Switch to the app

The fastest, easiest way to book tours

tourradar.com
Sailing Tours & Trips in Aegean Islands
Sailing Tours & Trips in Aegean Islands

Sailing Tours & Trips in Aegean Islands

4.6 stars on(8,813 reviews)
Select Date

Select departure month

2025

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

2026

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
1 Adult2 Adults, 1 Child2 Children

Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0
  • Choose from 21 Aegean Islands tours
  • 150+ verified reviews from TourRadar travelers
  • 24/7 customer support
  1. 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 $3,339

    25% Off
    NZ$2,504
    You save $835
    View tour
  2. 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 $2,359

    25% Off
    NZ$1,769
    You save $590
    View tour
  3. 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, Ios, Amorgos, Cyclades, Naxos, Syros, Mykonos, Sifnos, Folegandros
    Age Range Ages 15+
    OperatorIntrepid Travel

    From $3,760

    20% Off
    NZ$3,008
    +$217 local payments
    You save $752
    View tour
  4. 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, Naxos, Syros, Cyclades, Amorgos, Ios, Santorini
    Age Range Ages 15+
    OperatorIntrepid Travel

    From $2,845

    20% Off
    NZ$2,276
    +$198 local payments
    You save $569
    View tour
  5. Sailing & Hiking the Dodecanese IslandsMap of Sailing & Hiking the Dodecanese Islands
    Sailing

    The Hanse 370 yacht Armida takes you through secluded bays and pristine coves of the Aegean. The 120-nautical-mile journey from Kos to Rhodes includes stops at Gyali's crystal waters and Symi's historic harbor. Professional crew guides you through the Dodecanese archipelago.

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

    From

    20% Off
    NZ$7,212
    View tour
  6. 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

    20% Off
    NZ$8,476
    +$780 upfront costs
    View tour
  7. Sailing the Greek MediterraneanMap of Sailing the Greek Mediterranean
    Sailing

    The crystal waters of the Aegean stretch from Lavrion to Hydra and Spetses. Master sailing basics while visiting car-free islands and hidden bays. The trip includes professional instruction, yacht accommodation, and personalized route planning for optimal conditions.

    Duration 8 days
    DestinationsLavrion, Kea, Serifos, Milos, Sifnos
    Age Range Ages 20-40
    Operated in English, German
    Operatorsailwithus

    From

    20% Off
    NZ$1,521
    +$494 local payments
    View tour
  8. Mykonos Party at SeaMap of Mykonos Party at Sea
    Sailing

    From Laurium port, the Aegean Islands await, with stops at Makronisos for swimming and Vourkari village exploration. Lively nights unfold in Ermoupoly and Mykonos town. The journey includes 7 nights on gulet with daily brunches for ages 18-35.

    Duration 8 days
    DestinationsLavrion, Kea, Kythnos, Mykonos
    Age Range Ages 18-35
    OperatorEncounters Travel

    From

    20% Off
    NZ$1,420
    View tour
  9. Southern Cyclades Cruise 2025Map of Southern Cyclades Cruise 2025
    Sailing

    Waters stretch from Piraeus to Milos' volcanic coastline and Folegandros' cliff-top towns. Santorini's caldera reveals itself by day, with sunset views from Fira at 220 meters above sea level. Modern amenities complement outside access in each cabin.

    Duration 8 days
    DestinationsAthens, Milos, Folegandros, Santorini, Astypalaia, Ios, Serifos
    Age Range Ages 8+
    Operated in English, German
    OperatorRunning On Waves

    From

    20% Off
    NZ$6,520
    +$780 upfront costs
    View tour
  10. 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 $3,139

    40% Off
    NZ$1,883
    You save $1,256
    View tour
Want to explore even more?

Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0

Select departure month

2025

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

2026

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