Waterway Guide's contributing editors are a special breed. They spend time exploring America's waterways and beyond in all kinds of conditions and aboard variously equipped vessels. We asked five of our editors to provide one of their favorite cruising destinations from 5 of the regions that Waterway Guide covers with its publications and mobile app. If you haven't been where they recommend, plan on visiting. They've done the homework and Waterway Guide has all the details you need. Now get out there and enjoy.

Mackinac Island - Great Lakes
Emily Kiser

I'm always looking for destinations where we can park our sailboat in a beautiful place and go ashore to explore. As a Michigander, I've been spoiled by an amazing local destination – Mackinac Island. The island is in northern Lake Huron, between Michigan's upper and lower peninsulas.

Mackinac Island has long been known as a playground for the rich and famous, which for cost-conscious cruisers like me, might sound unattainable. Luckily, there are many ways to enjoy the island no matter your budget, particularly if you love nature. The main boating facility on the island is a reasonably priced marina operated by the state. Slips are usually available by online reservation, except on the island's busiest summer weekends. Anchoring is possible in light winds.

The marina gives you easy access to the best of the island. You will find horses, carriages and lots of people but no cars (they've been banned since 1898!). Walk a block west and you'll be in "downtown" with many restaurants, bars, fudge and souvenir shops. Walk a block east and you'll find yourself ogling beautiful historic buildings with eye-popping gardens. Head up the bluff north of the marina and you'll be immersed in the history of Fort Mackinac, built in 1780 by the British. Keep walking (or biking) a half a mile in any direction and you'll be in the Mackinac State Historic Park, which comprises more than 80% of the island. Within the park, there are countless trails that will take you along dramatic bluffs, near interesting rock formations, through historical landmarks and forests full of stately trees. There's so much to explore that it would take weeks for you to see it all.

These are just some of things that make Mackinac Island an unforgettable destination and one of my favorite places.

I've cruised in Maine and have come to love the unmatched scenery, the secluded anchorages, and abundant wildlife. You can spend a summer in Maine and anchor at a different location every night. My favorite anchorage is Seal Bay on Vinalhaven. The entrance is unmarked with no buoys to guide you, but the charts are accurate as you search for a spot deep enough to withstand a 12 foot drop in depth at low tide. You are rewarded with seals of all colors on the nearby ledges and one time I was greeted by a bald eagle as he dived for his dinner not more than 10 feet off my port side. The famous granite rocks in Maine are perfect picnicking spots. One night when checking the anchor, the air was still as it often is at night in Maine, which offered a perfect reflecting pool for the overhead stars on a moonless night. The boat was floating in a sea of stars, a stunning sight I'll never forget. It's a special place that will always be my favorite anchorage in Maine.  

However, Maine does present challenges to those not familiar with the area. Fog is a constant possibility, especially in the morning but it usually burns off later in the day. Then there's the ever  present lobster pots that are more numerous than anywhere else on the east coast. Just to make it more interesting, each lobster pots has a toggle that could be as long as 50 feet with a line just below the surface connecting to the lobster pot buoy, ready to snag the keel or prop of unwary boaters. You learn to always pass the pots on the up current side and look 300 feet ahead for planning a path through the pots. 

As with many things in life, the price of a treasured memory comes with some learning challenges, but it's well worth the effort for cruising in Maine.

Dismal Swamp Canal - Mid-Atlantic
Scho & Jo

Don't let the "dismal" name put you off; the Dismal Swamp Canal should be included in your 2025 boating plans. It's our favorite type of trip, a unique, historical adventure that you'll remember for years to come.

The Dismal Swamp Canal is the oldest operating man-made canal in the United States and connects the Chesapeake Bay with the Albemarle Sound through a 22-mile-long waterway. The most famous investor in the canal was none other than George Washington, and its impact on U.S. history is noticed throughout time.

We recommend taking the trip in the spring or fall for two completely different experiences. In the spring, boaters travel north, starting from the Harbor of Hospitality, Elizabeth City. The weather isn't too hot and you can enjoy hiking and local fauna in Dismal Swamp State Park, while in the fall, boaters start from Norfolk or Portsmouth and can cruise through beautiful fall foliage. The reflection of the tree lines as you cruise down the center of the canal is truly magical. The route includes many great, protected anchorages and free docks from start to finish. 

The entire Dismal Swamp Canal can be done in a day or on a weekend, depending on your available time, but we recommend spending at least one night on the canal. The Dismal Swamp Welcome Center is a great place to spend the night as you have facilities and access to the Dismal Swamp State Park. Crossing the canal to the state park provides a beautiful boardwalk trail and great biking trails. Always check the Dismal Swamp Welcome Center and Waterway Guide Navigation Alerts to confirm status of the waterway. 

The St. Johns River - Southern
Capt. Mac Rubel & Deb Boswell

Cruising the Intracoastal Waterway (ICW) in Florida gives us the chance to go on one of our favorite side trips: the St. Johns River. Port 32 Marina on Ortega River just south of Jacksonville serves as a good starting point.  As you head upriver you might get to see a squadron of anti-submarine patrol planes taking off or landing at Jax Naval Air Station. Green Cove Springs and Palatka are good stops as you continue south.  Upstream of Palatka the river narrows and the connection between boater and river becomes more intimate.  Birds, fish, manatees, alligators, and scenery abound.  The cruising is easy, the water is deep, navigation is straightforward, the sights amazing, and the history is remarkable.  People have lived on the banks of the St. Johns River for thousands of years.  

For deeper draft boats the head of navigation is Lake Monroe, 160 miles upriver.  Get a slip at the Downtown Sanford Marina and plan to spend a week or more traveling around the center of Florida (we spent a month).  The bike trails and state parks in the area are worth the visit.  You can also spend time on the hook exploring side creeks and springs by dinghy.  Some of our favorite anchorages include Mill Cove – Doctors Lake, G-31 Seven Sisters, R-70 Blue Springs State Park, R-36 Catfish Bend, and R-112 Butchers Bend.  Even after three trips we have plenty of places left to explore.  Salt Spring in the northwest corner of Lake George and Crescent Lake are just two on our list.   Take inspiration, like we did, for a slower paced cruise from John and William Bartram who paddled the St. Johns in the eighteenth century in expeditions to record the flora and fauna of this incredible river.  We are looking forward to our next St. Johns cruise.

St. Michaels, MD is one of my favorite towns on Chesapeake Bay due to its protected location, the highly rated Chesapeake Bay Maritime Museum (CBMM), and local restaurants and shops. I've never been disappointed when visiting. All of the waterfront is within walking distance of the town's main district. Whether you anchor or stay at a marina or at the Museum, St. Michaels is a delight. If you plan far enough in advance you may want to join the Museum, which means that you are eligible to use the docks there. It is charming to walk the Museum campus and see not only exhibits, but also the working shipwrights advancing various projects.

As for the town, we've always enjoyed the local restaurants and pubs, gift shops, and ice cream store. Arriving by boat provides few options for going far and that's the attraction. There may be a taxi somewhere nearby, and there's certainly not an Uber that I've located, so be prepared. You may be able to locate a friendly local who can get you to the grocery store, which is a few miles out of town.

Call ahead for reservations during peak season. And check the calendar at the CBMM for its festivals and programs so you can time your visit accordingly. The annual Antique and Classic Boat Society festival is delightful each Father's Day weekend as boats from around the Bay make their way to be judged and owners show off their work.

Learn more about St. Michaels at https://www.stmichaelsmd.com/.

Hope to see you there…