From Our Blog

The Best of the Best in Galena

Weekend Winery Getaways Near our Galena Bed and Breakfast

Before we get to the busy holiday season, it’s time to plan a weekend winery getaway in Illinois, and our Galena Bed and Breakfast is the ideal lodging for the adventure. We’re located steps away from downtown Main Street where you’ll find a few choice tasting rooms, as well as the nearby winery and vineyards for a Galeana wine tour. While as a guest at our Galena Bed and Breakfast, you’ll also get to indulge in our wine and snacks service, brought directly to your door, and the perfect mid-afternoon reprieve before your evening adventures.

Jail Hill Inn is one of the country’s highest-rated bed and breakfast experiences (in 2019, we received the honor of the number one B&B in America!). Not only is our historic building unique and meticulously maintained, but you’ll experience a level of service from our Innkeeper and staff that is unparalleled. The morning meals are delectable with generous portions and perfectly brewed coffee. The six spacious suites exude luxury with king beds dressed in fine linens, spa-grade en suite baths, and beautiful furnishings that whisk you away. Staying at our Galena Bed and Breakfast is the ultimate addition to a weekend wine getaway.

Start planning your next adventure in Illinois, and book Jail Hill Inn today!

Galena Bed and Breakfast

Fantastic Wine Tasting near our Galena Bed and Breakfast

As a guest at our Galena Bed and Breakfast, you’ll be within walking distance of a handful of downtown Galena wine tasting options. There are local wine tour options or easy self-guided routes for exploring the wineries in the surrounding areas. It’s the perfect weekend wine getaway from Chicago, and we would love to host you.

Here are five ways to enjoy a weekend wine getaway in Galena:

  • Galena Cellars: There are two ways to experience the wines of Galena Cellars: the downtown tasting room and the countryside vineyard just about ten minutes from our Galena Bed and Breakfast. The tasting room encompasses three floors of the historic downtown brick building offering flights of their locally grown wines, tasty small share plates, and live music.
  • Massbach Ridge Winery: This local Illinois winery also offers a downtown Galena tasting experience, as well as a vineyard tour just over 30 minutes from our Galena Bed and Breakfast. Pop into the tasting room on Main Street
  • Galena River Wine and Cheese: This local wine and cheese shop is one of our favorite businesses in downtown Galena (we feature their products on our afternoon tray service). The spacious store has an impressive selection of wines from around the world, olive oil tastings, a large cheese case with exciting finds, and great gifts to bring home with you.
  • Stone Cliff Winery: If you happen to make it out to Dubuque during your stay, check out this winery in the historic Star Brewery building along the Mississippi River. Grab a spot under the hanging flowering baskets on the patio or inside at the bartop.

Galena Bed and Breakfast

  • Galena Wine Tours: Perhaps one of the best ways to experience a weekend winery getaway in Galena is to book a wine tour with this local company. These knowledgeable and friendly guides will take you through the Upper Mississippi wine region, giving an incredible insight into the cold weather varietals grown here. Better yet, they take care of your transportation so that you can focus on tasting the vino without a care in the world. After your weekend winery tour, we’ll await your return at our Galena Bed and Breakfast with our afternoon tray service of housemade sweet and savory treats.

Galena Bed and Breakfast

Relaxing Spaces at our Galena Bed and Breakfast

Every suite at our Galena Bed and Breakfast is 700 to 800 square feet of luxury—when we designed the layout of the Inn, we made sure that each room offered a seating area, spacious en suite bath, and elegant sleeping quarters. Our custom-made furnishings, artwork, and attention to detail create a space where one can entirely relax and unwind. While we encourage using your time to unplug, each room has a 43-inch Samsung Smart TV and Bluetooth-enabled sound system. Join us in Galena for your next weekend winery getaway, and come see for yourself why we’re one of the best bed and breakfasts in the country.

Head over to our reservations calendar and book your next stay today!

Scroll to Top

Give The Gift of Jail Hill Inn This Christmas

Give your loved one a very special gift of a stay at Jail Hill Inn .  We offer gift certificates in many amounts.