Called “the San Francisco of the Midwest,” Duluth blends urban cultural activities with easy access to outdoor activities. (Outside Magazine named it one if its “Best Towns Ever” in 2014.) Stay at Park Point, the longest freshwater sandbar in the world, or right downtown at Pier B, the new resort and restaurant with available slips. Along the downtown waterfront, you’ll find festivals and concerts at Bayfront Park and unique dining, shopping, and galleries in Canal Park. In this outdoor mecca, the paved Lakewalk extends for miles along the shoreline. Farther up the hill, you’ll find plenty of city parks with trails for hiking, running, and biking; recently developed trails by the Cyclists of Gitchee Gumee Shores have made Duluth’s wilderness a mountain biking paradise.
Thunder Bay, Ontario
The largest city on Lake Superior offers ideal amenities for boaters, as well as access to the arts, restaurants, and the incredible natural environment of this northern Great Lakes metropolis. From your slip at Prince Arthur’s Landing at Marina Park, you can wander through the lakefront’s outdoor art and sculptures, enjoy live concerts and movie nights, tour the Baggage Building Arts Centre, and even run through the wildly popular splash pad. About a half-hour drive from the marina, you’ll find Kakabeka Falls Provincial Park, where the second highest waterfall in Ontario plunges more than 130 feet and endangered lake sturgeon spawn at the base. Fort William Historical Park, one of the largest living historical attractions on the continent, recreates the days of the North West Company and the Canadian fur trade. And if you’re looking for a day cruise, head over to Sleeping Giant Provincial Park on Sibley Peninsula.
La Pointe, Wisconsin
If you’re looking for the easygoing pace of island life, you’ll find it on Madeline Island, the largest of the Apostle Islands. This haven is quite possibly the sweetest place to spend a weekend—or a month. Stay at the municipal marina, where a short walk down the main street will get you to shopping, restaurants, and galleries. You can rent kayaks and bikes, or just hang out on one of the laid-back sand beaches. Head over to Big Bay State Park on the other side of the island, where there are plenty of places to anchor, more sand beaches, and beautiful trails. While you’re there, take a class at the Madeline Island School of the Arts, ranked one of the top five arts and crafts schools in the United States.
The third largest city in the U.S. offers irresistible opportunities for anyone visiting by boat. Stay on a mooring in downtown Monroe Harbor and tour the many world-class museums, like the renowned Art Institute of Chicago, and parks like Millennium Park with the “Cloud Gate” sculpture, nicknamed “The Bean” for its iconic shape. A walk up the Magnificent Mile will take you to the John Hancock Center, where you can relax with a drink and take in the incredible view from the Signature Room on the 95th floor. Take the “L” or a cab to one of Chicago’s many neighborhoods and enjoy food from around the world. One of the best things about visiting Chicago by boat is that you may never have to leave the hook—the cityscape and the fireworks over Navy Pier may be all the excitement you need for a private Great Lakes getaway.
Port Washington, Wisconsin
Just north of Milwaukee, this port will woo you with its open-arms hospitality and art deco lighthouse, but you’ll stay for the fishing. Coho and Chinook salmon and lake, rainbow, and brown trout fill the charter boats. (The charter captains are even known to go fishing on their off days.) On the third weekend of July, almost 30,000 people flock to the lake shore for Fish Day. Right next to the marina you’ll find historic downtown Port Washington, featuring pre–Civil War buildings and a self-guided walking tour. Local dining and shops line the street. Shipwreck enthusiasts will love the Port Exploreum with its interactive Lake Michigan Table showing the locations of 50 shipwrecks between Milwaukee and Two Rivers, Wisconsin. The 1860 Light Station Museum features tales of a 19th-century lighthouse keeper.
The natural beauty of this port draws artists and art enthusiasts of all kinds. Named by USA Today as a “Best Small Coastal Town,” Saugatuck offers a multitude of galleries, studios, and art spaces to inspire you. The Saugatuck Center for the Arts (SCA) houses concerts, films, and professional theater productions in its 400-seat theater. The SCA also offers children’s classes, culinary and pairing events for adults, and a farmers market from May through September. The Chamber Music Festival of Saugatuck presents traditional and contemporary chamber music on Thursday and Friday evenings in July and August. Trek up Mount Baldhead for its exceptional views, take a dune ride tour at Saugatuck Dunes State Park, or wander the 10 miles of gorgeous shoreline, including renowned Oval Beach.
Port Stanley, Ontario
If beaches are your passion, Port Stanley offers some of the best sands anywhere. The popular Main Beach, recipient of a prestigious Blue Flag for its exceptionally high water quality, is well known as one of Ontario’s best beaches. Little Beach features shallow, well-protected waters, making it perfect for families with little swimmers. Erie Rest Beach, less than a half mile west of Main Beach, is quieter and more private. From the shore, view the 1937 King George VI Bascule Bridge and listen to live bands during the summer. The Elgin Hiking Trail, running 25 miles from Port Stanley to Payne’s Mills, will take you through forests and valleys. You can also visit the Moore Water Gardens, where they grow water lilies and aquatic plants for wholesale and retail and also offer tours, special events, and speakers.
Derived from a Lenape name meaning “river of many fish,” the Ashtabula River lives up to this description. At the point where it flows into Lake Erie, the river teems with bass, steelhead, yellow perch, and especially walleye. But Ashtabula may have an even bigger attraction these days: wineries. Once the busiest iron and coal shipping port on the Great Lakes, today the area is known for its Lake Erie shoreline and rich soil, making it a perfect microclimate for growing grapes. Ashtabula County grows 75% of the grapes grown in the state. What were once mainly crops of Concord grapes have been replaced by a wider range of grapes used in riesling, merlot, pinot, syrah, and chardonnay. You can visit 25 wineries in the county, including the century-old Debonne Vineyards, Ohio’s oldest and largest. The county also boasts Ohio’s largest collection of covered bridges.
Sarnia, Ontario and Port Huron, Michigan
At the juncture where Lake Huron flows into the St. Clair River, you’ll find amazingly blue water that looks more like the Caribbean than the Great Lakes. Welcome to the international sister cities of Sarnia and Port Huron. The water’s exquisite hue is the combination of a natural limestone lakebed, clear water, and the precise water depth through which reflected sunlight casts a larger range of blue rays. Joined by the suitably named Blue Water Bridge, the cities offer events for boaters all summer long. In July, people flock to see the start of the Bayview Mackinac Race, one of the most challenging freshwater yacht races in the world. In August, they come for the Sarnia–Port Huron International Powerboat Festival. And in September, Sarnia’s Jazz & Blues in the Village is the highlight. On first Fridays, make your way to Sarnia’s downtown for the “cultural walkabout” of food, art, and events. In Sarnia you can also tour the Stones ‘N Bones Museum and the Wawanosh Wetlands Conservation Area. Port Huron’s acclaimed museums cater to the nautically minded; visit the Huron Lightship Museum to see the last lightship on the Great Lakes–and the only lightship designated as a National Historic Monument. You can also tour USCGC Bramble, the Port Huron Museum, and the Fort Gratiot Lighthouse. But with water as blue as the Caribbean, you might not want to leave the flybridge.
For history buffs, there’s no better port than Kingston, Ontario’s oldest city and the first capital of Canada. There are more than 20 museums in the vicinity. Visit Fort Henry, where 19th century military life carries on with special ceremonies, events, and precision military demonstrations by the Fort Henry Guard, a group of university students trained as 1867 British soldiers. Take a guided tour of Kingston City Hall, built in 1844 when Kingston was the national capital, or visit the Bellevue House, where guides in period costume will show you the 1840 National Historic Site that once housed Canada’s first prime minister, Sir John A. Macdonald. In July and August, Confederation Park offers free concerts during the lunch hour and in the evenings. The port city is especially popular among boaters, as it sits midway between Toronto, Ottawa, and Montreal, and is the entry to the Rideau Canal and the Thousand Islands of the St. Lawrence River.
Prince Edward County, Ontario
If you’re looking for a night sky full of stars, the island that makes up Prince Edward County is your heaven on earth. With 500 miles of shoreline, the island is home to three main towns and a handful of smaller villages. A variety of marinas, beaches, hiking and cycling trails, wineries, and shops offer boaters plenty to do in a delightful rural setting. Explore Closson Road, called the “Golden Mile,” a meandering country road with farmsteads and pastures, wineries, and specialized farm shops. At Karlo Estates, a vegan-certified vineyard about 25 minutes from the Prince Edward Yacht Club, the dry stone bridge is a popular place for picnickers. You can also see one of Ontario’s natural wonders, Lake on the Mountain, whose gorgeous waters and unbelievable setting defy all geographical and geological theory.