High Hopes Sportfishing
High 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.
- Hidden Gem
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, 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
Coastal Edge East Coast Surfing Championships
August 23, 2026 – August 30, 2026 · annual
The world's oldest continuously running surfing competition returns for its 64th year, turning the south end of the Oceanfront — from the 1st Street Jetty up to 10th Street — into a week-long surf carnival. More than 850 competitors surf pro and amateur divisions, including a WSL qualifying event, while the beach fills out with skate and BMX demos, live music, and tournament games. It's the anchor event of late summer at the beach and the best week of the year to watch serious surfing at the 1st Street break.
Virginia Beach Funk Fest Beach Party
August 28, 2026 – August 29, 2026 · annual
A free two-day beach party on the Oceanfront closing out August with funk, R&B, and soul acts on the sand. Part of the official Beach Events season, Funk Fest draws a big, dance-heavy crowd to the resort beach for one of the last major music weekends before Labor Day — no ticket needed, just claim a patch of sand.
American Music Festival
September 4, 2026 – September 6, 2026 · annual
Beach Events' Labor Day weekend concert series bills itself as the largest outdoor music festival on the East Coast, spreading national, regional, and local acts across a 60-foot stage at 5th Street plus free park stages at 17th, 24th, and 31st Streets along the boardwalk. Past headliners have included Sheryl Crow, the Doobie Brothers, ZZ Top, and Zac Brown Band, with tickets sold per show, as a three-day Passport Pin, or as VIP packages, while the park stages stay free. It's the Oceanfront's last big blowout of the summer season, timed to send visitors off before the crowds thin out after Labor Day.