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Sailing Tours & Trips in Mediterranean
Sailing Tours & Trips in Mediterranean

Sailing Tours & Trips in Mediterranean

Picture yourself sailing around the Mediterranean, taking in Croatia and Montenegro to name just two. Check out Diocletian's Palace in Split, Korčula (which claims to be Marco Polo's birthplace), and Montenegro's Bay of Kotor with its fjord-like vibes. Head to Podgorica, and enjoy Budva's beaches. So much to see, so little time!

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2026

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1 Adult2 Adults, 1 Child2 Children

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AdultsAges 18 or above

2

ChildrenUnder 18

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  • Ruth•traveled in July, 20265.0
    They can't do much better than our trip with Jiorgos
    Greece Sailing Adventure: Cyclades Islands
  • Peter•traveled in October5.0
    We had a great time meeting lots of new friends who all got on from many nationalities. At a restaurant one evening another group asked if we were a family which is how we ended up but without the disputes! Our skipper, Rita displayed wonderful leadership & sailing skills telling many interesting stories. Twice we has difficult dockings in strong crosswinds & other boats were messing it up big time but Rita nailed it both times & I was informed she received applause at Mykonos from the people on the dock. She also spent lot of time producing a video of our trip that she gave to us all. If your other CEO’s are half as good as her you have a very good team. Please note that you may only use my first name publically for this review, Peter!
    Sail Greece: Santorini to Mykonos
  • DaveHutchinson•traveled in August, 20265.0
    Superb trip with fun hilarious skipper. Good group. Lots of nice islands and swim stops. One day with strong winds. Strong winds can happen in cyclades July and August, so if you get seasick easily avoid these months. Of the year but definitely do the trip.
    Sailing Greece - Santorini to Santorini
  1. Greece Sailing Adventure: Cyclades IslandsMap of Greece Sailing Adventure: Cyclades Islands
    Sailing

    A 54-56ft yacht glides through Mediterranean waters, revealing hidden coves and vibrant harbors. Routes stretch from Santorini's caldera to Mykonos' coastline, featuring swim stops at secluded beaches like Paradisi and Gaidharos Bay.

    Duration 10 days
    DestinationsSantorini, Thera, Firostefani, Oia, Ios, Amorgos, Katapola, Koufonisia, Iraklia, SchoinousaSee all destinations
    Age Range Ages 15+
    OperatorIntrepid Travel

    From

    US$2,883
    +$124 local payments
    View tour
  2. Sail Greece: Santorini to MykonosMap of Sail Greece: Santorini to Mykonos
    Sailing

    A 56ft yacht sails from Santorini's dramatic cliffs to Mykonos's bustling harbor. Professional skippers guide you through the region's most scenic routes, stopping at hidden coves and historic ports over 8 unforgettable days.

    Duration 8 days
    DestinationsSantorini, Ios, Amorgos, Koufonisia, Iraklia, Naxos, Syros, Mykonos
    Age Range Ages 15+
    OperatorIntrepid Travel

    From

    US$2,112
    +$113 local payments
    View tour
  3. Sailing Greece - Santorini to SantoriniMap of Sailing Greece - Santorini to Santorini
    Sailing

    A 57-foot yacht provides intimate Mediterranean adventures through crystal-clear waters and ancient harbors. The route includes Magganari Beach, Homer's tomb on Ios, and Mykonos' Little Venice, perfect for groups of 8.

    Duration 10 days
    DestinationsSantorini, Ios, Naxos, Mykonos, Syros, Paros, Sifnos, Folegandros
    Age Range Ages 16+
    OperatorG Adventures

    From

    US$2,549
    View tour
  4. Sailing Greece - Mykonos to MykonosMap of Sailing Greece - Mykonos to Mykonos
    Sailing

    The 56-ft yacht sails Cyclades waters from Mykonos' windmills to Santorini's caldera. The voyage reveals hidden coves near Folegandros and ancient ruins in Paros, combining nautical skills with cultural discoveries.

    Duration 10 days
    DestinationsMykonos, Syros, Paros, Folegandros, Santorini, Ios, Naxos
    Age Range Ages 16+
    OperatorG Adventures

    From

    US$2,499
    View tour
  5. 15-Day Private, Premium Tour of TURKEY | Gulet Sailing, Serenity & VIP Road Trip | May to October  | by ANGELS VACATIONSMap of 15-Day Private, Premium Tour of TURKEY | Gulet Sailing, Serenity & VIP Road Trip | May to October  | by ANGELS VACATIONS
    Sailing
    Duration 15 days
    DestinationsIstanbul, Cappadocia, Uchisar, Goreme, Konya, Antalya, Olympus, Demre, Kekova, SimenaSee all destinations
    Age Range Ages 12+
    OperatorAngels Vacations

    From $9,033

    5% Off
    US$8,581
    View tour
  6. Med Sailing in Croatia (from Split to Dubrovnik)Map of Med Sailing in Croatia (from Split to Dubrovnik)
    Sailing

    The Oceanis 48 yacht cuts through crystal-clear Adriatic waters. Highlights include Hvar's Hula Hula bar, Vis's Blue Caves, and Mljet's saltwater lakes with professional crew support.

    Duration 8 days
    DestinationsSplit, Brac, Hvar Island, Vis, Korcula Island, Pomena, Mljet Island, Dubrovnik
    Age Range Ages 18+
    OperatorMed Sailing Holidays

    From

    5% Off
    US$1,565
    View tour
  7. Med Sailing in Croatia (from Dubrovnik to Split)Map of Med Sailing in Croatia (from Dubrovnik to Split)
    Sailing

    An Oceanis 48 yacht carries you through the Mediterranean's clearest waters. Hvar's iconic Hula Hula bar, Vis's famous caves, and cycling through Mljet National Park highlight the journey. Fresh meals accompany discoveries of hidden bays and authentic konoba restaurants.

    Duration 8 days
    DestinationsDubrovnik, Mljet Island, Pomena, Korcula Island, Vis, Hvar Island, Maslinica, Split
    Age Range Ages 18+
    OperatorMed Sailing Holidays

    From

    5% Off
    US$1,677
    View tour
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Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0

Select departure month

2026

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2027

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2028

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec