8 Romantic Midwest Getaways in Minnesota & Wisconsin

by Jenny Javitch, Founder of Global Game Plan

Disclosure: Please note that some of the links below may be affiliate links, and at no additional cost to you, I earn a commission if you make a purchase. I am also the owner of Stillwater Airbnbs and a partial owner of a Grand Superior Lodge cabin, both mentioned below.

 

Looking for a charming small town, Midwest spa resort, or a romantic cabin getaway?  The Midwest USA is home to many hidden gems – you don’t want to overlook these spots when planning a romantic getaway with your significant other!  You have resorts on Gull Lake, Minnesota North Shore lodging on Lake Superior, glamping opportunities and romantic Wisconsin getaways in Door County and Bayfield. The Midwest has it all!

If you live in the middle of the USA you can easily create a romantic getaway in the Midwest, right in your backyard!  If you live farther away, it’s easy to fly into a nearby airport. Or, if you prefer, take a longer Midwest road trip and make your way to any of these destinations in Minnesota or Wisconsin.

Every Midwestern romantic getaway mentioned in this article is recommended based on my own personal trips with my significant other.  You may be celebrating an anniversary, planning a birthday vacation, honeymoon, mini-moon or baby-moon: we’ve got you covered!  Even if you’re only looking to get away from the kids or just want to spend time together, all of these romantic Midwest getaways are a great choice.

 

Romantic Getaways in Minnesota


Duluth & North Shore

 

Nearest major cities in Minnesota - by distance to Duluth:  Minneapolis (155 miles) and St. Paul (150 miles); additional distance to Minnesota North Shore lodging past Duluth

There is no shortage of Minnesota North Shore resorts for a romantic stay, and Odyssey Resorts has plenty of highly rated options from which you can select.  Gain access to hot tubs, heated pools, spacious rooms, and beautiful views of Lake Superior! Choose from the best of Minnesota’s North Shore lodging at Beacon Pointe in Duluth, Larsmont Cottages and Grand Superior Lodge in Two Harbors, and additional properties all the way up to Grand Marais.  If you prefer, the North Shore is also a fun place to go glamping in Minnesota. 

In Duluth you can walk hand in hand with your honey for miles along the newly updated Lakewalk, or along the rocky shoreline at any of the resorts or North Shore cabin rentals.  

In autumn you will see stunning fall colors; while in the summer, you can sail and sea kayak along Lake Superior or visit unique attractions like the pink rocks at Iona’s beach and the Split Rock Lighthouse.  During wintertime, enjoy the peaceful silence while you snowshoe or hike the winter trails, and ski or snowboard at Lutsen Mountains, the biggest ski area in Minnesota.

In any season, access to eight Minnesota State Parks plus the Superior Hiking Trail on the North Shore provides scenic access to nature at its finest. This includes waterfalls, rivers and gorgeous views of Lake Superior – the largest freshwater lake in the world.  Stop at local craft and gift shops, enjoy the local restaurants and beer, and grab a slice of homemade pie to round out your MN North Shore romantic getaway.

Brainerd Lakes Area

 

Nearest major cities in Minnesota:  Minneapolis (131 miles); St. Paul (142 miles); Duluth (110 miles)

There are so many year-round things to do in Brainerd, MN, and in the next-door town of Nisswa, MN.  It can get busy in the summer months, as it’s an awesome family vacation spot, so this is the perfect place for a Minnesota winter getaway for couples.

If you’re not a fan of winter, plan a couple’s trip during the spring or fall. However, winter enthusiasts will love a stay at either the Quarterdeck Resort or Grandview Lodge Spa and Golf Resort, two of the best Nisswa resorts on Gull Lake.  The Quarterdeck Resort has beautifully appointed suites decorated in a nautical theme, with large windows that overlook Gull Lake.  They come with a full kitchen and a living room area to relax, and there is also a restaurant on site.  At Grandview Lodge you can rent a cabin or stay in their modern North hotel. Don’t miss an opportunity to eat dinner outside in Grandview’s festive winter igloos, relax in their indoor and outdoor hot tubs, or visit their on-site Glacial Waters Sps for a couple’s massage. 

Spend some time shopping in Nisswa, eat lunch at the Main Street Ale House, and bring home a local souvenir from the cute gift shops. Oh, and don’t forget to book the romantic ice fishing house for two which will complete your romantic Midwest getaway.

Stillwater

 

Nearest major cities in Minnesota:  Minneapolis (26 miles); St. Paul (21 miles)

You will find the perfect escape in this charming town, one of the most romantic getaways in Minnesota.  Set on the scenic St. Croix River, Stillwater is known as the Historic Birthplace of Minnesota.  Experience the height of romance in a hot air balloon, glide down the river on a couple’s Venetian gondola ride or walk hand in hand or bike across the famous lift bridge.  Explore the local antique shops, hike the nearby trails, or attend a local festival in this four-season destination. 

Tasty food and drink options are aplenty in downtown Stillwater! You can enjoy a fine dining or a casual meal, drinks on a rooftop bar, wine tasting at a local vineyard, craft beer at their taprooms, ice cream shops and several old-school candy stores. 

Choose from a variety of lodging options and stay at a Bed and Breakfast, boutique hotel or charming Airbnb on Main Street.  Many a marriage proposal (and weddings) have occurred in this beautiful town. There are multiple local venues and vendors to create a special day for the couple and their guests.  You can’t go wrong by visiting this popular Minnesota romantic getaway. 

Crosby

 

Nearest major cities in Minnesota:  Minneapolis (131 miles); St. Paul (142 miles); Duluth (110 miles)

If you’re not a huge fan of camping, but you’re looking for something more adventurous than a typical hotel or lodge, try glamping in Minnesota at Cuyuna Cove.  In the spirit of “glamorous camping,” they make it easy and special with their glamping tents available May through October. Each tent is creatively named after local hot spots.  The bathrooms are amazing and the tents come with their own private hammock, firepit, cooking utensils and coffee maker! 

For active couples who love exploring the outdoors, this is a perfect Minnesota romantic getaway. Cuyuna Cove also offers boutique cabins if glamping in Minnesota isn’t your thing.  There is plenty to do in Crosby and the Cuyuna Country State Recreation Area, famous for its red dirt and mountain biking.  Rent bikes from the Red Raven shop, which also showcases craft coffee and tasty fruit smoothies, to explore the nearby Cuyuna Mountain Bike Trails.  At the end of your day, hike to Miner’s Point to watch a beautiful sunset.

Check out the building murals while walking around in the historic downtown, and don’t forget to stop at Victual for some lactose-free ice cream, other specialty foods and fun gifts.  Grab some dinner at the Iron Range Eatery and then a drink at the Hard Water Lounge (try the smoked old fashioned) or Cuyuna Brewing Company.

Romantic Wisconsin Getaways

Sundara Inn & Spa

 

Nearest major cities:  Madison (52 miles); Milwaukee (120 miles); Green Bay (144 miles); Rochester, MN (159 miles); Chicago (190 miles); St Paul (209 miles)

Although Sundara Inn & Spa is located in an area famous for its plentiful waterparks, this Wisconsin Dells spa couldn’t feel farther away from that type of atmosphere. Just drive right past all the waterparks in favor of a Wisconsin Dells romantic getaway and head to a very lovely weekend getaway at one of the best spas in the Midwest.

Offering spacious rooms and a variety of places to relax and read throughout the property, you can sip complimentary coffee or tea, enjoy some snacks and lounge around all day in your matching robes and slippers. You will feel welcomed in this space that includes multiple hot tubs and pools, a unique ritual bath process that’s not be missed before each of your treatments, and can anyone say swim up bar??

Since Wisconsin is a cold winter destination, you will be pleased to know that all of the resort amenities can be found on-site and inside the main building of the spa. In the summer they open an additional saltwater pool and multiple outdoor firepits, and the nearby trails allow you to explore and hang out on the grounds. This is truly a great experience year-round! 

Don’t forget to book a couple’s massage or a couple’s facial to make your romantic Wisconsin getaway extra special. You can enjoy tasty meals at their on-site restaurant so you don’t have to leave the grounds, but if you’d like a break, the local Del Bar steakhouse followed by some whiskey or wine at the Kilbourn Cork is a good time.  The next day, visit a local winery such as the Drumlin Ridge on your way home to Madison or Chicago, or wherever your next Midwest road trip destination may be! 

Door County

 

Nearest major cities:  Green Bay (44 miles); Milwaukee (156 miles); Madison (183 miles); Chicago (245 miles); St. Paul (314 miles); Minneapolis (322 miles)

Another popular Midwest road trip destination, a romantic getaway in Door County, is best experienced during the spring, summer or fall.  Whether you’re looking for a quiet cabin, bed and breakfast, cozy Airbnb, or just a place to enjoy over 300 miles of shoreline of Lake Michigan, Door County is the place to be.

Each town in Door County has its own vibe, with numerous tasty food and drink options, cute shops, and proximity to the water.  Enjoy activities ranging from a picnic on the beach or a fishing trip to a walk across the Sturgeon Bay bridge at sunset and a ferry ride to Washington Island where you can visit the lavender fields.  Outdoor adventurous couples will want to hike the Cave Point Lakeside trail at Whitefish Dunes State Park or take a Segway tour through Peninsula State Park.  Pick up some Door County coffee and tea as a souvenir of your romantic getaway in Wisconsin.  There are so many places to stay and activities to choose from that you can return again and again to relive your Door County romantic getaway. 

Bayfield & the Apostle Islands

 

Nearest major cities: Ironwood, MI airport (61 miles); Duluth (85 miles); St. Paul (212 miles); Minneapolis (226 miles); Green Bay (280 miles);

The best lodging in Bayfield, Wisconsin is the Wild Rice Retreat, where you can stay in a beautifully Scandinavian-designed tiny home (that’s actually pretty big).  Be sure to reserve at least one night of dinner at their on-site restaurant, and you’ll want to take advantage of the sauna experience and included classes like yoga on the deck. They also have other nature-filled amenities designed to help you relax.  As a bonus, this retreat is for adults-only!

A little north of Bayfield, if you’re into gambling with a view (of the lake!), the Legendary Waters Resort & Casino is worth a stop.  Nearby, you can drive the Bayfield Fruit Loop and choose from multiple apple orchards, cider drinking and wine tasting experiences.  

Be sure to grab some drinks overlooking the water in downtown Bayfield at the Bayfield Inn lakeshore deck.  They even have a Bayfield WI webcam if you want to check it out from home before you go!  Shop on Main Street and pick up some souvenirs at the Keeper of the Light gifts.  I’d also recommend you visit the Good Thyme restaurant in nearby Washburn for a Friday night fish fry, but you can visit any night of the week for delicious fare. 

If you’ve never been sea kayaking then taking an Apostle Islands kayaking tour will be an incredible way to explore Lake Superior that showcases the stunning views of the nearby rocks.  Take the ferry to Madeline Island to visit the local shops and explore the trails at Big Bay State Park. Trust me, this is a romantic getaway in Wisconsin you won’t want to miss.

Canoe Bay

 

Nearest major cities:  St. Paul (103 miles); Minneapolis (108 miles); Madison (221 miles); Green Bay (223 miles); Milwaukee (289 miles); Chicago (361 miles)

As one of the most romantic Wisconsin getaways, if you’re looking for a relaxing cabin retreat in the middle of nature and suited on acres of lakefront property, you’ve found it!  This couples-only romantic getaway, one of the resorts in Chetek, WI, offers a variety of beautiful accommodations to choose from. Whether it be a private cottage, wood-paneled guest room, or tiny home, you’ll have access to cozy fireplaces and beautiful views of the Wisconsin outdoors.  Canoe Bay is rated highly by travel magazines and is the only Midwest lodging member included in the Relais & Chateaux association  for good reason.

The food is amazing, with breakfast and lunch included in your stay. It’s comprised of fresh ingredients from an on-site garden that is also perfect for an afternoon walk.  Enjoy a smoke-free and pet-free experience in nature where you can use the provided paddleboards, kayaks or canoes on the lake. You can also take a walk around or appreciate the lakeview from your deck, or enjoy the sights from the lofted library – perfect for enjoying a book or just spending quality time together.  Although Wisconsin is a cold destination in the winter, this romantic cabin getaway near Chicago and other Midwestern cities is a cozy, year-round destination. 

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Ideas to enhance your romantic Midwest getaway:

Considering a trip outside of the Midwest? These are the factors to consider when choosing your vacation destination!

Destinations, U.S. TravelJenny JavitchWisconsin, Minnesota, Midwest, Couples, Activities, Glamping, Lodging, The Great Outdoors, Winter