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Our destinations near Chester, MD

In addition to the best offers we have for boat and yacht charters in Chester, MD, see also options available for rent in these nearby locations:

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Chester, MD - a yachting playground perfect to explore with Sailo

Planning a sailing vacation in Chester? Enjoy the freedom of the open water on a private yacht charter from Sailo. Rent a boat from a couple of hours to a full day, to really explore Maryland from Chester. With a licensed captain driving your boat rental with, you’ll be able to relax and discover those hidden gems with your friends or family. Prefer to skipper your yacht rental? Use our advanced filters to find your perfect bareboat charter on Sailo!

Our premium selection of private boat rentals in Chester, MD

There are currently 9 Sailo yacht charters waiting for you in Chester, MD. From a day trip on the water, to a week exploring (or more), it’s easy to find the perfect boat for you on Sailo. Our inventory includes 5 beautiful sailboats waiting to take you away. You’ll find numerous catamarans to charter in Maryland. If you prefer, in Chester, Maryland you’ll also have the choice of 2 motor yachts for an unforgettable trip. Throw the party of the year in Maryland on the deck of your own party boat rental suitable for more than 13 guests: search the 2 options in Chester with Sailo and book the one for you.

Great boating experiences happen on the right yacht. Find it now!

Sailo has the most advanced filters to help you find the perfect boat rental for an amazing experience on the water in Chester, MD. Start your search by choosing your start trip date, duration and number of guests. For a great day trip with your family or friends, you have the option to select 2, 4 hours or full day rentals. Depending on your preferences and budget, you may narrow your results by boat type and price range. The 'crew' filter allows you to check the boat rentals with the captain included in the price, skipper optional (paid as extra) or bareboats that you’ll captain yourself (boating resume required). Once you have laid your eyes on a boat you like in Maryland, click on it to read the description, reviews and see more pics. We also recommend using our direct 'Message Owner' feature that allows you to start a conversation with the boat representative to ask away everything you want to know before you submit a booking request.

How much is it to charter a Chester, MD yacht for a day?

Whether you are looking to rent a yacht for a city sightseeing tour, a romantic sunset cruise or an active day on the water with your family or friends, we're confident you’ll find the best one for you on Sailo. The average starting price to charter a yacht in Chester is $1100. You can however find excellent affordable rentals from $250 and also elegant yacht charters that can go up to $6500 (service fee and mandatory extras not included).

Can I rent a yacht in Chester with a captain?

When you rent a Sailo boat with captain, you set yourself and your guests for a relaxed, worry-free trip, with a professional skipper making sure that you all have an amazing experience on the water. Currently we offer 7 boat and yacht rentals with captain in Chester.

Tips for responsible boating

If you’re looking to explore our beautiful planet, a yacht charter is a great place to start. Explore coral reefs with your snorkel, discover hidden bays and islands and generally enjoy the view of nature. Remember, that sailing motto: 'Take only photos, leave only wake' (OK, so we paraphrased). To be a responsible sailor, remember:
  • Don’t disturb coral or sealife
  • Take your trash home (and don’t throw anything in the sea)
  • Respect the locals and their customs wherever you go
Read more about responsible boating.