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Sailing Tours & Trips in Aegean Islands
Sailing Tours & Trips in Aegean Islands

Sailing Tours & Trips in Aegean Islands

Picture sailing between Greek islands in the Aegean, waking up in different harbors. Sailing trips mean living aboard catamarans or monohulls, visiting islands tour boats skip, and swimming straight from the boat. Could be Cyclades (Mykonos, Paros, Naxos), Dodecanese (Rhodes, Kos), or Sporades. Sail during days, anchor in secluded bays, hit island towns for evenings. It's active but relaxed, with stunning scenery constantly.

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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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  1. Greece Sailing Adventure: Cyclades IslandsMap of Greece Sailing Adventure: Cyclades Islands
    Sailing

    A 54-56ft sailing yacht takes you through Aegean waters from Santorini to pristine coves. The itinerary features swimming at Gaidharos Bay, visits to Amorgos' 11th-century Moni Hozoviotissis monastery, and hands-on sailing between islands. Share authentic maritime life with 11 fellow passengers.

    Duration 10 days
    DestinationsSantorini, Oia, Ios, Amorgos, Katapola, Koufonisia, Iraklia, Schoinousa, Naxos, SyrosSee all destinations
    Age Range Ages 15+
    OperatorIntrepid Travel

    From

    US$2,555
    +$128 local payments
    View tour
  2. Sailing Greece - Santorini to SantoriniMap of Sailing Greece - Santorini to Santorini
    Sailing

    The 57-ft yacht glides through Aegean waters, visiting eight distinct islands over 10 days. Highlights include snorkeling in secluded coves, Homer's tomb on Ios, and Venetian ruins in Paros. From Mykonos' iconic windmills to Sifnos' ceramic workshops, this voyage showcases authentic Greek maritime life at approx. $230 per day.

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

    From $2,599

    50% Off
    US$1,300
    You save $1,300
    View tour
  3. Sail Greece: Santorini to MykonosMap of Sail Greece: Santorini to Mykonos
    Sailing

    The bluest Aegean waters carry you from Santorini to Mykonos on a sleek 54ft yacht. Sailing skills improve between Ios's pristine Manganari Beach and Amorgos's rugged coastline. Traditional ports in Koufonisia and sunsets from Syros's hilltop Ano Syros village highlight the journey.

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

    From

    50% Off
    US$1,715
    +$116 local payments
    View tour
  4. 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

    50% Off
    US$4,903
    +$425 upfront costs
    View tour
  5. Journeys: Discover the Greek Islands National GeographicMap of Journeys: Discover the Greek Islands National Geographic
    Sailing

    Ferries connect the Aegean Islands, with nights in Mykonos and Naxos before reaching Santorini's dramatic cliffs. The marble Portara gateway stands as remnants of Apollo's 6th-century BC temple, while Little Venice in Mykonos features famous windmills and the Church of Panagia Paraportiani.

    Duration 8 days
    DestinationsAthens, Mykonos, Delos, Naxos, Santorini, Palea Kameni Island, Nea Kameni Island, Oia
    Age Range Ages 12+
    OperatorNational Geographic Expeditions with G Adventures

    From $3,649

    25% Off
    US$2,737
    You save $912
    View tour
  6. Northern Cyclades Cruise 2026Map of Northern Cyclades Cruise 2026
    Sailing

    A comfortable group cruise takes you through the heart of the Cyclades, visiting the UNESCO-listed Delos archaeological sanctuary and stopping at hidden spots like the Cave of Katafyki in Kythnos and Kolona Beach's striking sand strip. From Piraeus Port, the route goes through crystal-clear Aegean waters to Amorgos, where the cliff-hanging 11th-century Monastery of Panagia Hozoviotissa hangs above the sea. Swimming near the Olympia shipwreck in Liveros Bay offers a unique underwater view. This 8-day sailing adventure welcomes families and travelers ages 8+, with stops in medieval Syros' Ermoupoli, the glamorous shores of Mykonos, and Naxos' hillside kastro. Pottery workshops in Kea and thermal springs in Loutra add variety to the journey.

    Duration 8 days
    DestinationsPiraeus, Kea, Ioulida, Syros, Ermoupouli, Galissas, Delos, Mykonos, Amorgos, ChoraSee all destinations
    Age Range Ages 8+
    OperatorRunning On Waves

    From

    25% Off
    US$4,903
    +$425 upfront costs
    View tour
  7. Sailing Greece - Santorini to MykonosMap of Sailing Greece - Santorini to Mykonos
    Sailing

    The 57-ft luxury yacht sails for 8 days between Santorini and Mykonos. Folegandros offers cliff-side exploration, while Sifnos showcases ceramic workshops. Hidden coves provide perfect snorkeling spots, with beach time at Magganari on Ios and stunning sunsets over Hora's whitewashed buildings.

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

    From $1,849

    35% Off
    US$1,202
    You save $647
    View tour
  8. Sailing Greece - Mykonos to MykonosMap of Sailing Greece - Mykonos to Mykonos
    Sailing

    A state-of-the-art 57-ft yacht takes you through the Aegean's azure waters, from Mykonos' Little Venice to Folegandros' clifftop villages. The route passes through Santorini's volcanic caldera, with stops at Ios' Magganari Beach and Naxos' ancient Temple of Dimitra.

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

    From $2,549

    40% Off
    US$1,529
    You save $1,020
    View tour
  9. Sail Greece: Mykonos to SantoriniMap of Sail Greece: Mykonos to Santorini
    Sailing

    A modern yacht carries travelers from Mykonos's Little Venice to Thirasia's volcanic shores. The route includes hands-on sailing through the Small Cyclades, stops at Amorgos's ancient port of Katapola, and visits to Ios's protected Kolitzani Beach. The trip balances sailing adventures with island exploration.

    Duration 8 days
    DestinationsMykonos, Syros, Naxos, Amorgos, Ios, Santorini
    Age Range Ages 15+
    OperatorIntrepid Travel

    From

    40% Off
    US$1,795
    +$116 local payments
    View tour
  10. Sail Greece: Skiathos, Skopelos & AlonnisosMap of Sail Greece: Skiathos, Skopelos & Alonnisos
    Sailing

    A 44-46ft private catamaran sails through the Sporades archipelago, visiting Skiathos, Skopelos, and Alonnisos over 8 days with an expert skipper. The iconic Agios Ioannis church featured in Mamma Mia sits along the route, then stand-up paddleboarding happens in the National Marine Park of Sporades where Mediterranean monk seals and dolphins swim alongside you. Remote Kyra Panagia island, inhabited only by monks, offers complete disconnection from the world. Anchoring in Planitis Bay provides total isolation and quiet.

    Duration 8 days
    DestinationsSkiathos, Skopelos, Alonnisos
    Age Range Ages 15+
    OperatorIntrepid Travel

    From

    40% Off
    US$3,520
    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
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