Dreamy Date Ideas for Late Autumn and Winter

There’s something about autumn and winter dates that just have me hooked, more than any other time of year.

It’s that time of year when I’m thinking about cozy season. Dates together snuggled up and keeping warm in each other’s embrace, lingering kisses, long train rides and sharing cups of hot chocolate.

You may be wondering what the best ways are to keep cozy with your favorite companion as it cools down- so much exciting going on to choose from, especially with the holidays coming up!

And well, while I can’t speak for every companion: here’s a few of my favorite ways to keep each other company as the leaves finish changing and the lights go up around the city-


  • Cool weather glamping (perhaps in a heated yurt like this one)
  • Drive through holiday lights (or walk through!)
  • Christenkindl markets for mulled wine or hot cocoa, good food and cheer
  • Museums! Good for all year, but especially in times where the weather is a bit too chilly for enjoyment.
  • FMTY to warmer places
  • Cat cafes!

Planned Cold Weather Dates for Philadelphia and New York

And if you don’t want to do any of the work of planning (mood, I get it) here’s winter dates for us in Philly and NYC that I did all the work for you! You just have to reach out..

A cozy winter weekend in Philly:

Why don’t we make a weekend of it? We’ll start with a wonderful walk around Morris Arboretum, then spend the rest of the day and evening under the magical spell of the Christmas markets at the Christmas Village, hand in hand, hot chocolate and laughing like children.

On Sunday, let’s go ice skating before we cruise into the sunset on a romantic dinner cruise for two.



An erotic evening in NYC:

Setting the mood for our date, let’s have some fun at the Museum of Sex and go to the erotic carnival!

Once we’ve worked up an appetite, we can head for some delicious afternoon tea (maybe at Prince Tea) or some cocktails to share at one of my favorite speakeasies, before finishing our evening out at a Burlesque show, getting us both hot under the collar.

Life is short, so let’s start ticking things off our bucket lists! We’ll take photos to look back on with wide smiles and laughter, making each moment count now ❤️

Written by ellesutton

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