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Weekend in Virginia Beach

Weekend in Virginia Beach

Trip Overview

This 48-hour sprint pairs sunrise paddle-outs with sunset cocktails, tracing Virginia Beach's three-mile boardwalk from First Landing's pine-shaded trails to the neon clam bars of 24th Street. Expect salt on your skin, Old Bay on your fingers, and a steady ocean soundtrack in the background. The rhythm is brisk but never rushed, plenty of time to watch dolphins arc past the pier while nursing a cold local lager.

Pace
Moderate
Daily Budget
$200, 250 per day
Best Seasons
May through October for warm water; December for uncrowded walks and oyster roasts
Ideal For
Couples, Weekend escapees from D.C., Beer-and-beach lovers

Day-by-Day Itinerary

A complete plan for every day of your trip

1

First Landing to First Shuck

North End & Chesapeake Bay
Morning hike where English settlers first stepped ashore, afternoon surf school on glassy Atlantic rollers, sunset oysters on the bay.
Morning
Cape Henry Trail at First Landing State Park
Walk the shaded maritime forest trail past gnarled live oaks and Spanish moss. The briny scent of the bay filters through the pines before you emerge onto a quiet crescent of sand where only gulls keep watch.
2.5 hours $10 per vehicle entry
Arrive by 8 a.m. to beat crowds and snag the shaded parking loop near the trailhead
Lunch
Blue Seafood & Spirits
Chesapeake seafood
Afternoon
Surf lesson at 1st Street Jetty
Take a private lesson with VB Surf Sessions. Your instructor paddles you past the break where dolphins slice through emerald water and the boardwalk shrinks to a string of pastel motels.
2 hours $90
Book the day before. They provide boards and spring suits
Evening
Sunset oysters and craft beer at The Shack on 8th
Sit on the dock, watch the sky turn sherbet over the bay while slurping Rappahannock River oysters and a citrusy Commonwealth Brewing lager

Where to Stay Tonight

North End on Atlantic Avenue between 40th and 60th Streets (The Cavalier Hotel, Autograph Collection)

Art-deco grande dame with adult-only infinity pool overlooking the ocean, walkable to quieter beaches

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Ask hotel concierge for a side-door shortcut to the beach that skips the boardwalk crowds
Day 1 Budget: $230
2

Boardwalk Miles to Neon Nights

Oceanfront & ViBe District
Sunrise bike cruise, street art safari, afternoon kayak among bottlenose dolphins, late-night speakeasy jazz.
Morning
Sunrise bike ride on the Boardwalk
Rent fat-tire cruisers at Cherie's Bike Rentals and glide the wooden planks as orange light burns off the overnight mist. Smell waffle cones mixing with salty air and hear the metallic clink of fishing lines dropping off the pier.
1.5 hours $15 rental
Reserve bikes after sunset the day before for guaranteed availability at 6 a.m.
Lunch
Commune
Farm-to-table sandwiches
Afternoon
Dolphin kayak tour in Rudee Inlet
Paddle calm inlet waters with Chesapean Outdoors. Bottlenose dolphins surface beside your kayak, exhaling with a wet trumpet sound while marsh grasses tickle the plastic hull.
2.5 hours $65
Morning tide slots fill first, book online a week ahead
Evening
Craft cocktails at The Hunt Room followed by live jazz at 24th Street's Cobalt Grille Lounge
Start with a bourbon smoked over cherrywood, end with saxophone solos echoing against brick walls

Where to Stay Tonight

Oceanfront between 20th and 30th Streets (Hilton Virginia Beach Oceanfront)

Rooftop infinity pool facing the pier, elevator drops you directly onto the boardwalk for midnight stargazing

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Skip the elevator at 7 p.m. and take the back stairwell, the top floor fire escape door opens to an unmarked rooftop deck with unobstructed sunset views
Day 2 Budget: $220

Practical Information

Everything you need to know before you go

Getting Around
Virginia Beach is built for cars. But the oceanfront grid and boardwalk make walking faster. Lyft costs $8, 12 between the North End and ViBe District. Bikes handle the three-mile oceanfront stretch in fifteen minutes flat.
Book Ahead
Surf lessons, dolphin kayak tour, and weekend hotel stays, at The Cavalier, sell out during May to August.
Packing Essentials
Reef-safe sunscreen, quick-dry shorts, light hoodie for breezy nights, waterproof phone pouch for kayak spray, beach cruiser-friendly backpack
Total Budget
$450, 500 for the weekend including lodging, meals, activities, and rides

Customize Your Trip

Adapt this itinerary to your travel style

Budget Version
Camp at First Landing State Park ($30/night), swap surf lessons for free public beaches, and hit Crocs 19th Street Bistro for $5 happy-hour oysters.
Luxury Upgrade
Book an oceanfront suite at The Cavalier with private cabana service, charter a sunset sail out of Rudee Inlet, and reserve the chef's tasting menu at Terrapin with Virginia wine pairings.
Family-Friendly
Switch dolphin kayaking for the calmer Back Bay Wildlife Refuge pontoon cruise, add the Virginia Aquarium and a late-night ice-cream crawl along Atlantic Avenue.
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Things to Do

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Getting Around

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