High Hopes Sportfishing
Hidden GemHigh Hopes Sportfishing is a fishing outdoor recreation and watersports operator in Oceanfront, Virginia Beach, located at 200 Winston Salem Ave. Rudee Inlet's oldest continuously running charter — a 58-foot Gary Davis sportfisherman chasing marlin and tuna offshore, flounder and drum inshore.
High Hopes is the oldest continuously running charter operation out of Rudee Inlet, running a 58-foot custom Gary Davis sportfisherman with twin 735-horsepower turbo diesels under Captain Dave Wright. The boat, which carries up to 15, chases blue and white marlin, sailfish, wahoo, mahi-mahi, and tuna offshore, and bluefish, Spanish mackerel, cobia, flounder, and drum inshore, with the best season running May through October. Beyond standard charters, High Hopes books bachelor and bachelorette trips, corporate outings, family outings, and burials at sea.
Amenities
- 58-foot Gary Davis sportfishing vessel
- Carries up to 15 guests
Know Before You Go
- Best for: the oldest continuously running charter out of Rudee Inlet
- Best for: large groups (carries up to 15)
Visit
- Address: 200 Winston Salem Ave, Virginia Beach, VA
- Phone: (757) 286-3842
- Website: https://highhopessportfishing.com/
Last verified 2026-07-10.
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While You're in the Area
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Upcoming Events Nearby
Neptune Festival Boardwalk Weekend
September 25, 2026 – September 27, 2026 · annual
Virginia Beach's signature festival closes out September with its 52nd Boardwalk Weekend, spreading across the Oceanfront between 1st and 35th Streets. The headline draw is Neptune's International Sandsculpting Championship — 22 large-scale works by sculptors from around the world — alongside an art and craft show with more than 200 artisans, twenty-plus musical acts across festival stages, the Grand Parade, Neptune's 8K, and a surfing competition at the jetty. Most of it is free to attend, and it reliably fills the resort area for one last big weekend of the season.
Virginia MOCA Boardwalk Art Show
October 9, 2026 – October 11, 2026 · annual
One of the longest-running outdoor art shows on the East Coast marks its 70th year along the Virginia Beach Boardwalk. Produced by the Virginia Museum of Contemporary Art, the juried show brings artists from across the country to sell painting, sculpture, photography, glass, and fine craft directly to visitors with the Atlantic as the backdrop. Hours run 10am–6pm Friday, 10am–5pm Saturday, and 10am–4pm Sunday, and October's thinner crowds make it an easy, walkable browse.
Wicked 10K Weekend
October 30, 2026 – October 31, 2026 · annual
Coastal Virginia's largest Halloween race weekend starts at the Convention Center on 19th Street and finishes on the Boardwalk near 20th, with runners in costume covering the flat, fast oceanfront course for the 10K, a Wicked 5K, or the shorter Monster Mile. A costume contest and a post-race beach party with food and drink follow the finish line. Presented by Sentara and run by J&A Racing — the same organizer behind the Yuengling Shamrock Marathon Weekend — it's the Halloween counterpart to that spring race on the same stretch of Boardwalk.