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Luxury Dates for the Holidays – 10 Outsized, Upscale Ideas

Romance is the best cure to the winter blues. Whether you’re the crackling fireside type or a snowy outdoor adventurer, we’ve put together a list of the best luxury dates for the holidays. Why stay stuck inside when you can indulge in the most upscale winter experiences? So go ahead and let the cold winds blow because you and your sugar plum are about to enjoy the holiday season in style!

Horse-drawn Carriage Ride

Grab your boots and a hat, it’s time for you and your snowbird to take the most romantic ride of your lives. For an evening that feels right out of a fairy tale, book a horse-drawn carriage to pick the two of you up right at your doorstep.

You can ride around your local park, check out the holiday lights, or head to your downtown area. No matter where you go, the idea is to make warm memories together. And if it gets chilly, you just snuggle up close to your date!

Holiday Concert Experience

Music sets the soundtrack to any romantic evening. From your city’s Philharmonic holiday show to a concert by your favorite artist, wintertime celebrations are especially magical with live music.

To make the whole evening unforgettable, remember to include dinner before or after the concert. And don’t hesitate to dress up for the occasion! You’ll probably want to snap some pictures of this special night to remember this holiday luxury date.

Magical Ballet Performance

The best ballet companies save their most beautiful productions for the holiday season. And it’s not just The Nutcracker! Sure, this might be the most famous. But if you’re in the mood for something different, see what your local company has to offer.

Some of the most popular wintertime ballets include:

  • The Sleeping Beauty
  • A Christmas Carol
  • A Cinderella Story
  • Les Patineurs
  • The Snow Queen
  • Hansel & Gretel
  • Giselle

All of these ballet performances would be considered perfect luxury dates for the holidays.

Rooftop Ice Skating

This holiday season, leave the skating rink to the teenagers and choose the upscale version, instead. Rooftop ice skating is all the rage with the grown-ups nowadays, and it makes for a spectacular holiday date. Plus, it’s a chance to get outdoors and stay active together.

Hold hands as you glide along the ice and take in the panoramic views of your city. When you need a break, hit the bar for warm cocktails to keep you cozy and make this romantic experience one of a kind.

Weekend Winter Getaway

You know you need a weekend getaway. You deserve a break before the holidays. Your significant other could also use a break. Why not a holiday luxury date away from the hustle and bustle?

When a night out’s not enough, book a dreamy cabin and treat yourselves to an intimate mountain getaway! From skiing to walking around a charming town or spending the whole day in the hot tub – the options are endless! 

Snowmobile Ride in the Slopes

Looking for a real winter thrill? Get out of the city and chase the backcountry powder with a snowmobile ride! It’s the best way to play in good company, away from the city and the distractions of everyday life.

But be warned: this isn’t your typical resort hangout. This date idea is for those daredevils who want to turn the slopes into their playground. 

Lux Movie Date

Wondering how to make holiday movies feel posh? How about you rent out the entire cinema for you and your bae? From classics like the Gremlins to modern favorites like Elf, there’s no better way to upgrade your “dinner and a movie” date this holiday season.

This holiday luxury date idea’s so extra, it’s guaranteed to send shivers down your partner’s spine! Perfect for wrapping your arm around them and making out when the lights dim inside the theater. 

Holiday Couples Spa

The holiday season can get pretty stressful. Why not pamper yourselves with a couples spa day? Before you spend hours around the table with relatives you haven’t seen all year, make time for some well-deserved R & R.

This one’s especially nice if your skin gets dry in the wintertime. Plus, the spa is always more fun when you get side-by-side massages and sip on champagne. Hydrotherapy while it snows outside? Yes, please!

Shop ‘Til You Drop

This luxury holiday date idea is a classic that never fails. Especially during the holiday season, with so many great offers and gifts to buy for everyone on your list.

But don’t forget to put each other at the top of your list. And if you don’t mind spoiling the surprise, just let your date handpick their own present. That way, you’ll know you’re getting them something that brings a smile to their face. 

Plane Ride with a View

If you ask us, the best way to see New Year’s Eve fireworks is from a private jet! If you want to welcome 2022 in serious style, charter a flight to enjoy fireworks and an unforgettable New Year’s celebration. Whether you invite a group of friends or throw a party in the sky for two, this is sure to be the most amazing experience.


With all the flurries and fun of the season, the holidays are filled with opportunities for the most wonderful dates. During this season of giving, treat your partner to the experience of a lifetime and add some romance to your season. Remember, the best part about the holidays is spending time with those who make you feel special. Seeking can help you find that special someone.

For more dating stories, advice, and tips, be sure to check out the rest of the Seeking Blog.