I’ve always adored the magic of themed hotels—they’re playful, indulgent, and oh-so-romantic. Imagine us taking a little road trip together, slipping away to one of my favorite spots like the Don Q Inn outside of Madison, the Atlantis in the Dells, or the Sunset Inn in Illinois. Each offers a room with its own special charm—perfect for escaping reality.

If you’d rather not leave Milwaukee we can always book a stay at the Saint Kate—an artsy boutique hotel right downtown.

I’ll bring the candles and bath oils so we can soak together in a jetted tub before melting into soft sheets. There’s something deliciously naughty about mirrored ceilings, and I can think of no better way to enjoy them than in the arms of a lovely gentleman who knows how to spoil me.

$1,500 for the night, plus hotel and dinner on you.

There’s something so romantic about boarding a train together—watching the scenery blur by as we slip into our own little world. Let’s take a trip to Chicago, where you can whisk me off to the Art Institute to lose ourselves among the masterpieces. As an art student, I could happily spend hours wandering the galleries, sharing which pieces inspire me and listening to what stirs you.

Instead of rushing back, let’s spend the night in the city—at the historic Palmer House or the charming Ray’s Bucktown B&B. After all, what could be sweeter than ending such a dreamy day curled up together in a beautiful room?

$1,500 for the night, plus hotel and dinner on you.

I’m a country girl at heart, so a simple, sweet date outdoors always delights me. I’ll pack us a basket full of charcuterie and meet you by the water with my fishing pole in hand. We’ll cast a line, drink a beer, and let the day stretch out slow and easy.

After a long, lazy day in the sun I’ll be flushed, glowing, and more than a little worked up. By sunset, I won’t just be ready for a picnic—I’ll be aching for something more indulgent, something only you can satisfy…

$1,000 for the day