Cyclades Greece Sailboat Tours & Trips
Explore a wide diversity of tours through Cyclades Greece. We have 18 tours that vary from 4 days to 15 days. With the greatest number of departures in May, this is also the most popular time of the year.
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Cyclades Greece Sailboat Tours & Trips
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Sailing Greece - Mykonos to Santorini
"Great tour, would do it all over again."
Instant BookingJust $99 deposit- destinations
- Mykonos, Naxos, Paros, Antiparos, Ios, Sifnos, Folegandros, Santorini+5 more
- starts/ ends in
- Mykonos / Santorini
- age range
- 12 to 70 year olds
- accommodation
- Berth / Cabin
- transport
- Ship, Boat
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Travel style
- Sailboat, Discovery
- operator
- G Adventures
-20%- Duration
- 8 days
- Price per day
- $145
- From $1,449
- US$1,159
Sign up to save $33628 Apr 20192 spaces left5 May 20194 spaces leftMore informationSailing Greece - Santorini to Mykonos
"Great country, excellent tour leader but very poor comfort...so think about it twice..."
Instant BookingJust $99 deposit- destinations
- Santorini, Folegandros, Sifnos, Ios, Antiparos, Paros, Naxos, Mykonos+7 more
- starts/ ends in
- Santorini / Mykonos
- age range
- 12 to 70 year olds
- accommodation
- Berth / Cabin
- transport
- Ship, Boat
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Travel style
- Sailboat, Discovery
- operator
- G Adventures
-20%- Duration
- 8 days
- Price per day
- $143
- From $1,429
- US$1,143
Sign up to save $3321 May 20198 spaces left5 May 20196 spaces leftMore informationSail Greece: Mykonos to Santorini
"Fantastic trip! Highly recommend"
Instant BookingJust $99 deposit- 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
- $185
- From
- US$1,482
- +$113 local payments
You save $3818 May 20197 spaces left1 Jun 20197 spaces leftMore informationHidden Cyclades Sailing Adventure
10 day sailing tour through Athens, Serifos, Sifnos and 4 other destinations in Greece
Instant BookingJust $99 deposit- destinations
- Athens, Serifos, Sifnos, Kimolos, Polyaigos, Kythnos, Kea+5 more
- starts/ ends in
- Athens / Athens
- age range
- 15 to 99 year olds
- accommodation
- Berth / Cabin
- transport
- Ship
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Travel style
- Adventure, Sailboat, Discovery+1 more
- operator
- Intrepid Travel
- Duration
- 10 days
- Price per day
- $185
- From
- US$1,848
- +$125 local payments
You save $4711 May 20192 spaces left21 May 20197 spaces leftMore informationSantorini to Mykonos - Sailing Greece
"A really great experience with top service - 100% recommendation! brgds MS"
Instant BookingJust $99 deposit- 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
-24%- Duration
- 7 days
- Price per day
- $163
- From $1,508
- US$1,141
- +$129 local payments
You save $3671 Jun 20198 spaces left8 Jun 20198 spaces leftMore informationPride Sailing in Greece (Mykonos)
8 day gay travel tour through Mykonos, Paros, Ios, Santorini, Naxos in Greece
Instant BookingJust $99 deposit- destinations
- Mykonos, Paros, Ios, Santorini, Naxos+2 more
- starts/ ends in
- Mykonos / Mykonos
- age range
- 18 to 55 year olds
- accommodation
- Berth / Cabin
- transport
- Boat
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Travel style
- Sailboat, Sailing
- operator
- Med Sailing Holidays
- Duration
- 8 days
- Price per day
- $410
- From
- US$3,278
You save $10117 Aug 20196 spaces left24 Aug 20195 spaces leftMore informationSailing & Hiking Explore Cyclades Greece
"Sailing the Greek Islands was wonderful. The small group (we had 8) experience was..."
Instant BookingJust $99 deposit- 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+1 more
- operator
- Personality Journeys Greece
- Duration
- 8 days
- Price per day
- $135
- From
- US$1,083
You save $3413 Apr 201910 spaces left4 May 201910 spaces leftMore informationAegean Sea Sail and Hike Tour
9 day sailing tour through Athens, Serifos, Milos and 3 other destinations in Greece
Just $99 deposit- destinations
- Athens, Serifos, Milos, Sifnos, Kythnos, Sounio+4 more
- starts/ ends in
- Athens / Athens
- age range
- 15 to 80 year olds
- transport
- Boat
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Travel style
- Adventure, Yoga, Sailboat, Hiking & Trekking+1 more
- operator
- Aegean Outdoors
- Duration
- 9 days
- Price per day
- $671
- From
- US$6,037
You save $18718 May 20198 spaces left25 May 20198 spaces leftMore informationMykonos - Paros 6 nights - 7 Days Tour.
"A glorious week sailing between beautiful unspoilt islands, staying in small quiet..."
Instant BookingJust $99 deposit- destinations
- Mykonos, Delos, Naxos, Iraklia, Koufonissia, Antiparos, Paros+4 more
- starts/ ends in
- Mykonos / Paros
- age range
- 12 to 80 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
- Blue Aegean Sailing
- Duration
- 7 days
- Price per day
- $173
- From
- US$1,210
- +$1,219 local payments
You save $375 May 20196 spaces leftMore informationParos Flexi 4 day Sailing trip
"We had a lovely time and Petros made everything extra special. His knowledge of the..."
Just $99 deposit- 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
- $379
- From
- US$1,518
You save $476 Apr 20196 spaces left13 Apr 20196 spaces leftMore informationSailing Adventure Cyclades Long Weekend
5 day sailing tour through Athens, Kea, Kythnos, Loutra, Serifos in Greece
Instant BookingJust $99 deposit- 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+1 more
- operator
- Personality Journeys Greece
- Duration
- 5 days
- Price per day
- $126
- From
- US$632
You save $2019 Apr 20196 spaces left24 Apr 201910 spaces leftMore informationNaxos Flexi 5 day Sailing trip
5 day sailing tour through Naxos, Mykonos, Paros, Ios in Greece
Just $99 deposit- 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
- $304
- From
- US$1,518
You save $4728 Mar 20198 spaces left4 Apr 20198 spaces leftMore informationSailing Greece - Santorini to Santorini
"The group dynamic was terrible, and the guide lacked the leadership/people skills..."
Instant BookingJust $99 deposit- destinations
- Santorini, Ios, Naxos, Mykonos, Syros, Paros, Sifnos, Folegandros+5 more
- starts/ ends in
- Santorini / Santorini
- age range
- 12 to 70 year olds
- accommodation
- Berth / Cabin
- transport
- Ship, Boat
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Travel style
- Sailboat, Discovery
- operator
- G Adventures
-20%- Duration
- 10 days
- Price per day
- $148
- From $1,849
- US$1,479
Sign up to save $4292 May 20198 spaces left12 May 20195 spaces leftMore informationSailing Greece - Mykonos to Mykonos
10 day sailing tour through Mykonos, Syros, Paros and 4 other destinations in Greece
Instant BookingJust $99 deposit- destinations
- Mykonos, Syros, Paros, Folegandros, Santorini, Ios, Naxos+4 more
- starts/ ends in
- Mykonos / Mykonos
- age range
- 12 to 70 year olds
- accommodation
- Berth / Cabin
- transport
- Ship, Boat
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Travel style
- Sailboat, Discovery
- operator
- G Adventures
- Duration
- 10 days
- Price per day
- $185
- From
- US$1,849
Sign up to save $748 May 20195 spaces left18 May 20196 spaces leftMore informationSailing Greece - Santorini to Athens
"Incredible trip. Skipper was fantastic, knowledgeable, and looked after our every..."
Instant BookingJust $99 deposit- destinations
- Santorini, Folegandros, Ios, Kimolos, Sifnos, Antiparos, Paros, Naxos, Mykonos, Syros, Kythnos, Kea, Hydra, Aegina, Athens+14 more
- starts/ ends in
- Santorini / Athens
- age range
- 12 to 70 year olds
- accommodation
- Berth / Cabin
- transport
- Ship, Boat
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Travel style
- Adventure, Sailboat, Discovery+1 more
- operator
- G Adventures
-20%- Duration
- 15 days
- Price per day
- $142
- From $2,659
- US$2,127
Sign up to save $61712 May 20197 spaces left15 May 20196 spaces leftMore information
Cyclades Greece Sailboat Tour Reviews
"It was a very good experience to visit the islands of Greece by boat. The team was..."
Sailing Greece - Mykonos to Santorini"Great country, excellent tour leader but very poor comfort...so think about it twice..."
Sailing Greece - Santorini to Mykonos"Fantastic trip! Highly recommend"
Sail Greece: Mykonos to Santorini"Great overall experience! still in touch with the group i met there. we will repeat..."
Santorini to Mykonos - Sailing Greece"Sailing the Greek Islands was wonderful. The small group (we had 8) experience was..."
Sailing & Hiking Explore Cyclades Greece"A glorious week sailing between beautiful unspoilt islands, staying in small quiet..."
Mykonos - Paros 6 nights - 7 Days Tour.