While it’s hard to explain to non-boaters, some of the best boating on the Chesapeake happens in September and October. Waterfront festivals and fairs crowd the shorelines. Cooler weather means you can leave the dock even if you don’t have air conditioning. And the jellyfish … well, they’re not as bad.
If you aren’t currently a boat owner or your smaller boat doesn’t allow for comfortable long-term cruising, you can charter one just like vacationers do in the Caribbean. And thankfully there are multiple charter agencies operating on the Chesapeake, from big, beamy cats to sleek monohulls designed for gunkholing. There’s a perfect boat for every adventure.
Whether you want to go out for a couple of hours or an entire week, if you’re celebrating a big birthday or needing a weekend of quiet solace, you can find a boat that fits your budget and your itinerary. And while bareboating is great fun, getting a fully-crewed charter allows you to sit back and relax without the stress of driving or provisioning. From picnic boats to fishing boats, you can enjoy your time on the water without a care in the world.
Here are our tips for getting the most out of your Bay-region charter.
Choose Your Adventure (Ahead of Time)
While most of us consider the Bay to be our own backyard, it’s also the largest estuary in the world. You could spend your entire life exploring its waters, so having a game plan for what you want to cover during your charter experience is a good call. Charters are available in daily, overnight, and weeklong packages, and charter operators can help you get the most out of your time on the boat.
One thing to note: prices for hourly charters will be significantly higher than a multi-day rate. Opting for an overnight, if time allows, is more financially conscious.
Even though you may have an entire week, it’s impossible to see everything the Bay has to offer. Listening to expert advice on where to go and how long to spend there is helpful. Sail Solomons lists itineraries on their website, and Haven Charters is known for their local knowledge. Our Weekends on the Water section has inspiration for mini-trips to towns from the top of the Bay to the bottom.
Chesapeake charter fleets are more disparate than what you may find in the Caribbean. This is partly because the Bay’s waters are diverse: what might be great for exploring creeks won’t be as powerful for a lengthy Bay transit. Talk to your operator ahead of time to make sure your boat can handle exactly what you want to do.
Ask for the Add-Ons
There’s great fall fishing to be had on the Bay! Many charter operators will happily send you off with a tackle box and some rods for a small add-on fee, saving you the hassle of bringing all your gear with you. Water toys, paddleboards, kayaks, and more, can also be arranged with some lead time.
If you’re coming into town and don’t have time to provision, ask your charter company about having the boat entirely set for you. Groceries and supplies can be arranged before your trip for added costs, but these will save you time on the front end of your adventure. In some areas, particularly on the Eastern Shore, general provisions can be a car trip away.
Work with the Local Experts
There are multiple Airbnb-type websites linking boat owners to clients, and these are great for experienced boaters. Issues do come up, and without the infrastructure of a charter operator, you may be up a creek without a paddle (quite literally). Make sure you do your due diligence before casting off the dock. However, if you’re trying to explore a specific creek or want to do some easy fishing, these rental opportunities are ideal.
To find a great experience in any area of the Bay, see below for highly recommended operators with decades of experience providing superior service.
Haven Charters
Haven Harbour Marina, Rock Hall
With a fleet of almost 20 power and sailboats all in excellent condition, the team at Haven Charters are friendly and helpful in getting you on the water quickly and safely. From Rock Hall, you can check out the Magothy and Chester Rivers as well as the Middle Bay, head up to Baltimore, or sweep over to Annapolis. It’s worth it to ask owners David and Jacki for their opinions on your float plans, as they have decades of local knowledge to help you get the most out of your vacation. Fleet includes Beneteaus, Catalinas, Hunters, and Sabres.
Bay Sail
Based out of Tidewater Marina, Havre de Grace
A charter operator that is also a sailing school, BaySail has more than 20 keelboats to get you out and exploring the upper Bay. Boats are in good condition and offer quick access to the Sassafras River, Worton and Fairlee Creeks, and more. Boats are available either bareboat or captained for full- and half-day rentals.
Sail Solomons
Safe Harbor Zahnisers, Solomons, MD
One of the perks of chartering through a sailing school is that boats are regularly maintained and serviced. Sail Solomons has a fleet of Beneteau, Jeanneau, Catalinas, and a nice big Seawind catamaran at their disposal, and one thing that makes the boats stand out is Safe Harbor’s attention to detail (extremely clean conditions, and a memory foam mattress are the little things that make us excited). If you’re traveling to Solomons from far away, you can ask about staying on the boat the night prior for a low rate rather than needing a hotel.
Waypoints Yacht Charters in Annapolis
Waypoints offers a more elevated charter experience, with a fleet full of luxury yachts, both power and sail. Bareboats available include Fontaine Pajot cats as well as Dufour, Jeanneau, and Sun Odyssey monohulls, all 40 feet and bigger. Waypoints offers an element of luxury to your adventure for daily, weekend, and week-long dream trips.
South River Boat Rentals
If you’re looking for a quick escape, South River Boat Rentals offers easy access to the South River and the greater Chesapeake from their port in Edgewater. The fleet is a robust mix of powerboats, from pontoons to trawlers. There’s even a classic deadrise perfect for parties. And if you need to hire a captain to drag your kids around on their tubes, South River Boat Rentals captains understand the importance of family time on the water and can really deliver a great experience.
