Discover Dewey Beach - Sun, Surf & Spirited Nights on the Delaware Coast

• Morning (10:00 AM - 1:00 PM) Arrive in Dewey Beach and kick off your ultimate party weekend! Head straight to the main public beach access at Dagsworthy Street (or your preferred entry point) on Dewey Beach. Set up your spot on the sand. You can rent beach chairs and an umbrella from local vendors usually patrolling the beach or near accesses (expect to pay around $35-45 for two chairs and an umbrella for the day). Spend the morning soaking up the sun, swimming in the Atlantic, and shaking off any travel stress. Everything is extremely walkable in Dewey, so your hotel/rental will likely be just a short stroll (0.1-0.5 miles) from the sand.
• Afternoon (1:00 PM - 5:30 PM) For a quintessential Dewey lunch, take a short walk (0.2 miles) from the beach to Woody’s Dewey Beach on Coastal Highway. Famous for their Crab Cake Sandwich and Lobster Rolls, it’s a casual, delicious start. Budget about $60-75 for lunch for two. After refueling, head to Dewey Beach Watersports (located bayside on Dickinson St, about 0.3 miles from Woody’s). Rent paddleboards or kayaks for an hour or two to explore Rehoboth Bay. This offers a different perspective of Dewey and is a fun active break. Expect to pay around $70-90 for a 1-hour rental for two people.
• Evening As the sun begins to set, get ready for Dewey’s legendary nightlife! Start with dinner at Nalu Hawaiian Surf Bar & Grille (on Coastal Hwy, ~0.1 miles from Woody’s). Nalu offers a vibrant atmosphere and delicious Pacific-inspired dishes. Budget $80-100 for dinner for two, including a couple of drinks. After dinner, it’s time to hit the main strip. Your first stop must be The Starboard (Coastal Hwy, ~0.1 miles from Nalu). This iconic Dewey institution is famous for its Orange Crushes and lively crowds. Enjoy a few drinks and the live music. Later, if you’re up for more, walk just a few steps down the road to the Bottle & Cork or Rusty Rudder (both on Coastal Hwy, <0.1 miles apart) for more live entertainment and dancing. Budget $150-200 for drinks and cover charges (if applicable) for the evening.

• Morning (10:30 AM - 1:00 PM) After a late night, it’s time for Dewey’s most famous hangover cure: The Starboard’s Bloody Mary & Mimosa Bar Brunch. Head back to The Starboard (Coastal Hwy) for their epic brunch buffet, complete with an expansive build-your-own Bloody Mary bar and endless mimosas. This is a must-do experience in Dewey. Budget $100-120 for two people, including drinks and gratuity. It’s the perfect way to ease into your second day.
• Afternoon (1:00 PM - 4:00 PM) With a full stomach, take a leisurely stroll back to Dewey Beach (0.1-0.3 miles depending on your starting point) for some more relaxation. Enjoy the sun and waves one last time, or simply walk along the shore. If you’re feeling peckish, grab a casual, classic beach lunch. Grotto Pizza (Coastal Hwy, <0.1 miles from Starboard) is a Dewey staple, perfect for a quick and satisfying slice. Budget $30-40 for a pizza and sodas for two. Alternatively, grab some ice cream from Vanderwende’s Farm Creamery for a sweet treat (Coastal Hwy, ~0.1 miles from Grotto).
• Evening Before heading out, enjoy a final Dewey Beach experience. Make your way to Northbeach (on the bay side, end of McKinley St, ~0.4 miles from Grotto Pizza) for sunset drinks. Northbeach offers fantastic bayfront views and a relaxed atmosphere to watch the sun dip below the horizon. Budget $60-80 for cocktails for two. For your farewell dinner, walk a short distance (0.1 miles) to the Rusty Rudder (on the bay side, adjacent to Northbeach). Known for its great food, often live music, and excellent bay views, it’s a perfect spot to cap off your weekend. Enjoy fresh seafood or a hearty meal. Budget $100-120 for dinner for two. After dinner, you’ll be perfectly positioned to head home with incredible Dewey memories.

Day 1: Sun-Kissed Welcome & Coastal Stroll

• Morning (9:00 AM - 12:30 PM) Begin your Dewey Beach escape by heading straight to the oceanfront. Find an accessible beach entrance (many public access points along Coastal Highway, e.g., McKinley Street or Read Street). Settle in for some classic beach time – building sandcastles, boogie boarding in the gentle waves, or simply relaxing with a book. Lifeguards are typically on duty from Memorial Day to Labor Day. If you didn’t bring your own, boogie boards can be rented from local shops like Dewey Beach Surf Shop (2000 Coastal Hwy) for approximately $15-20 for the day.
  • Practical Tip: Parking can be metered or permit-required; if staying in Dewey, walking is often the easiest option.
  • Cost: Free beach access, ~$15-20 for boogie board rental.
• Afternoon (12:30 PM - 5:30 PM) For a casual, family-friendly lunch, walk over to Woody’s Dewey Beach Bar & Grill (1904 Coastal Hwy, a short walk from most beach accesses). They’re famous for their crab cakes and relaxed atmosphere. Expect to spend $40-60 for two. After lunch, take a leisurely stroll along Coastal Highway, browsing the surf shops and boutiques. Consider a ride on the Jolly Trolley (seasonal, check schedule and availability) to explore a bit of Rehoboth Beach Boardwalk without the hassle of parking. The trolley runs regularly between Dewey and Rehoboth.
  • Distance: Woody’s is centrally located, easily walkable. Jolly Trolley stop is usually near the Bottle & Cork.
  • Cost: Lunch ~$40-60, Jolly Trolley ~$4-5 per person per ride ($16-20 round trip for two).
• Evening Enjoy a delicious dinner with bay views at The Rudder at the Lighthouse (207 Dickinson St, Dewey Beach). This waterfront spot offers fresh seafood and a pleasant ambiance, perfect for winding down after your first day. Expect to spend around $80-120 for two including drinks. After dinner, treat yourselves to a scoop (or two!) of ice cream at The Ice Cream Store (1900 Coastal Hwy), known for its creative flavors.
  • Cost: Dinner ~$80-120, Ice Cream ~$10-15.

Day 2: Bay Breezes & Crabby Adventures

• Morning (9:30 AM - 1:00 PM) Today, shift your focus to the calmer waters of Rehoboth Bay. Head to Dewey Beach Watersports (120 Dickinson St, Dewey Beach) for a fun paddleboarding or kayaking excursion. You can rent single or tandem kayaks, or stand-up paddleboards. It’s a fantastic way to explore the bay, spot wildlife, and get some exercise. Allow about 1.5-2 hours for your rental and paddling.
  • Practical Tip: Wear swimwear, bring water, and apply sunscreen. Life vests are provided. It’s a very short walk from most Dewey accommodations to Dickinson Street.
  • Cost: Kayak/SUP rentals typically $25-35 per hour; budget ~$70-90 for two for 1.5 hours.
• Afternoon (1:00 PM - 5:30 PM) Grab a unique, laid-back lunch at Nalu Hawaiian Surf Bar & Grille (1308 Coastal Hwy, located bay side, a short walk from Dewey Beach Watersports). Their Hawaiian-inspired menu is a refreshing change. Expect to spend $40-70 for two. After lunch, embrace a classic Delaware tradition: crabbing! Pick up a basic crab trap, line, and bait (chicken necks or fish heads work well) from a local tackle shop. You can often find supplies at some convenience stores or hardware stores in the area. Find a public pier on the bay side (such as near Dickinson Street) and try your luck. It’s a fun, patient activity that often yields some catches!
  • Cost: Lunch ~$40-70, Crabbing supplies ~$20-30.
• Evening Enjoy the serene sunset over Rehoboth Bay, followed by dinner at the Lighthouse Restaurant (124 Dickinson St, Dewey Beach). This spot offers excellent bay views and a varied menu, often with live music. It’s known for its seafood, but also offers other family-friendly options. Budget $70-100 for two. After dinner, take a relaxing walk along the bay side to soak in the evening atmosphere.
  • Cost: Dinner ~$70-100.

Day 3: Farewell Waves & Sweet Memories

• Morning (9:00 AM - 12:00 PM) Start your last day with a final, refreshing dip in the Atlantic Ocean or a peaceful morning stroll along the beach, collecting seashells and enjoying the calming rhythm of the waves. Afterward, take some time for souvenir shopping. Browse the local gift shops along Coastal Highway, like Dewey Beachwear (2000 Coastal Hwy) or similar independent stores, to find a memento of your trip.
  • Cost: Free (beach), ~$20-40 for souvenirs.
• Afternoon (12:00 PM - 3:30 PM) For lunch, venture back to Rehoboth Beach for a classic boardwalk experience. Take the Jolly Trolley (if operating) or a short drive. Indulge in iconic boardwalk treats like Thrasher’s French Fries and a slice of pizza from Grotto Pizza on the boardwalk. Take a final stroll along the Rehoboth Boardwalk, maybe play a quick arcade game or two at Funland (check seasonal hours). This offers a different coastal vibe before you head home.
  • Distance: Trolley ride is ~10-15 minutes to Rehoboth Ave.
  • Cost: Jolly Trolley ~$4-5 per person per ride ($16-20 round trip for two), Lunch ~$30-50.
• Evening Before hitting the road, enjoy one last casual and comforting meal. Head back to Dewey Beach for dinner at Mama Maria’s Restaurant (1608 Coastal Hwy, Dewey Beach). This local staple serves delicious Italian comfort food in a family-friendly setting, perfect for a relaxed farewell dinner. Expect to spend $50-70 for two.
  • Practical Tip: Allow ample time for traffic if departing on a Sunday afternoon during peak season.
  • Cost: Dinner ~$50-70.

Day 1: Bay Breeze & Brews

• Morning (10:00 AM - 1:00 PM) Kick off your adventure with a refreshing start on Rehoboth Bay. After a light breakfast or coffee, head to Dewey Beach Watersports (110 Dickinson St) for kayak or stand-up paddleboard (SUP) rentals. Enjoy 1.5 hours exploring the calm bay waters, paddling past homes and local wildlife. No prior experience needed, and the staff provides quick instructions.
  • Practical Tip: Wear a swimsuit, sunscreen, and bring a hat. Rentals typically include life vests.
  • Distance: Dewey Beach Watersports is centrally located on the bay side, easily walkable from most Dewey accommodations.
  • Cost (Estimate for 2 people): ~$105 for 1.5 hours (e.g., 2 single kayaks/SUPs at $35/hour each).
• Afternoon (1:00 PM - 5:00 PM) After your paddle, grab a casual lunch at Nalu Hawaiian Surf Bar & Grille (1308 Coastal Hwy) known for its vibrant atmosphere and delicious fish tacos or poke bowls. Post-lunch, unwind on the pristine sands of Dewey Beach. Find a spot near one of the public access points along Coastal Highway, swim in the Atlantic, or simply relax with a good book.
  • Distance: Nalu is a short walk from the bay to the ocean side of Dewey, and beach access is just across the street.
  • Cost (Estimate for 2 people): ~$50 for lunch with non-alcoholic drinks.
• Evening As the sun begins to set, head to The Rusty Rudder (113 Dickinson St) for dinner. This iconic bayfront restaurant offers fantastic views of Rehoboth Bay, fresh seafood, and a lively atmosphere. Enjoy a diverse menu with options from crab cakes to steaks, paired with a local craft brew or a classic cocktail as you watch the sunset.
  • Distance: Located directly on the bay, a pleasant evening stroll from most of Dewey Beach.
  • Cost (Estimate for 2 people): ~$120-150 for dinner and drinks.

Day 2: Thrill-Seeking & Taproom Delights

• Morning (9:30 AM - 12:30 PM) Get your adrenaline pumping with a thrilling water sports experience! Head back to the bay side for either Jet Skiing with Dewey Beach Watersports (110 Dickinson St) or Parasailing with Dewey Beach Parasail (3908 Highway One). Jet skiing offers the freedom to zip across the bay, while parasailing provides breathtaking aerial views of the coastline.
  • Practical Tip: Book your slot in advance, especially during peak season. Arrive 30 minutes prior to your reservation.
  • Distance: Dewey Beach Watersports is centrally located. Dewey Beach Parasail is a short drive north on Coastal Hwy or an accessible bike ride.
  • Cost (Estimate for 2 people): ~$200-240 for one hour of jet skiing (can often be shared by two) OR ~$190-200 for parasailing for two people.
• Afternoon (1:00 PM - 5:30 PM) Refuel with a laid-back lunch at Hammerheads Dockside (13206 Coastal Hwy). Known for its casual, friendly vibe and bay views, their menu features delicious burgers, fresh salads, and their famous crab dip. Afterwards, enjoy more time lounging on Dewey Beach, or explore the small boutiques and surf shops along Coastal Highway for unique finds.
  • Distance: Hammerheads is on the bay side, a short walk from the ocean and shopping.
  • Cost (Estimate for 2 people): ~$60 for lunch with drinks.
• Evening Prepare for a true craft beer experience at Dewey Beer Co. (2100 Coastal Hwy). This popular brewery is a mecca for beer enthusiasts, offering an innovative selection of IPAs, sours, and unique brews on tap. Their kitchen also serves up delicious, elevated pub fare like gourmet tacos and smash burgers perfect for pairing. Enjoy the lively atmosphere, often with indoor/outdoor seating options.
  • Distance: Located right on Coastal Highway, easily walkable or a very short ride from anywhere in Dewey.
  • Cost (Estimate for 2 people): ~$120-150 for dinner and several rounds of craft beers.

Day 3: Lazy Morning & Lobster Rolls

• Morning (9:30 AM - 12:00 PM) Start your final day with a classic Dewey Beach brunch experience at The Starboard Restaurant (2009 Coastal Hwy). Famous for its lively atmosphere, fantastic breakfast menu, and legendary Bloody Mary Bar, it’s a must-do. Enjoy hearty portions of breakfast favorites or a delicious brunch dish.
  • Practical Tip: The Starboard can get busy, especially on weekends, so be prepared for a short wait or arrive earlier.
  • Distance: Centrally located on Coastal Highway, easy to find.
  • Cost (Estimate for 2 people): ~$70 for brunch with coffee/juice (Bloody Marys would be extra).
• Afternoon (12:00 PM - 3:00 PM) For your farewell lunch, indulge in some of Dewey’s best seafood at Woody’s LBC (1904 Coastal Hwy). Known for its mouth-watering lobster rolls and fresh, casual seafood menu, it’s the perfect way to cap off your coastal culinary journey. Take your time, savor the flavors, and reflect on your Dewey Beach adventures before heading home.
  • Distance: Just a block or two down Coastal Highway from The Starboard.
  • Cost (Estimate for 2 people): ~$80-100 for lunch, especially if opting for lobster rolls.
  • Practical Tip: Grab any last-minute souvenirs from local shops before departing, or take one last stroll on the beach.