Island Getaways


Madeline Island

In island getaway fantasies, the sand is white, the ocean aquamarine, and the blazing sun so hot that an umbrella-topped cocktail is an absolute necessity. There are always palm trees, often a hammock, and sometimes thatched-roof huts with open sides to better draw the breezes.

There are breezes here, too, en route to my Lake Superior island getaway just off the coast of Bayfield, Wisconsin, albeit of the chilly variety. It’s mid-May, and I’m on the Madeline Island car ferry, holding my breath and clutching the rail every time the steel hull thunks over another chunk of ice. The strait looks as if a glacier fell from the sky and shattered into a million pieces.

This is the earliest I’ve ever ventured out to Madeline, the largest of the Apostle Islands at 14 miles long and 3 miles wide. It’s the only Apostle open to private ownership and commercial development (the other 21 islands are part of a protected national lakeshore), yet it tends to be sparsely inhabited until the summer residents and tourists arrive. Crowds peak between July 4th and Labor Day, when cool breezes off the lake offer respite from the humidity and heat.

This ferry passage is among the first of the 2014 season, and the boat is loaded with a dozen cars and even a horse trailer—its owner, clad in cowboy hat and boots, drinking a beer, is chatting up a guy in a suit on his way to officiate a wedding. In the winter, when Madeline’s population dips below 250, it’s linked to the mainland by an ice road, which is typically viable for about a month. Island crossings aren’t always so convenient; between the ferry and ice-road seasons, limited trips are made via a passenger-only wind sled. Neither is the passage reliably safe; last winter, three locals perished after falling through the ice.

Less than half an hour later, the ferry docks at Madeline’s hub, the tiny town of La Pointe, home to a post office, police/fire station, a few restaurants, art galleries, and one real-estate agent’s office that is itself for sale. Most seasonal businesses don’t open until Memorial Day weekend, and current traffic levels are so sparse that my husband and I see two drivers meet on the road, stop, roll down their windows, and engage in a lengthy conversation. The island’s slow pace and compact geography make it ideal for bicycle travel; in fact, we decided to make this trip without our car and just stuffed a change of clothes into our panniers.

Our first stop is the island’s most infamous: Tom’s Burned Down Cafe (, which looks like the aftermath of a tornado tossing a pontoon boat into a trailer park, or a grownup’s tree fort crashed to earth—scrap wood and pilfered street signs slapped together to create a big open deck with a bar in the middle.

We join a handful of regulars on wobbly bar stools and order a couple of Red Stripes. “Have you been to Mexico?” the bartender asks, warning us that the water isn’t yet turned on, so if we’d like to use the restrooms, we’ll have to do a bucket flush. Everything at Tom’s that appears to defy building and health codes probably does. So the story goes: After the original Tom’s burned down and its replacement surfaced, its namesake’s connections to political authorities encouraged regulators to look the other way.

Tom’s isn’t really a “café,” just a bar that serves pizza. Wild Rice Restaurant ( in Bayfield is the only area eatery that’s truly destination worthy—discriminating gourmands may want to pack a cooler when they come to the island. Still, there are better dining options than Tom’s. The Beach Club’s ( menu is mostly basic bar food, but its Lake Superior fish fry is terrific. The Pub ( has a more upscale menu than its name suggests, including scallops, steaks, and crispy pork belly, but not ordering the local trout or whitefish here  feels like a missed opportunity. Cafe Seiche ( takes the most contemporary approach to dining, offering a tightly curated menu focused on local ingredients and seasonal dishes.

Visiting with a few locals at Seiche, we get the sense that Madeline’s tourists aren’t so much embraced as endured by some (I’d repeat the term one barfly used, but it’s not exactly appropriate for publication). The attitude is understandable: Peak-summer visitors clog the streets, pack the restaurants, and leave little to the locals besides the real out-of-the-way joints such as the Island Oasis bar (715-747-3192), which has the vibe of your grandpa’s fishing shack—if he charged for his Miller Lights. As the Oasis’s second and third customers of the season, our experience feels less like that of tourists than anthropologists, observing a culture whose lifestyle exists in more isolation than would seem possible just a few miles from the mainland.

Madeline’s tourist infrastructure doesn’t offer a lot for entertainment, but island businesses recognize the limits of a locals-only customer base, and warmly roll out the welcome mat. Since Bayfield’s inns outnumber those on Madeline, most island visitors are day-trippers, stopping just long enough to have an ice cream cone and browse the art galleries—the Bell Street Gallery’s ( painting, pottery, and glass are exquisite. Those staying longer tend to be groups renting vacation homes and doing a whole lot of nothing: sharing meals and conversations, or meditating on the gorgeous views.

Making the 6-mile trek to Big Bay’s crescent-shaped beach is the best on-island activity (if you didn’t bring your own wheels, rent a scooter at Motion To Go, Out here, soft sand meets pristine, icy-blue water extending all the way to the horizon. It’s the prettiest spot on the island, and readily explored in one of the kayaks or canoes parked between the bay and the lagoon (some are rentable on the honor system, in character with the island’s easy-going style).

This is why we’ve come to Madeline: It’s less about the island itself than its liquid surrounds. The truly beautiful spots are out on the water, among the smaller, wilder Apostles. These islands offer the most peace and seclusion, with one drawback: If you want to wake up in their paradise, you’ll have to sleep in a tent.

If you don’t have your own boat, there are sailing charters, canoe or kayak tours, or day cruises to position you just between the lake’s majestic dark blue and the sky’s bright azure. From this vantage point, you can get a good view of the area’s famous sea caves, a honeycomb array of chambers and arches carved out of the striped red sandstone shoreline. The lake, as it turns out, is an artist, too, having created this spectacular Badlands on the water. • –RH


The Covington Inn, Harriet Island, St. Paul

Truth be told, Harriet Island is no longer an island. The channel that once separated it from St. Paul’s West Side was backfilled in the ’50s. We don’t mind fudging this one a bit however, because, c’mon: a retired towboat-turned-inn, floating on the Mississippi River in St. Paul for almost 20 years? How have you not heard about this place?

The Covington Inn’s four rooms are bigger than you’d expect, and each comes with its own fireplace, mini-fridge, and private bath. Appropriately nautical touches, such as brass fixtures and a skinny spiral staircase, are everywhere. The portholes in the Riverview Suite put you practically eye level with the river, and the original brass controls in the two-story Pilot House Suite’s upper lounge make it all but impossible not to play captain. 

The real selling point, though, has to be the unbeatable view. You can’t get any closer to the river than being on the river, and you’re directly across from downtown, with the Cathedral of Saint Paul peeking between buildings in the distance. Most rooms have attached outdoor space, and all have access to the large, shared deck, full of waiting chaises on which to plop down and river-watch.

Owner Liz Miller calls her seaworthy baby a “grab- a-six-pack-and-hang-out-on-the-deck kind of place,” urging guests to invite their friends to drop by or have a pizza delivered. Casual romance plays out nicely here, too, especially when it involves a walk or cab ride across the Wabasha Street Bridge for dinner and drinks downtown. Go all in and spring for the Romance Package: flowers, locally crafted truffles, and a bottle of wine or bubbly for 60 bucks.

Breakfast—baked French toast with caramel-apple sauce, fresh fruit, whipped cream, and sausage—is served between 9 and 10 a.m., further proof of the inn’s late-and-leisurely style. Early risers, rest assured that the coffee’s on and the Mississippi right out the window is a fascinating, if taciturn, companion. • –BT


Stout’s Island

From the shores of a lake near Spooner, Wisconsin, the boat ride to Stout’s Island lasts less than 10 minutes, but it rewinds the clock a century. Just up the boathouse steps and across a great lawn, guests encounter a stately, log-and-stone Adirondack-style lodge fit for a titan of the industrial era. In fact, this rustic retreat was built by an heir of what was once the largest lumber company in the world: Frank D. Stout commissioned the compound for his family (and service staff) to find respite from the sweltering Chicago summers. Construction cost a fortune—$1.5 million in 1915 dollars—but the resulting lodge and cabins, built with thick cedar timbers, wide plank floors, and massive stone fireplaces, possess a vintage grandeur impossible to replicate. It’s a rare case of powerful architecture hidden in relative seclusion. 

Stouts island

After Stout’s children sold the property, it was at times both left vacant and host to a youth camp before being seized by the government after its unscrupulous owner went to prison for embezzlement. But the island has emerged from hard times primed to be a luxe couples’ retreat. While antsy kids might want more activity than paddleboats and a swimming beach provide, those operating at a more relaxed pace can easily fill a weekend with romantic nature walks, tennis, leisurely meals, and fireside nightcaps. 

Stout’s current ownership has experience with historic properties (the developer John Rupp has preserved several St. Paul darlings, including W.A. Frost and the Saint Paul Athletic Club). Even so, the maintenance of the expansive, aged Stout’s is an immense undertaking, from weeding the clay tennis court to keeping the moss-covered roofs watertight. Early in the season, before the grounds are manicured, the pantry fully stocked, and the temporary staff up to speed, the challenges are more visible—like, what self-respecting Wisconsin bar doesn’t know how to mix an old-fashioned and have the ingredients on hand?
Admittedly, such disappointments are likely the result of guests having flipped too many pages of Martha Stewart Living or searched for images of “rustic-chic weddings” on Pinterest: The popularity of American heritage style has created fantasies of casual elegance that are far more difficult to curate than they appear. We now expect a simple breakfast of yogurt and granola to be presented with the perfectly imperfect aesthetic of the photographs in Saveur. (Stout’s house-made granola is, in fact, delicious, though the enthusiastic wait staff can’t quite match the kitchen’s polish.)

With a few tweaks, Stout’s could fully reclaim its original magnificence. Starting with a stylist’s edit of the 1990s-era cabins’ eclectic-chic décor, such that overstuffed armchairs with Southwest-print upholstery don’t compete with pink floral bedspreads. (And while you’re at it, cull the dog-eared tomes with Goodwill stickers from the lodge’s library shelves.) While Stout’s newer cabins are perfectly suitable, they lack the resort’s essence of historic luxury. There’s really nothing like spending a night in one of the rooms from Frank Stout’s era, lying on a canopy bed or looking up at a wood-paneled ceiling and imagining growing up here, on your own private playground. • –RH


The Nicollet Island Inn, Minneapolis

There’s a notable abundance of clinking champagne glasses throughout the Mississippi-facing dining room. It’s not unusual to pass a bride (or three) in the lobby. And the staff estimates that special occasions drive a whopping 9 out of 10 guest visits here. Translation: The Nicollet Island Inn is typically just an anniversary or two away from a 100-percent celebration rate.

Bring your fancies, because this party’s upscale. Damask wallpaper, floor-length draperies, and floral still lifes work with the 121-year-old building’s exposed brick and tin ceilings to create a historic elegance. Though each of the 23 rooms is unique, all come with a lovely view of the river, Nicollet Island Park, or the Minneapolis skyline.

As your views suggest, you’re in one of the Twin Cities’ most tourist-worthy locations. Right behind the inn, the compact, red iron Merriam Street Bridge connects the island to the cobblestone of the St. Anthony Main Riverfront District, which puts a Nice Ride bike rental station, Segway tours, a few river-facing restaurants, and St. Anthony Falls all within easy walking distance. The historic Stone Arch Bridge links St. Anthony to the Guthrie Theater, Mill City Museum, and greater downtown Minneapolis.

However, no one would blame you for remaining in your celebration bubble. The window-walled bar area offers views of the river and the park, often eclipsed by the sight of a horse-drawn carriage whisking away a couple hitched minutes earlier at the neighboring pavilion. The little piano lounge springs to life on Saturdays, and diners have been known to abandon their roasted chicken to slow dance right next to their tables. The outdoor patio’s a beaut as well.
People come from all over the Twin Cities specifically for the inn’s three- or five-course Sunday brunch, which also is included with several package stays. Choices include crème brûlée French toast, lobster bruschetta, and strip steak with fingerling hash. Just don’t forget the bubbly. –BT


Ludlow’s Island

If you arrive at the shores of Lake Vermilion to find a dimly lit parking lot and an empty dock, forget about relying on your cell phone for directions. Network service here is spotty; you’re better off resorting to last century’s technology, with the antique phone that instructs: “Crank hard for five seconds, lift receiver, and wait for answer.”

You’ll soon be connected to the on-call water taxi, a vintage wooden speedboat that’ll shuttle you to your cabin. All 20 of Ludlow’s cottages have lake views, a perk of island geography, and range in size from a cozy honeymooners’ suite to a four-story tower designed by SALA Architects. (Though the buildings were constructed throughout the decades, a wood-paneling and cabin-kitsch aesthetic endures that’s more forgivable during the deeply discounted low season than at peak pricing.) The resort staff can book you a massage, recommend the best pizza place on the mainland (the Vermillion Club, in Tower), and drop off a newspaper in the morning. Otherwise, they’ll leave you alone to explore the lake or simply relax. There’s no need even to carry your wallet—if you take groceries from the pantry or bait from the fish shack, you simply write your name in a notebook.

Ludlow’s has been a family-run operation for three generations, and is big on entertaining kids. Parents can safely lengthen the leash on older ones, knowing they can’t go far. And when the kids tire of leaping off the floating playground or taking part in planned activities (hikes, crafts, marshmallow roasts, rides on the resort’s amphibious car), they can spend a night on Ludlow’s tiny camping island, outfitted with a tent and sleeping bags. A safely adventurous separation is not something the kids will soon forget—and neither will their chaperones. • –RH


Big Island, Lake Minnetonka

“Grab my hand,” the guy said, in the heat of last year’s Fourth of July. “C’mon, grab my hand!” And the girl with the patriotic micro-bikini flopped aboard his boat like a tattooed walleye, yanked open her Stars and Stripes, and, as Kid Rock howled “All Summer Long” on a nearby stereo, jiggled her all-American assets. They’re the coin of the realm in Cruiser’s Cove, off Big Island, an alley of several hundred lashed-together boats that peels apart and reforms every weekend, like an endless sunburn.

Kim Kardashian partied here three years ago, with Kris Humphries and a posse of Eurotrash: “Like Vegas on the lake,” she tweeted. Maybe the truest thing she’s ever said. It’s a relatively safe place to play at vice, the chest-high water roiling with babes, beefcake, and the occasional bluegill. The boats are just expensive coolers.

A nature park opened on Big Island a few years ago, reclaiming a remnant of its native woods, free of invasive species—“It has the Boundary Waters vibe,” said a supporter, who perhaps had not been to the BWCA. The island is eroding from the waves of more and bigger boats; trees and bluffs are falling into the lake. But the island isn’t essential to the scene. It’s a buoy marking the spot. A good thing, because imagine if the party traveled, rattling windows and moralists alike. This way, it’s predictable. Like the moment the shy patriot bends over, a huge, pink bow tattooed over her rear—gift-wrapped—and jiggles again. If you want that, you know where to find it, all summer long. –TG


Treasure Island Resort & Casino, Red Wing

Don’t be fooled. The causeway, the lack of beach, the free shuttle that picks you up almost anywhere in the Twin Cities and deposits you at the door like driftwood—this doesn’t mean Treasure Island is a misnomer. An island is nothing if not an escape from reality. And Treasure Island is about as real as a coconut bra, at once enticing and weird. An island by reason of isolation, cut off from such mainland mainstays as the sun, smoking bans, and judginess.

Here’s what you do. You pull your Pontiac up to the valet, step into the hallucinatory clangor of the main slots hall, rimmed with ersatz Caribbean balconies, and check the monitor showing which games have recently hit big. The Legend of Gaucho, perhaps, or the Golden Monkey. You drop a couple hundo, go up two grand, lose it all four hours later before joining the buffet line, 80 people deep, for prime rib night, $16.95. Or, if you really lose big, the casino café offering chai tea pancakes, $7.29. Take a dip in the pool, catch Louis Anderson in the event center, try some late-night Bingo Gone Wild (drink specials, live deejay, “may contain adult content”). Repeat.

You’re thinking: What kind of sad bastard mistakes paradise for dropping coin at a casino? Listen: You could sit at the opera waiting for magic to happen or you could do it here, with a Bud and free soda, smoking your godforsaken lungs out. It’s a place where you can take major risks in public, and there are fewer and fewer of those left—islands, really. • –TG