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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

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ChildrenUnder 18

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  • Ruthtraveled in July, 20265.0
    They can't do much better than our trip with Jiorgos
    Greece Sailing Adventure: Cyclades Islands
  • Petertraveled 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
  • Chloetraveled in July, 20265.0
    You won’t regret booking this tour. Steph is the best tour leader, good accommodation and space on the boat and some great activities involved.
    Croatia Sail Adventure
  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, Oia, Ios, Amorgos, Katapola, Koufonisia, Iraklia, Schoinousa, Naxos, SyrosSee all destinations
    Age Range Ages 15+
    OperatorIntrepid Travel

    From $2,563

    14% Off
    US$2,198
    +$127 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 $2,102

    28% Off
    US$1,507
    +$115 local payments
    View tour
  3. CROATIA SAIL - Split to Dubrovnik (The Southern Discovery)Map of CROATIA SAIL - Split to Dubrovnik (The Southern Discovery)
    Sailing

    Cruise the Mediterranean's crystal waters on an A+ category vessel with private en-suite cabins and sundeck lounging. Zlatni Rat beach, Hvar's historic quarter, and Mljet's National Park highlight the journey, accompanied by freshly prepared Croatian cuisine and daily swim stops.

    Duration 8 days
    DestinationsSplit, Bol, Hvar Island, Makarska, Korcula Island, Mljet Island, Dubrovnik
    Age Range Ages 25-40
    OperatorKoda Sail

    From

    28% Off
    US$1,675
    +$121 local payments
    View tour
  4. Delicious Amalfi Coast - Luxury Sailing Catamaran ALL INCLUSIVEMap of Delicious Amalfi Coast - Luxury Sailing Catamaran ALL INCLUSIVE
    Sailing

    A luxury 43ft catamaran carries you through Mediterranean waters, past hidden caves and secluded bays. Professional crew guides through Gulf of Naples highlights while offering sailing instruction. Modern amenities and spacious outdoor areas ensure optimal comfort.

    Duration 7 days
    DestinationsCastellammare di Stabia, Procida, Ischia, Forio, Capri, Positano, Amalfi, Sorrento, Pompeii
    Age Range All Ages Welcome
    Operated in English, Italian
    OperatorSail And Experience

    From

    28% Off
    US$8,664
    +$346 local payments
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  5. Sailing Croatia Catamaran Cruise: Dubrovnik, Ston, Korcula Mljet, Lastovo and islandsMap of Sailing Croatia Catamaran Cruise: Dubrovnik, Ston, Korcula Mljet, Lastovo and islands
    Sailing
    Duration 8 days
    DestinationsDubrovnik, Ston, Korčula, Lastovo, Mljet Island, Sipan Island
    Age Range Ages 18+
    OperatorSailing Adriatic

    From

    28% Off
    US$2,022
    +$404 local payments
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  6. 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

    28% Off
    US$1,721
    View tour
  7. Sail Greece: Mykonos to SantoriniMap of Sail Greece: Mykonos to Santorini
    Sailing

    Crystal waters carry the 54-56ft yacht from Mykonos to Santorini. The route includes secluded Gaidharos bay, traditional fishing villages in Small Cyclades, and iconic ports like Katapola in Amorgos.

    Duration 8 days
    DestinationsMykonos, Syros, Ermoupouli, Naxos, Ano Koufonisi Island, Iraklia, Schoinousa, Amorgos, Katapola, ChoraSee all destinations
    Age Range Ages 15+
    OperatorIntrepid Travel

    From $2,087

    19% Off
    US$1,693
    +$115 local payments
    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