Galena, Illinois Romantic Getaway: Charming Inns and a Vineyard Tour

There’s nothing gloomy about this 1878 former county jail, which has been converted into an elegant six-suite bed-and-breakfast in the heart of downtown. Retaining much of its characteristic charm, Jail Hill’s architecture features original wooden beams, vaulted ceilings and many of its antique 2.5-meter-high windows. Upon arrival, guests are met with wine and cheese, only to find champagne and chocolates waiting in their luxury suites, which are appointed with fine linens and a wet bar. Unwind on the deck in the evenings and wake up to a made-from-scratch gourmet breakfast in the gracious first-floor dining room. You can also buy a bottle of wine and enjoy it in front of the ornate gas fireplace in your suite.

Like something out of a fairy tale, this dreamy inn is set on an 80-hectare working farm surrounded by bucolic countryside. When you aren’t feeling cozy in one of the inn’s guest rooms or any of its five private cottages, you can explore the grounds and on-site trails, get a massage or relax by the campfire. Irish Hollow features a seasonal menu and a full country gourmet breakfast served every morning in the Old General Store, but you can also have breakfast in bed. The Inn offers food delivery straight to your cottage, as well as picnic preparations and the option to have your suite fully stocked with everything you need to make breakfast. 

Located just 18 kilometers from downtown Galena, this vineyard and winery gives guests a sense of remove in a picturesque setting where it’s all about the wine. It’s an ideal day trip for couples. Tour the grounds with the winemaker herself, learning about 22 different types of grapes and sampling from 40 varietals. The farmhouse has been turned into a tasting room where you can sip a glass while taking in the view from the wrap-around deck. Time your visit to coincide with one of several wine-centric events held on the property each year. Stay in the Cellars’ Vineyard Suite or Country Farmhouse to extend your tasty visit to this award-winning winery that’s been impressing guests for three generations.

Galena is a three-hour drive northwest from Chicago. Fly in to O’Hare (ORD) or Midway (MDW) airport, both of which welcome flights from hundreds of international destinations. Rent a car, and take Interstate 90 and US-20 to Galena. Around Rockford, you can drive the Old Stagecoach Trail for a more scenic route.