Sailing Tours & Trips in Cyclades
Get ready to hoist the sails on a sailing tour of Cyclades. Whether you are island hopping or gliding along the coast, with 32 sailing holidays lasting from 4 days up to 15 days, we have made finding the right sailboat tour a breeze!
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32 Sailing trips in Cyclades with 624 reviews
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Greek Island Hopping
"This was my first Contiki and it was one of the greatest experiences I've ever had...."
Instant BookingFlexible Payments- destinations
- Athens, Mykonos, Santorini, Ios+2 more
- starts/ ends in
- Athens / Athens
- age range
- 18 to 35 year olds
- accommodation
- Hotel
- transport
- Train & Rail
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Travel style
- Boat
- operator
- Contiki
-20%- Duration
- 13 days
- Price per day
- $153
- From $2,482
- US$1,986
Sign up to save $54623 Aug 20191 space left26 Aug 20191 space leftMore informationSailing Greece - Mykonos to Santorini
"Highly recommend doing a Sail Greece. It was a week packed full of activities, Islands..."
Instant BookingFlexible Payments- destinations
- Mykonos, Naxos, Paros, Antiparos, Ios, Sifnos, Folegandros, Santorini+5 more
- starts/ ends in
- Mykonos / Santorini
- age range
- 16 to 70 year olds
- accommodation
- Berth / Cabin
- transport
- Ship, Boat
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Travel style
- Family, Sailboat, Discovery+1 more
- operator
- G Adventures
-20%- Duration
- 8 days
- Price per day
- $160
- From $1,599
- US$1,279
Sign up to save $35225 Aug 20191 space left15 Sep 20192 spaces leftMore informationSailing Greece - Santorini to Santorini
"The group dynamic was terrible, and the guide lacked the leadership/people skills..."
Instant BookingFlexible Payments- destinations
- Santorini, Ios, Naxos, Mykonos, Syros, Paros, Sifnos, Folegandros+5 more
- starts/ ends in
- Santorini / Santorini
- age range
- 16 to 70 year olds
- accommodation
- Berth / Cabin
- transport
- Ship, Boat
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Travel style
- Family, Sailboat, Discovery+1 more
- operator
- G Adventures
-30%- Duration
- 10 days
- Price per day
- $136
- From $1,939
- US$1,357
Sign up to save $61620 Aug 20192 spaces left30 Aug 20195 spaces leftMore informationSail the Greek Cyclades
"This was an excellent tour! The Aegean Sea and Greek Islands are beautiful. We went..."
Instant BookingFlexible Payments- destinations
- Athens, Kea, Kythnos, Loutra, Serifos+2 more
- starts/ ends in
- Athens / Athens
- age range
- 15 to 99 year olds
- accommodation
- Berth / Cabin
- transport
- Boat, Mini-coach
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Travel style
- Adventure, Sailboat, Discovery, Hiking & Trekking+2 more
- operator
- Personality Journeys Greece
- Duration
- 5 days
- Price per day
- $149
- From
- US$743
You save: $239 Oct 20194 spaces left19 Oct 20195 spaces leftMore informationSailing & Hiking Explore Cyclades Greece
"Sailing the Greek Islands was wonderful. The small group (we had 8) experience was..."
Instant BookingFlexible Payments- destinations
- Lavrion, Kea, Kythnos, Syros, Serifos+2 more
- starts/ ends in
- Lavrion / Lavrion
- age range
- 15 to 99 year olds
- accommodation
- Berth / Cabin
- transport
- Boat
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Travel style
- Adventure, Sailboat, Discovery, Hiking & Trekking+2 more
- operator
- Personality Journeys Greece
- Duration
- 8 days
- Price per day
- $147
- From
- US$1,179
You save: $3621 Sep 20191 space left12 Oct 201910 spaces leftMore informationGreece Sailing Adventure: Cyclades Islands
"My daughter and I just got back from sailing around 9 greek islands starting in Santorini..."
Instant BookingFlexible Payments- destinations
- Santorini, Ios, Amorgos, Cyclades, Naxos, Mykonos, Sifnos, Folegandros+6 more
- starts/ ends in
- Santorini / Santorini
- age range
- 15 to 99 year olds
- accommodation
- Berth / Cabin
- transport
- Boat
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Travel style
- Motor boat, In-depth Cultural+1 more
- operator
- Intrepid Travel
- Duration
- 10 days
- Price per day
- $185
- From
- US$1,848
- +$122 local payments
You save: $478 Sep 20191 space left18 Sep 20191 space leftMore informationSail Greece: Mykonos to Santorini
"Fantastic trip! Highly recommend"
Instant BookingFlexible Payments- destinations
- Mykonos, Naxos, Cyclades, Amorgos, Ios, Santorini+4 more
- starts/ ends in
- Mykonos / Santorini
- age range
- 15 to 99 year olds
- accommodation
- Berth / Cabin
- transport
- Boat
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Travel style
- Motor boat, Sailboat, Discovery+1 more
- operator
- Intrepid Travel
- Duration
- 8 days
- Price per day
- $180
- From
- US$1,438
- +$111 local payments
You save: $3716 May 202010+ spaces left30 May 202010+ spaces leftMore informationSailing And Yoga in West Cyclades Greece
8 day sailing tour through Kea, Kythnos, Sifnos and 4 other destinations in Greece
Instant BookingFlexible Payments- destinations
- Kea, Kythnos, Sifnos, Kimolos, Serifos, Syros, Lavrion+4 more
- starts/ ends in
- Kea / Lavrion
- age range
- 18 to 70 year olds
- accommodation
- Berth / Cabin
- transport
- Boat
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Travel style
- Adventure, Beach
- operator
- Med Sun Yachts (PC)
- Duration
- 8 days
- Price per day
- $93
- From
- US$743
You save: $2324 Aug 20194 spaces left31 Aug 20195 spaces leftMore informationGreece Lightning
7 day sailing tour through Athens, Mykonos, Ios in Greece
Instant BookingFlexible Payments- destinations
- Athens, Mykonos, Ios
- starts/ ends in
- Athens / Athens
- age range
- 18 to 39 year olds
- accommodation
- Hostel, Hotel, Berth / Cabin+1 more
- transport
- Ferry
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Travel style
- Beach, Discovery
- operator
- Topdeck
- Duration
- 7 days
- Price per day
- $186
- From
- US$1,299
Sign up to save $3227 Aug 201910+ spaces leftMore informationSantorini to Mykonos - Sailing Greece
"Everything was well organized."
Flexible Payments- destinations
- Santorini, Ios, Naxos, Mykonos, Paros+2 more
- starts/ ends in
- Santorini / Santorini
- age range
- 18 to 60 year olds
- accommodation
- Berth / Cabin
- transport
- Boat
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Travel style
- Adventure, Sailboat, In-depth Cultural+1 more
- operator
- Yacht Batch
- Duration
- 7 days
- Price per day
- $194
- From
- US$1,361
- +$120 local payments
You save: $4224 Aug 20198 spaces left31 Aug 20198 spaces leftMore informationExplore Cyclades islands on board the MS Galileo
"We were a couple, took 1 cabin. It was unique and glorious vacation, I enjoy any..."
Flexible Payments- destinations
- Piraeus, Poros, Poliegos, Folegandros, Santorini, Antiparos, Paros, Delos, Mykonos, Syros, Kythnos+9 more
- starts/ ends in
- Piraeus / Piraeus
- age range
- 1 to 100 year olds
- accommodation
- Berth / Cabin, Houseboat
- transport
- Ship, Boat
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- operator
- Global Yacht Rentals
-22%- Duration
- 8 days
- Price per day
- $404
- From $4,165
- US$3,232
You save: $93323 Aug 201910+ spaces left30 Aug 201910+ spaces leftMore informationParos Flexi 4 day Sailing trip
"We had a lovely time and Petros made everything extra special. His knowledge of the..."
Flexible Payments- destinations
- Paros, Ios, Koufonissia, Naxos+2 more
- starts/ ends in
- Paros / Naxos
- age range
- 18 to 65 year olds
- accommodation
- Berth / Cabin
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Travel style
- Adventure, Sailboat, Discovery+1 more
- operator
- YachtHop
- Duration
- 4 days
- Price per day
- $371
- From
- US$1,485
You save: $4614 Sep 20196 spaces left21 Sep 20196 spaces leftMore informationGreece Cyclades Explorer: Superior Catamaran From Paros
7 day sailing tour through Paros, Antiparos, Ios and 5 other destinations in Greece
Flexible Payments- destinations
- Paros, Antiparos, Ios, Naxos, Mykonos, Syros, Kea, Athens+5 more
- starts/ ends in
- Paros / Athens
- age range
- 18 to 65 year olds
- accommodation
- Berth / Cabin
- transport
- Boat
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Travel style
- Sailboat, Discovery
- operator
- Yacht Getaways
-11%- Duration
- 7 days
- Price per day
- $143
- From $1,125
- US$1,004
- +$103 local payments
You save: $12130 May 20208 spaces left6 Jun 20208 spaces leftMore informationNaxos Flexi 5 day Sailing trip
5 day sailing tour through Naxos, Mykonos, Paros, Ios in Greece
Flexible Payments- destinations
- Naxos, Mykonos, Paros, Ios+1 more
- starts/ ends in
- Naxos / Ios
- age range
- 18 to 65 year olds
- accommodation
- Berth / Cabin
- transport
- Boat
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Travel style
- Adventure, Sailboat, Discovery+1 more
- operator
- YachtHop
- Duration
- 5 days
- Price per day
- $297
- From
- US$1,485
You save: $4626 Sep 20198 spaces left3 Oct 20198 spaces leftMore informationGreece Cyclades Explorer: Superior Catamaran From Athens
7 day sailing tour through Athens, Kea, Syros and 5 other destinations in Greece
Flexible Payments- destinations
- Athens, Kea, Syros, Mykonos, Naxos, Ios, Antiparos, Paros+5 more
- starts/ ends in
- Athens / Paros
- age range
- 18 to 65 year olds
- accommodation
- Berth / Cabin
- transport
- Boat
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Travel style
- Discovery
- operator
- Yacht Getaways
- Duration
- 7 days
- Price per day
- $157
- From
- US$1,097
- +$103 local payments
You save: $3430 May 20208 spaces left6 Jun 20208 spaces leftMore information
Cyclades Sailing Tour Reviews
"Greek Island Hopping was an amazing tour which I would not have enjoyed without the..."
Greek Island Hopping"It was a very good experience to visit the islands of Greece by boat. The team was..."
Sailing Greece - Mykonos to Santorini"Sailing the Greek Islands was an amazing experience. I had been to Greece several..."
Sailing Greece - Santorini to Santorini"Amazing week, the good weather helped, Alex was the best sort of captain, eager to..."
Sail the Greek Cyclades"Sailing the Greek Islands was wonderful. The small group (we had 8) experience was..."
Sailing & Hiking Explore Cyclades Greece"The trip was the best holiday I have ever done . Great skipper who made sure we all..."
Greece Sailing Adventure: Cyclades Islands