Yes, you can—and for many charterers, choosing a skippered charter makes the whole experience more enjoyable. You don’t need to be a sailor to enjoy the sailing holiday of a lifetime. With a carefully selected professional skipper on board, you can set sail in confidence and comfort.

A skippered bareboat means you still have the boat to yourselves, but with an expert at the helm. Your skipper will take care of the navigation and boat handling, so you can focus on the fun, the scenery, and the adventure. They also bring invaluable local knowledge—pointing out hidden gems, the best anchorages, and places to eat ashore. And as experienced tourism professionals, they’re often great company too.

Hiring a skipper is a smart option not just for beginners or those with limited experience, but also for seasoned sailors who want to fully relax without the responsibilities of command. You can be as involved in the sailing as you like—or not at all.

A paid skipper offers:

• Peace of mind with expert navigation and safe boat handling
• Local insights and recommendations for a richer experience
• A stress-free holiday—even for experienced sailors
• An opportunity to learn sailing basics in a relaxed, hands-on way
• Whether you're new to sailing or just keen to unwind, adding a skipper is a great way to enhance your yacht charter.

"The highlights of the trip were, for sure, the knowledge of the skipper who shared special harbour destinations and information with us. His knowledge was impeccable and we got to see destinations that we would not have seen without him." Trudie, South Africa, who chartered in the Bay Of Naples, June 2024

"Our guide Carlos was extremely knowledgeable -- we learned so much about aquaculture. He pointed out whales and turtles, and gave us a lot of info on flora and fauna. He made our trip phenomenal!!!" Kerrie, USA, who sailed in La Paz, Mexico, August 2024."

Related FAQs

Do I need a sailing qualifications to bareboat charter in the Caribbean?

In most of the Caribbean, you do not need a formal sailing qualification such as an ICC (International Certificate of Competence) or RYA certificate in order to take a bareboat charter. What you do need is to demonstrate sufficient sailing experience and practical knowledge to the charter operator Continue Reading...

Are one-way sailing charters a good option in the Mediterranean?

One-way sailing charters can be a fantastic option in the Mediterranean, especially if looking to experience a greater variety of coastlines and cultures without retracing your route. By starting in one port and finishing in another, you avoid the need to sail back to your original base Continue Reading...

Can Sail Connections match prices I see on other charter websites for the Mediterranean?

Yes, Sail Connections can usually match and often improve on prices listed on large charter booking websites. We access the same global databases and work directly with all major operators across the Mediterranean or any destination. Continue Reading...

Should I choose a bareboat, skippered, or fully crewed charter in the Mediterranean?

Choosing between a bareboat, skippered, or fully crewed charter in the Mediterranean depends on your sailing qualifications, group preferences, and the type of holiday you want. Continue Reading...

How do I book a yacht charter?

Booking a yacht charter with Sail Connections is a simple yet personalised process. Our aim is to match you with the perfect sailing experience for your group of holidaymakers. Continue Reading...

What happens if there’s a problem with the boat during our trip?

Problems on a charter are rare, but should something go wrong, rest assured you're not on your own. At Sail Connections, we only work with established, reputable operators who maintain their fleets to high standards. Continue Reading...

What are some less well known Mediterranean sailing destinations worth exploring?

Beyond the well-patronised waters of Greece, Italy, and Croatia, the Mediterranean offers a host of hidden gems ideal for those seeking a more off-the-beaten-path yacht charter. Continue Reading...

Is the Mediterranean suitable for families taking their first sailing holiday?

Yes, for the most part he Mediterranean is one of the best places in the world for a family-friendly sailing holiday — especially if it’s your first time. Continue Reading...

What are the differences between catamaran and monohull for Mediterranean sailing?

The choice between chartering a catamaran or a monohull comes down to what kind of sailing experience you are looking for. Continue Reading...

Can you help plan my Mediterranean sailing holiday itinerary?

Absolutely. At Sail Connections, we're here to make your Mediterranean sailing holiday seamless from the moment you get in touch. With years of experience and in-depth knowledge of the region, Continue Reading...