How to Plan a Perfect Staycation in Madison

Madison staycation

By Shelby Deering | Photography courtesy of Destination Madison, © Focal Flame

Going on a vacation to a new place is always exciting, but it can be just as fun being a tourist in your own town. Perhaps there are areas of Madison that you are longing to explore a little more—there are four lakes here after all, waiting to be discovered. From fresh restaurants to standby favorites, activities in the water to near the water, to places that are (slightly) off the beaten, lakeside path, here’s the ideal Madison itinerary from Friday to Sunday.


12 p.m. To kick off your perfect lakeside weekend, start at The Boathouse at The Edgewater for lunch. Arrive by boat and anchor it at The Edgewater Pier, or plan to enjoy downtown on foot before and after lunch. Sit right next to the water, watch the sailboats drift by and keep it light (plan on dessert later!) with coconut shrimp and parmesan truffle fries.

2 p.m. As a Madisonian, or someone who lives nearby, you’ve probably already visited the Terrace at the University of Wisconsin-Madison’s Memorial Union. But have you ever truly sat in one of the iconic chairs without having somewhere else to be or grabbing a bite as you head to your next destination? If not, it’s an idyllic way to spend a Friday afternoon. People-watch to your heart’s content, pet some dogs and soak up flawless waterfront views. And, don’t forget to pick up some Babcock Dairy ice cream from Daily Scoop.

4 p.m. For the full campus-meets-lakefront experience, walk from the Memorial Union to Picnic Point along the Lakeshore Path. As you listen to the waves from Lake Mendota, meander along the path until you reach Picnic Point, Madison’s iconic peninsula that happens to be one of the best spots in town for sunset viewing.

7 p.m. Not far from campus, end your evening on a high note at a rooftop locale. Camp Trippalindee at the Graduate Madison Hotel has a summer camp vibe — something that seems all too appropriate for a lakeside weekend. With Lake Mendota vistas in the distance, park yourself in an old-school red chair, claim a fire pit and look at the stars as you roast marshmallows.


8 a.m. If you love the Dane County Farmers’ Market and still want to support local farmers while the Saturday market on the Capitol Square is suspended due to COVID-19, order goodies through the WhatsGood app and pick them up at the Alliant Energy Center from 8-11 a.m. Simply drive through and farmers will place your fresh food right in your car!

9 a.m. It’s time to head to Lake Monona. Whether you’re biking, rollerblading or if you’re a long-distance runner or walker, circle the entire lake on the 11-mile Lake Monona Loop. Enjoy watery scenery next to the Monona Terrace and take in picturesque lakefront neighborhoods as well.

11:30 a.m. Once you’ve completed the loop and are back near Monona Terrace, head to La Kitchenette, a cute French café with stellar comfort food. It’s hard to narrow down what to try, so you’re on your own on this one. But, keep it light — there’s plenty more to do!

1 p.m. Get out on the lakes. There are several kayak or canoe rental spots in the area to see the sights from the water — Marshall Boats on Lake Mendota, Brittingham Boats on Lake Monona or Wingra Boats on Lake Wingra.

4 p.m. The convenient part of taking a staycation right in town is that after kayaking or canoeing all afternoon, you can head home to freshen up before a waterside dinner.

6 p.m. With views that are stunning both indoors and out, Paisan’s is a Lake Monona mainstay. Originally founded in 1950, its lakeside residence is its fourth locale and still serves up the same Italian specialties it did back in the day. Manicotti, mushroom alfredo, specialty pizzas with Paisan’s famous spicy cheese — you’ll be well-fed. And, their patio has great views and plenty of outdoor seating.

8 p.m. Conclude your Saturday night with a glass of Chateau de Cruzeau 2016 at Fresco, located on top of the Madison Museum of Contemporary Art.


10 a.m. Spend your Sunday morning trying something new on the water. Rent a stand-up paddleboard from Rutabaga Paddlesports or the UW-Madison’s Wisconsin Union, or take it up a notch with some stand-up paddleboard yoga. For something really new, take a log-rolling class with Madison Log Rolling on Lake Wingra.

12 p.m. Sure, you can be all about the lake, but for a change of waterside scenery, enjoy lunch at Breakwater on the Yahara River. Between two levels of patio seating, live music and tasty pub fare, you’ll experience weekend bliss.

2 p.m. After lunch, pretend you’re a kid again at the Henry Vilas Zoo. Polar bears, penguins and the university’s famous mascot (the badger!) are all on view.

3 p.m. With its proximity to Lake Wingra, take a walk from the zoo to Vilas Beach, where you can dig your toes into the sand and peacefully watch the waves.

4 p.m. End your weekend on a high note at the Lake Vista Café at Monona Terrace. It’s a perfect early-evening destination, with its rooftop gardens, local brews and pristine views of the lake Monona.

This article originally ran in the 2020 spring/summer issue of Lakeshore Living magazine, a Nei-Turner Media Group-owned publication.

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