The Best Boat Rentals in Hampton

Expect most captained sightseeing or fishing trips to run about $150–$300 per hour, with smaller sailboats often around $100 per hour and mid-size motor yachts commonly $200–$350 per hour. Half-day outings typically land in the $500–$900 range, while full days can run from about $1,000 to $2,000+ depending on size, season, and crew. Rates may be higher on holiday weekends. Your booking generally includes the boat, required safety gear, and a licensed captain when applicable; fuel, docking, and gratuity may be extra. Check each listing for what’s included and any holiday surcharges before you book. (getmyboat.com, hamptonroadsboatcompany.com)

You’ll find a good mix suited to the Chesapeake Bay and Hampton Roads: center consoles and fishing boats for angling or quick harbor hops, comfortable pontoons and party-style boats for relaxed cruising, classic sailboats for a breezy afternoon, and mid-size yachts for celebrations. Many options are offered as captained charters, with some smaller boats available for qualified self-drivers.

For stress-free planning, a captained trip is the easiest choice—especially in a busy working harbor with shipping lanes and naval security zones. Captains handle navigation, docking, and weather calls so you can focus on your group. Confident boaters may self-operate smaller vessels where allowed, but remember that you must follow navigation rules and keep clear of large commercial and naval traffic.

Popular pickup points include The Docks at Downtown Hampton on the Hampton River, Safe Harbor Bluewater (formerly Bluewater Yachting Center) near the river entrance, the Marina at 37 North at Fort Monroe (Old Point Comfort Marina), and Salt Ponds Marina Resort by Buckroe Beach. Your captain will confirm the most convenient dock and parking details after booking. (downtownhampton.com, shmarinas.com, fortmonroe.org, saltpondsmarinaresort.com)

Highlights include the stone walls of historic Fort Monroe, the Old Point Comfort Lighthouse at the mouth of Hampton Roads, the Hampton Roads Bridge–Tunnel, and the red sparkplug-style Thimble Shoal Light out in the Bay. On many days you’ll watch ships moving to and from the Port of Virginia, and in warmer months you may spot ospreys fishing or dolphins surfacing as you cruise. (nps.gov, en.wikipedia.org, dhr.virginia.gov, whro.org, vims.edu, umces.edu)

If you book with a captain, you don’t need a license. For self-operated rentals, Virginia requires boating safety education for anyone operating a motorboat of 10 hp or more. Renters typically meet this requirement through the rental business’s safety orientation and by being listed as the authorized operator on the rental agreement—carry the provided documentation while operating. When in doubt, ask your host or choose a captained charter. (dwr.virginia.gov, law.lis.virginia.gov)

Yes—family outings are common. Boats carry U.S. Coast Guard–approved life jackets for all passengers, and most captains can provide child sizes if you share ages and weights in advance. Federal rules require children under 13 to wear a life jacket when a boat is underway on most local waters, so expect your crew to help with proper fit before departure. (dwr.virginia.gov, uscgboating.org)

Most charters are BYO for snacks and non-glass beverages, and many boats have a cooler or can add ice on request. Moderate alcohol is often allowed for adults, but the operator may not be under the influence; Virginia treats boating under the influence much like driving, with a 0.08% BAC limit and strict enforcement. If you plan to celebrate, book a captained trip and confirm your host’s rules.

Many captains welcome well-behaved dogs—just ask in your inquiry and bring a leash and a pet life jacket. Downtown docks are pet-friendly, but if you plan to stop ashore, note that some nearby beaches restrict pets seasonally, including Grandview Nature Preserve (no dogs on the beach May 15–Sept 15). (downtownhampton.com, dwr.virginia.gov)

Summer brings warm water and frequent fair days, but afternoon sea breezes can kick up chop or spark pop-up storms; your captain will watch the marine forecast and may reschedule if conditions aren’t safe. Hurricane season runs June 1 to November 30, with the highest odds of tropical systems from mid‑August through early October. Always review your listing’s weather policy and, for the smoothest ride, consider morning departures. (en.wikipedia.org, nhc.noaa.gov)

Absolutely. Captained boats are ideal for stress‑free celebrations, with easy downtown pickup spots and short cruises to scenic landmarks for photos. Share your headcount, desired vibe (laid‑back cruise or lively playlist), and any food or décor ideas in the inquiry so your captain can tailor the route and timing.

Peak boating season runs roughly May through September, with comfortable shoulder months in April and October. Holiday weekends—Memorial Day, July 4, and Labor Day—book early and may carry premium pricing. Local waterfront events to plan around include the Blackbeard Pirate Festival in late May/early June, Norfolk Harborfest in early June, and the Crabtown Seafood Festival in mid‑September; December brings a lighted boat parade for winter cheer. Weekday mornings are usually calmer and less crowded than weekend afternoons. (downtownhampton.com, festevents.org, visithampton.com, hampton.gov)

Ask your captain about a lighthouse loop past Old Point Comfort and Thimble Shoal Light, or a relaxed anchor in fair weather off the Grandview/Factory Point area for a swim. These are beautiful but sensitive shorelines—follow posted signs protecting bird‑nesting areas and stay off the dunes if you go ashore. With luck, you might spot ospreys diving for menhaden or dolphins riding the bow wake along the way. (nps.gov, dhr.virginia.gov, dwr.virginia.gov, vims.edu, umces.edu)