Sailing 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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Fiona • traveled in October, 2025
The actual trip was amazing. The skipper was very knowledgeable and safety conscious. You have to allow 2 days for adjusting to boat life.
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 - S
Sarah • traveled in August, 2024
Wonderful trip with wonderful crew!
Sailing Greece - Santorini to Santorini
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95 Sailing trips in Greece with 389 reviews
Compiled by
MelissaGreece travel expert at TourRadar
- Greece Sailing Adventure: Cyclades Islands
- Sail Greece: Santorini to Mykonos
- Cyclades Luxury Sailing Adventure (Catamaran)
- Sailing Greece - Santorini to Santorini
- Southern Cyclades Sailing Cruise 2026
- Saronic Sailing Luxury Adventure
- Yoga Sailing in Greece - Ionian Sea
- Sailing the Ionian Islands
- Sailing Adventure through the Saronic Gulf
- Greece: Sail & Swim
Greece Sailing Adventure: Cyclades Islands
20 Reviews by TourRadar travelers“The natural beauty of Greek Islands and amazing local experiences offered us friendship and camaraderie.”
Simon, 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, Ios, Oia, Amorgos, Katapola, Cyclades, Koufonisia, Iraklia, Naxos, SyrosSee all destinations Age Range Ages 15+ Operator Intrepid Travel From
- US$2,840+$129 local payments
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
- US$2,015+$117 local payments
Cyclades Luxury Sailing Adventure (Catamaran)
3 Reviews by TourRadar travelers“Trip was amazing and defiantly the trip of a lifetime. HIGHLY recommended.”
Kimberly, traveled in August
The luxury catamaran departs Athens Marina for the Cyclades archipelago. The route includes Milos's volcanic formations, Sifnos's medieval Kastro, and Kythnos's thermal springs. Professional skipper guides 209-nautical-mile adventure over 8 days.
Duration 8 days Destinations Athens, Sounio, Serifos, Kimolos, Polyaigos, Milos, Sifnos, Kythnos Age Range All Ages Welcome Operator Trails Beyond From
- US$2,856
Sailing Greece - Santorini to Santorini
30 Reviews by TourRadar travelers“Excellent tour, great skipper, Marios and great group participation. Though travelling alone, I never felt left out.”
Liam, traveled in June
The modern 57-foot yacht reveals secluded bays and ancient harbors throughout Greek waters. Stops include Magganari Beach on Ios, Mykonos' Little Venice, and Naxos' Temple of Dimitra. Rated 4.5/5 by previous travelers.
Duration 10 days Destinations Santorini, Ios, Naxos, Mykonos, Syros, Paros, Sifnos, Folegandros Age Range Ages 16+ Operator G Adventures From $2,349
25% Off- US$1,762You save $587
Southern Cyclades Sailing Cruise 2026
1 Review by TourRadar travelers“cozy tour that i would like to repeat next year.”
Igor, traveled in May
Duration 8 days Destinations Athens, Milos, Folegandros, Santorini, Astypalaia, Ios, Serifos Age Range Ages 8+ Operator Running On Waves From
25% Off- US$4,903+$425 upfront costs
Saronic Sailing Luxury Adventure
5 Reviews by TourRadar travelers“Swimming & snorkelling in the beautiful clear waters was out of this world.”
Catherine, traveled in July
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$2,774
Duration 8 days Destinations Lefkada, Ithaca, Sami, Fiskardo, Meganisi, Kalamos, Lefkas Age Range Ages 18+ Operator Med Sailing Holidays From
25% Off- US$2,329
The 25-passenger gulet awaits in Corfu's UNESCO Old Port for a trip costing around $1,100. Highlights include Sivota's Blue Lagoon, Antipaxos's Voutoumi beach, and Paxos's hidden coves. The 8-day voyage features snorkeling, beachfront taverna dinners, and Ionian Sea views.
Duration 8 days Destinations Corfu, Sivota, Parga, Antipaxos Island Age Range All Ages Welcome Operator Encounters Travel From
25% Off- US$995
Duration 8 days Destinations Athens, Aegina, Ermioni, Spetses, Hydra, Poros, Epidaurus Age Range Ages 10+ Operator Joyride Charters From
25% Off- US$3,725
A traditional motorized vessel takes you through Greece's Saronic Gulf to six distinct islands. The itinerary features Aegina's Temple of Apollo, swimming in Poros' secluded bays, and walks through Hydra's car-free streets. Daily swim stops and fresh Greek cuisine included.
Duration 8 days Destinations Athens, Aegina, Poros, Ermioni, Spetses, Hydra Age Range Ages 18-32 Operator Topdeck From $2,539
10% Off- US$2,289You save $250
What our customers ask about Sailing 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."
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