5 Awesome Places To Go Sailing In America You Didn’t Know About

Are you looking for a new sailing destination? Maybe you’ve been to all of the sailing hotspots like Martha’s Vineyard, Nantucket, and even Montauk. Or maybe you’re a new skipper looking to test out your new boat on some waters, but you’re not sure where to start.

Sometimes, it’s a worthy investment to look for waters that may be less traversed by other sea dogs such as yourself. You’ll be able to make special memories that you can take home with you and inspire other ship captains to look for new horizons. Here are some places where you can go sailing that you may have never considered before.

Gloucester, Massachusetts

No, that’s not just the town in west England. It’s also a beautiful coastal city and one of a few to be home to Cape Ann. Not only is it a great birding spot and host to many unique artists, but there are so many other elements of this city to discover! By the way, it’s pronounced gloss-ter so you can fit right in with the locals and don’t get laughed at right out to Gilligan’s Island.

Brush up on your maritime trivia by visiting the legendary 122’ schooner which has become a national landmark. Originally built in Essex in 1926, it has undergone a full restoration so you can marvel at its beauty. This ship is a real educational resource for any young shipmates that want to have something to take back to school for show and tell after a family vacation.

If you’re looking for a break from singing sailing songs and getting sprayed with water from high winds, consider taking a walk on the Harriet Webster Wharf. It reaches right into the harbor where you can catch a romantic sunset and watch different fishing boats float by. Maybe you’ll even catch a deal for a fresh-caught dinner.

For even more history to cram into your noggin, check out the Cape Ann Museum. One of the must-see areas is the 19th-century captain’s house. With many different exhibits coming and going throughout the year, you’re sure to find something of interest for everyone in your crew.

Rock Hall, Maryland

After staying a couple of nights in this town jutting out over the water, you will see why it is aptly named “the Pearl of the Chesapeake”. Even with current conditions, there are still plenty of fun things to see and do around the area. Multiple schools offer sailing instruction if you want to fine-tune your knowledge. Which part of the boat is the stern again? There are also stand-up paddle-boarding classes available.

If you want to hand off the captain duties to someone else for a while, you can go out on one of a couple of available, private charters. It’s a perfect way to stay out in the fresh air and get a scenic tour of the surrounding area. You are guaranteed to fall in love with the Chesapeake, so much so that you’ll be begging for another ride around the water.

This town is filled with quaint lodging, as well as different activities and a vibrant nightlife to explore and experience. Why not stay in a cottage or a condo overlooking the harbor? There’s even a working lighthouse to stay in, with amazing views out of the giant windows! With the sound of the water lapping at the sailboats in the distance and the cry of seagulls to wake you up in the morning, this will make a perfect destination for any boating enthusiast.

There is certainly no shortage of great food to be had in this town and from a variety of different venues. Come support local businesses by trying the famous Lester waffle at the Muskrat Alley cafe, or some crab imperial stuffed shrimp at the Osprey Point Restaurant. No matter what you try, you will soon be raving about it to your friends and begging them to join you on your next vacation.

Savannah, Georgia

A place where many beautiful Southern girls get their name, Savannah, Georgia is a gorgeous coastal city with charming historical architecture. At any seafood restaurant you stop by to eat, you can be rest assured that you’re served local and fresh fish caught right out on the surrounding waters. There are also pristine beaches that need no introduction but are still worth checking out.

Located just twenty minutes from downtown, you might consider checking out Tybee Island for a sea-worthy sailing trip. Catching stunning sunsets and maybe a bass, snapper, or more at the pier are just a couple of activities that you can brag to all of your friends about. If you’re lucky, you might be able to spot some dolphins whilst on a private tour!

When the sun has finally gone down and all of the fish are asleep, landlubbers can still find a wide variety of entertainment onshore. If you’ve never seen “Dueling Pianos” before, you can catch them in the historic landmark district for a show that will leave you screaming your favorite songs and getting jiggy with your loved ones. If you want to get down with the sailor culture, there’s White Whale Craft Ales where you’re sure to find a new brew to try.

With all of that history surrounding the area and all of the stories that are embedded into the city itself, it doesn’t surprise anyone to hear that it is the most haunted city in America. If you’re looking for some great ghost stories on your next evening voyage at sea, go ahead and book a ghost tour. Some can even take you inside haunted buildings, so this is a must-have on your to-do list when you visit!

Beaufort, North Carolina

Another town that is jam-packed with history is America’s own “Coolest Small Town” winner, Beaufort. Standing proudly as the fourth oldest town in North Carolina, it started as a fishing village and port of safety district back in the late 1600s. There are plenty of water-based and land-based activities to do around here, and once you spend enough time here, you will understand why this town deserves all of the accolades it has collected over the years. Another fun fact, remember to pronounce it as bow-fort.

Since this state is right on the east coast, it might not surprise you to find out that there are not one, nor two, but three maritime museums! Luckily, one is conveniently located in Beaufort, and you can finally go check it out. For those who are more interested in what lurks beneath the water’s surface, this museum has plenty of sea monster exhibits to explore.

Now for some real natural fun, consider taking a peek at Cape Lookout. These barrier islands are only accessible by boat and they carry activities that the whole family will enjoy. Whether you’re more of a bird-watcher, camper, fisherman, or if you just like climbing a ton of stairs in order to obtain a stunning view of the water as a reward, this getaway will make you feel like you’re on a private island.

Have you ever seen one of those ultra-colorful parachute-looking things dragging people out over the water as you’re getting your tan on at the beach? That daring activity is kiteboarding at its finest, and one of many water-related activities that you can find on the Crystal Coast. You can even take either a self-guided or a charter tour of the coastline. Just look out for the pirates!

Stonington, Connecticut

Here you will find the only Connecticut town facing the Atlantic Ocean, so boaters from all walks of life visit in order to look at yachts, gain a sailing education, and check out the historic mill in town. There’s also a nice-looking cafe that may let you pull up to their docks in your boat. You might just find the perfect accents for your home in one of the many quaint shops.

Being stuck in a boat for long periods of time may leave your legs feeling a bit stiff. A great way to counteract that annoying sensation is to rent a bike and ride along one of the many routes that you can take. This way, you can explore other towns and find even more places that will make a perfect scenic post for Instagram.

A museum that you won’t want to miss is the Captain Palmer House. This was once home to a man who discovered the Antarctic peninsula, so anyone who comes through will surely be inspired by his ventures and his living space. There’s so much more to see than just his model ships and gardens, however. There are also dollhouses that are so intricate, you’ll have trouble praying your little ones away from them to move on to the next room.

Fun for the whole family

These wonderful towns and cities are great for solitary sailing journeys or romantic getaways, but they are also spots packed with activities that the whole family can enjoy. If you’ve got someone in your crew who isn’t as enthused about maritime history as you are, there are plenty of shopping districts around, art museums to peruse, and beaches to relax on.