Trap Pond State Park

Southern Delaware Getaway – A Four-Day Itinerary for Sussex County, Delaware

Head to one of Delaware’s famous beaches. Rehoboth Beach, Lewes, Bethany Beach, Dewey Beach and Fenwick Island each offer something unique to offer. Play on the wide, sandy beaches (rated the cleanest in the nation); wander the wooden boardwalk; or go sailing, kayaking or canoeing along the preserved bays and waterways bordering historic downtown districts. Immerse yourself in charming beach communities, indulge in tax-free shopping at the Tanger Outlets and eclectic shops, discover coastal lighthouses plus, enjoy the beautiful scenery of rural Sussex County. 

Trap Pond State ParkBeyond the sand, take a tour and sample savory craft beer at the Dogfish Head Brewery, enjoy live entertainment at the Freeman Stage at Bayside, play a round of golf at Baywood Greens or paddle through Trap Pond State Park home to the northernmost natural stand of baldcypress trees. 

Whether you’re enjoying fun festivities, fine dining, breathtaking views of a vibrant sunset or enjoying arcade games with the family on the boardwalk, southern Delaware makes for a truly memorable getaway. 

Day 1: Rehoboth Beach

Rehoboth Beach Boardwalk

  • Morning: Get an early start on retail therapy: Go shopping at Tanger Outlets (discount prices on designer names) and eclectic boutiques in downtown Rehoboth Beach, where you’ll find one-of-a-kind gifts, artwork and beach fashions.
  • Lunch: Head to Fork and Flask for creative American cuisine or Pickled Pig Pub, a gastropub with local craft beer always on tap.
  • Afternoon: If you aren’t soaking in the sun on the beach, kids of all ages will enjoy go-karts, giant water slides, bumper boats and a lazy river at Jungle Jim’s, which boasts 16 acres of waterpark attractions. Or head to the Rehoboh Beach boardwalk for arcade games and classic amusement rides at Funland.
  • Evening/Dinner: Stroll the boardwalk, play a round of mini-golf, grab some ice cream, Thrasher’s French Fries, or a slice of Grotto Pizza and just take in the sights and sounds of Rehoboth Beach. (Travel tip: Many of the local restaurants and bars have live entertainment, check their schedules to up to date information).
  • Where to stay: For oceanfront views, book a stay at the Boardwalk Plaza or Atlantic Sands Hotel. Or for a more boutique style hotel within waking distance to the beach, check out The Bellmoor or Hotel Rehoboth.

Day 2: Bethany Beach

Bethany Beach Delaware Sunrise

  • Early Morning: Set the alarm and wake up early to watch the sunrise over the ocean. From an orange sliver of the sun peaking above the water to the changing colors of the sky, you won’t want to miss nature’s big show! Add the sounds of the waves crashing and the smell of the salt water and you’ll be whisked away to a moment of rest and relaxation.
  • Morning: Get out on the water! Try your hand at surfing, windsurfing, kitesurfing or stand-up paddleboarding. Rentals and lessons are available. Or take a guided kayak tour of the peaceful salt marshes of Assawoman Bay. Rehoboth Bay is considered ideal for small-boat sailing, so rent a Sunfish or Hobie and set sail.
  • Lunch: The oceanfront views from the decks at Mango’s embrace the boardwalk, bandstand, beach and Atlantic. Go for the fish tacos or other Caribbean-inspired eats.
  • Afternoon: For more than 150 years, the Fenwick Island Lighthouse has stood sentinel on the Delaware coast just north of the Maryland line. Built in 1859 to help mariners avoid the shoals off Fenwick Island, the lighthouse stands 87 feet tall and offers sweeping vistas of the barrier island and beyond.
  • Evening/night: For fresh seafood imaginatively prepared, including locally caught fish, crab and lobster, head to dinner at Bluecoast Seafood Grill in North Bethany Beach.
  • Where to stay: ResortQuest by Wyndham Vacation Rentals offers accommodations in several resort communities in the Bethany Beach area.

Day 3: Lewes

Lewes Cape Henlopen

  • Morning: Grab a cup of coffee and pastry from Second Street in downtown Lewes. Then, head out to Cape Henlopen State Park to claim your spot on the beach! Visitors can choose between a lifeguarded beach with a public bathhouse or drive on beach access for surf fishing. (Make sure to check out the Point for one of the best views of the coastline).
  • Lunch: Enjoy handmade pizza at Half Full or Touch Of Italy, both located on Second Street in Lewes.
  •  Afternoon: Visit the Lewes Historical Society to learn about history behind the first town in the First State. With rich maritime history, you’ll walk through preserved homes and museums near the canal front on fun and educational tours. (During the late spring through early fall season, make sure to visit the Lewes Farmers’ Market located in the historic dishes for great local flavor). 
  • Evening/Night: Take the Cape Water Taxi out for a sunset cruise from the Lewes marina and will set sail along the coastline for a 90-minute peaceful ride. When you return, dine out at Agave for fresh Mexican cuisine or Striper Bites Bistro for fresh seafood.
  • Where to stay: The Inn at Canal Square is a ‘nantucket-style’ retreat located on the waterfront in Lewes.

Day 4: Dewey Beach

Dewey Beach Delaware

  • Morning: Walk along the beach, go for a bike ride or take the Jolly Trolley into Rehoboth Beach for an early morning stroll on the boardwalk. Stop in a couple shops and galleries before heading back to Dewey Beach.
  • Lunch: Grab a bite at Woody’s Bar and Grill. Definitely try the crab cakes and homemade chips.
  • Afternoon: Spend some time soaking in the sun and having fun on the water! Dewey is a skimboarding hot spot and a great location for jet skiing, parasailing, wake boarding and of course, relaxing on the beach.
  • Dinner: Admire the sunset with a laid back soundtrack at the Rusty Rudder or for fine dining, visit Two Seas with high scale cuisine and rooftop bar with scenic views.
  • Evening/night on Dewey Beach: Dance the night away at lively beach bars including; the The Starboard (which serves late-night eats until 1 a.m. nightly including Build a Burger on Friday nights or Build your own Bloody Mary for Sunday brunch), Bottle and Cork, which dubs itself “the Greatest Rock and Roll Bar in the World” or Nalu for an open air Hawaiian surf bar vibe. 
  • Where to stay: Enjoy oceanfront views and easy beach access at the Atlantic View Hotel or stay at the Hyatt Place Dewey Beach, located on the bay and steps away from the ocean.
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