3 Days on the Delaware Shore: A Hidden Gem

If you’ve dreamed of an East Coast beach vacation, it’s probably been to places like, Cape Cod, Virginia Beach, or the Outer Banks. But tucked quietly between New Jersey and Maryland lies a stretch of sand that feels like a hidden gem among those in the know: the Delaware shore. The three towns of Lewes, Rehoboth Beach, and Dewey offer history, charm, great food and simple pleasures. They’re close enough together to feel like siblings, yet each one has its own distinct personality. And 3 Days on the Delaware Share really does feel like a hidden gem, especially if your tour guide is your son.

Whether you’re walking the quaint streets of Lewes, savoring oysters at a chic Rehoboth bistro, or watching the sunset from a Dewey bayside bar, three days on the shore will linger in your memory long after you’ve gotten the last of the sand from your shoes.

Why choose the Delaware shore?

Unlike the more famous beaches of the East Coast, Delaware’s shorelines feel approachable. They’re family-friendly without being overwhelming, and lively without being chaotic. You won’t find massive resorts looming over the sand; instead, boutique inns, independent restaurants, and local shops dominate the scene. There’s a feeling here like everyone you see has been coming here forever and chooses to keep it to themselves.

Begin your 3 days in Lewes

Lewes holds the distinction of being the first town in the first state, founded in 1631. It has weathered pirate raids, colonial battles, and shipwrecks. Today, its historic district feels like a living museum, where you can wander past clapboard houses, visit the Zwaanendael Museum, or step into the Ryves Holt House, Delaware’s oldest surviving building.

Rehoboth, once dubbed the “Nation’s Summer Capital” thanks to its popularity with Washingtonians, retains a classic Americana boardwalk vibe. And Dewey, with its youthful energy and bayside concerts, represents the lighter, more playful side of the Delaware shore.

Getting there

One of the reasons the Delaware shore is most known to those close-by is that Delaware has no airport of its own. Visitors either drive from the D.C. area, ferry from Cape May, New Jersey, or land in one of three airports. This gives these beautiful beaches a sense of being for those who have been, returned, and don’t need to shout about it.

• Philadelphia International Airport (PHL): The closest major airport, about a 2-hour drive to Lewes and Rehoboth.
• Baltimore-Washington International (BWI): Roughly 2.5 hours by car, and often offers more direct flights from other U.S. hubs.
• Washington, D.C. airports (DCA and IAD): Both around 3 hours by car, making them good options if you want to combine your beach trip with a city visit.

The drives themselves have their own kind of charm. You’ll pass through stretches of farmland, marshlands dotted with egrets, and small Delaware towns before you hit the coast. It’s the kind of journey where the transition from city life to seaside quiet feels gradual, easing you into vacation mode.

Where to stay on the Delaware shore

Lewes is a town that whispers rather than shouts, and its lodging reflects that. The Dogfish Inn is a quirky, modern boutique inn created by the famous Dogfish Head Brewery. Located on the Lewes-Rehoboth Canel, the rooms are filled with nautical touches, beach chairs on the lawn, and the atmosphere is as laid-back as it gets. Their website describes the Dogfish Inn as “an off-centered basecamp for beer lovers and adventure seekers alike (like there’s a difference).”

And, if you prefer something steeped in history, Lewes has several B&Bs housed in colonial homes, where creaking floorboard add to your experience.

I stayed at the Beacon Inn, close to the beach, and somehow arrested in what I’d guess to be the 1970s. The lobby area and the rooms are spacious and charming in a local, lost-in-time way. The bedspreads, art, and even the lamps are beachy and retro. The hall carpets could use a refresh but everything else was clean, and retro-fitted to provide enough plugs for charging and the room even had a mini-fridge.

Staying in Rehoboth

Rehoboth offers a bit more variety. For indulgence, the Avenue Inn & Spa pairs coastal charm with spa amenities, and it’s only a block from the beach. It’s the kind of place where you can slip from a beach walk to a massage in the same afternoon. The Boardwalk Plaza Hotel is, as its name suggests right on the Boardwalk. Here you’ll get oceanfront views and Victorian-inspired elegance. Finally, Mar Bella Boutique Hotel offers a more affordable, garden-style stay.

Stay in Dewey if you want a more lively experience

In Dewey, the accommodations are more in line with the town’s lively, youthful vibe. Hyatt Place Dewey Beach combines comfort with proximity to both ocean and bay. The Atlantic View Hotel caters to a youthful crowd and has beach access just steps away. If you want to be near music and late-night energy, Dewey is your best bet.

Where to eat on the Delaware shore

There is no shortage of great food in the Lewes, Dewey, Rehoboth Beach area. My youngest picked me up at the Philadelphia airport, with chilled water tucked into my door! We headed straight to Rehoboth Beach to grab dinner. One of the many perks of young adult kids is when visiting them, you get a perspective wholly unlike what you might have experienced on your own. In our case, we usually get taken to the restaurants they’ve wanted to hit but have saved for Mom and Dad’s treat!

Our first stop the night I arrived was Cafe Azefran, a Mediterranean-Spanish inspired gem, run by a father and son. It’s tucked into a quiet side street in Rehoboth Beach, and worth every minute we spent looking for parking.

Like so many of the spots we tried that weekend, the place was populated not by tourists but by people who seemed to know the menu, as well as many of the other patrons, and everyone seemed to know what to order. Apparently, Espresso Martinis were a specialty, and while I’ve never had one before dinner, that’s what we did. They were the best I’ve ever had.

We over-ordered with a starter of a delicious cheese board, followed by duck breast tapas, and rib-eye paella. Everything was first-rate and would make for amazing leftovers for Sawyer, after I left.

Morning began with lunch

We tended to grab coffee in the a.m., then head straight into lunch. Our first morning, we headed to Rehoboth Beach where my youngest said he’d been told we had to hit Woody’s, in Dewey Beach, for the best clam cakes around.

I will say, I’ve never had a crab cake with less filling, more crab, and a fresher, just-caught taste than this one. We sat outside in the bustling cafe, filled with locals who knew the menu by heart. Crab cakes here are served on a brioche roll with house-made chips. This was a lunch to remember.

We spent the afternoon walking the quaint streets of Dewey, and then heading to my son’s place so I could finally meet Pyra, his rescue kitten.

I could go on and on about Pyra, but instead, I’ll just show you.

Evening 2

Lewes was our dinner destination our second night. Although the town is not large, there are a number of amazing restaurants, some of which we’d tried before. We began with a cocktail at the Bramble & Brine, located in a Victorian home on a quaint corner in Lewes.

Probably because we’d been here before and loved it, we headed to Kindle for dinner, where their tagline is “Eat. Drink. Glow.” Fresh fish seemed like the way to go and we had halibut and swordfish, both perfectly cooked and amazingly fresh.

Day 3 on the Delaware shore

Today was beach day and although we again began our day with lunch, post-lunch, we joked we took an 18-mile trek down the beach and back to wear it off.

302 Social was our lunch spot, a cute 2nd story eatery with outside seating that meant we could watch all the passers-by as we ate. Our waitress approached to take a drink order and Sawyer quickly responded, “I’ll have a 302 Spritz.” The waitress was gone before I could even ask what that was, but clearly my son had been here before.

The 302 Sprint is their take on an Aperol Spritz, and it clearly trumps the Aperol Spritz. Their version is made with Aperol, grapefruit juice, and Prosecco.

Lunch was great but we were off to the beach. Hurricane Erin had swept up off the eastern coast just a day or two earlier and rip tides kept most out of the water. But it didn’t stop an intrepid few from venturing out too far, which meant we witnessed somewhere between four and five (successful) lifeguard rescues.

Our final evening on the Delaware shore

It was a perfect evening for what came next. Sawyer had reserved spots for us on a Sunset Dolphin Cruise out of Fisherman’s Wharf in Lewes.

We boarded the boat, climbed the completely vertical ladder to the upper deck, and found a place to sit amidst the lifeboat, cushions and lines. From the lower deck, the captain called out the sights and all we could hear was the buzz of his voice. It was perfect.

Thanks to the remnants of Hurricane Erin, the breeze was brisk, the sea choppy, and apparently the dolphins stirred up. Suffice it to say, I’ve seen my share of dolphins, but I’ve never had a show like this one, just off the railing of the boat. A dozen dolphins and few calves put on a playful display where they swam in circles, jumping in perfect arcs before diving back in, nose-first. We were close enough to see one had a deformed fin, but he seemed none the worse for wear.

We passed historic lighthouses and learned a couple were slowly sinking into the sea. There wasn’t enother boat in sight and we watched the sun go down below the horizon. It was a beautiful finish to an amazing 3 Days on the Delaware Shore, with Sawyer.

Our final dinner on the Delaware shore

We had reservations at the Lewes Oyster House, clearly the place to be. We sat at the bar awaiting our table and the bartenders made our evening. A little bit seaman, a little bit rogue, a little bit standoffish, they seemed to warm to us as we asked questions about their creative drink menu.

Dinner was outstanding. Seared scallops with the most perfect succotash beneath, and Parker house rolls baked to order, which meant no room for dessert.

Limitless possibilities for fun

Of course, this was just our itinerary. But there’s no end to the activities possible along the Boardwalk, in the museums, the historic districts and the carnival-like offerings. My trip was near the end of peak-season, just before Labor Day Weekend. But one can imagine this would be a beautiful spot in the fall or even winter, when there’d be no crowds, and an even more laid-back vibe.

Final thoughts

The Delaware shore is not the loudest or most famous of East Coast destinations, but that may be precisely why it’s so appealing. Lewes, Rehoboth, and Dewey each offer their own shade of coastal life, and together they create a three-day getaway filled with character, flavor, and beauty. Whether you’re drawn by history, food, nature, or simply the lure of the ocean, these towns remind us that sometimes the most meaningful escapes are found not in the obvious places, but in the hidden corners waiting to be discovered.

And, I would say, they are made all the more special when you get to experience them with a grown child, one who makes you beam with pride.