotel.
Food: £50-£100 per day depending on where you eat.
Attractions: £20-£30 per person for most museums and tours.
Nightlife: £50-£100 per night if you're drinking.
Transport: Around £30 for a 7-day MetroCard (unlimited subway/bus).

Overall, budget £2,000-£3,000 for two people for 5 days, including flights.

Do I need to tip everywhere?

Yes. Coming from the UK, tipping culture in the US is a shock. Expect to tip 18-20% at restaurants, $1-2 per drink at bars, and a few dollars for hotel porters or taxi drivers. Factor this into your budget—it adds up quickly.

Is Times Square worth staying in?

Yes, if you want to be central. It's touristy, loud, and overwhelming, but it's also convenient. You can walk or subway to most attractions easily. If you prefer a quieter vibe, look at Chelsea or Greenwich Village instead.

Are there LGBTQ+-friendly hotels in New York?

Loads. Most hotels in Manhattan are LGBTQ+-friendly as standard, but if you want specifically queer-owned or queer-focused hotels, look at The Out NYC or The Bowery Hotel.

How do I get from JFK to Manhattan?

Take the AirTrain to Jamaica Station, then the LIRR to Penn Station or Grand Central. It costs around $15.50 during peak hours and takes about 35 minutes. Don't make our mistake and take the subway.

Quick Travel Guide

Money & Costs

New York is expensive. Budget accordingly. Credit cards are accepted everywhere, but carry some cash for tips and smaller vendors. Contactless payment works on the subway.

Getting Around

Buy a 7-day unlimited MetroCard for $34. It covers all subway and bus journeys. Download the MTA app for live updates. Taxis and Ubers are expensive—use the subway wherever possible.

When to Visit

June for Pride. September/October for great weather. Winter for Christmas vibes and fewer crowds. Avoid July/August if you hate heat and tourists (we went anyway and loved it).

What to Pack

  • Comfortable shoes. You'll walk 15,000+ steps a day.
  • Sunscreen and a refillable water bottle (essential in summer).
  • Layers. Air conditioning indoors is freezing, but it's scorching outside.
  • A small backpack for carrying water, snacks, and a jacket.

Sun & Weather Safety

New York in summer is hot. Drink water constantly, wear sunscreen, seek shade during peak hours (12-3pm), and don't underestimate how draining the heat can be.

Language & Culture

English, obviously. New Yorkers have a reputation for being rude, but we found most people to be helpful and friendly. Just don't walk slowly in the middle of the pavement.

Must-Try Experiences (Top 5)

  1. Walk the Brooklyn Bridge at sunset.
  2. See a Broadway show.
  3. Visit the Eagle or another classic gay bar.
  4. Do a speed boat tour of the Hudson River.
  5. Spend an afternoon in Central Park with no agenda.

Final Thoughts: Is 5 Days in New York Worth It?

So. Is 5 days in New York as a gay couple worth it?

Absolutely. Without question. New York is one of those cities that lives up to the hype. It's big, it's loud, it's overwhelming, and it's brilliant. We made mistakes (subway disaster, museum timing disaster), we spent too much money (Fifth Avenue, we're looking at you), and we definitely didn't see everything. But we loved every second of it.

For LGBTQ+ travellers, New York is one of the safest, most welcoming cities in the world. You'll feel visible, accepted, and celebrated. The nightlife is excellent, the history is important, and the energy is infectious. Whether you're here for Pride, Broadway, culture, or just to say you've been, New York delivers.

We'll be back. Probably sooner than we should be, given how much we spent. But that's New York for you.

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Travel with us, always with love and a little luxe. 🌈✈️

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