Sunsail Bareboat vs. Flotilla vs. Skippered Vacations: Which Fits You?

Updated

Sunsail offers three main ways to sail: bareboat charters, flotilla vacations, and skippered vacations. The right choice depends on your sailing experience, how independent you want to be, and whether you want company on the water. Bareboat gives qualified sailors full control of their own yacht and itinerary; flotilla combines independent sailing with a lead yacht and crew plus a social group; skippered puts a Sunsail skipper at the helm so you can relax or learn. The sections below compare them on the same dimensions so you can decide.

Side-by-Side Comparison

Dimension Bareboat Flotilla Skippered
Who sails the yacht You (must be qualified) You, with an expert lead yacht and crew guiding the group A Sunsail skipper
Itinerary control Full freedom to set your own route Social sailing guided by the lead yacht; new 2026 flotilla dates added Skipper takes control; you decide how involved to be
Best for Experienced sailors who want independence People who want to sail with others and have support nearby Newcomers to sailing or anyone who wants to unwind
Social element Private, self-directed Group-based and social Private, with crew aboard

Bareboat Yacht Charters

Choose bareboat if you have the sailing experience to handle a yacht yourself and want the freedom and flexibility to set your own itinerary and sail independently. This is the most self-directed option: you plan the route, make the calls, and run the boat. If you are not confident in your ability to skipper and crew a yacht on your own, this is not the right starting point.

Flotilla Vacations

A flotilla is social sailing in some of the world's best destinations, guided by an expert lead yacht and crew. You sail your own yacht but stay with a group, which suits travelers who want companionship and a safety net without giving up the feeling of sailing themselves. Sunsail notes new 2026 flotilla dates have been added, so check current availability if this appeals to you.

Skippered Vacations

A skippered vacation lets a Sunsail skipper take control. It is described as perfect for those new to sailing or looking to unwind. You get the destination and the water without the responsibility of running the yacht, and you can still be as hands-on as you like.

How to Decide

  • You are a qualified, confident sailor who wants your own route: bareboat.
  • You want to sail but also want a group, guidance, and company: flotilla.
  • You are new to sailing, or you want to relax while someone else handles the yacht: skippered.

Practical Notes Before Booking

Sunsail's site lets you search by departure date, number of nights (from 5 up to 14), and number of passengers (2 to 12), across more than 20 destinations. Current promotions shown include up to 15% off BVI charters when booked by November 2, and a BVI skipper special saving $1,000 on skipper services for BVI charters departing through July 31, 2027, booked by November 2, 2026; terms and conditions apply. Offer details and eligibility can change, so confirm the current terms on the site before you book.