Wine Lover’s Guide to Sailing in Greece: Sip, Sail & Soak in the Sun

If you’ve ever dreamed of combining your love for wine with the magic of the Greek islands, this is your sign to make it happen. Med Sailing Holidays’ Wine Week in Greece is an unforgettable adventure that blends the best of both worlds—lush vineyards and sun-soaked sailing across the Ionian Sea.

For one incredible week, you’ll island-hop in luxury, swim in crystal-clear waters, and indulge in some of the most delicious wines and local dishes Greece has to offer. Here’s what your wine-filled escape looks like:

Day 1: Lefkas to Spartochori, Meganissi

Your journey kicks off in Lefkas Marina, where the first toast is served—Prosecco in hand as you board your fully crewed catamaran. From there, we set sail to the charming island of Meganissi. The tiny village of Spartochori welcomes you with its whitewashed homes, blooming bougainvillaea, and authentic tavernas where you’ll dine like a local.

Day 2: Vathy, Ithaka

Morning swim? Yes, please! You’ll dip into the Blue Caves before sailing to Atakos for lunch. Then it’s on to Vathy, the vibrant capital of Ithaka. Here, you’ll head to WineLand for an intimate tasting session paired with local bites. It’s the perfect intro to Greek winemaking—and trust us, your tastebuds will thank you.

Day 3: Sami, Kefalonia

Today, we anchor in Sami, a postcard-perfect port on Kefalonia. Wine lovers, this is your moment—Orealios Winery awaits with its legendary Robola varietals. You’ll swirl, sniff, and sip your way through their best bottles before exploring the mysterious Melissani Caves, where sunlight dances on turquoise waters. Simply magical.

Day 4: Fiskardo, Kefalonia

We arrive early in glamorous Fiskardo, a colorful fishing village that oozes charm. But today is all about hands-on culture. Tour a family-owned vineyard, take part in a wine tasting, and then roll up your sleeves for a Greek cooking class. Learn to make traditional dishes, then enjoy them with a perfectly paired glass of vino.

Day 5: Sivota, Lefkada

Back to the sea! You’ll enjoy multiple swim stops before docking in the tranquil bay of Sivota. Tonight’s highlight? Another exclusive wine tour and tasting, because no two wineries—or their wines—are alike. It’s all part of the discovery.

Day 6: Kalamos

Relax and recharge with a full day of sailing, snorkeling, and hidden bays. In the evening, you’ll choose: a laid-back beach BBQ under the stars, or a luxe three-course dinner with expertly paired wines onboard. Either way, it's the perfect celebration of an epic week.

Day 7: Return to Lefkas

The journey wraps up with one last sail back to Lefkas, but the adventure isn’t over yet. You’ll end the trip in style with sunset cocktails at FlyMe, a trendy mountaintop bar with panoramic views and handcrafted drinks.

Whether you're a wine connoisseur or just someone who loves the finer things in life, Wine Week Greece is the sailing holiday you didn’t know you needed. Ready to sip and sail your way through paradise?

Visit Med Sailing Holidays – Wine Week Greece to book your spot.