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Romantic Winter Date Ideas- 25 Dates to Celebrate the Holiday Season

Our romantic winter date ideas are perfect for when the weather gets colder and you just want to enjoy the season with that special someone.

Around the holidays, everything is more festive and there are so many more events to choose from for your date night. We also added some of our favorite winter date ideas NYC if you are nearby or planning a visit.


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Winter Date Ideas


Visit our themed date nights that will inspire you to create the best dates to keep that spark alive! They include menus a playlist, games and so much more!


Best Date Ideas Guide

Hygge Fondue Date Night

Hallmark Movie Night   (as long as your SO likes these movies! We do include a drinking game to make it even more interesting)


Play this Christmas playlist when you are spending time at home decorating or cooking a special meal for that perfect winter date.


Winter date ideas- Rockefeller Center Tree NYC
Winter date ideas- Rockefeller Center Tree NYC


  1. Visiting the city sights

Or town sights. Act like a tourist in your  home town and celebrate the season. Do some window shopping and take it all in.

No matter where you live, you have those special places that you love to visit especially when they are all decked out with decorations and lights.


Visit the Cipriani Dolci  for a cocktail at Grand Central Station to people watch.


Winter date ideas- Grand Central Station NYC
Winter date ideas- Grand Central Station NYC


  1. Sleigh or Carriage Ride

Create your own perfect winter moment by going for a horse and carriage or sleigh ride. Obviously you will get some of the most perfect photos from your outing.

Pure romance!


  1. Ice Skating

Find an outdoor rink and enjoy! It’s like riding a bike, if you learned it as a kid, you will likely do just fine after a few minutes. It’s lots of fun to enjoy as a couple.

Every season we enjoy watching  the movie Serendipity. We recreate it most years by ice skating at Wollman rink at night and getting frozen hot chocolate from Serendipity 3. It’s a true magical NY moment.

While there are many places to ice skate in the city, Wollman in Central Park has the most amazing setting and is best visited during the week at the holidays. 

Rockefeller Center is a must see for the tree, the rink is usually insanely busy, so I would visit but not skate at that location. 


Winter date ideas- Rockefeller Center NYC
Winter date ideas- Rockefeller Center NYC


  1. Snowball fight

In the movie Elf, they have an iconic snowball fight which is so much fun! Try to recreate your own version of a snowball fight. In the movie they did some damage  (just don’t pack the snow too much so its rock hard!)


  1. Drive to various light displays

Check online for recommended places to visit in your area or neighboring towns. Plan a drive to see some local elaborate light displays or visit some decorated shopping areas. You may find some gems that you have never seen before.


  1. Visit a festive restaurant

There are some restaurants that are known to dress up at this time of the year. Maybe its a historic hotel that really looks amazing or a small cafe that is decorated like a jewel box. 

 You don’t always have to go for a dinner, you can go for dessert or just drinks & enjoy each other’s company.


Winter date ideas- Johns Pizza NYC
Winter date ideas- Johns Pizza Times Square NYC


  1. Find a holiday concert or show

Enjoying a holiday concert or play is a perfect winter date idea. Whenever you go to an event like this you will definitely get in the spirit of the season.

Many churches and synagogues offer holiday concerts to check out. 

There are many classic holiday shows available including seeing the Rockettes Christmas Spectacular at the Radio City Music Hall.


Winter date ideas- Radio City Music Hall NYC
Winter date ideas- Radio City Music Hall NYC



  1. Holiday or winter movie marathon

Make some hot chocolate, perhaps spiked and enjoy a movie marathon. Find your favorite holiday or binge worthy shows.

Netflix will be showing both classic and original movies this season, of course you can head over to Amazon for your favorites if you can’t find them on scheduled on TV.


  1. Visiting a tree farm

Cutting down your own tree is a special tradition to share. If you’re lucky enough to find a tree farm that has some food & drinks then that will make it all the more fun. 

Most of these winter date ideas are ready made for some fabulous photos opportunities.


  1. Attend a charity event

Whether it is volunteering at a food bank or dressing up for a holiday gala, Google to see what events are happening in your area. 

Do something good as a couple, while really enjoying the experience.


Winter date ideas- St Patrick's NYC
Winter date ideas- St Patrick’s NYC


  1. Romantic cooking date w/ cocktails

We designed many theme dates that include menus, conversation starters, games and crafts. There are two that have perfect menus for you to create together.

Fondue recipes with brown bread – Spicy chocolate fondue & spiked hot chocolate

Brie with onion jam + apples & honey

Mac & Cheese


  1. Snowmobiling & Sledding 

Renting snowmobiles can be so much fun! Better yet if you have some friends with snow mobiles that you can use or borrow. Many resorts will have some options for both snowmobiling or sledding.

You can also find a hill and have some fun. Sleds and snow tubes are easy to use are not expensive with the benefit of not needing a lot of snow to have a blast.


  1. Skiing & Snow Tubing

Most ski resorts offer both skiing and tubing. You don’t have to be a great skier to have a great time on the slopes. Whether you rent or have your own ski equipment there are ways to make it more affordable.

 Check out your local Groupon to find some deals that may be offered at your local ski resorts.



  1. Winter festival

Find a festive winter or holiday festival in your area or a nearby location. Usually these festivals are held in December, January & February.


  1. Think cozy! Find that perfect coffee shop or cafe

Everyone loves the smell of coffee. Take your date to a cozy coffee shop, grab a pastry  and better yet if there is a fireplace.

It’s simple and so comforting. This is especially nice as a morning date. Perhaps a cafe with a great brunch that would make a romantic date to remember.


  1. Holiday market

Visiting a holiday market is a great way to spend a  winter date night. Grab some hot cocoa or cider while roaming around the craft huts will this a romantic evening.

There are many festive Christmas markets in the US to visit and enjoy.

In NYC visit  the Columbus Circle & Bryant Park holiday markets.


Winter date ideas- Columbus Circle NYC
Winter date ideas- Columbus Circle NYC



  1. Visit a botanical garden

Enjoy an afternoon at a local botanical garden. Many botanical gardens have amazing holiday displays. If you are near Longwood Gardens they have spectacular displays that are a must see.

After the holidays the gardens are just as beautiful. Being indoors with the gorgeous greenhouse plants will  definitely lift you up and be a bright spot in the cold weather.


  1. Celebrate a tradition from you or your partners family heritage 

In our family we make Kiffles and Struffoli. One for our Austrian side and the other for our Italian. Find some traditions that you  would like to keep alive and create some of them together. 


  1. Take a walk in the snow

When the snow falls there is a silence that is very special. As long as the snowblowers are quiet! 

Everything looks different when covered in snow and you and your date could have a thoughtful conversation while appreciating nature.


  1. Romantic night in

We have everything that you need to create the perfect romantic night in at home. We include decor, menus plus many more details. 

So many ideas for you to choose from to bring an extra dose of romance to your relationship.


romantic night at home


  1. Winter photo shoot

Each one of these winter date ideas creates picturesque settings for photos. Some tips for a successful photo shoot can be found here.

Use the photos in a special album or for posting on your Instagram. We have Instagram captions to use that are sentimental and sweet to add to your photos. 


Winter date ideas- photo shoot


  1. Holiday Traditions

We all have holiday traditions that we enjoy. But creating traditions as a couple will be something that you will treasure every year.

  1. Making a favorite cookie together.
  2. Craft a new ornament each year.
  3. Creating a Christmas Eve for just the two of you (or any holiday celebration that you can make special for you both as a couple.)
  4. Take time to talk about your goals & dreams for the new year. Maybe write them down to read at a later date.


  1. Holiday cocktail trail

Create your game plan before you head out  and decide what you would like to sample at different restaurants. Whether it is cocktails, apps or desserts. 

You could also visit one place that is famously known for desserts and another for interesting appetizers. The idea is to do something different for the fun of it!


  1. Couples game night

We have 100’s of fun questions to ask  to inspire interesting conversations as part as your game night. We also chose some favorite couples games for you to choose from.

 If you have a favorite game that you haven’t played in a while, now is the time to bring it out for an evening of fun.

This laid back date night would be great with pizza & beer or any other drink of choice.



winter date ideas- weekend cabin getaway


  1. Plan a cozy couples getaway

Whether its a day trip or an overnight getaway the key is to savor your time together.


A cozy cabin in the mountains, a luxury spa trip or a charming B&B. There are many specials that are available at this time of year especially if you get a black Friday or cyber Monday deal.

Spending some intimate time together will be a terrific way to reconnect and recharge.


Conclusion Winter Date Ideas


Enjoying any of the dates here will create special moments to remember for a long time.

The goal is always to find ways to keep that spark alive. 


Sometimes in the winter we tend to just want to hibernate. While this can create wonderful moments, taking the time to plan something special will make  wonderful memories. 

Enjoy these winter date ideas! Cheers 😊


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