1. Sand Valley Golf Resort, Nekoosa, Wisconsin
Distance from Milwaukee: 170 miles (about 2 hours, 45 minutes) by car
This 12,000-acre resort is home to Scandi-style rooms, an Italian-themed fine-dining restaurant and a buzzy bar with a view of the sand dunes, as well as the main feature: four golf courses. If tee time’s not your jam, there are marked hiking and fat-mountain-bicycling trails to explore, as well as bocce-ball courts and lakes for swimming. Also offered on property is glow golf (night golfing), and the resort is pet-friendly, too, so there’s no need to drum up a pet sitter: just bring the dog along.
2. Saugatuck, Michigan
Distance from Milwaukee: 245 miles (about four hours) by car
To reach this posh resort town on the other side of Lake Michigan, you have two options: battle Chicago traffic or take the Lake Express Ferry, which dumps you off an hour North. The newest lodging spot is the 11-room Wickwood Inn, owned by Chicago interior-design firm Soucie Horner (yes, it’s fancy but also like you’re staying at your cool cousin’s lake house). Scaling the dunes at Saugatuck Dunes State Park is a must, as is poking into the town’s many art galleries (such as J. Petter Galleries, spanning several adjacent buildings) and boutiques, as is grabbing a carrot-cake latte from Woosah and Outside Coffee (if you love camp-apparel and clothing, this is your place to shop) and renting a vintage, candy-colored electric boat from Retro Boat Rentals.
3. Cape Cod, Massachusetts
Distance from Milwaukee: Two-hour flight, then 88 miles (about two hours) by car
If you’re not familiar with this part of the country, there are three distinct vacation areas: Cape Cod, Nantucket and Martha’s Vineyard. Cape Cod is the only one not an island (hence, no ferry or plane ride necessary). You can just rent a car at Boston’s Logan International Airport and head Southeast. Ocean Edge Resort & Golf Club offers a resort vibe—including lobster rolls and lobster quiche, plus an intimate spa with beach-y decor—and is right on the sand in Brewster, and down the road from Brewster Store, dating back to 1866, as well as Cape Cod Museum of Natural History and Cape Cod Museum of Art. Nearby towns include Chatham, home to Chatham Lighthouse and adorable boutiques.
4. Door County, Wisconsin
Distance from Milwaukee: 180 miles (about three hours) by car
If you’ve been to Door County more times than you can remember during the summer months and are looking for something new, the 15-room Fresh Coast Motel in Fish Creek is a revamp of a 1940s property that opened its doors last month. Cultured is celebrating its second season in Sister Bay with just-out-of-the-oven bagels, five flavors of focaccia, sourdough bread and sandwiches. Then, in tiny Ephraim, a new restaurant – Anatolia – is solely focused on Mediterranean and Turkish cuisine, and founded by an Azerbaijan native, serving everything from spanakopita to baklava. That said, a trip to Door County isn’t complete without visiting the classics, such as Wilson’s Restaurant and Ice Cream Parlor, dishing up ice cream in Ephraim since 1906.
5. St. Petersburg, Florida
Distance from Milwaukee: 2 hours and 35 minute flight, then 20 miles (about 30 minutes) by car
With so many direct flights to Tampa, the travel time to this region of Florida is not that much longer than driving to Door County’s Northern tip. Go big by booking at The Vinoy Resort and Golf Club, celebrating its centennial this year and hosting fun experiences on property like afternoon tea, straddling the best of both worlds: a resort setting within walking distance to four art museums (Museum of Fine Arts, Museum of the American Arts and Crafts Movement, The Dali (Salvadore Dali Museum) and The James Museum of Western and Wildlife Art) as well as many waterfront restaurants.
6. Honolulu, Hawaii
Distance from Milwaukee: Varies, but will likely take most of a day to fly
Despite summer being Hawaii’s high season, there’s a lot of hotel rooms in Honolulu, particularly in walkable Waikiki Beach on the island’s Southeastern shoreline where fun dining spots are within a few blocks. Outrigger Reef Waikiki Beach Resort is a rare hotel smack-dab on the beach in Waikiki Beach and with a restaurant by a James Beard Award-winning chef (Peter Merriman) called Monkeypod Kitchen, serving up Mai Tais with beach views. Given that Honolulu is a big city, there’s something for everyone, such as art aficionados (Honolulu Museum of Art), history buffs (Pearl Harbor National Memorial) and outdoor-adventure lovers (hiking Diamond Head State Monument).
7. Nassau, Bahamas
Distance from Milwaukee: Varies, but will likely take five to seven hours of flying time
If Caribbean travel seems intimidating, and you’re not sure if an all-inclusive is right for you, Baha Mar is a development with three resorts that are not all-inclusive resorts, and yet everything is all in one place: SLS Baha Mar, Rosewood Baha Mar and Grand Hyatt Baha Mar. There’s also a casino, waterpark, and 45 bars and restaurants. Resident flamingos and an art studio hosting classes in figure drawing and landscape painting are two perks you’d be hard-pressed to find at most resorts. As well, there are two spas and a bunch of outdoor-recreation activities, from golf and mini-golf to bocce ball and croquet.
