A couples' sailing vacation in Greece

A couples’ sailing vacation in Greece offers the ultimate blend of romance and adventure, featuring private cabins on luxury catamarans or monohulls. These curated trips focus on secluded swimming coves, sunset dinners at traditional island tavernas, and flexible itineraries across the Cyclades and Ionian seas, perfect for honeymoons or romantic escapes in 2026.

Sailing vacations for couples

 A journey through the Greek Islands on a skippered sailboat charter

If you’re looking for an exciting and unforgettable adventure with your significant other, look no further than Greek Water Yachts! We offer the best private sailing trips with a captain in the stunning Greek islands, and our trips are perfect for active couples of all ages, from young and adventurous to middle-aged or retired.

Imagine exploring the Aegean Sea with your loved one, swimming in the crystal-clear waters, and discovering new islands every day. Sip on a pre-dinner drink on your yacht, and then indulge in the delicious flavors of Greek cuisine during your trip.

At Greek Water Yachts, we can customize your sailing trip for 2 to suit your preferences. Whether you prefer to relax on the sun deck with a glass of champagne, take in the sights and sounds of the islands, or explore hidden bays, we’ve got you covered.

With our sailing tour by boat in Greece for couples, you can rent a yacht and enjoy a memorable trip filled with exciting activities and new experiences. Instead of visiting the same places every day, you’ll discover a unique Cycladic site each day.

Don’t just take our word for it – read our glowing sailing Greece reviews from satisfied customers who have experienced the magic of the Greek islands with us.

Book your private sailing trip with Greek Water Yachts. Rent a yacht with skipper and create memories that will last a lifetime!

 

What to expect during your private trek while sailing the Greek Cycladic Islands with your partner:

  • you explore every day a new island , drive around with a rental or go jogging, hiking , cycling, windsurfing,diving and of course going out for night life.
  • together we will head for sandy beaches under the hot sun of the Aegean traveling from island to island
  • sipping cocktails on deck watching the full moon
  • swimming in the crystal clear water , snorkeling around and experience the hospitality of the locals at all the small islands we will visit.
  • try the delicious dishes of seafood and all the local recipes at the recommended tavernas.

  • enjoy nudism, as Greek Water Yachts is friendly to naturists guests(check also our spin-off Greek Naturists Yachts)

With your captain giving the best directions according to your interests, the only thing that you and your mate has to do is to relax and enjoy your sailing excursion in the Cyclades with a private skippered yacht.

Roaming After Sixty

Moments in the Cyclades: Couples’ Sailing Trip Highlights

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Happy is the man, I thought, who, before dying, has the good fortune to sail the Aegean sea.
― Nikos Kazantzakis, Zorba the Greek

 

 

Yacht prices with skipper

Prices are for the 40ft sailboat Beneteau40 for a week charter

Discount available for 7-day charters on certain dates. Contact us!

Total Prices for 7-Day All-Inclusive Charter October May, June, July & Sept August
For 2 people €3805 €4445 €4765
For 3 or 4 people €4055 €4755 €5095
Departure / Arrival Paros / Paros

✓ What is included in this total?

We believe in transparent pricing. The totals above already include:

  • Fixed Essentials: Yacht rental, Professional Skipper, and 24% VAT.
  • Operational Extras: All diesel fuel consumption and Marina/Port fees for the full week.
  • Convenience: Final cleaning of the yacht and high-speed onboard Wi-Fi.
  • Skipper Care: Full food compensation for your skipper is already covered.
  • Peace of Mind: Full yacht insurance and all credit card commission fees.

Note on Experience: Unlike standard charters where you pay for fuel and port fees at the end of the trip, these rates are pre-calculated for your convenience. You won't need to handle a "kitty" for boat expenses or worry about the skipper's meals—just step aboard and sail.

⚠️ What is NOT included: Food & drinks for the clients. You may bring your own provisions for the yacht or enjoy dinner at local tavernas.

*USD prices are approximate based on real-time exchange rates and rounded to the nearest $10.

Table: Greek skippered sailboat rental price for a week.

Escape Together: Tailored Cyclades Itineraries for Couples

Your private boat cruise is always flexible, customized in your profile in order to get the maximum pleasure. We are absolutely sure that you will have such a good time that you will add us in your every year couples vacation plan.

 

 

Rent a sailboat in Greece and cruise the Greek islands.

Shared Memories: Real Experiences from Our Couples’ Sailing Vacations

This was the trip of a lifetime.

My boyfriend and I sailed with Antonis and his wife, Poppy, for seven days (six nights) in the Minor Cyclades.

We took the ferry from Athens to Paros and boarded the sailboat in Paros.

Antonis had two rules on the boat: firstly, no watches allowed because, on this vacation, time does not exist, and secondly, there are no rules! Antonis was THE MOST capable captain and made both of us feel incredibly safe and comfortable. I cannot express how important this part was. On the ferry from Athens to Paros, the seas were unusually rough and I became very seasick. You can imagine our anxiety about the impending seven days on a sailboat. We worried for nothing because we had Antonis on the sailboat! He personalized our trip to give us the best experience in Greece imaginable.

Private beaches, beautiful coves for swimming, and the most charming islands comprised our trip. Once we told him that I was nervous swimming in deep water, he made it his business to find the most magnificent beaches for me to snorkel in. We have memories that will last a lifetime thanks to Antonis. Making the trip even more fantastic was the sailboat we took to reach these spectacular places each day. Antonis even let us help let out and bring in the sails and taught us so much about sailing in general.

The trip was so incredible, we will definitely be doing this again!

Stephanie

Check more at TripAdvisor

Sailing trips through Greece with 42 reviews

Our Pick for Two: The Ideal Private Yacht for a Couples’ Escape

Yachts_for_sailing_the _greek_islands_with_greekwateryachts
Yachts_for_sailing_the _greek_islands_with_greekwateryachtsThe yachts of your chartered sailing holidays in Greece
Drawing of your chartered yacht
Sailing Yacht from Greek Water Yachts (4)-min
Sailing Yacht from Greek Water Yachts (3)-min
Full equipent kitchen
Year: 2010
Length: 40 feet
Crew:skipper
Base: Paros (Cyclades)
Cabins : 3 doubles
Shower/Head: 2
Accommodation: 4 guests + skipper
 

Booking Form

Make your introductory reservation request for your Greek islands sailing tour by filling out the contact – booking form.  We will respond within 24-48 hours.

FAQ-Sailing holidays Greece

Check out our questions and answers section about tips and deals for a couple sailing vacations in the Greek Islands with a professional captain.

Greek island boat tours for couples

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Greek Water Yachts