The Best Boat Rentals in Annapolis

Most small powerboats and basic harbor cruises in Annapolis start around $100 to $150 per hour, mid-size captained boats and classic sailboats are commonly $150 to $300 per hour, catamarans and premium cruisers tend to run $300 to $500 per hour, and larger yachts for celebrations can range from about $500 up to $1,000+ per hour. Pricing usually includes the boat, standard safety gear, and—if listed as captained—the captain’s time. Fuel is often included for short harbor routes but may be added for longer Bay runs. Taxes, gratuity, and optional extras like pickup at a different dock, water toys, or catering are typically additional. Book a 2–4 hour window for the best value and availability.

You’ll find a strong mix tailored to the Chesapeake: comfortable sailboats for cruising the Severn River and Bay, spacious catamarans for groups, center consoles and bowriders for sightseeing or sandbar stops, plus motor yachts ideal for birthdays, bachelorettes, and corporate outings. Many listings are captained, and there are also options for qualified renters to self-operate smaller powerboats and sailboats.

Both options are available. Captained charters are the easiest—just show up with your crew and enjoy. If you want to operate the boat yourself, owners typically require solid boating experience and, for motorized vessels, Maryland’s boating safety education certificate for operators born on or after July 1, 1972. Expect a brief checkout on handling and local rules before departure; if you’re unsure, book with a captain to keep planning simple.

Common pickup points include City Dock on Ego Alley in downtown Annapolis, marinas in Eastport such as Annapolis City Marina on Spa Creek and Port Annapolis Marina on Back Creek, and larger facilities around Back Creek like Safe Harbor Annapolis and Horn Point Harbor. Your exact meeting spot will be confirmed after booking and is usually chosen for easy access and parking.

Typical routes glide past the U.S. Naval Academy and historic downtown, into Spa Creek’s Ego Alley, and out the Severn River toward the Chesapeake Bay. Many charters cruise by the Bay Bridge and the iconic Thomas Point Shoal Lighthouse, with frequent views of ospreys and herons in season. Sunset trips add skyline views and golden light on the dome of the Maryland State House.

If you book a captained charter, no license is required. To operate a motorized vessel yourself in Maryland, anyone born on or after July 1, 1972 must hold a state-approved boating safety education certificate (or a recognized equivalent). Owners may ask for proof of experience and can decline self-operated requests if conditions or skill level aren’t a safe match.

Yes—families are welcome on most boats. Every charter carries U.S. Coast Guard–approved life jackets, and reputable captains can provide child sizes on request. Maryland requires children under 13 to wear a life jacket when underway on smaller vessels; regardless of boat size, it’s smart to have kids jacketed anytime you’re outside the cabin. Let your captain know your children’s ages and weights so the right sizes are ready at boarding.

Most charters allow you to bring snacks, coolers, and beverages. Some offer ice and water; others can arrange catering for special occasions. Glass is often discouraged, and the operator must remain sober at all times. If you have a cake, décor, or special setup in mind, mention it in your booking so the crew can plan a clean, safe space.

Many owners are pet-friendly with advance approval. Policies vary by boat, but small to medium, well-behaved dogs are commonly allowed. Expect to keep pups leashed on docks, bring a towel and water bowl, and budget a possible cleaning fee. If anyone in your group has allergies, just flag this during booking.

Your captain monitors conditions on the Chesapeake, which can bring pop-up summer thunderstorms and breezy afternoons. If unsafe weather is forecast, most charters will proactively reschedule or refund per the listing’s policy. Morning departures are usually calmer; build a little flexibility into your itinerary, especially in late spring and summer.

Absolutely. Captained yachts, catamarans, and roomy powerboats make celebrations easy. Tell the host your headcount and vibe—chill cruise, swim stop, or photo-forward sunset lap—and they’ll suggest an itinerary and pickup spot that keeps logistics simple. Many crews can help you set up playlists, décor, and toast-worthy timing at golden hour.

Peak season runs May through September, with warm water July to early September. Big boating holidays—Memorial Day weekend, July 4th, and Labor Day—sell out quickly, and October brings the famous Annapolis boat shows that fill City Dock. Weekdays usually have more availability and friendlier rates, mornings are smoother on the water, and sunset charters are the most requested. Spring and fall shoulder months offer cooler temps and gorgeous light with fewer crowds.

Yes—many crews offer special trips for Blue Angels practice and show days in late May, and they book out well in advance. Expect heavy boat traffic and temporary safety zones on the Severn River; captains know where to stage for great views while staying within the rules. Plan extra time for docking and rideshare after the show, and secure your date as early as you can.