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Narrated trolley tour of Main Street in downtown Galena

Illinois

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

By: Amy Nance

Illinois Office of Tourism
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  • States:
    Illinois

Idyllic Galena is a vibrant, progressive community nestled along its namesake river in Illinois.

The city has been wooing travelers looking for a pastoral retreat since it was settled 1821. Today’s visitors still enjoy downtown’s characteristic 19th century architecture, unique shops, restaurants and scenic beauty. These favorite spots are all the invitation you’ll need to plan your own romantic retreat.

Jail Hill Inn

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.

Afternoon wine and cheese at Jail Hill Inn, a downtown bed-and-breakfast

Afternoon wine and cheese at Jail Hill Inn, a downtown bed-and-breakfast
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Inn at Irish Hollow

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. 

Romantic Inn at Irish Hollow, a country resort on a working farm

Romantic Inn at Irish Hollow, a country resort on a working farm
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Inn at Irish Hollow
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Galena Cellars Vineyard & Winery

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.

Grapevines at Galena Cellars Vineyard & Winery, open for tours and tastings

Grapevines at Galena Cellars Vineyard & Winery, open for tours and tastings
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Illinois Office of Tourism

Getting There

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.

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