Mediterranean Sailing: 10 Must-Visit Islands

I have a confession to make. I LOVE ChatGPT. I mentioned this to a friend recently, and she asked, “What’s that?” It’s simple. You can ask “ChatGPT” questions on your trusty laptop or phone and get an answer within seconds. I decided to illustrate how this works in this week’s post by using AI. I got this when I asked for the 10 best islands to sail around in the Med!

Here’s a list of the 10 best islands to sail around in the Mediterranean. Each offers a unique mix of scenery, culture, anchorages, and charm. They are perfect for any sailing adventure.

1. Corsica, France

Why sail here: A dramatic blend of rugged mountains and turquoise waters. The island’s wild beauty and mix of French and Italian culture make it a standout.

Highlights: Bonifacio’s fjord-like harbour, crystal-clear bays in the north, and protected marine reserves.

2. Mallorca, Spain (Balearic Islands)

Why sail here: A perfect mix of vibrant cities, quiet coves, and scenic coastline.

Highlights: Palma’s chic marina, the hidden Calas on the east coast, and the stunning Tramuntana mountains rising behind the shore.

3. Santorini, Greece

Why sail here: Iconic whitewashed villages perched over a volcanic caldera, and unforgettable sunsets.

Highlights: Anchor near the red and black beaches, soak in hot springs, and explore ancient ruins in Akrotiri.

I might disagree with this choice. After spending six months sailing around Greece and its many beautiful islands, I feel there are perhaps better options.

4. Sardinia, Italy

Why sail here: Wild beaches, upscale marinas, and a rugged coastline perfect for sailing.

Highlights: The Maddalena Archipelago for pristine anchorages, Costa Smeralda for luxury stops, and secluded beaches like Cala Luna.

5. Hvar, Croatia

Why sail here: Glamour, nightlife, and sun-drenched charm — Hvar is the jewel of the Adriatic.

Highlights: Buzzing Hvar Town, the Pakleni Islands for swimming and snorkelling, and lavender-scented hills inland.

6. Ibiza, Spain (Balearic Islands)

Why sail here: World-renowned for its nightlife, Ibiza also offers calm coves and bohemian beach vibes.

Highlights: Sunset anchorage at Cala Comte, beach bars in Cala Jondal, and scenic Formentera just a short sail away.

7. Lefkada, Greece (Ionian Islands)

Why sail here: Ideal for relaxed sailing with short distances between stunning anchorages.

Highlights: Porto Katsiki Beach, sheltered bays perfect for swimming, and easy access to nearby islands like Meganisi and Ithaca.

I know that many sailors “winter” their boats in Lefkada, which is a popular choice.

8. Elba, Italy

Why sail here: Rich history (Napoleon’s exile island) meets stunning natural beauty and clear waters.

Highlights: Charming Portoferraio, peaceful moorings in Biodola Bay, and great hiking inland.

9. Mljet, Croatia

Why sail here: A tranquil and green escape, often considered Croatia’s most beautiful island.

Highlights: National Park with saltwater lakes, lush pine forests, and uncrowded coves for anchoring.

10. Symi, Greece (Dodecanese Islands)

Why sail here: A hidden gem with a postcard-perfect harbour and a slow, authentic pace.

Highlights: Neoclassical pastel houses lining the harbour, clear bays for swimming, and proximity to Rhodes for a larger sailing itinerary.

Bonus tip:

These islands are best explored as part of a chain. For instance, you can sail the Cyclades, the Ionian islands, or Croatia’s Dalmatian Coast. Plan your route according to your pace, weather, and interests — history, nightlife, tranquility, or wild beauty.

Now, this information may feel quite “generic.” However, I do believe there are some interesting options listed. These can be used as a starting point when considering your journey. We have looked up many things using ChatGPT (most are free). These include mechanical problems on the boat and “how-to” boat questions. Of course, we also searched for the very useful “where is the cheapest store to buy beer near me?”

Whether we love it or hate it, view AI with trepidation and horror (where is the personal input and expression in using AI?), or accept it as the future, AI is here to stay. That’s “Artificial Intelligence,” for those who are wondering. It’s a bit of an oxymoron, isn’t it?

I would love to hear your views. Please comment: your thoughts on AI, or tell us your favorite places to sail in the Mediterranean?

Happy sailing wherever you are, ocean or armchair!

Captain Mike and Mermaid.