Earning Stripes is a beautifully maintained 1986 Hatteras 45 Sportfishing yacht, perfect for those seeking adventure and relaxation on the water.
"Captain Greg absolutely exceeded our expectations in every way!" — Kathleen,
An evening sunset cruise and a fishing charter with Big Dog Charters are two completely different trips. A sunset cruise is for relaxing, sightseeing, music, dancing, taking pictures, making TikToks, and enjoying the sunset.
"Captain Rocky was amazing. At the beginning of the trip he offered for the kids to “drive the boat." — Lauren,
Step aboard Is That Right Sport Fishing, a beautifully restored 2001 Luhrs 36ft Sportfishing, fully refreshed in 2021, and experience the waters of Virginia Beach like never before.
"Ryan and his crew gave my family one incredible and safe experience out on the water - one trip my boys will remember for a lifetime." — Samantha,
Experience the ultimate Virginia Beach adventure aboard Dream Chaser Charters, a fully restored 2000 Glacier Bay 2670 Island Runner Walkaround (restored 2022).
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Captain Donny has gone above and beyond to make our trip came true with a short notice!" — (Donna)Diep,
Step aboard Reel Release Sportfishing, a beautifully restored 1992 Privateer 30ph Pilothouse, freshly upgraded in 2024 and based in vibrant Virginia Beach! This versatile vessel accommodates up to six guests and is powered by a robust 350 HP diesel inboar
Step aboard Charter Boat Partners LLC, a well-maintained 1995 Regal 400 Commodore Cruiser based in Hampton, offering the perfect blend of comfort, space, and classic cruising style for up to 6 guests.
Step aboard Beast Light Tackle Sport Fishing, a well-maintained 2005 Regulator 26’ center console based in Norfolk, built for both serious fishing and relaxed coastal cruising.
Step aboard Four Winds Chartering for a memorable adventure on the waters of Hampton! This 1997 Evans Downeast vessel, beautifully restored in 2021, combines classic charm with modern amenities, ensuring a comfortable and stylish experience for up to 19 g
"Thank you, guys, for a truly awesome, beautiful, time. It was perfect!" — Deidre,
Set sail on an unforgettable adventure aboard the luxurious 2021 Axopar 37 XC Motor Yacht – your ultimate getaway from Hampton, VA. With a capacity for up to 13 guests, this sleek vessel offers both thrilling performance and exceptional comfort.
"We had a great time on our boat with Darby! Our charter was to celebrate a bachelorette party and it definitely delivered!" — Katie,
Discover Cape Charles, Virginia, a charming Eastern Shore harbor town where calm Chesapeake Bay waters meet miles of inviting coastline. With gentle winds, broad horizons, and spectacular sunsets, it's an easygoing base for sailing, powerboating, and family-friendly getaways. Cape Charles boating charters offer access to protected bays, scenic inlets, and sandbar anchorages that are perfect for swimming, shelling, and relaxed afternoons on the water.
Anglers appreciate the seasonal action around channels and nearshore structure, while wildlife lovers often spot ospreys, pelicans, and playful dolphins along the bow. Clear, shallow stretches make this destination welcoming for first-time captains, yet there's plenty of open water for experienced crews to stretch their sea legs. From sunrise cruises to golden-hour sails, every outing delivers big-sky views and camera-ready moments.
On land, the walkable waterfront and historic streets pair effortlessly with a day on the bay. Plan a beach picnic between outings, stroll the marina for local flavor, or step off your charter to enjoy fresh coastal fare. With easy access to launch points and marina services, Cape Charles boating charters simplify logistics so you can focus on the fun—whether that's a guided nature tour, a sandbar swim stop, or a celebratory cruise at sunset.
Ready to chart your day? Choose from captained trips for stress-free exploring or bareboat options for confident skippers. Create your own itinerary—cast a line, find a secluded cove, or simply drift and watch the sky change colors. Cape Charles welcomes you with smooth sailing, friendly docks, and the kind of shoreline adventures you'll want to repeat season after season.
