9-Day Virginia Beach Itinerary for Two: Beachfront Stays, Scenic Hikes, and Deep Sea Fishing Adventure

Day 1: Arrival & Beach Relaxation

Virginia Beach, Virginia on May 30, 2025

10:00am

Drive from Holland, Indiana to Virginia Beach, Virginia

Begin the trip with a scenic drive heading east approximately 8-9 hours to Virginia Beach.
C0, 9h0m

7:00pm

Check-in Beachfront Hotel or Condo

Settle into a comfortable hotel or rental condo situated within 2-3 blocks of the beach for great ocean access and views.
C150, Overnight

8:00pm

Dinner at Waterman’s Surfside Grille

Enjoy fresh seafood and beautiful oceanfront dining in a relaxed atmosphere.
C60, 1h30m
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Day 2: Beach & Hiking

Virginia Beach, Virginia on May 31, 2025

8:00am

Breakfast at Doc Taylor’s

Start the day with locally loved breakfast dishes in a cozy beachfront eatery open from 7:30am.
C30, 1h0m

9:30am

Hiking at First Landing State Park

Explore the beautiful 0.5-mile manageable hiking trails that offer scenic views of Chesapeake Bay and natural coastal forests. Park opens at 8:00am.
C8, 2h0m

12:00pm

Lunch at Signal 19

A casual spot famous for tacos and local seafood, great for a laid-back lunch near the beach.
C40, 1h0m

2:00pm

Leisure on the Beach

Spend the afternoon relaxing on Virginia Beach’s sandy shores or take a swim in the Atlantic Ocean.
C0, 3h0m

6:30pm

Dinner at The Atlantic on Pacific

Enjoy elegant, seafood-focused cuisine just a block from the beach with excellent ambiance.
C70, 1h30m
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Day 3: Aquarium & Boardwalk

Virginia Beach, Virginia on June 1, 2025

7:30am

Breakfast at The Bee & The Biscuit

Delight in a hearty southern-style breakfast before a day of exploration. Opens at 7:00am.
C30, 1h0m

9:00am

Virginia Aquarium & Marine Science Center

Discover marine life exhibits and nature trails; the center opens at 9:00am and is ideal for a 2-3 hour visit.
C30, 3h0m

12:30pm

Lunch at Waterman's Brewing Co.

Grab a casual lunch with great craft beers and sandwiches near the oceanfront.
C40, 1h0m

2:00pm

Visit the Virginia Beach Boardwalk

Stroll the 3-mile boardwalk featuring shops, street performers, and ocean views; open all day.
C0, 3h0m

6:30pm

Dinner at Terrapin Restaurant

Dine on locally sourced, upscale dishes with waterfront views; reservation recommended.
C80, 1h30m
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Day 4: Fishing Excursion Day

Virginia Beach, Virginia on June 2, 2025

6:00am

Breakfast Quick Bite at Hotel/Condo

Grab a quick breakfast or prepare a light meal before the early fishing trip.
C20, 0h30m

7:00am

Deep Sea Fishing Excursion

Spend 6-8 hours on a chartered deep sea fishing boat exploring Atlantic waters; includes gear and expert captain. Typically returns 2-3pm.
C250, 8h0m

3:30pm

Relaxing Afternoon at Beach or Condo

After the excursion, unwind with a beach walk or rest at your accommodation.
C0, 2h0m

6:30pm

Dinner at Catch 31

Enjoy elegant seafood dining in an oceanfront setting, perfect for post-fishing celebration.
C75, 1h30m
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Day 5: Cultural Day

Virginia Beach, Virginia on June 3, 2025

8:00am

Breakfast at Louis' Morning Kitchen

Start your day with hearty southern breakfast classics in a casual setting, opens at 7:30am.
C30, 1h0m

9:30am

Visit the Military Aviation Museum

Explore a unique collection of WWII aircraft and engage in history-rich exhibits; open from 9am to 5pm.
C15, 2h0m

12:00pm

Lunch at Taste Unlimited

Casual lunch spot offering diverse sandwiches and salads, ideal for a light afternoon meal.
C30, 1h0m

1:30pm

Art Walk at Virginia Museum of Contemporary Art

Enjoy contemporary exhibits and small galleries; open 11am–5pm Tuesday to Sunday.
C10, 2h0m

5:30pm

Evening Stroll on the Boardwalk

Take in the sunset views and lively atmosphere with street vendors and music.
C0, 1h0m

7:00pm

Dinner at Tautog's Restaurant

Classic Virginia seafood dining with ocean views, perfect to round out your cultural day.
C70, 1h30m
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Day 6: Leisure & Local Exploration

Virginia Beach, Virginia on June 4, 2025

8:00am

Breakfast at Commune

Eclectic breakfast in a cozy setting, opens at 7:30am.
C30, 1h0m

9:30am

First Landing State Park Bike Rental and Ride

Rent a bike to explore scenic trails less taxing than hikes, rental open 9am–5pm.
C20, 2h0m

12:00pm

Lunch at Catch 31 Fish House & Bar

Popular seafood spot with fresh daily catches, great for lunch.
C40, 1h0m

2:00pm

Visit Chesapeake Bay Beach

Smaller less crowded beach area perfect for a relaxing afternoon.
C0, 3h0m

6:30pm

Dinner at BlackFinn Ameripub

A blend of American classics and pub fare with a selection of craft beers.
C50, 1h30m
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Day 7: Nature & Shopping

Virginia Beach, Virginia on June 5, 2025

8:00am

Breakfast at Simply Thai

Start your day with unique Thai breakfast options, opens at 8:00am.
C30, 1h0m

9:30am

Visit Back Bay National Wildlife Refuge

Great for easy hikes and spotting native wildlife on .5 to 2 mile trails, refuge open at 8am.
C0, 2h0m

12:00pm

Lunch at Bay Local Eatery

Fresh local ingredients served in a small bistro setting.
C35, 1h0m

1:30pm

Shopping at Town Center at Virginia Beach

Enjoy afternoon shopping at this popular mall with a variety of stores and cafes.
C0, 3h0m

6:30pm

Dinner at Blue Seafood & Spirits

Modern seafood dining with river views; reservation recommended.
C75, 1h30m
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Day 8: Free Day & Beach

Virginia Beach, Virginia on June 6, 2025

8:00am

Breakfast at Hotel or Nearby Cafe

Enjoy a relaxed breakfast with ocean views.
C30, 1h0m

9:30am

Relaxing Beach Day

Spend the day enjoying the beach, swimming, sunbathing, or taking gentle 0.5 mile walks along the shore.
C0, 6h0m

3:30pm

Explore Local Art Galleries

Visit several local art galleries along the boardwalk showcasing regional artwork.
C0, 2h0m

6:30pm

Dinner at Le Yaca French Restaurant

Experience fine French dining for your special last evening in Virginia Beach.
C85, 2h0m
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Day 9: Departure

Virginia Beach to Holland Indiana on June 7, 2025

8:00am

Breakfast and Final Beach Walk

Have a leisurely breakfast and take a final stroll on the beach.
C20, 1h0m

10:00am

Check out and drive back to Holland, Indiana

Depart Virginia Beach for the drive home, concluding the 9-day trip.
C0, 9h0m
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