7-Day Ultimate Coastal and Cultural Getaway in Rehoboth Beach and Surrounding Delaware

Day 1: Beach and Boardwalk

Rehoboth Beach, Delaware on May 30, 2025

8:00am

Breakfast at The Green Man Juice Bar

Start your vacation with fresh and healthy smoothies, juices, and breakfast bowls at this local favorite just steps from the beach.
USD10, 1h

9:30am

Stroll Rehoboth Beach Boardwalk

Experience the vibrant atmosphere with ocean views, boutiques, and family-friendly amusement rides along the mile-long boardwalk.
Free, 2h

12:00pm

Lunch at Henlopen City Oyster House

Enjoy top-quality local seafood specialties, including fresh oysters and savory fish dishes in an inviting upstairs setting.
USD25, 1h30m

2:00pm

Visit Rehoboth Beach Museum

Dive into the area's history and learn about its evolution from a small fishing town to a beloved beach resort (open 10:00am–5:00pm).
USD5, 1h

4:00pm

Relax on Rehoboth Beach

Unwind on the soft sandy beach—swim, sunbathe, or simply enjoy the peaceful ocean breeze.
Free, 2h

7:00pm

Dinner at Dogfish Head Brewings & Eats

Sample creative dishes paired with craft beers from the iconic brewery in an upscale yet casual setting.
USD40, 2h
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Day 2: Nature & Hiking

Cape Henlopen State Park, Delaware on May 31, 2025

7:30am

Breakfast at Jellyfish Macaron Boutique

Begin with exquisite macarons and a variety of breakfast pastries paired with artisanal coffee near Rehoboth.
USD15, 1h

9:00am

Explore Cape Henlopen State Park

Hike scenic trails, visit the WWII observation towers, and enjoy ocean views; the park opens at 8:00am and closes at sunset.
USD10 per vehicle, 5h

2:30pm

Picnic Lunch at Gordon's Pond

Pack or pick up a lunch to enjoy a serene picnic by the pond surrounded by coastal wetlands within the park.
USD20 (to-go meal), 1h

4:00pm

Visit Seaside Nature Center

Explore native wildlife and marine exhibits; center is open until 5:00pm for a relaxing late afternoon visit.
Free, 1h

7:00pm

Dinner at Big Fish Grill

Relish sustainable, locally sourced seafood dishes in a lively yet comfortable atmosphere near the park.
USD35, 2h
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Day 3: History & Shopping

Lewes, Delaware on June 1, 2025

8:00am

Breakfast at The Green Room

Enjoy a traditional American breakfast featuring fresh eggs, pancakes, and coffee within Lewes’ charming historic district.
USD18, 1h

9:30am

Zwaanendael Museum Tour

Discover Delaware’s Dutch colonial roots and Lewes’ heritage through engaging exhibits in this beautifully preserved museum (open until 4:30pm).
USD8, 1h

11:00am

Downtown Lewes Shopping & Galleries

Explore charming boutiques, art galleries, and artisan shops showcasing local craftsmanship in the historic district.
Free, 2h

1:00pm

Lunch at Kindred Spirits

Savor a menu blending American classics with Southern flair in a cozy and inviting setting close to town center.
USD30, 1h30m

3:00pm

Afternoon on Lewes Beach

Take a relaxing swim or sunbathe on this lesser-crowded beach featuring calm waves and scenic views.
Free, 2h

7:00pm

Dinner at Agave Mexican Cocina

Enjoy vibrant Mexican flavors and fresh ingredients in a festive atmosphere, open until 9:00pm.
USD30, 1h30m
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Day 4: Discovery & Small Town Charm

Milton and Delmarva Discovery Center, Delaware on June 2, 2025

8:00am

Breakfast at DiFebo’s Italian Eatery

Enjoy fresh baked goods and Italian-inspired breakfast dishes in Milton’s quaint town center.
USD15, 1h

9:30am

Visit Delmarva Discovery Center

Engage with interactive exhibits highlighting the Delmarva Peninsula’s ecology, history, and culture; open 9:00am–5:00pm.
USD10, 2h

12:00pm

Lunch at Broadkill River Company

Dine on sumptuous seafood and farm-to-table dishes along the scenic Broadkill River waterfront.
USD30, 1h30m

2:00pm

Explore Historic Milton

Walk this charming town known for its historic architecture, unique shops, and scenic trails along the Broadkill River.
Free, 2h

7:00pm

Dinner at Agave Nuevo

Indulge in an innovative spin on classic Mexican dishes at this casual, modern spot in Milton open evenings until 9pm.
USD30, 1h30m
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Day 5: Park & Beach Fun

Delaware Seashore State Park and Fenwick Island, Delaware on June 3, 2025

7:30am

Breakfast at Fractured Prune Donuts

Grab fresh, custom-made donuts and coffee to fuel up for a day of outdoor adventure near Fenwick Island.
USD10, 1h

9:00am

Delaware Seashore State Park Activities

Enjoy swimming, kayaking, or hiking; the park has scenic bayside and oceanfront areas. Open 8:00am until sunset; entrance fee USD10 per vehicle.
USD10, 4h

1:00pm

Lunch at The Starboard

Savor seafood specialties with bay views, located near the park and open for lunch until 3:00pm.
USD25, 1h

2:30pm

Fenwick Island Exploring

Visit the Fenwick Island Lighthouse area for history, beach walks, and relaxed coastal charm.
Free, 2h

7:00pm

Dinner at Seared Steak & Seafood

End your day with succulent steak and seafood dishes served in a sophisticated atmosphere in Fenwick Island.
USD40, 2h
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Day 6: Historic Exploration

New Castle, Delaware on June 4, 2025

8:00am

Breakfast at Back Burner

Fuel your morning with hearty breakfast classics made from fresh, local ingredients in historic New Castle.
USD18, 1h

9:30am

Explore Historic New Castle

Tour the colonial-era streets, visit the Old New Castle Court House Museum, and explore Battery Park along the Delaware River.
Museum entry USD8, 3h

12:30pm

Lunch at Delaware House Restaurant

Enjoy comfort food with a colonial twist in New Castle’s historic downtown, offering classic American fare.
USD25, 1h30m

2:30pm

Visit Amstel House

Step inside a beautifully preserved historic home showcasing 18th-century architecture and furnishings (open until 5:00pm).
USD6, 1h

4:00pm

Relax at Battery Park

Enjoy the scenic waterfront park with views of the Delaware River, perfect for a relaxing afternoon stroll or picnic.
Free, 1h

7:00pm

Dinner at Vesuvio Ristorante

Cap off your historic tour with classic Italian dishes and an extensive wine list in warm ambiance.
USD40, 2h
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Day 7: Dover & Departure

Dover and Return to Rehoboth Beach, Delaware on June 5, 2025

7:30am

Breakfast at Batter'd & Fried

Start your day with traditional southern-inspired breakfast favorites featuring fried chicken and waffles in Dover.
USD18, 1h

9:00am

Visit the Air Mobility Command Museum

Explore military aviation history and aircraft exhibits at this free, must-see museum at Dover Air Force Base; open 9:00am–4:00pm.
Free, 2h

11:30am

Tour Dover Historical Society Museum

Discover Delaware’s political history and local artifacts in this compact museum in downtown Dover.
USD5, 1h

1:00pm

Lunch at The Green Lantern Tavern

Enjoy a casual American lunch featuring burgers and sandwiches in a friendly tavern atmosphere.
USD20, 1h

2:30pm

Return to Rehoboth Beach

Drive back to Rehoboth Beach for last-minute shopping or beach time before departure.
Free, 1h30m

5:00pm

Final Walk and Dinner at Boardwalk

Enjoy a last stroll along the Rehoboth Beach Boardwalk followed by dinner at Fins Fish House & Raw Bar, known for fresh seafood and raw bar options (open until 9:00pm).
USD40, 2h
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