How To Charter a Boat
Sponsored by Chronic Sailing
Want to feel the wind in your hair for a few hours, celebrate a special occasion, or take a few days to explore the Chesapeake Bay? Charter a boat where there are options to suit every type of traveler. Learn a few tips in advance about how to charter a boat, and you will soon be off for an unforgettable adventure. Charter is just a fancy word for renting, and your rental can include a lovely boat and a captain to take you where you want to go, along with catered food and a spectacular, stress-free experience.
Whether you’re looking to relax on a three-hour sunset cruise or a week-long excursion, with various destinations and unique towns to explore, the Chesapeake offers many chartering experiences. Before you set out, it’s essential to consider what type of itinerary best matches your interests, from leisurely cruises to more active excursions. No matter your preference, a boat tour of the Chesapeake Bay promises an incredible, immersive adventure.
Boat chartering has become a preferred way to enjoy sailing without the commitment and expense of owning a boat. It offers flexibility and tailored experiences that set it apart from static land-based holidays. Whether it’s a fully crewed yacht or a bareboat charter, the industry has seen an uptick in interest thanks to the personalized nature of such holidays.
What is a Charter? And What is “Bareboat”?
When you charter, you’re renting a boat.
Bareboat means you rent the boat and captain it yourself. OR you can bareboat charter AND hire a professional captain. A “Crewed” charter is a bit more of a luxury upgrade – you will have a professional captain, chef, and possibly other staff, depending on the vessel size and experience.
Hiring a captain is often a good way to go, even if you are experienced, because the captain knows all the cool places to go. A cook is also a great idea while you are on vacation; they are experienced at whipping up culinary delights in a cramped galley (kitchen).
What certification do I need to charter a yacht?
None! Charter companies like Chronic Sailing provide you with a list of pre-approved captains for you to choose from. You are welcome to bring your own licensed captain. You will be responsible for paying the captain’s fees + any tips directly to the captain at the end of the charter.
How long are we on the water?
Custom trips range from 3-8 hours or overnights, or a custom itinerary can be created for your trip.
What is included in the trip?
The trip cost includes the yacht, amenities, parking, access to the marina pool, restrooms, and showers. Fuel is included for single-day charters but not for multi-day charters.
What is not included in the trip?
The trip cost does not include the captain’s fees, tip, additional dockage fees, or provisions (food/drinks). Fuel is included for single-day charters but not for multi-day charters.
What is not allowed on the yachts?
Sprayable sunscreen is not allowed on any of the yachts, only lotions. Red wine and other dark-colored juices or drinks are also not allowed on the yachts. Any stains from either will require special cleaning services and are subject to additional fees paid by the charterer.
Can we bring food and drinks on our charter?
You are always welcome to bring drinks and pre-cooked food! The galley’s appliances are available to keep food warm and drinks cold, but are not to be used for cooking during single-day charters. Charter companies also offer catering from local restaurants and chefs.
Charter Packages on the Chesapeake Bay with Chronic Sailing
Spend multiple days and nights on board your private yacht or just a few hours to watch the sunset. Bring your own snacks and drinks or have a meal delivered or catered on board. Arrive in style at your favorite dock bar. Go for a swim or relax and enjoy the view.
Chronic Sailing wants you to have your perfect day on the Bay, whatever that means to you. That’s why there are a variety of itinerary options to choose from. Have something specific in mind? Just ask!
Tour Options
- 3 hours (2-13 people)
- 3-8 hours (2-13 people)
- Overnight sails from 1 – 7 nights (2-8 people)
Are you looking for a longer trip and wanting to experience a night on the water? Chronic Sailing can help you “get your feet wet” with an overnight sail. We will depart from our docks and sail to the destination of your choice. Popular options include St. Michaels, downtown Annapolis, and northern Chesapeake Bay. An overnight cruise is an enjoyable way to experience all the best sailing, from adventures on the water, shopping on dry ground, sunset cocktails, sleeping under the stars, and waking up to the sounds of nature and fresh coffee brewing.
Depending on the boat, there will be two or three staterooms with private heads and showers, a family saloon area, and a kitchen. Boats often have tvs and a variety of board games and cards.
Visit Chronic Sailing to get your charter started.
TUNESDAY
Come to Back Creek for Tunesday, a Floating Concerts Series, every Tuesday 5/20-8/26/2025, 6:30-8pm for a free concert sponsored by Chronic Sailing. A new artist takes the stage on board Starz, the catamaran, each week. Come out in your kayak, canoe, boat, paddle board, or listen from the shore at the Ellen Moyer Nature Park in Annapolis.
