1. Sand Valley Golf Resort, Nekoosa, Wisconsin
Distance from Milwaukee: 170 miles (approximately 2 hours and 45 minutes) by car
This 12,000 acre complex is home to Scandinavian-style rooms, an Italian-themed fine-dining restaurant, and a lively bar with views of the sand dunes, as well as the main feature: four golf courses. If departure time isn't your thing, there are marked hiking trails and mountain bike trails to explore, as well as bocce courts and lakes for swimming. Glow Golf (night golf) is also offered on the property, and the resort is also pet-friendly, so there's no need to hire a pet sitter—just bring the dog with you.
2.Saugatuck, Michigan
Distance from Milwaukee: 245 miles (about four hours) by car
To reach this chic resort town on the other side of Lake Michigan, you have two options: brave Chicago traffic or take the Express Lake Ferry, which drops you off an hour north. The most recent accommodation is the 11-room Wickwood Inn, owned by Chicago interior design firm Soucie Horner (yes, it's chic, but it's also like staying at your cool cousin's lake house). Climb the dunes Saugatuck Dunes State Park is a must, as is visiting the city's many art galleries (such as J. Petter Galleriesspanning several adjacent buildings) and boutiques, just like grabbing a carrot cake latte at Woosah and outdoor cafe (if you like camping clothes and gear, this is your place to shop) and rent a candy-colored vintage electric boat from Retro boat rental.
3. Cape Cod, Massachusetts
Distance from Milwaukee: Two hours 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 that is not an island (so no ferry or plane ride is necessary). You can simply rent a car at Boston Logan International Airport and head southeast. Ocean Edge Resort & Golf Club offers a resort ambiance — including lobster rolls and lobster quiche, plus an intimate spa with beach decor — and is right on the sands of Brewster, and down the road from Brewster Storedating from 1866, as well as Cape Cod Museum of Natural History And Cape Cod Museum of Art. Nearby towns include Chatham, home to the Chatham Lighthouse and adorable shops.
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 at Fish Creek is a revamp of a 1940s property that opened last month. Cultivated celebrates its second season at Sister Bay with freshly baked bagels, five flavors of focaccia, sourdough bread and sandwiches. Then, in little Ephraim, a new restaurant – Anatolia – is focused solely on Mediterranean and Turkish cuisine and founded by an Azerbaijani 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 Parlorserving ice cream in Ephraim since 1906.
5. St. Petersburg, Florida
Distance from Milwaukee: 2 hours and 35 minutes flight, then 20 miles (about 30 minutes) by car
With so many direct flights to Tampa, the travel time to this area of Florida isn't much longer than going to the northern tip of Door County. Go big by booking on Le Vinoy Resort and Golf Clubcelebrating its centennial this year and hosting fun on-property experiences like afternoon tea, straddling the best of both worlds: a resort setting within walking distance of four art museums (Museum of Fine Arts, Museum of the American Arts and Crafts Movement, The Dalí (Salvador Dali Museum) and The James Museum of Western and Wildlife Art) as well as numerous waterfront restaurants.
6. Honolulu, Hawaii
Distance from Milwaukee: Varies, but will probably take almost a day to fly
Although summer is peak season in Hawaii, there are plenty of hotel rooms in Honolulu, especially on walkable Waikiki Beach on the island's southeast coast, where fun restaurants are located a few blocks away. Outrigger Reef Waikiki Beach Resort is a rare hotel right on the beach at Waikiki Beach and with a restaurant run by a James Beard Award-winning chef (Peter Merriman) called Monkeypod Kitchen, serving Mai Tais overlooking the beach. Since Honolulu is a big city, there is something for everyone, such as art lovers (Honolulu Museum of Art), history buffs (Pearl Harbor National Memorial) and lovers of outdoor adventures (hiking Diamond Head State Monument).
7. Nassau, Bahamas
Distance from Milwaukee: Varies, but will likely take five to seven hours to fly
If traveling to the Caribbean seems intimidating and you're not sure if an all-inclusive package is right for you, Baha Mar is a development comprising three resorts that are not all-inclusive resorts, yet everything is in one place: SLS Baha Mar, Rosewood Baha Mar and Grand Hyatt Baha Mar. There is also a casino, a water park and 45 bars and restaurants. Resident flamingos and an art studio offering classes in landscape drawing and painting are two perks you'd be hard-pressed to find at most resorts. Plus, there are two spas and plenty of outdoor leisure activities, from golf and mini golf to bocce and croquet.
