Captained Sailing Vacations

Leave the Navigating To Us

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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.

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 Apostle Islands 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.

The accommodations are comfortable aboard all of our yachts and we will work with you to select the right boat for your party. Typically, you will sleep onboard the boat in the harbor, with complimentary boarding the evening prior to the first day of your captained charter. The boat you charter may accommodate up to six persons and the captain will be allotted their own private cabin while onboard. You will need to bring your own bedding and towels. There are heads and a galley on all boats.

The provisions are brought by you and your party as with all bareboat charters. For the most part, meals are prepared and eaten on board the boat. Please include your captain in your meal plans.

To make your booking experience a breeze, please use the filter option below to find the best sailboat for your group size!

Please review the important reservation information below.

Select From Our Most Popular Sailboats

To Find the Best Boat For Your Needs, Please Use the Filter Option Below.