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Celebrating a big birthday in New York: a 4-day-guide for an unforgettable trip

From the hotels to the sights to the secret local hotspots: this is the ultimate guide to marking a significant birthday with a trip to the Big Apple


Celebrating a big birthday in New York: a 4-day-guide for an unforgettable trip
Updated: May 5, 2025
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Turning 50 brings a mix of emotions but one thing I was sure of was that myself and my best friend, who I’ve known for most of those years, and who has been with me through all of life’s ups and downs, deserved to mark the occasion somewhere fun and exciting. And nowhere seemed to say ‘celebration of a lifetime’ as much New York, the city that never sleeps. It had a lot of expectations to live up to, but the Big Apple delivered on all counts: some fun, some luxury, some excitement, some culture, and lots and lots of amazing food, drink and laughter.

We spent four nights in the sparkling city and feel pretty confident we had the best four days there that you could possibly hope to have. Here are our recommendations for a trip of a lifetime, whatever big birthday you are celebrating. 

Day 1: Getting there in style – with cocktails!

Starting the trip with a celebration
Starting the trip with a celebration

We started our journey in the most fabulous way possible, flying Virgin Atlantic. We treated ourselves to a glass of champagne in the lounge, followed by another glass once we entered the plane - it felt like a fitting way to kick off our celebrations! I imagine you feel special whoever you are, but telling the cabin crew this was a special occasion ensured we arrived in NYC feeling like true VIPs. 

Once we’d made our way through immigration, we headed straight to our home for the next two nights, the Gansevoort Hotel in the trendy Meatpacking District. This hotel is spectacular. Luxury and elegance from the moment you walk into the lobby. The rooftop pool, with its breathtaking views of the city skyline, is like something out of Sex and the City. It was the perfect spot to unwind and let the New York vibe sink in. After a refreshing swim (it’s open all year round, come rain, snow or shine), we treated ourselves to an indulgent dinner at Saishin Sushi, the hotel’s rooftop restaurant, paired with a couple of expertly crafted cocktails. The sushi, prepared in front of us as we sat up at the bar, was out of this world.

Dinner at Saishin Sushi
Dinner at Saishin Sushi

Day 2: Exploring the Big Apple on foot

The next day, we started things gently with a leisurely walk along the High Line, the beautifully landscaped park built on an old elevated rail track, offering sweeping views of the city below. The walkway leads to Hudson Yards, where there is an amazing shopping centre, perfect  for a little window shopping. The architecture at Hudson’s Yards, with the awe-inspiring Vessel, are a must-see.

Walking on the High Line in the snow
Walking on the High Line in the snow

By mid-afternoon, we found ourselves at Chelsea Market, enjoying a lunch of New York bagels with lox and cream cheese. An afternoon strolling the shops – and popping for a quick photo call at Samantha from Sex and the City’s Meatpacking district apartment - was all we could squeeze in before returning to our hotel for a drink and an early dinner at the rooftop loft, in preparation for a very special birthday treat of an evening.

NYC moments at the top of the Gansevoort
NYC moments at the top of the Gansevoort

The Gansevoort is such a spectacular hotel you’ll definitely want to earmark plenty of time to spend enjoying it. The art is incredible – we had completely missed the Banksy towering over the  check-in desk before it was pointed out to us. But the cool vibe was something we hadn’t overlooked. Our visit happened in February, when the weather was chilly, and even then, it was hard to tear ourselves away from the (enclosed) rooftop bar and pool. But the barman explained it was even more amazing in the summer, when the roof of the bar peels back and the city’s coolest visitors hang out sipping cocktails, while dipping in the pool to cool off.  

The Banksy at check in
The Banksy at check in

We enjoyed our late afternoon dinner at the loft (with a side of espresso Martini to kick the jetlag into touch), but the evening had actually only just begun for us. Planning a 50th birthday treat makes you consider what you want to do more than anything else. For me, a theatre lover, a trip to Broadway was a must. The reality of watching Hamilton in the city it was first made for, despite having seen it in London a few times already, was something I couldn’t have prepared for. It was an utterly spellbinding experience and a show on Broadway is something I’d advise anybody to experience. There are so many theatres, you’ll be spoit for choice, but if you have the opportunity to see Hamilton, on Broadway, take it. It will be worth all the effort you expend in getting hold of the tickets.  

Hamilton on Broadway......unbelievable
Hamilton on Broadway......unbelievable

Day 3: A spot of culture and a change of scenery

Day three was all about culture. We started by visiting the Whitney Museum (with thanks to the Gansevoort concierge for assisting with tickets), where we marvelled at works by American icons like Edward Hopper and Georgia O’Keeffe. The museum’s stunning collection was the perfect backdrop for some self reflection, and just a few blocks from our hotel.

The Whitney Museum on a crisp winter's morning
The Whitney Museum on a crisp winter's morning

From culture, we moved back to sightseeing – with a difference. Retracing our steps on the Highline, we returned to Hudson’s Yards, this time to climb to the top of the building that houses the shopping centre, to visit Edge NYC. The VIP experience is definitely worth it – they whisk you through the crowds and treat you to a glass of champagne as the most incredible views of the city open up in front of you. This sky scraper offers both awe-inspiring views and viral social content opportunities aplenty. You can even walk over a transparent floor and see the city down below you – not for the faint-hearted. By far the best skyscraper viewing point in the city, and with a café and flowing champers, you can really make an afternoon of it.

Looking out over New York from the top of The Edge
Looking out over New York from the top of The Edge

After soaking in those views, we changed accommodation locations – this time checking into the Freehand New York, a cool, budget-friendly spot with a relaxed, artsy vibe. Our room was a cunning solution to the problem of family-friendly accommodation in a city with a price tag as big as its reputation. Bunk beds, but not as you know them! A full family double bed underneath and a kid, teen or adult friendly upper bunk means any combination of roommates can bunk up together. For the two of us, the room was surprisingly spacious and the ensuite perfectly appointed.

Ready for our next adventure, and keen to feel like locals, we jumped on the subway to enjoy a sunny afternoon stroll around Central Park. It was freezing cold, but the sun came out and it was the perfect way to take in the beauty of the city. A power walk round the reservoir (another familiar SaTC location) was followed by a bus trip to our second art museum of the day, MoMA, where we admired masterpieces from Van Gogh to Picasso. By the evening we were exhausted and happily collapsed into a cozy cocktail lounge at the Freehand, where we sipped margaritas and then reminisced on our art-filled day over Latin American food at Comodo

Central Park's reservoir
Central Park's resevoir

Day 4: Reconnections and settling into life as a New Yorker

Our final day started with an emotional reunion with an old primary school friend who now calls NYC home. We shared a delicious brunch at The Smith, a local hotspot. It was great to get a taste of what life is really like for a native New Yorker and to marvel at how the passage of time barely matters when you reconnect with a good pal.

Next, we explored the Fashion District, getting swept up in the energy of New York Fashion Week. The streets were alive with the chicest clothes and boldest personalities. While coinciding a trip to NYC with fashion week can make some arrangements trickier as the city is so busy, it’s worth it for the incredible people-watching. We were lucky enough to score one of the hottest tickets in town, to the alice + olivia show: fashion culture immersion and a highlight of our stay. The models, the outfits and the vibes were unforgettable.

Inside the alice + olivia NYFW show
Inside the alice + olivia NYFW show

Keen to get out on the water during our trip, and to try and grab a glimpse of the Statue of Liberty, we’d booked ourselves for a trip on a City Cruises boat – one which included dinner. To say that this event surpassed expectations is an understatement. This is an experience not to be missed! As we set sail on the Hudson, with a bottle of bubbles and a tasty buffet, things were already fun. But it’s hard to describe the elation we felt as we popped up onto deck for a spot of sightseeing, only to find Liberty herself lit up in the night sky right above us, Alicia Keys's 'Empire State of Mind' ringing out across the load speaker and then, to really take things to another level, a snowstorm started falling on us from the heavens. It felt like a moment of pure magic.

The wonderful Statue of Liberty from the boat
The wonderful Statue of Liberty from the boat

To cap off our trip, after mooring up at Chelsea Harbour, we followed a friend’s advice and ventured to Marie's Crisis, a lively piano bar in the West Village. If you’re a Broadway fan, you will love this small, understated LGTBQ+ venue, welcoming anyone who is prepared to line up to get in, and join in with a song. We sang show tunes until 4 a.m., belting out classics with locals and fellow travellers, from Disney hits to classic Sondheim and everything in between. With smiles as big as the bags under our eyes, we headed to the hotel to pick up our luggage, and then onto JFK for our homeward flight.

As we boarded our 6 a.m. flight back home there was no doubt in our (tired) minds that we’d made the absolute most of the past 4 days. It had been a lot of fun, but more than that, a reminder of the value of our friendship and the importance of living life to the full, whatever age you are.

Friends on top of the world in NYC
Friends on top of the world in NYC

It was a trip so jammed full of memories we’ll be reliving it for decades to come. That's if the New York 2.0 trip doesn't come along too soon! We had so much fun I have a funny feeling we’ll be back in the Big Apple before too long, even without the excuse of a very big birthday to get us there. You only live once, and this is definitely a great way of living. 

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