There are plenty of opportunities to rent a boat at prices accessible to all budgets, exploring enchanting places you might have only seen on postcards.
It’s interesting to note that in the post-pandemic era, the trend of choosing this type of holiday has risen sharply—likely because it perfectly captures that sense of freedom many of us missed during the pandemic years.
Sailing Holidays: With or Without a Skipper?
When it comes to yacht charters, there are essentially two options: bareboat charter (no crew on board) or charter with a skipper.
Wondering which one to choose? It depends entirely on what you want from your holiday. Neither option is objectively better—it’s just a matter of your needs. Keep in mind, if you don’t have a boating license, having a skipper on board is mandatory.
If you have your license and want to be fully independent—solo or just with friends and family—the bareboat option is perfect. On the other hand, even if you do have a license, you may prefer to leave every detail to a professional and simply enjoy the sea, beaches, sun, and coastal towns. In that case, a skipper-charter is ideal. Plus, sailing with an experienced skipper is a great way to improve your sailing skills.
Sailing with a skipper also means you’ll have expert support during any unexpected situations, such as strong storms, tricky docking, or port negotiations. Plus, thanks to their deep knowledge of the area, an experienced skipper can suggest hidden gems and less touristy spots to explore. They’re also a valuable source for tips on water activities like fishing, diving, or water sports.

Sailing Yacht Charter: Which Are the Most Sought-After Destinations?
Those looking for a sailing holiday have many choices; according to data from Sailogy, the leading online boat rental platform, the most popular Italian destinations are Sicily, Sardinia, and Tuscany. For international destinations, the top picks are—perhaps unsurprisingly—Croatia, Greece, and the Balearic Islands.
Sailogy, for example, manages a fleet of around 22,000 vessels and offers as many as 800 different sailing destinations—so there’s no shortage of options!
In terms of timing, most Italians book August departures, followed by July. Foreign visitors, however, tend to come in the second half of summer.

