Yacht Charter FAQs

With so many Mediterranean sailing holiday destinations, where do I begin to look?

It’s true—the Mediterranean is packed with incredible sailing options, each appealing in its own special way. From the history-rich coastlines of Greece and Italy to the stunning islands of Croatia and the turquoise bays of Turkey, you're spoiled for choice. The key is to match your destination to your group’s interests, sailing experience, and timing.

Start by asking yourself:

  • What kind of experience are we after? Island-hopping, cultural exploration, quiet coves, or vibrant nightlife?
  • What time of year do we want to travel? The Med sailing season runs from May to October, with each month offering different pros and cons.
  • How experienced is our crew? Some regions, like the Ionian Islands or the Dalmatian Coast, are ideal for first-timers. Others, like the Cyclades, can be more challenging.

At Sail Connections, we help you narrow the field by considering your sailing level, budget, and travel logistics. Whether you're drawn to the romantic Amalfi Coast, the cultural gems of the Balearics, or the variety of the Greek Islands, we'll recommend destinations—and boats—that suit you best.

Need help deciding? Talk to [email protected] for personal one-to-one support. With over 30 years of sailing knowledge and first-hand experience across the Med, Robert will help you get started on your perfect yacht charter holiday.

Related FAQs

Which Mediterranean destinations are most popular for charter sailing holidays?

The Mediterranean is a dream sailing destination Continue Reading...

How much does a sailing holiday in the Mediterranean cost?

The cost of a sailing holiday in the Mediterranean can vary widely Continue Reading...

Do I need a licence to charter a yacht in the Mediterranean?

Yes, if you're planning a bareboat charter (where you skipper the yacht yourself) Continue Reading...

What are the benefits of booking a sailing holiday through a broker like Sail Connections?

Booking through a trusted yacht charter broker offers many advantages Continue Reading...

What sailing qualifications are required to bareboat charter in the Caribbean?

Most Caribbean destinations do not require a formal sailing licence to charter a bareboat. Continue Reading...

Am I responsible for damage to my chartered boat?

From time to time, damage can occur during a yacht charter. Continue Reading...

When should I book a charter boat in the Caribbean and Bahamas?

The best time to charter in the Caribbean and Bahamas is from December through July Continue Reading...

What do you recommend about boat chartering in the Caribbean?

Chartering a boat in the Caribbean is one of the most rewarding sailing experiences Continue Reading...

What are your favourite Mediterranean sailing spots?

When it comes to sailing in the Mediterranean, we're totally sold! Continue Reading...

When should I book a charter boat in the Mediterranean?

For the Mediterranean It’s best to book 6 to 12 months in advance. Continue Reading...

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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.

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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.

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