Make this trip your own
Create your own free, personalized itinerary in seconds — then sign up to save and edit it.
Create my version

5-Day Rehoboth Beach, DE Itinerary — Beaches, Boardwalk & Cape Henlopen Highlights

Viewed by 147 travelers

Day 1: Boardwalk & Beach

Rehoboth Beach, USA on September 4, 2025

8:00am

Breakfast at The Buttery

Classic local bakery and café known for fresh pastries, breakfast sandwiches and strong coffee — a great start before hitting the boardwalk. Opens early (typically 7:00am); good for take-away if you plan a beach sunrise.
USD15, 1h0m

9:30am

Stroll the Rehoboth Boardwalk & Beach

Walk the iconic boardwalk, swim or relax on the beach — the boardwalk is open year-round and the beach is public (hours effectively sunrise–sunset). Perfect to get a feel for the town and sand.
USD0, 2h30m

12:15pm

Lunch at Grotto Pizza (Boardwalk)

Local favorite pizza chain with a strong boardwalk presence — casual, quick and family-friendly for a mid-day refuel. Most locations open daily for lunch (midday hours).
USD20, 1h0m

1:30pm

Shopping on Rehoboth Avenue & Browse Boutiques

Explore independent shops, surf stores and galleries along Rehoboth Avenue; ideal for souvenirs, beach gear and local goods. Most shops are open from late morning through early evening (hours vary by store).
USD0, 2h0m

4:00pm

Relax at your hotel or optional bike rental

Return to your hotel for a rest or rent a bike to explore the neighborhoods; rental shops typically open by mid-morning and run into the evening.
USD15, 1h30m

6:00pm

Dinner at Big Fish Grill

Casual seafood restaurant popular with visitors — reliable fresh seafood dishes and a lively atmosphere close to the boardwalk. Dinner service usually starts by 5:00pm and continues into late evening.
USD35, 1h30m

8:30pm

Evening at the Rehoboth Bandstand / Sunset

Catch live music (seasonal) or simply enjoy the sunset from the bandstand near the boardwalk; many outdoor events happen in summer and early fall, check local schedule.
USD0, 0h30m

Day 2: Cape Henlopen & Lewes

Cape Henlopen State Park & Lewes, USA on September 5, 2025

7:30am

Breakfast at a local café (The Buttery recommended)

Grab a hearty breakfast and coffee before heading to Cape Henlopen; cafés open early (usually 7:00am–8:00am) so you can be at the park at first light.
USD15, 0h45m

8:30am

Cape Henlopen State Park — trails, beaches & WWII towers

Explore coastal trails, Gordon's Pond (excellent for birding) and the WWII observation towers; the park is open sunrise–sunset and offers scenic overlooks and easy hikes.
USD0, 3h0m

11:45am

Visit Fort Miles / Lewes Historical Sites

Learn local military and maritime history at Fort Miles (museum hours commonly around 10:00am–4:00pm) and stroll Lewes' historic district for preserved 18th–19th-century buildings.
USD6, 1h30m

1:30pm

Lunch in Lewes — Crooked Hammock Brewery or waterfront café

Casual lunch with local beers or waterfront views in Lewes; many restaurants in the Harbor area are open midday and offer seafood and sandwiches.
USD22, 1h0m

2:45pm

Lewes downtown walk & Cape Henlopen lighthouse viewing areas

Wander the boutiques and small museums in Lewes, and visit viewpoints near the lighthouse area; small shops typically stay open through the afternoon.
USD0, 1h30m

5:30pm

Return to Rehoboth & sunset beach time

Head back to Rehoboth for one last beach sunset; evening beach access is open to the public (sunset hours vary seasonally).
USD0, 1h0m

7:00pm

Dinner at Henlopen City Oyster House

Local favorite for oysters and creative seafood plates with a cozy neighborhood feel — reservations recommended for evenings (opens for dinner service around 5:00pm).
USD40, 1h30m

Day 3: Dewey & South Beaches

Dewey Beach → Bethany Beach, USA on September 6, 2025

8:00am

Breakfast at Nectar Café or The Buttery

Light, fresh breakfast options to fuel a day of water activities; cafés typically open by 7:30–8:00am during season.
USD15, 0h45m

9:30am

Water sports in Dewey Beach (SUP, kayak or rented jet ski)

Choose stand-up paddleboarding or a guided kayak tour of the canals, or rent a jet ski for faster fun — most rental operators run 9:00am–5:00pm in season and require reservations for busy days.
USD40, 2h0m

12:00pm

Lunch at Dewey Beer Company or waterfront spot

Casual lunch and craft beer at a popular local spot in Dewey; patios and outdoor seating are common and open through afternoon.
USD20, 1h0m

1:45pm

Drive south to Bethany Beach — stroll the boardwalk & shops

Short scenic drive to Bethany for a quieter boardwalk, shops and possibly an outdoor concert depending on the schedule; boardwalk accessible year-round.
USD0, 2h0m

4:15pm

Fenwick Island viewpoint or state park short hike

If you have energy, continue to Fenwick Island for quieter beaches and nature viewing; small trails and dunes are ideal for late-afternoon walks (open sunrise–sunset).
USD0, 1h0m

6:30pm

Dinner at Salt Air Kitchen or similar seafood spot back in Rehoboth

Return to Rehoboth for dinner at a neighborhood seafood restaurant serving fresh local catches — many open for dinner starting 5:00pm; reservations recommended on weekends.
USD35, 1h30m

Day 4: Lewes → Cape May Ferry Day

Lewes (ferry) → Cape May, NJ day trip on September 7, 2025

7:00am

Early breakfast & drive to Lewes Ferry Terminal

Grab a quick breakfast and arrive at the Lewes Ferry terminal early — ferry schedules vary by season and departures often begin in the morning (confirm online and book ahead).
USD15, 0h45m

9:00am

Lewes–Cape May Ferry (foot passenger or vehicle)

Enjoy the scenic roughly 80-minute ferry crossing to Cape May, NJ; check the official Delaware River & Bay Authority schedule (seasonal times) and purchase tickets in advance — foot & vehicle fares differ.
USD25, 1h20m

11:00am

Explore Cape May — Washington Street Mall & beaches

Stroll the historic streets, boutique shops and cafes of Cape May and relax on the beach; many shops and museums open by 10:00am and stay open into the afternoon.
USD0, 2h30m

1:30pm

Lunch in Cape May — seaside café or seafood bistro

Enjoy a mid-day meal at a Cape May bistro or seaside café — popular spots fill up quickly so consider reservations or an early lunch.
USD28, 1h0m

3:00pm

Historic lighthouse visit or trolley tour

Visit Cape May Lighthouse or take the trolley for a quick overview of historic neighborhoods; hours for attractions are typically afternoon-friendly but check individual sites for exact times.
USD12, 1h30m

5:00pm

Ferry back to Lewes — return crossing

Return on a scheduled ferry crossing to Lewes; arrive back in Delaware in the early evening and drive to Rehoboth for dinner.
USD25, 1h20m

7:30pm

Dinner at a Rehoboth favorite (Henlopen City or Big Fish if not tried)

End the day with a relaxed dinner back in Rehoboth — choose a familiar seafood spot or try a new local restaurant; evening hours are typically 5:00pm–10:00pm.
USD35, 1h30m

Day 5: Relax & Depart

Rehoboth Beach, USA on September 8, 2025

7:00am

Sunrise & light beach walk

Enjoy a final sunrise stroll on the beach or a quick morning swim; beaches are accessible from sunrise and are a peaceful way to start departure day.
USD0, 0h45m

8:00am

Brunch at The Buttery or local café

Have a leisurely brunch and pack up — The Buttery or a nearby café offers easy, fresh options before checkout; brunch hours typically begin 8:00–9:00am on weekdays.
USD20, 1h0m

9:30am

Last-minute shopping or boardwalk souvenir stops

Grab any final souvenirs or a quick coffee on the boardwalk before heading out; many shops open by mid-morning and this is a convenient time to pick up gifts.
USD0, 0h45m

11:00am

Check-out & departure

Return to your lodging for check-out and depart — allow time for seasonal traffic on routes north or west off the peninsula.
USD0, 0h30m

12:00pm

Optional: quick stop at Cape Henlopen overlook (if time permits)

If your schedule allows, stop at a scenic overlook or short trail near Cape Henlopen on the way out for one last look at the coast; parks are open sunrise–sunset.
USD0, 0h30m
0
Like this trip? Make your own version.
A free, personalized itinerary in seconds — sign up to save and edit it.
Create my version