One of the Most Romantic Getaways in Illinois
If there’s one place for romantic getaways in Illinois that goes far beyond the rest, it’s our extraordinary Galena Bed and Breakfast. We all know that romantic getaways are special and a necessary part of any great relationship. They offer you a time to slow down, forget all of the stress of day-to-day life, and give you a chance to reconnect and rekindle that flame.
As important as it is to plan weekend getaways, it also matters where you choose to spend them. There’s truly nothing better than our romantic Bed and Breakfast in Illinois. The town of Galena itself has long been considered one of the most charming and romantic weekend getaways in Illinois for couples, filled with plenty of great things to see and do. Whether your idea of a perfect getaway is dining out, attending events, getting adventurous, or just shopping and browsing downtown stores, you’ll find that and more among the top Galena, IL things to do.
When it comes time for romance, no one does it better than Jail Hill Inn, considered by many to be one of the most romantic Illinois getaways. We have been rated the #1 Bed and Breakfast in the country and the #2 Bed and Breakfast in the world, let alone the best in Galena, and it’s precisely because of the incredible hospitality and romantic ambiance that we provide for our guests. From the moment you walk through our doors, you can expect an unparalleled lodging experience. Book one of the most romantic getaways in Illinois today!

Romantic Getaways in Illinois Start in Galena
It can be hard to truly disconnect in a world filled with distractions around every corner and with nearly constant notifications from phones and computers. This isn’t the case when you’re in Galena, though, and that’s what makes it such a wonderful destination for romantic getaways in Illinois.
From the moment you arrive in Galena, you’ll feel as though you’re living in an entirely different time and place. With its historic charm on display along Main Street and endless natural beauty in the surrounding countryside, there’s so much to enjoy about Galena that you’ll forget all about the busy world you left behind.
Between the beautiful natural surroundings, the incredible wine, great date-night restaurants, and plenty of fun attractions and things to do, there’s plenty to love about romantic weekends in Galena. Here are 8 of our top recommendations to enjoy your romantic getaways in Illinois:
- One of the best ways to enjoy your romantic getaways in Illinois is by wine tasting – and there are several great ones nearby. Enjoy wine tasting at Galena Cellars Vineyard and Winery, Massbach Ridge Winery, Fergedaboudit Winery, and Rocky Waters Vineyard & Winery.
- If wine isn’t your thing, we also recommend visiting nBlaum Bros Distillery, Galena River Wine & Cheese, Ms. Kitt’y Grape Escape, and Galena Brewing Co. for great drinks and a fun atmosphere.
- Enjoy dinner at one of the most romantic Galena restaurants, including Fritz and Frites and Fried Green Tomatoes. If you’re up for a short drive, Dubuque is home to some incredible restaurants, including Brazen Open Kitchen and Bar, and a classic supper club experience at Timmerman’s Supper Club.
- Browse the shops behind the historic facade of Galena’s Main Street. There are more than 100 unique shops to explore, and it’s one of our favorite ways to enjoy a quiet afternoon during romantic weekend getaways in Illinois.
- Enjoy the views over a romantic picnic at Galena’s Grant Park– the view is magnificent!
- Talk a walk together down Galena River Trail, or head out to one of the incredible parks and nature preserves surrounding Galena, including Horseshoe Mound Preserve, Casper Bluff Land and Water Preserve, and the Valley of Eden Bird Sanctuary.
- Enjoy a scenic drive along the Mississippi River and through the beautiful backroads of Illinois’ Driftless Area.
- Watch an incredible sunset at Chestnut Mountain Resort after you’ve raced each other on their alpine slide or mountain biked across their trails.
- Attend one of the many exciting events in Galena – a fabulous thing to plan your romantic getaways in Illinois around.

Our Galena Bed and Breakfast is the #1 Couples Getaway in Illinois
Our luxurious guest suites and attention to detail set the perfect stage for romantic getaways in Illinois. Couples choose Galena as a great getaway in Illinois time and time again. Once you discover our Galena Bed and Breakfast, you’ll never want to stay anywhere else. Upon arrival in your suite, you’ll find chilled champagne and a custom box of chocolates waiting for you, kickstarting what is soon to become one of the most romantic weekend getaways you’ve ever experienced.
From there, dim the lights, crank up the music on our Bluetooth-enabled sound system, turn on the fireplace, and get cozy in our luxuriously plush Frette robes. In the morning, we’ll start your day off right with a gourmet, 3-course breakfast. Is there anything more romantic than breakfast in bed? In the afternoon, enjoy more treats with our wine & cheese trays, delivered fresh to your room. It’s the perfect snack for afternoons and even late evenings.
In between those hours, how you make use of your time in Galena is entirely up to you. Whatever we can do to make this destination at the top of your list for romantic getaways in Illinois, we’ll do. Gracious hospitality and attention to detail are our specialties. We’re confident that one visit here is all it will take to make Galena your special place. Discover why our romantic Bed and Breakfast for couples is one of the top romantic getaway destinations in the Midwest. Book your room at our Galena Bed and Breakfast today!