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Sailing in Greece
Sailing in Greece

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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2026

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1 Adult2 Adults, 1 Child2 Children

Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

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  • E

    Elliot traveled in September, 2025

    5.0
    Amazing captain. He made this trip a fantastic sailing experience
    Greece Sailing Adventure: Cyclades Islands
  • M

    Marla traveled in May

    5.0
    It is impossible to express how much we loved our trip. By the end Mike and Andreas were like family. We stayed in Greece a week after and I got great advice on where we should go. This was a once in a lifetime trip for us. We saved up for our 25th anniversary and we made the right choice. Big thanks to the guys and Danae.
    Cyclades Luxury Sailing Adventure (Catamaran)
  • H

    Hannah traveled in July

    5.0
    Max was an amazing Skipper and went to great lengths to ensure we all had an amazing experience. I highly recommend this trip and will definitely be coming back for future adventures.
    Sailing Greece - Santorini to Mykonos
  1. Sail Greece: Santorini to MykonosMap of Sail Greece: Santorini to Mykonos
    Sailing

    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
    DestinationsSantorini, Ios, Amorgos, Koufonisia, Iraklia, Naxos, Syros, Mykonos
    Age Range Ages 15+
    OperatorIntrepid Travel

    From

    US$2,015
    +$117 local payments
    View tour
  2. Greece Sailing Adventure: Cyclades IslandsMap of Greece Sailing Adventure: Cyclades Islands
    Sailing

    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
    DestinationsSantorini, Ios, Oia, Amorgos, Katapola, Cyclades, Koufonisia, Iraklia, Naxos, SyrosSee all destinations
    Age Range Ages 15+
    OperatorIntrepid Travel

    From

    US$2,840
    +$128 local payments
    View tour
  3. Cyclades Luxury Sailing Adventure (Catamaran)Map of Cyclades Luxury Sailing Adventure (Catamaran)
    Sailing

    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
    DestinationsAthens, Sounio, Serifos, Kimolos, Polyaigos, Milos, Sifnos, Kythnos
    Age Range All Ages Welcome
    OperatorTrails Beyond

    From

    US$2,845
    View tour
  4. Sailing Greece - Santorini to MykonosMap of Sailing Greece - Santorini to Mykonos
    Sailing

    Your 57-ft yacht adventure spans from Santorini's caldera to Mykonos's windmills. The route connects islands like Folegandros and Sifnos, revealing hidden coves and remote beaches. Traditional harbors and local tavernas showcase spectacular Cyclades sailing.

    Duration 8 days
    DestinationsSantorini, Folegandros, Sifnos, Ios, Antiparos, Paros, Naxos, Mykonos
    Age Range Ages 16+
    OperatorG Adventures

    From $1,679

    25% Off
    US$1,259
    You save $420
    View tour
  5. Luxury Sailing & Archaeology adventure 8daysMap of Luxury Sailing & Archaeology adventure 8days
    Sailing

    The Saronic Gulf stretches 102 nautical miles, offering UNESCO site visits alongside island wonders. Peaceful coves near Agkistri provide anchorage, while Methana's volcanic beaches offer swimming spots. Traditional ports from Aegina to Hydra dot the route.

    Duration 8 days
    DestinationsAthens, Agkistri, Corinth, Mycenae, Palaia Epidavros, Epidaurus, Nafplion, Methana, Poros, HydraSee all destinations
    Age Range Ages 8+
    OperatorTrails Beyond

    From

    25% Off
    US$3,218
    View tour
  6. Sailing the Ionian IslandsMap of Sailing the Ionian Islands
    Sailing

    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
    DestinationsCorfu, Sivota, Parga, Antipaxos Island
    Age Range All Ages Welcome
    OperatorEncounters Travel

    From

    25% Off
    US$995
    View tour
  7. Set sail from ZakynthosMap of Set sail from Zakynthos
    Sailing

    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
    DestinationsZakynthos, Agia Efimia, Ithaca, Meganisi, Fiskardo
    Age Range All Ages Welcome
    OperatorEncounters Travel

    From

    25% Off
    US$995
    View tour
  8. Southern Cyclades Sailing Cruise 2026Map of Southern Cyclades Sailing Cruise 2026
    Sailing
    Duration 8 days
    DestinationsAthens, Milos, Folegandros, Santorini, Astypalaia, Ios, Serifos
    Age Range Ages 8+
    OperatorRunning On Waves

    From

    25% Off
    US$4,903
    +$425 upfront costs
    View tour
  9. Greece: Sail & SwimMap of Greece: Sail & Swim
    Sailing

    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
    DestinationsAthens, Aegina, Poros, Ermioni, Spetses, Hydra
    Age Range Ages 18-32
    OperatorTopdeck

    From $2,539

    10% Off
    US$2,289
    You save $250
    View tour
  10. Sailing & Hiking the Dodecanese IslandsMap of Sailing & Hiking the Dodecanese Islands
    Sailing

    The Hanse 370 yacht Armida sails 26 nautical miles from Kos to Nisyros. The route includes Symi's cosmopolitan harbor and secluded Alimia bay. Professional crew guides through 120 nautical miles of Aegean waters over 7 adventure-filled days.

    Duration 7 days
    DestinationsKos, Gyali Island, Nisyros Island, Tilos, Alimia, Chalki, Symi, Rhodes
    Age Range Ages 10+
    OperatorTrekking Hellas Rhodes

    From

    10% Off
    US$4,367
    View tour
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Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0

Select departure month

2026

Jan
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Apr
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2027

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2028

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