A Perfect Couple Of Grand-Gesture Trips For Valentine’s Day

Grand Geneva Resort & Spa
The heart-shaped lake at Grand Geneva Resort & Spa in Lake Geneva, Wisconsin

Grand Geneva Resort & Spa (grandgeneva.com) in Wisconsin wasn’t built for romance. It originally opened in 1968 as the country’s first Playboy Club-Hotel, an hour away from the Playboy Enterprises headquarters in Chicago. Hef entertained Bob Hope and Sonny and Cher, who arrived via the resort’s airstrip. Waitresses dressed like bunnies. And a pond was shaped like the famous rabbit logo.

All of those things have changed, but the beautiful property with an opulent Frank Lloyd Wright Prairie-style lodge is still an indulgent retreat, and the pond has been turned into a heart. For Valentine’s Day, you can arrange for a message to be written in the snow on the pond and take a helicopter ride to surprise your sweetheart with an aerial view of it. The 15-character maximum is just enough to say, “Will You Marry Me?” but you might want to wait until the pilot isn’t around to pop the question. In that case, the resort will write your initials in the snow or let you choose a message. Unfortunately, “Paint Me Like One of Your French Girls” won’t fit.

The lake message is part of the $5,500 Written In Snow package, which also includes a night in the Grand Suite, a photo shoot on the resort’s grounds, and a five-course dinner. The Grand Suite is the hotel’s largest and has a separate living room, fireplace, soaking tub, and private balcony overlooking the resort’s rolling landscape. It’s available throughout February.

Grand Geneva Resort & Spa
Skiing at The Mountain Top at Grand Geneva Resort & Spa in Lake Geneva, Wisconsin

For considerably less (around $400 per night, give or take, depending on the day), you can book the Love Is Grand package for a junior suite and keep the plush king bed, fireplace, and lovely views; skip the dinner, photo shoot, and lake message; and receive a bottle of Cava sparkling wine and a $100-per-night resort credit to use on activities, like sleigh rides, horseback rides, skiing, ice skating, snowshoeing, and sledding, all on the property. It’s an easy drive to The Mountain Top slopes, and the resort’s trolley can take you up there, too—chances are the driver has some stories from the Playboy days. Grand Geneva has a full spa and a large fitness center with a rock-climbing wall, pickleball, classes, and indoor tennis courts.

Lake Geneva is also one of the North American locations of the Ice Castle, a winter installation with rooms to explore, a slide, and an ice throne. Tickets are hot sellers, so if you want to go, check availability before booking the resort.

Bottleworks Hotel room
Bottleworks Hotel

Closer to home, the brand-new Bottleworks Hotel (bottleworkshotel.com) also has tempting Valentine’s Day packages starting at $264 per night. Love & Luxe includes champagne, truffles by the in-house chef, valet parking, late checkout, and a $100 credit for in-room dining. There’s no sexier hotel in town—dramatic dark-gray hallways with contemporary art and glossy cherry-red room doors set the tone. If you manage to extract yourself from bed, there’s a movie theater and some excellent shopping within the Bottleworks District. On February 8, the W Nail Bar (thewnailbar.com) is opening at the hotel with pampering pedicures and manicures using only all-natural and organic products.