7 Small Seaside Towns That You Need To Visit – And What To Do There

The most amazing places to visit are the small seaside watery towns around the world with local history, amazing views, and wonderful people. Here are 7 small seaside towns along the East Coast that you NEED to experience – and what to do when you’re there.

1.     Nantucket, MA 

Nantucket Lighthouse

Nantucket is a beautiful island off the coast of Massachusetts and popular summer destination for rich New Englanders. You can only get to the island by boat. The beaches are pristine and downtown has an old New England feel with beautiful cobblestone roads and views around the harbor that are out of this world. Go in September when the water is still warm but there are much less tourists. You can probably find places to stay at reduced rates especially during the week. There is also a really neat hostel that used to be a lifesaving station, check out HI-Nantucket Hostel.  Be sure to bring or rent a bike to get around and explore the island!

Nantucket Bay Scallops

MUST DO’s

Eat nantucket bay scallops, have a beer at Cisco brewery, check out the cranberry bogs, go to the beach, squid fish off the docks, kiteboard or SUP in the harbor.

2.     Montauk, NY

Montauk Fishing Fleet

Montauk is a fishing town. And a surfing town. And now a rich Hamptons summer town. Amazing fishing, beautiful bluffs, great waves, and fresh seafood. Bring a bike to explore Montauk’s quiet streets, trails, and harbor. There are a ton of amazing parks, unspoiled natural land and old historic sites thanks to Peconic Land Trust.

Montauk Coast Guard Cutter

MUST DO’s

Visit the Montauk lighthouse at the point and roll down the hill, see the fishing fleet in Montauk harbor, eat the seafood and embrace the smell, check out the cliffs at Camp Hero State Park, charter a fishing boat or go shark cage diving in the Great White breeding grounds off the point :-0.

3. Cape May, NJ

Cape May Water Tower

Cape May is another summer seaside town known for its Victorian Style houses, fishing, and beaches. The town is the southernmost point of New Jersey and has award winning beaches all along the ocean.

Cape May Victorian Houses

Bring a bike or skateboard to explore between the beaches, boardwalk, and up to the harbor where there are a bunch of fishing and recreational boats passing through to the Delaware Bay or out to the Atlantic Ocean. Cape May is also home to the Coast Guard Training base and you can see them running drills from the water all the time.

Cape May Ferry

MUST DO’s

Have a beer at the Rusty Nail, visit the Fisherman’s Memorial, go to the beach and surf, check out the Cape May Bird Observatory and go bird watching! You can also explore South Cape May meadows and once you are ready to move on to the next destination you can take the Cape May Ferry over to Delaware.

4. Annapolis, MD

Annapolis Sailboat

Annapolis is unofficially America’s sailing Capital. There are so many cool boats all over the place, great seafood, and home to the Naval Academy. There is a free trolley that runs all around town and is a great way to see places and get around. The nautical history around this seaside town is deep. I highly recommend visiting the U.S. Naval Academy museum to get a glimpse of the military history around Annapolis and the United States. For a ton more information about Annapolis visit visitannapolis.org. I stayed on my sailboat Tula in Glimmer Glass while I was in Annapolis but I’m sure you can find a cheap place to stay on couchsurfing.com or airbnb.com. Make sure you spend a good amount of time walking up and down the docks checking out all the amazing boats.

Annapolis Capitol Building

Must DO’s

Go to one of their famous boat shows, ride the FREE trolley, take a walking tour of the city, watch a sailing race, standup paddle board around the waterways, and walk the docks!

5. Oriental, NC

Oriental, NC

Being a simple cruising sailor, this is one of my absolute favorite small seaside towns in the world. They say there are more sailboats in Oriental than there are residents. Out of all the small seaside towns I have visited I felt the most at home in Oriental. There are so many old salts here that you could learn more about sailing and boating than from any course or book out there. One of the younger sailors warned me to be careful because this town is cursed to sailors. It is in the nature of sailors to keep cruising, exploring, and sailing. When Black Beared the pirate abandoned his crew centuries ago their ghosts began to haunt Oriental, grabbing hold of the souls of offshore sailors, forcing them to settle there and not leave.

Dinghy Dock

Every local here is just about the friendliest person you have ever met and will talk to you for hours. The single most important thing to do while you are visiting Oriental is walk along the town docks and talk to everybody. Hear their stories, ask questions, take pictures. Don’t forget to grab a cup of coffee at The Bean and go paddleboarding around Camp, Green, and Whittaker Creek.

6. Southport, NC

Southport, NC

Southport is a beautiful little town right on the Cape Fear River with Live Oaks and restored historical buildings everywhere. This beautiful town was the filming location for a bunch of popular movies such as “Safe Haven”.

Safe Haven Filmed in Southport

Walking along the River Walk and Marsh walk of Southport produce some amazing views of natural estuaries. Definitely be sure to check out the NC Maritime Museum to learn a bunch about the local history. Visit Southport-NC.com for a lot more information and some amazing pictures of Southport.

Labyrinth In Southport

Southport Maritime Museum

MUST DO’s

Walk along the River Walk, Marsh Walk, and Waterfront of Southport. Have a beer at Fishy Fishy Cafe. Visit the Maritime Museum. WALK THE LABYRINTH.

7. Savannah, GA

Savannah Riverfront

Savannah is one of the coolest and most unique waterfront towns that I have been to. It’s cobblestone streets and hundred year old buildings gives it a historic Southern feel. Antique shops, boutiques, pubs, restaurants and galleries line the streets of Savannah with large oaks, mossy gardens, and historic statues scattered around the historic district. You can feel the history, southern hospitality, art, culture, and beauty all around this small riverfront city. Be sure to spend some time on the actual riverfront and visit my friend Oji, the sweet-grass basket weaver. Keep your eyes peeled for the horse-and-buggies going down the streets.

Historic Savannah Statue

MUST DO’s

Walk through the galleries and museums that are scattered through the historic district. Watch ships from around the world go by on the riverfront. Spend lunch sampling the array of exotic peanuts at The Peanut Shop (no purchase necessary 😉 ). Visit the beaches of Tybee Island. Get the best grass-fed burger you’ve ever had from the Green Truck Pub.

And one more…

Jupiter, FL

Jupiter Lighthouse Paddleboarding

This amazing little ocean town can get crowded with snowbirds in the winter but holds a ton of magic if you know where to go. Jupiter is one of the last towns as you head South, with a lot of natural estuaries along the waterways. It feels like semi-tropical South Florida but without the high rises and noise of Ft. Lauderdale or Miami.

MUST DO’s

Paddleboard, paddleboard, paddleboard! Go on an incoming tide by Katos Bridge and keep your eyes peeled for Manatees. For a real thrill and to see some Gators paddle in Riverbend Park (watch your fins). Take a tour of the Jupiter Lighthouse. It’s only $9 for adults and $5 for kids. The view is well worth it! Try your hand at kiteboarding or just check them out on a windy day at beach access 33 just north of Juno Pier. Charter a fishing boat, there are a bunch off the docks by the new U-Tiki. Make sure you have a beer on the water at Square Grouper AND Guanabanas! For dinner, try the sweet potato crusted grouper cheeks at Food Shack!

Don’t forget to explore these towns in your own way. Find new places, venture off the beaten path, and EXPLORE! Take pictures and share some of your experiences with these wonderful towns in the comments below!