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A Sailing Adventure through the Greek Islands, cont’d

A couple of posts ago, I wrote about a sailing trip through The Sporades Islands of Greece. It was such a memorable trip, probably the most amazing vacation I’ve experienced, other than my Honeymoon in Bora Bora, that I thought I would share with you a quick rundown of our itinerary, chronicling our adventure across The Sporades. In Matt Barrett’s travel guides, he provides a really great overview of each of the islands I am about to take you through. Check out his site if you would like to learn more about The Sporades.

A Week of Sailing Bliss in the Greek Islands

Day 1: We set sail from Milina bright and early. There were 7 of us, 4 bedrooms and baths, in a 40’ catamaran. The sailboat was surprisingly spacious, never feeling too crowded. We had all just graduated from business school together and were ready for one last adventure before rejoining the working world. Note: I don’t recommend chartering a sailboat with other travelers that you do not know. If you don’t have a group, just hire a captain but keep your boat private. This sailing trip would be just as pleasant for two as it was for 7.

Today is going to be a long day of sailing. Once we get to The Sporades, we can easily sail from island to island in just an hour or so. But, the sailing part is half the fun! The scenery is just beautiful as we sail along. The less populated islands look like bright white, tree-capped rocks jutting out of aquamarine water. The water is so clear that you can see right to the bottom in the shallow areas. The weather is perfect. Not a cloud in the sky and a nice breeze to keep the bright, hot sun from cooking you.

That evening, we get to Skopelos. We moor, and its cocktail time! Enjoying a glass of Greek wine or a Mythos, Greece’s local beer, we sit back and watch the sunset. The sunsets are spectacular in the Greek Islands. These bright fiery orange hues reflect off the water and the islands turn a pretty pinkish purple against the sun. Just as the sun finished setting behind the island, we decide it’s time to jump on our dinghy and motor to the island for dinner. Here, our amazing dining experiences begin. I could subsist on nothing but Greek salad and grilled squid the entire vacation – it is so delicious, I just can’t get enough.

Day 2: Wake up refreshed with the freedom to do what we want when we want; no watches are needed. Time is completely irrelevant on our little floating paradise. After a refreshing dip in the ocean, we settle in for a cup of coffee and breakfast. From there, we have the day to do whatever we please. So, we get out the floaties, the kayaks, and the sunscreen, and enjoy a lazy day in the sun. Late afternoon, we set sail and head over to the other side of the island, where we moor up and head straight for the beach taverna where we eat right on the beach under the stars. Fresh, whole Mediterranean fish, calamari, greek salad, moussaka, you name it. And we feast. Back on the boat, we have one final toast under the stars before we head in for the night. Although small, the cabins are quite comfortable and the gentle rocking of the boat puts me to sleep instantly.

Day 3: After two full days on Skopelos, we decide it’s time to set sail once again and check out the other islands. Today, we are heading to Alonnisos. This is a smaller, less populated island. Alonnisos still has the low key, quiet island charm that you think of when you imagine the Greek Islands. Small fishing villages, no resorts and, best of all, minimal tourists. And it’s just beautiful. We tie up with some other sailboats right at the harbor. Alonnisos has several old towns, but the best in my opinion is Steni Vala. Its just a tiny fishing village, but has some of the best seafood tavernas in The Sporades.

Day 4 – 6: It’s time to party. We head to Skiathos where the nightlife and restaurants are abundant. This is the largest of the Sporades islands, they even have a small airport. It was quite a sight to see these commercial airplanes coming in for landing right over our sailboat! We spent two nights in Skiathos, mooring on each side of the island. Our first night, we moor the boat on the less populated side of the island and, unlike Skiathos Town, which is right on the water’s edge, we are the only ones around. In fact, once on the island, it is not clear where we can find civilization to eat! But, we just start walking and soon enough, we see signs for Koukounaries where we find a wonderful taverna set in a nice courtyard and have a fresh, delicious meal, like we’ve come to expect. Koukounaries is widely considered to have some of the best beaches in the world. The next night, which for us was the 4th of July, we decide its time to party it up so we sail over to Skiathos Town to check out the nightlife scene, which is definitely hopping. Skiathos is the Mykonos of The Sporades, so if you are looking for the party scene, you’ve got it right here.

Besides dining and restocking supplies, and the occasional beach bar, we hardly had a need to actually spend time on the islands. We spent our days floating in the cool water or hanging out on the boat reading a book or tooling around on a kayak. It was delightful. When we needed a bit more of an adventure, we’d go out sailing, watching the islands float by around us. In our floating hotel, we could explore the islands, play on the beaches, or just chill in the ocean.

Day 7: Sadly, we had to say goodbye to our sailboat and the Greek Islands and head back to Athens. But, we still had that last day to sail back to Milina and enjoy the air, the sun and the beautiful waters of the Aegean Sea.

If you’ve got a bit of an adventurous urge but still want a nice, relaxing vacation, charter a sailboat through The Sporades Islands in Greece. It really is a trip of a lifetime, combining all the best aspects of a perfect vacation: sunny weather, beautiful views, amazing dining experiences, and all the amenities needed to completely relax without a care in the world.


  1. Amanda says:

    Such a great guide to the Sporades! Totally different than the more crowded islands.

  2. Mary R says:

    I’m so happy to have found your blog and this guide to the Sporades!

    I got engaged in Tahiti, so if your experience compares to that, I am sold! My husband and I planned to do our honeymoon here, but one thing led to another and we didn’t get the chance to as we hoped. It’s still on our list though!

    Looking forward to reading more

    1. Sharman Wilson says:

      Hi Mary! Thanks for reading and commenting. The Sporades were absolutely amazing – so beautiful. You and your husband should definitely look into a trip there. Our sailing trip was right up there with our honeymoon in Bora Bora – I love the South Pacific as well! They are both amazingly beautiful and relaxing places.

  3. Ivan says:

    Greatings, Todo dinбmica y muy positiva! 🙂


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  10. Your trip to Greece looks unreal! Glad to hear you had a wonderful time. If you have another chance to go, check out Mykonos, I’ve written a few things about it on my blog. If you have any specific questions, let me know!

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