Relaxing 9-Day Virginia Beach Itinerary: Beachfront Stay, Gentle Hikes & Nearby Activities

Day 1: Arrival & Relax

Virginia Beach, Virginia on May 30, 2025

10:00am

Check-in at Oceanfront Hotel or Condo

Settle into a comfortable beachfront hotel or condo such as the Hilton Virginia Beach Oceanfront or a vacation rental condo. Enjoy ocean views and easy beach access.

USD150, 0h30m

11:00am

Breakfast at Doc Taylor's

Enjoy a delicious breakfast featuring fresh local ingredients at this well-known, friendly spot near the beach. Try the crab cake Benedict.

USD20, 1h

1:00pm

Virginia Beach Boardwalk Walk

Take a leisurely stroll down the iconic 3-mile boardwalk, enjoying ocean views, shops, and lively street performers. The walk is flat and easy.

Free, 1h30m

3:00pm

Relax at the Beach

Spend your afternoon unwinding on the sandy Virginia Beach, soaking up the sun and listening to the waves.

Free, 2h

6:00pm

Dinner at Waterman's Surfside Grille

Enjoy fresh seafood and ocean views at this popular oceanfront restaurant. The seafood paella is highly recommended.

USD35, 1h30m

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Day 2: Easy Nature Hike & History

Virginia Beach, Virginia on May 31, 2025

8:00am

Breakfast at The Bee & The Biscuit

Savor hearty Southern-inspired breakfast dishes in a cozy cafe setting, perfect for starting your day.

USD18, 1h

9:30am

Hiking at First Landing State Park

Explore several easy and beautiful hiking trails under 0.5 miles each, including the Beach Trail and Parker's Creek Trail, enjoying coastal forests and marsh views.

USD8 per vehicle parking, 2h

12:00pm

Lunch at Taste Unlimited

Have a relaxed lunch featuring fresh sandwiches and soups at this local deli with a casual vibe.

USD15, 1h

2:00pm

Visit the Military Aviation Museum

Explore one of the largest collections of WWI and WWII military aircraft, with some flights scheduled which bring the exhibits to life.

USD15, 2h

6:00pm

Dinner at Waterman's Museum Restaurant

Dine at a historical location with beach-inspired fresh dishes and a comfortable atmosphere just a short drive away.

USD30, 1h30m

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Day 3: Cultural & Waterfront Day

Virginia Beach, Virginia on June 1, 2025

8:30am

Breakfast at Bay Local Eatery

Start with locally sourced breakfast items with a modern twist in a casual setting near the water.

USD20, 1h

10:00am

Virginia Aquarium & Marine Science Center

Visit the aquarium featuring local marine wildlife and interactive exhibits, ideal for adults interested in the local ecosystem.

USD24, 2h

12:30pm

Lunch at Bubba's Seafood Restaurant & Crab House

Enjoy authentic local seafood specialties, including steamed crabs and shrimp, in a vibrant setting.

USD25, 1h30m

2:30pm

Stroll through Cape Henry Lighthouse and Beach Park

Tour the historic Cape Henry Lighthouse and enjoy an easy beachside walk with picturesque views.

USD8, 1h30m

5:30pm

Relax at the Hotel/Condo

Unwind and enjoy amenities such as the pool or private beach access to refresh before dinner.

Free, 1h30m

7:00pm

Dinner at Terrapin Restaurant

Dine on contemporary American cuisine with fresh, local ingredients and great service in an upscale environment.

USD40, 2h

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Day 4: Light Hiking & Shopping

Virginia Beach, Virginia on June 2, 2025

8:30am

Breakfast at Nick's Russian Restaurant

Experience a unique breakfast experience with authentic Eastern European dishes along with traditional options.

USD18, 1h

10:00am

Hiking at Back Bay National Wildlife Refuge

Enjoy short nature trails under .5 miles featuring sand dunes, maritime forests, and wildlife viewing in this tranquil refuge.

Free, 2h

12:30pm

Lunch at The Bee & The Biscuit

Return for a laid-back midday meal with fresh, homemade Southern comfort food.

USD20, 1h

2:00pm

Shopping at Town Center of Virginia Beach

Browse a variety of shops, boutiques, and cafes in this pedestrian-friendly shopping and dining area.

Free to browse, 2h

6:00pm

Dinner at Latitude

Enjoy coastal cuisine with a focus on sustainability and fresh seafood, located near the oceanfront.

USD35, 1h30m

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Day 5: Historic Sites & Local Brews

Virginia Beach, Virginia on June 3, 2025

8:30am

Breakfast at Doc Taylor's

Start your day at this beloved local spot known for hearty breakfasts and friendly atmosphere.

USD20, 1h

10:00am

Visit Edgar Cayce's A.R.E. (Association for Research and Enlightenment)

Explore this unique center dedicated to the work of Edgar Cayce, with tours, a library and gardens all easily walkable.

USD10, 1h30m

12:00pm

Lunch at Village Table

Enjoy fresh, farm-to-table fare in a relaxed environment with local ingredients.

USD22, 1h

2:00pm

Tour local breweries

Visit nearby breweries such as Back Bay Brewing Co. and Commonwealth Brewing Co. for tastings and tours of locally crafted beers.

USD15, 2h

6:30pm

Dinner at Waterman's Surfside Grille

Return to this oceanfront gem for a relaxing dinner with fresh seafood and cocktails.

USD35, 1h30m

View Hotel Availability

Day 6: Leisure & Light Activities

Virginia Beach, Virginia on June 4, 2025

9:00am

Breakfast at Taste Unlimited

Casual and convenient for a light yet satisfying breakfast with fresh sandwiches and coffee.

USD15, 1h

10:30am

Kayak Rental & Exploring Lynnhaven Inlet

Rent a kayak for a gentle paddle exploring calm waters and wildlife. Perfect for a relaxed morning activity close to the city.

USD30, 2h

1:00pm

Lunch at The Grilled Cheese Bistro

Enjoy gourmet grilled cheese sandwiches with creative toppings and sides in a cozy spot.

USD15, 1h

3:00pm

Relax at the Hotel/Beach

Spend your afternoon sunbathing, reading, or swimming at the hotel pool or on the beach.

Free, 2h

6:00pm

Dinner at Terrapin Restaurant

Indulge in a creative, upscale dining experience with an emphasis on local produce and seafood.

USD40, 1h30m

View Hotel Availability

Day 7: Art & Music

Virginia Beach, Virginia on June 5, 2025

8:30am

Breakfast at Bay Local Eatery

Enjoy a fresh, local breakfast to start your culturally focused day.

USD20, 1h

10:00am

Virginia Museum of Contemporary Art (MOCA)

Explore rotating exhibitions of contemporary visual art, perfect for a light cultural morning.

USD10, 1h30m

12:00pm

Lunch at Commune

Try their farm-fresh menu emphasizing local ingredients in a modern setting near the beach.

USD25, 1h

2:00pm

Attend a Live Music Event or Theater Performance

Check local listings for events such as live jazz at the Sandbar or performances at the Virginia Beach Little Theatre. Usually starts in the evening after 7pm but can have afternoon shows.

USD20, 2h