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

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...