One of the things that makes America’s Great Loop a bucket-list-worthy adventure is that it can be many things to many people. There are all the possible routes and side trips you might want to take. And then there’s the pace: For some, it’s a rush to get it done and set a record, while others prefer to go a slow as possible and savor the journey.
And then there’s another great debate — spend the night anchored or tied up at a marina? Everyone will do a little of both, but which do you prefer when you have the choice? It hints at a bigger question, one that is also measured on a spectrum: Do you prefer outdoorsy activities in nature, or the city life found in port towns?
Don’t be too quick to write off cities and towns that you’ve already explored by land. Every destination is different when you arrive by boat. Imagine cruising into old port towns via the waterfront, docking the boat, wandering cute downtown areas to discover unique cafes, restaurants, and local treats. It’s a completely different experience from flying into an airport, driving past ubiquitous strip malls and chain restaurants, and staying at a hotel in the suburbs.
Here’s a look at a handful of Looper favorite stops along the way to help you dream up your adventure.
Pick Your Activity, Pick Your Great Loop Towns to Visit
For the outdoorsy cruisers out there, you can find beaches, nature trails, hiking, biking, and kayaking along the route. Exploring creeks in your dinghy, or quiet nights swinging at anchor in quiet coves might be your scene. Dinner? Fire up the grill on the stern rail while the sunsets.
For the townies among us, marina life and dinners out are usually the solution. You can spend long afternoons strolling through shops and art galleries, finding hidden bars and museums to explore. Each town has its appeal, and the art of finding it is half the fun.
So, where do you land on the spectrum and what sort of Great Loop do you dream of?
Boater’s Favorite Stops on the Great Loop Route
It’s easy to get too focused on the technical side of things: the best Great Loop route or finding the perfect Great Loop boat. But the Loop is about the journey and the stops along the way.
So, with that in mind, here’s a list of favorite, interesting, and don’t-miss stops along the entire Loop. Some of these you might have heard about, while others might be boater secrets. It’s always a random choice where to start and finish your Loop, and for this article, we’re going to start in Chesapeake Bay and work counter-clockwise.
Tangier Island, VA — Hidden in Plain Sight on Chesapeake Bay
Tangier is the sort of place you’ll find written about by major news outlets and travel guides. Unique doesn’t begin to cover this little patch of sand in the middle of Chesapeake Bay. It’s so isolated that the locals have their own unique accent. It’s only accessible by boat, and the simple docks at Parks Marina allow you to tie up and walk around the place.
If that’s not enough, Smith Island offers a similar experience just across the state line in Maryland. That one is harder to visit, however, as there’s no good marina option.
Solomons Island, MD — Chesapeake Bay Stopover
Midway up Chesapeake Bay and just across the Maryland state line is an area called Solomon’s Island, even though it’s not an island. It’s a popular stopover simply for it’s convenience — halfway between Norfolk and Annapolis. But it’s a great port, with tons of marinas and boater services, restaurant choices, and pretty surroundings.
Solomons is home to the excellent Calvert Marine Museum, which is well worth your time for a look around. It’s got both classic bay boats to explore and an authentic screwpile lighthouse to explore. There are also exhibits about the Bay’s unique geology, with tons of fossils that have been found at nearby Calvert Cliffs State Park.
Annapolis, MD — Sailing Capital and Gateway to Washington, DC
Annapolis calls itself the Sailing Capital of the US (Newport, RI begs to differ, but I digress). It’s a popular stopover for all boaters, though, with a wide range of marina and mooring choices in the welcoming harbor. Downtown faces the harbor, and you instantly know that you’re in a town that really appreciates boaters.
One of the top tours here is the US Naval Academy, which also overlooks the harbor. A manic frenzy takes over in October when the Annapolis Sail and Powerboat Shows (on separate weekends) occur and take over the entire waterfront.
Annapolis is also a convenient place to dock and go on a land tour of Washington, DC. DC is a fantastic stop where you can get around on public transit and spend all day wandering through fantastic museums and monuments free of charge. You can take the boat up to DC via the Potomac River, but it’s a lengthy side trip.
New York City — Views Up the Hudson River on Your Way to the Erie Canal
Upon entering New York Harbor, you’ll transition from coastal cruising to canal and river boating — at least for a while. It seems a requisite part of every Great Loop adventure is to get a photo of your boat passing the Statue of Liberty, so make sure you have a buddy boat for the day to snap the photo for you.
Behind the statue on the New Jersey side of the Hudson is the Liberty Landing Marina, a favorite for Loopers staying and exploring the City. It’s an easy trip into Manhattan from there.
Georgian Bay — Canada’s National Park Paradise on the Great Lakes
If you decide to include a side trip through Canada on your Great Loop trip, you’ll definiately want to include some time in beautiful Georgian Bay. This part of Lake Huron feels like its own cruising world, with more than 30,000 islands and beautiful, clear water. You can hop from one protected anchorage to another and explore to your heart’s content. There are also welcoming boating towns all around the area, including Honey Harbour and Killarney.
Mackinac Island, Michigan — Gem of the Great Lakes
Mackinac Island is the place time forgot, and arriving by boat simply reinforces that notion. Cars aren’t allowed here, and the whole place is a wonderland for exploring on foot or by bike. There are tons of Victorian architecture, fun shops and restaurants, and beautiful scenery all around the island. Plus, the place is famous for its fudge. You can’t go wrong with that.
Charlevoix, Michigan — Michigan’s Sunset Coast
Charlevoix is a cute little town, one of the many summer resort towns along Lower Michigan’s Sunset Coast. In fact, it’s pretty easy to spend all summer hopping along this area from one amazing place to another.
Charlevoix is sort of the poster child for the whole lot: it’s got a walkable town that’s full of shops, galleries, and places to eat. It has an excellent marina that’s a Loop favorite. And the summer season is full of farmers markets, music festivals, and town events.
Sturgeon Bay, Wisconsin — Exploring Door County Peninsula
As you work your way south in Lake Michigan, you can choose to stick to the west coast of the Lower Michigan peninsula or cross the lake and explore the Door Peninsula in Wisconsin. The crossing isn’t as daunting as it might seem, and Door County has tons to explore.
The hub of the area is the town of Sturgeon Bay, where a canal takes you into Green Bay. There, the water is crystal clear, and cute towns and beautiful parks line the shores. If possible, gather a group of Loopers and order an authentic fish boil for dinner. It’s a pyrotechnic feast that is as much a show as a delicious meal.
Chicago, Illinois — Great Lakes to Great Rivers
Chicago marks another transition point, from exploring the Great Lakes to beginning your trek down the Western Rivers. That naturally makes it a good place to take a break, fix whatever has broken, and regroup before heading south. But it’s a vibrant city that has a lot to offer, and cruisers love their stops in Chicago.
Paducah, Kentucky — Inland Excursions (and maybe the Cumberland River)
This small town is located near the confluence of the Ohio, Tennessee, and Cumberland Rivers, and has fabulous city docks located right downtown. It’s one of those natural stopping points where you’re sure to meet other Loopers as everyone hangs out a little longer to take in the place. Shopping, restaurants, coffee shops, and art galleries — this town has plenty to explore.
Many also use this stop as another opportunity to rent a car and explore a little bit by land. Paducah, or nearby Grand Rivers, are only about 2 hours from Nashville. That’s of course if you aren’t into a 190-mile sidetrip up the Cumberland River to visit the city by boat.
Columbus, Mississippi — The Deep South on the Inland Rivers
This little town lies along the Tenn-Tom Waterway and has a wonderful, protected marina off the channel. The marina is outside of town, but it’s easy to find rides to explore. Mostly, it’s a popular Looper stopover where you’re bound to meet new and old friends. The town is welcoming, with walkable shops and restaurants once you get there, plus any supplies you might need for the rest of your trip to the Gulf.
Apalachicola and Carrabelle, FL — Florida’s Big Bend
Truthfully, we couldn’t narrow down the Florida Gulf Coast to just one specific town. From the rural and remote Big Bend area down to the swanky beach town of Fort Myers Beach, the entire west side of the Sunshine State is dotted with amazing ports of call. It’s considerably more laid back and boater-friendly here than other parts of the state, as well.
The areas around Apalachicola and Carrabelle are particular favorites with cruisers, as these are rural fishing villages that are, at least to some extent, off the beaten track. Most Loopers stage here to plan for their big Gulf crossing. Depending on your weather window, your next stop is likely to be Tarpon Springs, which is a unique treat for Florida: a walkable town with an amazing Greek heritage. From there, it’s down the Gulf Intracoastal Waterway.
Key West and the Florida Keys — America’s Tropical Paradise
Visiting the Florida Keys is a side trip that many Loopers decide to take, taking the alternate Great Loop route that circumnavigates the lower Florida peninsula. It means more time in open water than taking the protected Okeechobee Waterway, but it allows you to visit the port towns of Key West and Marathon (plus Miami, Fort Lauderdale, and West Palm Beach on the east coast). If you’re up for a real adventure, you can visit Dry Tortugas National Park, one of the most isolated and least visited places in the park system.
The Keys are home to the only living coral reef in the contiguous United States. The clear, warm water is fed from the Caribbean by the Gulf Stream, so snorkeling, diving, and fishing are what life centers around here. But don’t dismiss kayaking and sandbar hopping in the backcountry, where hundreds of mangrove islands dot the flat, shallow waters of Florida Bay. It’s a magical place to be a boater.
Key West is a special treat, too. There are multiple marinas, but they will cost you a pretty penny to stay. There’s also a city mooring field, but it can be rough and rolly. Walking around Key West and living on island time for a little while is worth it, though. You can also hang out at Marathon or Islamorada, more laid-back communities farther north in the Keys.
If you’re really digging the Keys, you might also want to extend your Great Loop and include a side loop through The Bahamas. Bimini is just 50 miles off the coast of Miami, and a tour of the Exumas or Abacos can be extended in anywhere from a few weeks to a few months.
St. Augustine, FL — History and Fun on the Atlantic Intracoastal Waterway
By land, St. Augustine on Florida’s East Coast is a crowded, tourist-centric town that borderlines on lame. But when you arrive by boat, you’ll tie up in the town marina (or on one of their mooring balls) and you’ll immediately be swept up by the place. It helps that you won’t be stressed out by the traffic, since all you have to do is step off the boat and walk into town.
St Augustine is the oldest city in North America, and the original Spanish fort, Castillo de San Marcos, still overlooks the harbor. If you happen to have one of the moorings under it, know that they also fire off the canon every few hours.
The town is fun to walk around in and has a little bit of everything. There’s great food and shops, but there are also tourist traps. Mostly folks seem to like wandering the streets and discovering new stuff.
Cumberland Island, Georgia — Natural Seashore Beauty
Cumberland isn’t the place to go find a coffee shop, but it is an incredible place to visit. The island is a national seashore located on the extreme south end of Georgia’s Sea Isles. It’s mostly undeveloped, except for one exclusive resort, a few campgrounds run by the park service, and the ruins of a huge Gilded Age mansion built by Thomas Carnegie. The island also has 17 miles of beautiful, pristine beaches, walking trails, and a herd of wild horses.
Cumberland is only accessible by boat or via the park service ferry from St. Marys, Georgia (another worthwhile stop while you’re in the area).
Charleston, SC — South Carolina’s Lowcountry
Charleston is one of the South’s most interesting port cities. The historic part of town lies on a peninsula that’s surrounded by marina options, all of which put you walking distance or a quick Uber away from the Battery, cobblestone streets, and the most beautiful parts of town.
And then, there’s the beautiful coastal areas around Charleston, referred to as the Lowcountry for its winding tidal marshes and creeks. Dolphins are a regular sight here, and the ICW winds past a few other beautiful port towns worth exploring: Beaufort and Georgetown, to name two. Don’t forget to sample the local cuisine, particularly if you can find any authentic Gullah dishes — the only shrimp and grits worth trying, in my opinion.
Beaufort, North Carolina — International Port of Call
Beaufort is a quintessential Carolina port town. It was a favorite haunt of Blackbeard, and his ship, the Queen Anne’s Revenge, was recently discovered where it had gone aground in the inlet here. You can learn about that at the excellent maritime museum right in town. But the point is, this port has a lot of history to it. You’re going to see yachts and sailboats here with flags from all over the world, as it’s a popular stopover before rounding Cape Hatteras, heading north or south.
It’s at Beaufort where the ICW will stop following the Atlantic coastline and tuck into the sounds and rivers of eastern North Carolina. You can stay on the docks right in downtown, anchor in the creek, or stay on the quieter back side at the popular Homer Smith Docks.
Ocracoke Island, NC — Visit the Famous Outer Banks
Exploring the Outer Banks of North Carolina by cruising boat isn’t as easy as it sounds — most of the water around here is too shallow. Plus, the ICW mostly bypasses them. You can take an alternate route through Pamlico Sound with stops in Ocracoke and Manteo, however. Both are great stops, but Ocracoke stands out.
It’s an island only accessible by boat or ferry. While it’s pretty busy during the summer, there aren’t very many year-round residents. The true island locals here have a unique dialect, or brogue, caused by centuries of being isolated so far from the mainland.
You can anchor in the harbor, Silver Lake, or take a slip from the park service or a private marina. It’s a fun stop just to wander around, and it feels a little more like New England than the rest of the Carolinas ever do.
Our Great Loop Destinations Methodology
Any list is going to alienate someone’s favorite, especially when boaters are concerned! We’ve endeavored to compile a list that includes a mix of cities, port towns, and natural areas that Loopers often comment on. We’ve scoured a ton of references, from Great Loop groups, and even asked AI for its opinions on the matter.
In the end, however, it came down to personal experience and knowing what boaters like more than anything. Preference was given to destinations with cute, walkable towns that are right on the waterway. The social component likewise should not be omitted, as one of the most popular elements of the Great Loop voyage is the camaraderie with other boaters.
Preference was also given to spots that you can’t get to any other way — there’s nothing more special than an island you can only get to by boat!
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