Yacht Charter FAQs

Can we have a skipper for our boat charter?

Yes, you can—and for many of our clients, 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

What is a fully crewed charter?

A fully crewed yacht charter is the ultimate sailing experience—combining comfort, service, and seamless travel. Your yacht comes with a dedicated professional crew, typically including a captain, cook/chef, and one or more hostesses or deckhands. Continue Reading...

What is a skippered bareboat charter?

A skippered bareboat charter gives you the freedom of a private yacht—without the responsibility of skippering it yourself. You hire a yacht and a licensed professional skipper joins your crew to manage the sailing, navigation, docking, and safety. Continue Reading...

What support is available during our charter?

You’re never alone at sea. Throughout your bareboat charter, you’ll have access to 24/7 technical support provided by the local charter base. Continue Reading...

What are the typical charter check-in and check-out procedures?

Most bareboat charters operate on a Saturday-to-Saturday schedule, although this can vary by destination and operator, particularly in quieter periods. Continue Reading...

How many people can a bareboat charter accommodate?

Most bareboat yachts are designed for groups of 4 to 12 people, depending on the size and layout of the boat. The average bareboat in popular destinations like the Greek Islands has around 4 cabins, though larger yachts with 5 to 8 cabins are available for bigger groups. Continue Reading...

What is a bareboat charter?

A bareboat charter is a yacht rental without a professional crew—giving you full responsibility for sailing, navigating, and provisioning the boat. It’s the ideal option for experienced sailors who want the freedom to plan their own itinerary and enjoy the adventure of skippering their own yacht. Continue Reading...

Can you assist with other aspects of our travel?

While we’re not a travel agency, we’re more than happy to assist with key elements that support your sailing holiday. Our expertise lies in organizing every aspect of your yacht charter—including transfers between the charter base and your arrival point or accommodation, as well as offering advice on provisioning your boat either remotely or upon arrival. Continue Reading...

How do we provision our bareboat charter?

Provisioning your bareboat is simple, and there are a few convenient options to choose from—depending on your destination and preferences. Continue Reading...

Can we board early at the start of charter?

Typically, your departure time is scheduled to give the operator enough time to prepare the yacht—ensuring it is clean, fully serviced, and technically sound before handover. Continue Reading...

Can we book a cabin on a crewed boat?

Yes, in many popular sailing destinations, it's possible to book a private cabin on a crewed yacht. Several charter operators offer scheduled cabin-share cruises, where you join like-minded travellers on a set itinerary with a professional crew. Continue Reading...

The Sail Connections Guarantee

One contact - every option - advice you can trust.


  • Matching any competitive offer
  • Sourcing boats with discounts available
  • Personalising our proposal just for you
  • Qualifying the operator as well as the boat
  • Advising without bias based on 25+ years of experience
  • We do more than just book yachts!

We will match any discount website offer on charter boat price, and still provide our customary high level of service.

Get in Touch

The Essential Guide to Sailing Holiday Charters

The Sail Connections Essential Guide to Bareboat and Crewed Sailing Holiday Charters is packed full of useful tips for getting the most out of your next boat charter. And it is FREE to download.

Download Guide

Enquire about a charter...

For a personal proposal structured to meet your needs, with advice on all aspects of your sailing charter.