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The Best of the Best in Galena

Plan the Best Romantic Getaway This Summer

Romantic Getaway Galena, IllinoisWhen people in the Midwest look for a romantic getaway destination, Galena is often the go-to place. Couples all across the Midwest are discovering Galena’s small town, romantic charm.  There is no doubt that love is in the air in Galena, a town practically built for the romantic in all of us. Galena is easily accessible, too, considered a “one-tank” getaway destination from several major cities, including Chicago & Milwaukee.  Book your room at our newly renovated, luxury Bed and Breakfast, and experience the romance of Galena this summer.

Summer’s Best Romantic Getaway

There are few better things to do this summer than bask in the warm Galena sun.  In no time at all, you’ll find your stress melting away.  Whether you like to hike, bike, boat, fish, horseback ride, take a hot air balloon ride, or simply spend the day talking and enjoying the beautiful scenery, this romantic and charming little town has something for everyone.

Dining Out

Great dining experiences are one of the simplest and often overlooked aspects of a romantic getaway.  Artisan dishes inspired from around the world are featured at many local restaurants, and farm-to-table hotspots will keep foodies come back again and again.  We love sending our guests to the friendly staff at Fritz and Frites, a wonderful French and German restaurant only a short 1/2 block away.  The Log Cabin Steakhouse, Galena’s oldest and longest running restaurant, is also an Innkeeper favorite.  If you’d like dinner with a view, we suggest taking in the breathtaking views at Chestnut Mountain Resort’s Sunset Grille.  For a unique dining experience, enjoy the masterful menu served up in a charming, historic church at The Holy Mackerel.  Other local favorites include Fried Green Tomatoes, Perry Street Brasserie, One Eleven Main, and Little Tokyo.

Wineries & Vineyards

Romantic Getaway Galena, IllinoisIf you long for the romance of Tuscany’s vineyard-covered hills, then you really must experience Galena’s wine country.  There are 4 beautiful vineyards nearby, providing the perfect backdrop for an afternoon picnic and/or wine tasting.  For breathtaking views out over the vineyards, head to either Rocky Waters Vineyard & Winery or Massbach Ridge Winery.  Fergedaboudit Vineyard & Winery is a boutique winery that focuses on dry-red-bold wines straight from their vineyards.  You also won’t want to miss your chance to take Illinois’ best wine at Galena Cellars Vineyard & Winery.


Reward yourself and your significant other with a luxurious massage or body treatment during your romantic getaway.  The added touch of indulgence will help you both to relax and focus on savoring this time spent together.  For the ultimate convenience, many Galena area spas offer mobile massage in any place you choose, whether it’s outside amidst breathtaking scenery, or in our private and luxurious guestrooms.  Guests of the Jail Hill Inn also receive special discounted services at Elle Day Spa, located just 3 blocks away from the Inn.


The old adage “A couple who plays together, stays together” couldn’t be more true, and the town of Galena is here to help.  There are so many activities to do in and around the Galena area, that we can’t possibly mention them all.  Here are a few fun ideas to get you started:

It won’t really matter what you choose to do in Galena.  All that matters is that you get here quickly, so you can enjoy a spectacular summer getaway.   Jail Hill Inn is Galena’s newest and finest Bed and Breakfast, conveniently located just steps from Galena’s Main Street.  Your romantic getaway will begin with a wine and cheese reception upon your arrival, followed by chocolates and chilled champagne in your room.  What follows will no doubt be charming getaway filled with fun.  Book your room at Galena’s best Bed and Breakfast today!


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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.