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A “Grown-Up” Family Holiday: Cruising and Exploring New York

A “Grown-Up” Family Holiday: Cruising and Exploring New York
21 Mar 2025
Orla Sutton
Canada, Enchanted Princess, Multi-generational Holiday, New York, Princess Cruises

This year, our Marketing Manager had the absolute pleasure of embarking on a special multi-generational holiday to celebrate her parents’ wedding anniversary.

We enjoyed a magical Cruise & Stay holiday as family. Kicking things off with a whirlwind city break in the Big Apple before boarding the magnificent Enchanted Princess for a breathtaking cruise through Canada and New England. It was a true family affair, my parents, my partner Jono, and I, all making unforgettable memories together.

New York: The City That Stole Our Hearts

Jenny’s Highlights: Fashion, Culture & A Boat Ride to Remember

As someone with a deep love for fashion, stepping into the Met Museum and the flagship Tiffany’s store felt like entering a dream. Every detail, every exhibit, it was all exquisite! I also adored wandering the charming streets of the West Village, home to Carrie Bradshaw from Sex and the City (a personal favourite of mine!). But one of the most spontaneous and delightful experiences was taking a cruise around Manhattan. It was the perfect way to give our feet a much-needed rest, soak in the glorious summer sun, and snap some stunning skyline photos, all while sipping on a cold beer. Bliss!

Jono’s Highlights: Food & Sports Paradise

For me, two moments in New York stood out above the rest. First up, Katz’s Deli. This place is legendary, and for good reason. The best sandwich I’ve ever eaten! Plus, as a movie lover, I couldn’t help but geek out knowing it was the setting of that famous scene from When Harry Met Sally—if you know, you know. The other highlight? A Yankees vs. Red Sox game! As a sports fan, watching this iconic rivalry unfold in Yankee Stadium was a dream come true. The atmosphere was amazing, and even though I wasn’t thrilled about the matching Yankees hats, I was thrilled to see them win. The girls loved it too, the music, dancing, and even a DJ between innings made it such a fun night.

Dad’s Highlights: A Surprising Love for NYC

I’ll be honest—New York never really appealed to me. I always imagined it as a shopping haven, which isn’t exactly my cup of tea. I’m more of a history lover, and Rome has always been my favourite city break. But, much to my surprise, New York completely won me over! There was an undeniable vibe, a buzz of energy, history, and excitement at every corner. One of the most poignant moments was visiting the 9/11 Memorial and Museum, made even more moving as our trip coincided with the anniversary of 9/11. A deeply humbling experience I will never forget.

Mum’s Highlights: A Magical Evening in Central Park

Choosing just one favourite moment from New York is nearly impossible! It’s a city that truly never sleeps, there’s always something happening. But if I had to pick, it would be our sunset tour of Central Park. We followed in the footsteps of famous film scenes, listened to violinists performing love songs under Bethesda Terrace, and ended with dinner at Tavern on the Green. Dining outside under twinkling fairy lights, surrounded by elm trees and the soft sounds of live jazz, was simply magical.

Cruising with the Enchanted Princess: Luxury & Relaxation

Jenny’s Favourite: Spa Heaven

After all the walking in New York, the onboard spa was a lifesaver! Mum and I treated ourselves to a spa pass for the week, and let’s just say we got our money’s worth, we went every single day, sometimes twice! It was the perfect way to unwind and rejuvenate.

Jono’s Favourite: Food, Fitness & The Best Pizza at Sea

I’m not a fussy cruiser. Give me good food, a gym, and a drinks package, and I’m set. But I have to mention the pizza onboard, it’s award-winning and for good reason! Hands down, the best pizza at sea. The gym facilities were also fantastic, and I could have joined some great fitness classes included in our Princess Plus package, which was definitely worth it.

Dad’s Favourite: The Perfect Balance

What I loved most about Princess Cruises was that even with a full ship, it never felt crowded. The service was impeccable, attentive yet relaxed. The food was top-notch, particularly the “casual dining” options included in our package. Plus, the entertainment was so varied, there was always something for everyone.

Mum’s Favourite: Speciality Dining & The Best Coffee at Sea

We’ve cruised with Princess before, but this was our first time trying the speciality dining, and I’m so glad we did! The food was spectacular, and it was so reasonably priced for the quality. Also, I swear Princess makes the best coffee at sea, I’m still dreaming about those iced lattes!

Our Itinerary: A Whirlwind Adventure

New York Highlights:
  • Tuesday 10 Sep: Arrival, Times Square, dinner at Carmines
  • Wednesday 11 Sep: Breakfast at Ellen’s Diner, 5th Ave shopping, Grand Central Station, Macy’s & sports bar, Top of the Rock
  • Thursday 12 Sep: Katz Deli, Brooklyn Bridge, 9/11 Memorial, Yankees Game
  • Friday 13 Sep: Met Museum, Tiffany’s, Central Park, Carriage Ride, Tavern on the Green
Cruise Highlights:
  • Saturday 14 Sep: Boarding Enchanted Princess
  • Sunday 15 Sep: Newport – scenic schooner cruise & walk
  • Monday 16 Sep: Boston – Hop-on Hop-off tour
  • Tuesday 17 Sep: Bar Harbour – Private Acadia National Park tour
  • Thursday 19 Sep: Halifax, Nova Scotia – Titanic & Fisherman’s Cove tour
  • Saturday 21 Sep: Back to NYC – City Tour & Airport Transfer

A Holiday to Remember

This trip was everything I dreamed of and more for a multi-generational holiday. A perfect balance of adventure, relaxation, and quality family time. I still get excited just thinking about the memories we made, from the vibrant energy of New York to the sheer luxury of our cruise. The only downside? It didn’t last long enough!

If you’re looking for the perfect multi-generational family holiday, I cannot recommend this combination enough. Whether you’re craving the hustle and bustle of a legendary city or the tranquillity of a world-class cruise, this trip delivers the best of both worlds.

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