Planning a long weekend trip to Virginia Beach? At Transcendent Stays, we believe that where you stay should be as memorable as what you do. That’s why we offer a lovely selection of boutique hotels and vacation rentals in Virginia Beach, VA. Here’s how to spend a long weekend in Virginia Beach, with a curated 3-day itinerary designed for effortless connection and maximum enjoyment.
Your 3 Day Itinerary for a Weekend Trip to Virginia Beach
Day 1: Arrival and Easy Exploration
Settle Into Your Stay
Arrive at your Transcendent Stays property and feel the difference immediately. From spacious layouts to elevated design details, every space is curated for travelers who value both comfort and style. Our homes are ideal for multigenerational groups, couples seeking privacy, or families looking for room to spread out during their weekend trip to Virginia Beach.
Evening at the Oceanfront
Ease into your Virginia Beach weekend getaway with a relaxing walk along the famous boardwalk. Watch street performers, snap a photo by the Neptune statue, and breathe in that unmistakable salt air.
For dinner, head to Waterman’s Surfside Grille, known for its fresh seafood and locally loved orange crush cocktail. With a kid-friendly menu and an oceanfront setting, it works for every kind of traveler.
Day 2: Beachside Adventure and Local Flavor
Start with Sunrise or Slow Sips
Early risers can catch the sun climbing over the Atlantic. Prefer something slower during your weekend trip to Virginia Beach? Ease into the day with a pour-over from Three Ships Coffee, a cozy café that is walking distance from our homes on 20th St. They serve handcrafted drinks and pastries with a local twist.
Midday in Nature
Take weekend getaways in Virginia Beach, VA, off the beaten path with a visit to First Landing State Park. The shaded trails are stroller-friendly and relaxing for older travelers, making it a great option for groups of all ages.
Optional Night Out
After dinner, couples or friends might enjoy a quiet drink at The Hunt Room, while families can gather back at your stay for games, dessert, or a movie night.
Day 3: Creativity and Connection
Delicious Brunch
Start your final day with brunch at Commune, a stylish spot in the ViBe District serving seasonal dishes made with locally sourced ingredients. It’s great for groups, accommodating kids, vegetarians, and everyone in between.
Explore the ViBe Creative District
Spend the morning discovering murals, boutique shops, and galleries in this walkable neighborhood. Teens and art lovers will find plenty to enjoy, while kids can do a mural scavenger hunt.
One Last Beach Moment
Before ending your weekend trip to Virginia Beach, return to the ocean for one last dip, walk, or moment of stillness. Or, if you’re looking for something educational and indoors, visit the Virginia Aquarium for interactive exhibits the whole family will enjoy.
