Bed and Breakfasts
© Buckingham Inn


As the Jackson Five spelled it out years ago—love is as easy as 1, 2, 3 and as simple as A, B, C. Deciding on a date night or weekend getaway may be a little tougher. Using the classic song as inspiration, read on for an alphabet’s worth of tips and ideas on how to spend time in Greater Madison with your loved one.


A romantic date night starts with the right restaurant serving amazing cuisine with a side of romantic ambiance. Madison’s culinary scene is adored by food critics and magazines, including Time Out Chicago, which recently ranked Madison as a “road trip for food-lovers.”  From nostalgic supper clubs to trendy bistros, Madison’s foodie scene will have your sweetie smitten!


Share the experience of handcrafted chocolate—you’ll be in for a real treat! Gail Ambrosius Chocolatier in the Atwood neighborhood specializes in single-origin dark chocolates, while Candinas Chocolatier in the heart of downtown imparts superior blends of rich flavors. Check out our Sweet Treats page for more sweet goodness like pie, cake and other desserts!


Take a tour of the city with your loved one at your side, and see the sights and sounds that encompass Madison’s charming character. Hop Head’s brewery tours literally give you a taste of the city, Madison Eats explores the area’s best eateries and Madison City Tours showcase the city’s ethnic roots and history. For a complete listing of the area’s tours, visit our Food Events and Tours page.


DUELING PIANOS                      
Do you love the nightlife? Madison’s entertainment scene is full of live, local music perfect for dancing, bellying up to the bar or cozying up in a booth. Couples connect at the Ivory Room piano bar for dueling pianos on Friday and Saturday nights.


Cold weather is no match for a love that burns bright! Spend the day together enjoying Madison’s winter sports (and use it as an excuse to cuddle up with hot cocoa and a fire afterwards). The city’s parks play host to ice skating, sledding, snowshoeing and cross-country skiing, and the more adventurous types will want to try snow kiting on one of the area’s five lakes.


Stroll through 16 acres of outdoor gardens and the indoor Bolz Conservatory on your next date at Olbrich Botanical Gardens. Smell the roses, feast your eyes on exotic flowers, or sit side-by-side while gazing at the beautiful Thai Pavilion. Another option for nature lovers is the UW-Madison Arboretum, the birthplace of ecological restoration (and many marriage proposals!). There are many walking trails, from wide and level paths to hilly trails.


Looking for a special gift for your loved one? Why not try Madison’s State Street, a pedestrian mall home to many local, boutique shops like Little Luxuries, which sells one-of-a-kind, unique gifts. Monroe Street also has many specialty stores like Orange Tree Imports, voted “Best of Madison” for more than 20 years. Read about our shopping centers, antique shops and more on our Shopping page. 


Need an excuse to get closer? Why not visit Cave of the Mounds, a dark and mysterious cave that may require some hand holding to navigate. This national landmark also hosts Fridays After Dark, a new series of themed events for those over 21. Each event includes a unique in-cave experience and a theme-related reception with a cash bar.

If you want to impress your date with your sophisticated knowledge of art, the Chazen Museum of Art is worth your time. In fact, the museum created this quiz to see how you’d fare on a stroll through their museum. If you score high, you’re ready for a night of impressionism at the Chazen!

Rubbing the nose of the honey badger statue at the entrance to the Supreme Court at the Capitol Building is considered good luck. Why not take it a step further and steal a kiss from your sweetie while touring the building? Experience the beauty and grandeur of Wisconsin’s Capitol building together with a free tour. The building, especially the scenic observation desk, is surprising romantic.


Our five lakes aren’t reserved just for summer. Many enjoy ice skating, ice fishing, snow kiting and other sports when the temperature drops. You can spend the whole day on Madison’s lakes—whether you’re looking for a sunset cruise with Betty Lou Cruises, or want to relax on one of Madison’s dozen beaches. Turn the romance up a notch with a sun-filled, relaxing day on our lakes!


Romance comes naturally with a candlelit moonlight snowshoe throughout the trails of the Aldo Leopold Nature Center. Hundreds of candles softly glow as you walk, plus you can snuggle up by a roaring bonfire afterwards. Even if you’re not in town during one of these moonlight walks, the center serves as a real treasure of natural beauty year-round.


Next time you visit Madison, consider a charming bed and breakfast. Located in the heart of downtown, The Livingston Inn was built in 1854 and was home to two Madison mayors. The Buckingham Inn is Madison’s newest B&B and a classically-restored 1911 residence located just steps away from the UW-Madison campus. These B&Bs and others are the perfect starting point for any romantic stay and booking a room is easy!


Madisonians love the color red. For many, it exemplifies their one true love: the Wisconsin Badgers. Cheer on the home team the next time you’re in Madison and you’ll fall in love, too! Badger fans are loyal, and it’s almost as fun to watch them as it is the sports teams. Plus, with many pre- and post-game options, you’re bound to have fun at USA’s Today’s top pick for best college football town.


When traveling, it’s exhilarating to find those hole-in-the-wall restaurants and secret hang-outs reserved for locals. Impress your travel companion by reading our like a local itinerary, which will give you the insider scoop on the places and things that create Madison’s unique culture.


Sure, it may be cliché to take your spouse for a day at the spa, but you’ll still win brownie points! Share a tender moment during a couple’s massage at one of Madison’s many spas and discover why Madison ranks among the best in the nation for quality of life.


If you have an undying love for movies, discover Madison’s theaters, which are home to much more than popcorn and soda. The Take Five Lounge at Marcus Point Cinema has dream loungers that provide maximum comfort and closeness, and Sundance Cinemas has a rooftop restaurant and bar that serves a tall glass of wine known as the “home pour.” Both theaters allow you to choose your seats when you purchase your tickets, plus you can enjoy food and beverage while watching.


Take your funny valentine to one of Madison’s comedy shows and give the gift of laughter! Ranked as TripAdvisor’s #1 nightlife attraction in Madison, the Monkey Business Institute improv shows create comedy by infusing audience suggestions. Another funny option is the Atlas Improv Company, voted “Best Comedy Group in Madison” by Madison Magazine.


If you’re searching for a non-traditional, wild way to spend the evening, catch a Mad Rollin’ Dolls roller derby bout. This fast-paced experience combines adrenaline and estrogen, sass and strength for a thrilling performance. The team plays at the Alliant Energy Center, which is also home to the Madison Capitols hockey team, another great contact sport!


…for more information? Check out the events calendar—searchable by category, date and location. Or visit the Things to Do page, chalk full of itineraries, free attraction ideas and more. Once in Madison, download the Visit Madison app for the latest information, including in-app features like “near me” or “call” to complete your planning process.