Sailing Tours & Trips in Greece
Set sail for a Greek island odyssey. Discover Mykonos, with its famous windmills, wander through the ancient temples of Naxos, and check out Syros's beautiful architecture. Of course, don't forget to get some R&R on Ios's pristine beaches. Watch spectacular sunsets from Santorini's caldera, tour Athens' Acropolis, swim in turquoise waters at Paros and the Saronic Gulf, and savor fresh seafood at harbor-side taverns. What a life!
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Elliot • traveled in September, 2025
Amazing captain. He made this trip a fantastic sailing experience
Greece Sailing Adventure: Cyclades Islands - A
Andrew • traveled in October, 2025
It was a fabulous yachting tour of the Greek Islands. I'll be recommending this to my friends.
Sailing Greece - Mykonos to Santorini - M
Michael • traveled in July
First time sailing and it was amazing!
Sailing Greece - Mykonos to Athens
10 best Sailing Greece tour packages
Compiled by
MelissaGreece travel expert at TourRadar
- Greece Sailing Adventure: Cyclades Islands
- Sail Greece: Santorini to Mykonos
- Sailing Greece - Mykonos to Santorini
- Sailing Greece - Mykonos to Athens
- Saronic Sailing Luxury Adventure
- Set sail from Zakynthos
- Pride Sailing in Greece (Ionian Sea)
- 6-Day Tour Athens & Santorini Island to Discover Greece's Charm
- Athens, Naxos & Santorini Sunset Cruise - Premium
- Greek Islands Explorer with Santorini Sunset Cruise - Premium
Greece Sailing Adventure: Cyclades Islands
21 Reviews by TourRadar travelers“Amazing Tour with an amazing skipper.”
Kaja, traveled in May
Your 54-56ft yacht connects 9 islands over 10 days, from Santorini's dramatic caldera to Mykonos' vibrant harbors. The journey includes secluded beaches like Paradisi and Gaidharos Bay, with basic sailing instruction throughout.
Duration 10 days Destinations Santorini, Oia, Ios, Amorgos, Katapola, Koufonisia, Iraklia, Schoinousa, Naxos, SyrosSee all destinations Age Range Ages 15+ Operator Intrepid Travel From $2,564
24% Off- US$1,955+$126 local paymentsYou save $609
Sail Greece: Santorini to Mykonos
1 Review by TourRadar travelers“We had a great time meeting lots of new friends who all got on from many nationalities. Without the disputes!”
Peter, traveled in September
The modern 56ft yacht carries you along Greece's most scenic routes. Highlights include Santorini's Red Beach, Ios's Manganari Beach, and Naxos's ancient temples. Seven nights of authentic maritime life guided by skilled skippers.
Duration 8 days Destinations Santorini, Ios, Amorgos, Koufonisia, Iraklia, Naxos, Syros, Mykonos Age Range Ages 15+ Operator Intrepid Travel From $1,712
19% Off- US$1,393+$114 local paymentsYou save $319
Sailing Greece - Mykonos to Santorini
54 Reviews by TourRadar travelers“Sailing from island to island was very cool, much more fun than just ferry hopping.”
Fabio, traveled in July
A modern 57-foot yacht takes you through Greece's crystal waters to secluded coves and hidden beaches. The skipper shares sailing expertise while visiting eight islands, including Naxos's ancient temples and Antiparos's caves.
Duration 8 days Destinations Mykonos, Naxos, Paros, Antiparos, Ios, Sifnos, Folegandros, Santorini Age Range Ages 18+ Operator G Adventures From $1,849
25% Off- US$1,387You save $462
Sailing Greece - Mykonos to Athens
20 Reviews by TourRadar travelers“This was the absolute best introduction to Greece and sailing.”
Debra, traveled in April
The 57-ft yacht sails from cosmopolitan Mykonos through the Cyclades. Your skipper guides visits to Hydra's car-free harbor, Kythnos' therapeutic springs, and Aegina's ancient temples. Eight-day adventure includes snorkeling gear.
Duration 8 days Destinations Mykonos, Syros, Kea, Kythnos, Hydra, Aegina, Athens Age Range Ages 16+ Operator G Adventures From $1,799
25% Off- US$1,349You save $450
Saronic Sailing Luxury Adventure
5 Reviews by TourRadar travelers“This trip was fantastic. Definitely 5/5 stars.”
Liam, traveled in August
A luxury yacht carries you through Greece's Saronic Gulf to the Temple of Aphaea and Ancient Epidaurus. The route connects Poros, Hydra, and Spetses islands, with swimming stops at secluded beaches. Limited to 8 guests.
Duration 8 days Destinations Athens, Poros, Ermioni, Spetses, Hydra, Aegina, Agkistri, Palaia Epidavros Age Range Ages 6+ Operator Trails Beyond From
25% Off- US$2,930
A traditional gulet carries you from Zakynthos to iconic Greek destinations. The route includes Fiskardo's white pebble beaches, Meganisi's hidden coves, and the famous Shipwreck Beach. Seven nights at sea with ensuite cabins and authentic Greek cuisine.
Duration 8 days Destinations Zakynthos, Kefallonia, Agia Efimia, Fiskardo, Lefkada, Nydri, Meganisi, Ithaca, Atokos Island Age Range All Ages Welcome Operator Encounters Travel From
25% Off- US$995
Ionian winds propel your Lagoon 42 catamaran along Greece's stunning coastline. The route between Lefkada's marina and Kefalonia's ports includes stops at Porto Katsiki's white-cliff beaches and Meganisi's secluded coves.
Duration 8 days Destinations Lefkada, Meganisi, Ithaca, Vathy, Kefallonia, Sami, Fiskardo, Sivota, Lefkas Age Range Ages 18+ Operator Med Sailing Holidays From
25% Off- US$2,387
What our customers ask about Sailing Tours & Trips in Greece
What is the best time of year to go sailing in Greece?
Greece's sailing season peaks from May to September with each month offering distinct advantages. The Ionian Sea maintains gentle winds throughout summer while the Cyclades experiences stronger gusts during July and August. Most travelers find June and September offer the best combination: temperatures hover between 25-30°C with less crowded ports in popular stops like Santorini and Mykonos. A TourRadar traveler notes: "We went in June and we had the perfect balance of wind for sailing and calm seas for swimming."
What are the top destinations covered on Greek sailing itineraries?
Greek sailing routes typically focus on two main island groups. The Cyclades circuit includes Mykonos Santorini and Naxos featuring distinctive white architecture and significant archaeological sites like Ancient Delos. The Ionian journey covers Lefkada Kefalonia and Ithaca offering sheltered waters and historical landmarks including Odysseus's home in Vathi. A TourRadar traveler shared: "Exploring hidden coves in Milos and visiting the Blue Caves of Lefkada were highlights - each island offered something unique and special."
How many people typically share a sailing vessel?
Greek sailing tours maintain small group sizes for comfort and personalization. Standard vessels like the Lagoon 42 catamaran host 8-10 guests while larger traditional boats such as the Running On Waves accommodate slightly more passengers. One TourRadar traveler observed: "Having just 8 people on board created a perfect dynamic - we became like family by the end of the trip."
What's the typical budget needed beyond the tour price?
Daily expenses beyond the tour cost average 50-60 USD covering non-included meals (mainly dinners) optional activities and local transport. Port fees may add around 395 USD per person on certain tours. Popular destinations like Mykonos and Santorini command higher restaurant prices. A TourRadar traveler advises: "Plan for around 30-40 USD per dinner at local tavernas plus extra for activities like wine tastings or archaeological site visits."