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Captained Sailing Vacations

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Want a carefree getaway or not qualified to sail on your own?

Superior Charters offers a roster of USCG Licensed Captains to skipper your boat on your Apostle Islands boating vacation!

This option is available on any of our sailboats and is the best choice for families or couples who don’t have extensive sailing experience and are looking for a unique vacation experience. So, leave the details to us at Superior Charters and we will help pair you with one of our professional U.S. Coast Guard licensed captains who are very familiar with the cruising grounds. They will safely take your group into the islands, anchor out or slip back into a marina – it’s up to you. Our boats are privately owned and therefore there is a limit of six passengers when you have a paid captain.

Accommodations:  Our fleet of late model sailboats offer our guests premium accommodations. Our wide variety of boats also means that we can meet your needs regarding crew size and budget. While out sailing, the captain will be allotted their own private cabin onboard, with the crew sharing the balance of the sleeping quarters. Guests should bring their own bedding and towels. Boats are equipped with all the creature comforts you could want, including heads on board.

Provisions:  Plan to bring your own food and beverage, and please include the captain in your meal plans. The galley will be equipped with pots, pans, utensils and dishes. You can prepare your meals on the stove, in the oven or on the grill. There will be a fridge on board your boat, so you’ll have safe storage for perishables. Guests typically bring water with them for drinking as well. We can talk through provision suggestions and meal plan ideas!

Schedule:  Trips vary in length from a minimum of 2 days to as many as 10 or 14 days! Crew arrives at the marina in the afternoon, just in time to meet the Captain and get situated on the boat before you spend the night on the boat in the marina, this is considered our complimentary sleep aboard. The adventure begins the next morning, when you set sail for the islands (that is, after a safety talk and introduction to the boat). Each night will be spent at anchor in the islands, with eating, living and sleeping on board with the Captain. The trip concludes on the last day, with crew off-boarding by 4:00 pm.

Cost:  Pricing ranges anywhere from $500 – $2000/person

Booking:  Custom, captained trips are meant to be booked directly with our office, where we can walk you through all the costs, options, itinerary and timing. We will also answer your questions that we may not have covered here. Call us at 715.779.5124

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Create your own custom trip! Choose a boat and let's craft an adventure!