Explore these four regions along America’s waterways
US Boating Destination #1:
Mackinac and Les Cheneaux Islands, Michigan
Enjoying the various US boating destinations is something everyone should experience. To begin, sailing around Mackinac and Les Cheneaux Islands in Michigan is an experience that encapsulates the essence of Great Lakes boating. It offers a chance of a journey with no purpose other than to explore. With dozens of islands to investigate, you can spend a day, a weekend, or even a full week lazily motoring from cove to cove, setting anchor at your leisure and returning to port refreshed and relaxed.
Mackinac Island
Mackinac Island, a car-free historical haven, is your best bet for home base. The state-run Mackinac Island State Harbor offers both transient and seasonal slips with water, 30- and 50-amp shore power, restrooms, showers, ice, Wi-Fi, pump-out, and a U.S. customs check-in if you’re coming from Canada.
Bring a bike, or be prepared to rent one, because once you get tied off at your slip you’ll want to explore. If you’re hungry, there are plenty of restaurants to choose from right next to the harbor, including the Caribbean-inspired Kingston Kitchen, Mighty Mac Hamburgers, and the equestrian-themed Seabiscuit Bar & Restaurant. The 1852 Grill Room, located inside the gorgeous Island House Hotel, offers dining on a sweeping veranda with water views, perfect for a cool Lake Michigan summer evening.
Hiking trails and golf are all within walking distance of the marina, and make sure to check out Biddle House, a look back in time to Mackinac’s founding that also includes the Mackinac Island Native American Museum. About a mile’s hike into the interior of the island will find you at Fort Holmes, the reconstructed replica of the island’s original 1817 fort.
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On the Water
You could easily spend the whole weekend strolling Mackinac Island, but it’s time to hit the water. Located northeast a short sail across Lake Huron are the Les Cheneaux Islands. With sheltered channels and secluded anchorages, they’re a boater’s paradise. This archipelago encompasses 36 islands filled with nature and history, and you’ll want to spend some time exploring both land and water. A tender, kayaks, or even stand-up paddleboards will be helpful in accessing the coastline.
It’s less than 20 nautical miles directly from Mackinac to Marquette Island, the largest and first of the Les Cheneaux Islands that you’ll reach, but a trip in this region just begs for a good meander. Pick up lunch in Mackinac and plan on spending a full day poking around the islands, or provision for a weekend spent on the hook in one of the hundreds of peaceful coves that dot the region.
Les Cheneaux Islands
The Les Cheneaux have a long boating history—keep an eye out for a classic Chris-Craft plying the waters. The Les Cheneaux Antique and Wooden Boat Show is the largest show of its kind in the world and is held each August in the small town of Hessel.
The Seiberling-Stewart Nature Preserve on Marquette Island is only accessible from the water and makes a great stop for a short hike and to check out some of the region’s flora and fauna. For a longer hike, make your way to Bush Bay and find the Narnia Trail, which begins at the Busy Bay Scenic Overlook. Follow the red arrows to find yourself transported to a world reminiscent of that in C.S. Lewis’ classic tale. The trail even boasts a lamppost marking your entrance to “Narnia.”
If you’ve worked up an appetite, there are a few options for grub in the region, mostly in the hamlets of Hessel and Cedarville, both of which have marinas. In Cedarville, check out Cattails Cove for a patty melt or a classic lake meal of fried perch. Stroll up to Ang-Gio’s for Italian-American comfort food, and pick up breakfast for the next morning at the Little Buoy Bakery & Cafe. If the mood calls for a drink or two, check out Les Cheneaux Distillers and sample its craft vodka, rum, gin, and whiskey, enjoy a cocktail, and pick up a bottle or two for sunset drinks back on your boat.
Over in Hessel, why not let the students at the Les Cheneaux Culinary School take care of you? The school has a restaurant where students can gain real-world experience, and the seasonally changing menu is easily one of the best in the region. The nearby Islander Bar is perfect for a happy hour cocktail and has Caribbean beach bar-meets-lake house vibes. NibbleLungen is a small, family-run convenience store with an American and Mediterranean menu and grab-and-go snacks, booze, and more. You’ll find it hard to resist picking up some baklava to take back to the boat.
Boating around Mackinac and Les Cheneaux Islands is an experience that almost requires no itinerary and a very loose idea of destination. Sure, you could easily just spend the day on the water, returning to the quaint charm of Mackinac as the sun sets, but why not hole up in a cozy cove and drift to sleep as the waves of Lake Huron lap the shore? Just point your finger toward the nearest island and go explore, or anchor near one of the many nature preserves and spend the day watching classic wooden boats and kayakers ply the waters. As the evening cools down and the haunting cries of the loons start up, you’ll understand why this little corner of the upper Midwest has been a beloved boating destination for generations.
US Boating Destination #2:
Portland to Boothbay Harbor, Maine
Sailing from Portland, Maine’s largest city, to the quintessential New England coastal town of Boothbay Harbor, is not merely a passage; it’s a voyage through time, nature, and the very essence of New England’s maritime soul. The roughly 170-nautical mile journey weaves through rocky islands topped with towering Balsam firs and past fishing villages that retain echoes of past lives spent on the water, but now are more likely to be populated by vacation homes than actual fisheries.
Departing Portland
Before you set sail, do yourself a favor and spend some time exploring Portland’s world-famous culinary scene. No visit to Portland would be complete without a stop at Eventide Oyster Company for a dozen (or few dozen) on the half-shell washed down with some cold beer. Additionally, a lobster is almost a legal requirement when in Maine, and it’s hard to beat the rolls and atmosphere at Luke’s Lobster on the Portland Pier. Central Provisions, located just off Commercial Street, has been lauded as one of the best restaurants in Maine, and Bar Futo offers unique twists on Japanese izakaya-style bar food alongside truly stellar craft cocktails. You could spend days just eating through Portland before you ever toss off the lines, so booking a room at one of the many downtown inns and hotels (Portland Harbor Hotel and the West End Inn being two of the most aesthetic stays) would be a good idea.
There are a handful of marine shops situated downtown, including a West Marine on the north end and Sawyer & Whitten Marine on the wharf. There are also plenty of small marinas and ports along the way in case of an emergency.
The Journey
The journey north to Boothbay Harbor can easily stretch into a longer voyage depending on how many of Maine’s picture-perfect coves you choose to explore along the way. Set a direct course across the Casco Bay toward Popham Beach if you’re in a hurry, or meander along islands like Long Island and Chebeague Island. The waters here are relatively deep, although the closer you pull to shore the more you’ll need to pay attention to rocky outcroppings. Keep an eye out for the Portland Head Light at the head of the Portland Harbor, and note the Coastal Maine Botanical Gardens on the map, a treasure truly worth doubling back via car to explore.
Depending on the time of year, you may be joined by a variety of resident and migratory seabirds and raptors like Osprey and Bald Eagles, playful harbor seals and porpoises, and perhaps even a whale or two. Crossing Casco Bay might be the perfect time to drop a line or two and see if you aren’t able to catch some dinner.
New England weather should also be taken into consideration. Even with much warmer summers due to climate change, the shoulder seasons can be particularly fickle, and the water itself rarely ever gets above 70 degrees Fahrenheit in the dead of August. It’s not uncommon for dense fog banks to roll in during the mornings as the temperature fluctuates wildly between air and sea.
Boothbay Harbor
In some ways, pulling into Boothbay Harbor is like sailing into a postcard of Maine’s past. If it’s docked, you won’t be able to miss the schooner Eastwind, a double-masted beauty built in 1999 as a replica of a 19th century ocean-going vessel. Tie up at Boothbay Harbor Marina, the best full-service option near the center of town. The marina can accommodate boats up to 100 feet in length and longer and offers showers, water hookups, washer/dryers, 30- and 50-amp shore power, free ice, free Wi-Fi, and more. It’s small though, so during the summer season reserve a slip well in advance. Boothbay Harbor Yacht Club is another option, although you will have to drive or tender yourself into town. There is no anchoring allowed in the downtown harbor itself.
Make sure you’ve packed your appetite, and as you might have guessed, seafood rules the day here. Kaler’s Restaurant is a great option for a relaxed pub vibe, while Mine Oyster right on the docks offers both a raw bar and sushi options. McSeagull’s Restaurant is something of a town institution, and if you’re ready for a somewhat wacky culinary adventure, head to Boathouse Bistro & Tapas Bar for an eclectic menu that runs the gamut from schnitzel to tacos (and yes, more seafood).
Strolling around town, be sure to keep an eye out for what the town calls its “Museum in the Streets,” historical placards that allow you to delve into the region’s rich history without paying a museum admission fee. There are also plenty of gift shops (make sure to stock up on saltwater taffy) and a trolley that runs during the high season and can get you to some of the more popular spots.
If you’re looking for a place to lay your head for a night or two that isn’t a rollicking V-berth, there are a few options ranging from understated luxury to down-home New England charm all within walking distance of the marina. For a well-deserved splurge, book a room at the Topside Inn, a five-star boutique hotel with excellent dining. Captain Sawyer’s Bed & Breakfast is located near the docks in a Victorian-era sea captain’s home, and the Tugboat Inn (also on the docks), offers comfortable rooms with water-view dining and transient slip rentals.
It can be hard to tear yourself away from all there is to see and do and eat in Portland, Maine, but once you hit that open water and start the journey up to Boothbay Harbor, the noise of the city melts away, and the salty history of the New England seaside hits you full force. In some ways, you’re able to experience all of Maine’s future, present, and past during those 170-odd nautical miles. You’d be hard-pressed to find a trip quite like it anywhere else in America’s waters.
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US Boating Destination #3:
Southport to Bald Head Island, North Carolina
Embarking on a journey from Southport, North Carolina, over to Bald Head Island, North Carolina, is an adventure that offers both serene beauty and a touch of challenge. While relatively short in terms of distance, the trip is rich with maritime culture and coastal charm. Southport is a quintessential coastal village, with plenty of shops and amenities to get you and your vessel ready to sail, while car-free Bald Head offers an almost-Caribbean atmosphere. Both locations are close enough to make it an easy day trip, although you’ll find yourself tempted to stay on Bald Head for a few days for some island exploration and world-class relaxation.
The Journey
There are numerous marinas in Southport at which to start your trip, including Deep Point Marina & Yacht Club and Cape Fear Yacht Club (located on the Intracoastal). Deep Point Marina is also where the Bald Head Island Ferry operates, so keep that in mind in terms of harbor traffic.
Bald Head Island itself is only two nautical miles off the coast, so depending on where you cast off from your actual journey will be fairly short. Upon approach, be sure to radio ahead. The entrance into Bald Head Island Marina is narrow and can be quite busy, especially during the summer. The marina can accommodate boats up to 100 feet in length, with 30-, 50- and 100-amp hookups, shower and laundry facilities, Wi-Fi, and gas and diesel fuel. Pump-outs are available, and some slips come with TV access. Note that this marina is the only option on Bald Head Island, and while it offers both overnight and day slips, it can fill up months ahead of time. Though the trip itself might be quick, it’s wise to reserve a slip well in advance.
Navigational Concerns
This part of the North Carolina coast is called Cape Fear for good reason, and there are plenty of shipwrecks that remain as evidence of these waters’ treacherous history. The sandbars can shift seemingly overnight, and though it might go without saying, staying within the marked navigational channels and paying close attention to your depthfinder is key here. The journey from Southport to Bald Head Island also traverses the part of the Intracoastal Waterway accessed by commercial cargo ships utilizing the Port of Wilmington just up the Cape Fear River. These behemoths are hard to miss; just hold back and let them pass.
What to Do
If you’re looking to top off with a good meal before hitting the water, Fishy Fishy Cafe in downtown Southport is a classic coastal eatery with docks available for mooring right next to the restaurant. There’s plenty of shopping, especially around the intersection of Moore and Howe Streets, and some larger marine supply stores just outside of the downtown area.
Once on Bald Head Island, there are a fair number of activities from which to choose. Pro tip: Bring bikes or plan on renting them, or call ahead and reserve a golf cart. There are restaurants, bars, and shops situated around the marina—Jules’ Salty Grub is a favorite of both visitors and island residents alike. Located next to the market in the middle of the island, Jailhouse Provisions offers delicious renditions of classics like Calabash-style fried seafood platters, burgers, crab cakes, and more. Bald Head Bottle is a great wine bar and shop, perfect for winding down with a crisp glass of rosé or stocking up on a few bottles for sunset back on your boat. There are also restaurants within the two private clubs on the island, some of which are open to the public with reservations depending on the day and time of year.
One not-to-miss experience is climbing Old Baldy, a historic lighthouse located within walking distance of the marina. First illuminated in 1817, climbing Old Baldy is a yearly tradition for many families, and the grounds and museum offer a glimpse into the fascinating history of Bald Head Island.
For those looking for more physically challenging activities, a paddle through the island’s interior marshes might be the right move. There are two locations at which to rent kayaks, one just off the main marina and another slightly deeper into the interior of the island. A bike ride to some of the beaches on the far end of the island will help build a sweat that can be cooled with a dip in the sea, and depending on the time of year, you might be able to see some carefully marked sea turtle nests. The Bald Head Island Conservancy offers sea turtle walks during the summer, starting during the egg-laying season and going through hatching season.
Lodging Options
Southport is home to a handful of charming inns like The Inn at Southport and Captain Newton’s Inn, both located within walking distance of downtown amenities. If you’ve found that the marina at Bald Head Island has filled up, consider basing yourself at one of these quaint B&Bs in Southport and just zipping over to Bald Head for a day trip.
On Bald Head Island, you’ll find a plethora of lodging options (if you choose not stay aboard your own vessel). Located right on the marina are both The Inn at Bald Head Island and The Marsh Harbour Inn. If you’re ferrying a crowd and find yourself short of berths, there are dozens of rental condos and houses spread across the island, all of which are rented through Bald Head Island Limited, LLC, the company that owns the vast majority of the island.
Though the journey itself might be short, the trip from Southport to Bald Head Island is at once a trip back in time as well as a true escape from the mainland. Pull into a slip at the Bald Head Island Marina and set your clocks to island time, embracing the long, languid lunches, golf cart rides, and sundowners on the back porch of a relaxed coastal restaurant or the deck of your own vessel. Less distance to traverse means more time to relax, something that every boater has a hard time turning down.
US Boating Destination #4:
Port St. Joe to Carrabelle, Florida
Offering warm Gulf of Mexico waters, gorgeous sandy beaches, and quaint towns that almost seem trapped in a bygone era, a leisurely cruise between Port St. Joe and Carrabelle on Florida’s Forgotten Coast should be on everyone’s sailing bucket list. At anywhere from 35 to 45 nautical miles, depending on your route, the journey is short enough to be an easy day trip, but has enough to do that you could easily make the trip last a long weekend.
Port St. Joe
Port St. Joe was once a bustling town known for its paper mill but is now better known for its laid-back atmosphere and tourist trade. Begin your cruise at one of two marinas, Point South Marina right off the downtown core or Captain’s Cove Marina located a bit farther up the coast. Point South offers in-slip pump-outs, gas and diesel fuel, laundry and shower facilities, a marina store, and more.
Before casting off, take some time to stroll around Port St. Joe’s compact downtown. Check out the Port St. Joe Lighthouse before heading into town for a bite to eat and some shopping. At Keeper’s Bistro & Bar (named in honor of the lighthouse keepers who manned the historic lighthouse), the menu offers plenty of seafood and some of the region’s famous oysters. Sand Dollar Cafe is your go-to for classic Southern cuisine, while Joe Mama’s Wood Fired Kitchen is a laid-back joint offering small plates (try the Chicken Parm Meatballs), pizzas, and a decent wine list.
If you’re looking to stay the night, The Port Inn and Cottages is your best bet. They have both rooms and small standalone cottages as well as a pool for cooling off after your downtown stroll. While there isn’t a dedicated marine supply store within walking distance of the marinas, there is an Ace Hardware downtown as well as Bluewater Outriggers, a fishing supply store that can get you sorted if you plan on casting a line or two once you hit the water.
The Voyage
Once you leave Port St. Joe, you’ll find yourself in the warm waters of the Saint Joseph Bay. Directly ahead lies the TH Stone Memorial Saint Joseph Peninsula State Park, offering expansive sandy beaches. You’ll need to hook around the peninsula and down past Cape San Blas on your way to Carrabelle. Note that part of this area is a military exclusion zone, so keep an eye on your charts and listen to the radio for any instructions.
Once you round Cape San Blas, continue cruising east toward Indian Pass. Use this cut, part of the Intracoastal Waterway, to enter the Saint Vincent Sound. To starboard will be St. Vincent Island, part of the St. Vincent National Wildlife Refuge and only accessible by boat. If you have some time, and stand-up paddleboards or kayaks, it might be well worth a slight detour for some wildlife viewing and exploration.
Continuing through the sound you’ll come to your first must-stop of the journey—at least, it’s a must if you’re an oyster lover. Apalachicola is world-famous for its oysters, and you can tie up at Up the Creek Raw Bar and quickly down a few dozen alongside a cold beer before moving on.
Once you’ve had your fill of oysters, point your bow northeast and continue past barrier islands and into the Saint George Sound. Dog Island will be on your starboard side as you turn toward port and head into Carrabelle.
Carrabelle
The entrance up the Carrabelle River can get narrow, so go slow and watch for boat traffic. Once in town, there are a few marinas to choose from, most an easy walk to all there is to see and do. On shore, Carrabelle’s vibe is laid-back Gulf Coast ease. Grab a bite at places like the Seafood Shack, Fathoms Restaurant, or The Fisherman’s Wife. The Carrabelle History Museum offers a glimpse into the past of this small town, while The World’s Smallest Police Station (a phone booth turned into a police station) is worth a peek for the Instagram pic alone.
Located just two blocks from the river, The Old Clarabelle Hotel is the best bet for a soft bed and some air conditioning after your trip, although there are some chain options just a short drive outside of town.
Sailing from Port St. Joe to Carrabelle is as much about the journey as it is the destinations. There are myriad spots along the way to drop anchor, go for a swim, or explore a barrier island. This corner of Florida has largely been spared the overdevelopment of some of its coastal neighbors to the West and South, hence the name Florida’s Forgotten Coast. Use this to your advantage and take the opportunity to get a feel for Old Florida.
-by Matt Lardie
