How to Search for a Sunsail Sailing Vacation on the Website

Updated

To search for a Sunsail vacation, use the search panel on the Sunsail USA homepage: pick a departure date, the number of nights, and the number of passengers, then select Search Vacations. The results show the charter vacations that match those three inputs. The date picker starts at October 2026 and runs through April 2028, so this search works for trips in that window, not for near-term departures.

What the search panel asks for

The panel has three dropdowns and one button. Each one narrows the results:

Field Options shown What it controls
Departure Date Monthly options from October 2026 through April 2028 The month your trip starts
No. of Nights 5, 6, 7, 8, 9, 10, or 14 nights Trip length
No. of Passengers 2 through 12 passengers How many people the vacation must fit
Button Search Vacations Runs the search

The night options are not continuous: 11, 12, and 13 nights are not listed. If you want a length that isn't offered, choose the closest option and check the individual vacation details before booking.

Step-by-step

  1. Set the departure month. Open the Departure Date dropdown and choose the month you want to sail. The list begins at October 2026, so earlier dates can't be selected here.
  2. Choose the trip length. Select the number of nights from the No. of Nights list. Seven nights is the standard option; 5, 6, 8, 9, 10, and 14 nights are also available.
  3. Set the group size. Choose 2 to 12 passengers. This matters most for bareboat charters, where the yacht has to have enough cabins for everyone.
  4. Select Search Vacations. The site returns vacations that match your date, length, and group size.
  5. Check the results against your plans. Confirm the destination, yacht, and price details on each result before you book. The homepage also lists current offers, such as the British Virgin Islands savings and the BVI skipper special, so compare those with what the search returns.

Expected result: a list of available sailing vacations for your month, trip length, and group size, which you can then open for details.

Before you search: decide which type of vacation you want

The search finds vacations, but Sunsail offers three formats, and your choice affects what you're looking for:

  • Bareboat yacht charters — you sail independently and set your own itinerary. Best if you have sailing experience and want full control.
  • Flotilla vacations — you sail in a group led by an expert lead yacht and crew. The site notes new 2026 flotilla dates. A good middle ground for sailors who want company and support.
  • Skippered vacations — a Sunsail skipper takes the helm. Suited to people new to sailing or those who want to relax rather than crew.

If you're unsure, search first with your dates and group size, then compare the formats that come back.

Common snags

  • Your dates aren't in the list. The departure picker only covers October 2026 to April 2028. If you want to sail before October 2026, this search won't find it.
  • Your trip length isn't offered. Only 5, 6, 7, 8, 9, 10, and 14 nights appear. Pick the nearest option and confirm the actual length on the vacation page.
  • Too few or too many passengers. The range is 2 to 12. Groups outside that range need to check with Sunsail directly rather than through this search.
  • Offers look better than the search results. Promotions like the BVI savings and the skipper special have their own booking deadlines and terms. Read the conditions on the offer before assuming the discount applies to your search result.

Once you have a shortlist, use the destination pages and the offer terms to choose between them, and confirm price and availability on the specific vacation before booking.