5 Fun and Toasty Sugar Date Ideas for the Winter

By Caitlin


Let’s be blunt: It’s freaking cold outside. You feel it, your sugar daddy feels it and you’re both feeling resigned to several months of hibernation and indoor vegging.

Except…that gets old. And there’s nothing like doing the same old boring routine to kill the passion in any arrangement – which is what you certainly want to avoid. Especially when there’s so many ways you could actually take advantage of this cold, cold winter to have fun and take your arrangement to new heights.

Here’s a few fun ideas to try this winter with your sugar daddy!

Spa & Hotel

Ah, a classic. This is always something fun to do in the winter. First off, with all the parties and events coming up to Christmas, who’s ever going to say no to a facial or a massage? The real fun in going to a spa with your sugar daddy is first taking full advantage of the heated indoor pool and if you pick a real winner, the hot tub!

Both always make for some sexy fun and they’re the perfect distraction from the bitter winter cold outside. The second major plus of going to a spa is that they’re typically in the most picturesque of places – the perfect setting for wrapping up warm and going for a walk through the snow with your man.

It means you can also round off your day by scurrying back to the hotel, putting on a fluffy white robe and enjoying a nice hot shower and a glass of champagne.

Tip: If you can find a spa with a novelty aspect, that makes it even more fun. Take a page from the Japanese and look for an onsen facility in your area!

Ice Skating

Come on, you didn’t think we were going to write an article about winter dates and not include ice-skating. It’s the ultimate winter activity and fun for everyone from beginners to professionals. It also gives you the chance to show off your skills or let your man show you the way around the rink.

A lot of ice rinks will have other activities around it too, think Winter Wonderland displays and hot chocolate stands. There’s always such an amazing atmosphere and you can spend a beautiful night strolling around, soaking it all in.

Romantic Carriage Ride

This is another must for winter. It can seem a little cliché but it’s a really romantic night and the cold is always a good excuse to snuggle into your man. I did it twice in New York and it was so much fun!

The first time I did it, I was with a sugar daddy I had been seeing for about a year so it was extra special as it was a kind of anniversary for us. We obviously got coffee and hot chocolate beforehand as it was absolutely freezing but once we got there, I found out that he had arranged a bottle of champagne, chocolate and fruit inside the carriage.

We bundled up and snuggled in the blankets and it was genuinely one of the most romantic dates I’ve ever been on. The second time I went, it was during the day but we went through the park and it was just as beautiful as doing it at night. We got to see the park covered in snow and went for a lovely dinner afterwards to warm ourselves back up.

Cosy Night In

This is one of the most simple, but one of the best, dates you can organize. There’s loads of things that remind me of winter but a cosy night in is definitely near the top of my list. The best thing about these kinds of dates is that you can tailor it to suit yours and your sugar daddy’s tastes.

I’d recommend ordering in his favorite food and also stocking up on alcohol – a good bottle of wine or his favorite beer works great.

Whenever I host these kind of dates, I also always make sure I have some ingredients for some sexy fun later that night. I usually like to get ice cream and chocolate and then you can feel free to get creative!

Next, I’d light a fire and bring some blankets in from your bedroom – this will allow you both to get nice and comfortable. Lastly, select your favorite movie (bonus points if you manage to find a Christmas one) and enjoy your night. An inexpensive way to give your sugar daddy a night to remember!


I debated including this one in this list but who doesn’t love an excuse to go shopping? Your sugar daddy will most likely be feeling a lot more generous around the holidays too, meaning there’s even more opportunities to get that purse you’ve had your eye on.

Christmas means a ton of parties and events you have to attend so try mentioning that you need a couple of new outfits or let him know you have a great idea for your Christmas present this year.

Your sugar daddy should want to spoil you and you might as well get a gift you’ve been wanting! However the same goes for him – he probably also has parties to attend so be sure to mention you’re keen to go shopping for him as well. What guy doesn’t love an ego boost?

Going shopping also means that you’ll get to take a walk around all the stunning Christmas lights and then you can round off your day with a lovely meal. Win-win!

This post is brought to you by one of our contributing SB writers, Aly, aka The Travelholic Sugar Babe. You can check out her sugar baby story here!

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