
Greek Islands Sailboat Tours & Trips
Explore a wide diversity of tours through Greek Islands. We have 27 tours that vary from 3 days to 15 days. With the greatest number of departures in September, this is also the most popular time of the year.

Greek Islands Sailboat Tours & Trips
Sailing Greece - Mykonos to Santorini
"Highly recommend doing a Sail Greece. It was a week packed full of activities, Islands..."
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 informationBig Fat Greek Holiday - Sailing Greece
"Such a lovely experience thanks to the guide David who was amazing!"
Instant BookingJust $99 deposit- destinations
- Lefkada, Ithaca, Kefallonia, Meganisi, Kalamos, Zakynthos+4 more
- starts/ ends in
- Lefkada / Lefkada
- age range
- 18 to 60 year olds
- accommodation
- Berth / Cabin
- transport
- Boat
- Islands
- Greek Islands, Ionian Islands+1 more
- Travel style
- Boat, Adventure, Beach, Sailboat+1 more
- operator
- Yacht Batch
-24%- Duration
- 7 days
- Price per day
- $163
- From $1,506
- US$1,140
- +$129 local payments
You save $3671 Jun 20198 spaces left8 Jun 20198 spaces leftMore informationSantorini to Mykonos - Sailing Greece
"Thanks guy for the unique experience!"
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 $1,506
- US$1,140
- +$129 local payments
You save $3671 Jun 20198 spaces left8 Jun 20198 spaces leftMore informationGreece Ionian 7 Days Sailing (Premier Plus)
7 day sailing tour through Gouvia Marina, Kassiopi, Sivota and 4 other destinations in Greece
Just $99 deposit- destinations
- Gouvia Marina, Kassiopi, Sivota, Parga, Antipaxos, Gaios, Lakka+6 more
- starts/ ends in
- Gouvia Marina / Gouvia Marina
- age range
- 18 to 35 year olds
- accommodation
- Berth / Cabin
- transport
- Boat
- Regions
- Greek Islands, Ionian Islands, Northern Greece+2 more
- Travel style
- Sailboat, Discovery
- operator
- MedSailors
-8%- Duration
- 7 days
- Price per day
- $127
- From $969
- US$892
- +$98 local payments
You save $768 Jun 20196 spaces left15 Jun 20193 spaces leftMore informationMed Sailing in Greece
8 day sailing tour through Lefkada, Meganisi, Ithaca and 4 other destinations in Greece
Instant BookingJust $99 deposit- destinations
- Lefkada, Meganisi, Ithaca, Sami, Fiskardo, Lefkas, Kalamos+5 more
- starts/ ends in
- Lefkada / Lefkada
- age range
- 18 to 80 year olds
- accommodation
- Berth / Cabin
- transport
- Boat
- Islands
- Greek Islands, Ionian Islands+1 more
- Travel style
- Sailboat
- operator
- Med Sailing Holidays
- Duration
- 8 days
- Price per day
- $171
- From
- US$1,369
You save $428 Jun 20194 spaces left15 Jun 20194 spaces leftMore informationGreece Ionian 7 Days Sailing (Catamarans)
7 day sailing tour through Gouvia Marina, Kassiopi, Sivota and 4 other destinations in Greece
Just $99 deposit- destinations
- Gouvia Marina, Kassiopi, Sivota, Parga, Antipaxos, Gaios, Lakka+6 more
- starts/ ends in
- Gouvia Marina / Gouvia Marina
- age range
- 18 to 35 year olds
- accommodation
- Berth / Cabin
- transport
- Boat
- Regions
- Greek Islands, Ionian Islands, Northern Greece+2 more
- Travel style
- Sailboat, Discovery
- operator
- MedSailors
-8%- Duration
- 7 days
- Price per day
- $143
- From $1,085
- US$1,000
- +$111 local payments
You save $858 Jun 20192 spaces left22 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$3,277
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$1,084
You save $3313 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 informationCorfu Flexi 7 day Sailing trip
7 day sailing tour through Corfu, Sivota, Paxos, Lefkas, Preveza in Greece
Just $99 deposit- destinations
- Corfu, Sivota, Paxos, Lefkas, Preveza+2 more
- starts/ ends in
- Corfu / Corfu
- age range
- 18 to 65 year olds
- accommodation
- Berth / Cabin
- Islands
- Greek Islands, Ionian Islands+1 more
- Travel style
- Adventure, Sailboat, Discovery+1 more
- operator
- YachtHop
- Duration
- 7 days
- Price per day
- $280
- From
- US$1,957
You save $6113 Apr 20196 spaces left20 Apr 20196 spaces leftMore informationSailing and Climbing in The Greek Islands
8 day sailing tour through Kos, Kalymnos, Astypalaia, Nisyros Island in Greece
Just $99 deposit- destinations
- Kos, Kalymnos, Astypalaia, Nisyros Island+2 more
- starts/ ends in
- Kos / Kalymnos
- age range
- 18 to 99 year olds
- transport
- Boat
- Islands
- Greek Islands, Dodecanese Islands, Aegean Islands+2 more
- Travel style
- Adventure, Sailboat, Hiking & Trekking+1 more
- operator
- Rug and Rock Adventures
- Duration
- 8 days
- Price per day
- $294
- From
- US$2,355
You save $7313 Apr 20198 spaces left8 Jun 20198 spaces leftMore information
Greek Islands 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"Such a lovely experience thanks to the guide David who was amazing!"
Big Fat Greek Holiday - Sailing Greece"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