Unlock up to $350 offMember's Saving - Unlock up to $350in extra savings
Greek Islands Sailboat Tours & Trips
Explore a wide diversity of sailboat tours through Greek Islands. We have 17 tours that vary from 5 days to 15 days. With the greatest number of departures in September, this is also the most popular time of the year.
17 Greek Islands Sailboat trips with 102 reviews
Sailing Greece - Mykonos to Santorini
- destinations
- Mykonos, Naxos, Paros, Antiparos, Ios, Sifnos, Folegandros, Santorini
- Group size
- Max 8
- age range
- 16 to 70 year olds
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Travel style
- Family, Sailboat, Discovery+1 more
- operator
- G Adventures
Download brochure-15%- Tour length
- 8 days
- From $1,479
- US$1,257
Sign up to save $247
Sailing Greece - Santorini to Mykonos
- destinations
- Santorini, Folegandros, Sifnos, Ios, Antiparos, Paros, Naxos, Mykonos
- Group size
- Max 8
- age range
- 16 to 70 year olds
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Travel style
- Family, Sailboat, Discovery+1 more
- operator
- G Adventures
Download brochure-15%- Tour length
- 8 days
- From $1,479
- US$1,257
Sign up to save $247
Sail Greece: Mykonos to Santorini
- destinations
- Mykonos, Naxos, Cyclades, Amorgos, Ios, Santorini
- Group size
- Max 11
- age range
- 15 to 99 year olds
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Travel style
- Motor boat, Sailboat, Discovery+1 more
- operator
- Intrepid Travel
Download brochure- Tour length
- 8 days
- From
- US$1,520
- +$111 local payments
Sail Greece: Santorini to Mykonos
- destinations
- Santorini, Ios, Amorgos, Cyclades, Naxos, Mykonos
- Group size
- Max 11
- age range
- 15 to 99 year olds
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Travel style
- Sailboat, Discovery
- operator
- Intrepid Travel
Download brochure- Tour length
- 8 days
- From
- US$1,475
- +$111 local payments
Western Cyclades & Santorini Sailing Week
- destinations
- Paros, Ios, Santorini, Folegandros, Kimolos, Milos, Sifnos
- Group size
- Max 8
- age range
- 6 to 75 year olds
- Islands
- Greek Islands, Aegean Islands, Cyclades Greece+2 more
- Travel style
- Adventure, Sailboat, Discovery+1 more
- operator
- YachtHop
Download brochure- Tour length
- 7 days
- From
- US$1,732
You save: $32Med Sailing in Greece
- destinations
- Lefkada, Meganisi, Ithaca, Sami, Fiskardo, Lefkas, Kalamos
- Group size
- Max 8
- age range
- 18 to 80 year olds
- Islands
- Greek Islands, Ionian Islands+1 more
- Travel style
- Sailboat
- operator
- Med Sailing Holidays
Download brochure- Tour length
- 8 days
- From
- US$1,353
You save: $28Sail the Greek Cyclades
- destinations
- Athens, Kea, Kythnos, Loutra, Serifos
- Group size
- Max 10
- age range
- 15 to 99 year olds
- 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
Download brochure- Tour length
- 5 days
- From
- US$800
You save: $15Sailing & Hiking Explore Cyclades Greece
- destinations
- Lavrion, Kea, Kythnos, Syros, Serifos
- Group size
- Max 10
- age range
- 15 to 99 year olds
- 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
Download brochure- Tour length
- 8 days
- From
- US$1,302
You save: $24Small Cyclades & Mykonos Sailing Week
- destinations
- Paros, Antiparos, Iraklia, Koufonissia, Naxos, Mykonos
- Group size
- Max 8
- age range
- 6 to 75 year olds
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Travel style
- Adventure, Sailboat, Discovery+1 more
- operator
- YachtHop
Download brochure- Tour length
- 7 days
- From
- US$1,732
You save: $32Pride Sailing in Greece (Mykonos)
- destinations
- Mykonos, Paros, Ios, Santorini, Naxos
- Group size
- Max 8
- age range
- 18 to 55 year olds
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Travel style
- Sailboat, Sailing
- operator
- Med Sailing Holidays
Download brochure- Tour length
- 8 days
- From
- US$1,674
You save: $34Greece Ionian 7 Days Sailing (Catamarans)
- destinations
- Gouvia Marina, Kassiopi, Sivota, Parga, Antipaxos, Gaios, Lakka
- Group size
- Max 8
- age range
- 18 to 35 year olds
- Regions
- Greek Islands, Ionian Islands, Northern Greece+2 more
- Travel style
- Sailboat, Discovery
- operator
- MedSailors
Download brochure- Tour length
- 7 days
- From
- US$1,079
You save: $18Greece Ionian 7 Days Sailing (Premier)
- destinations
- Gouvia Marina, Kassiopi, Sivota, Parga, Antipaxos, Gaios, Lakka
- Group size
- Max 8
- age range
- 18 to 35 year olds
- Regions
- Greek Islands, Ionian Islands, Northern Greece+2 more
- Travel style
- Sailboat, Discovery
- operator
- MedSailors
Download brochure- Tour length
- 7 days
- From
- US$697
You save: $11Sailing Greece - Santorini to Santorini
- destinations
- Santorini, Ios, Naxos, Mykonos, Syros, Paros, Sifnos, Folegandros
- Group size
- Max 8
- age range
- 16 to 70 year olds
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Travel style
- Family, Sailboat, Discovery+1 more
- operator
- G Adventures
Download brochure-15%- Tour length
- 10 days
- From $1,849
- US$1,572
Sign up to save $309Sailing Greece - Mykonos to Mykonos
- destinations
- Mykonos, Syros, Paros, Folegandros, Santorini, Ios, Naxos
- Group size
- Max 8
- age range
- 16 to 70 year olds
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Travel style
- Family, Sailboat, Discovery+1 more
- operator
- G Adventures
Download brochure-15%- Tour length
- 10 days
- From $1,849
- US$1,572
Sign up to save $309Sailing Greece - Athens to Santorini
- destinations
- Athens, Aegina, Hydra, Kythnos, Kea, Syros, Mykonos, Naxos, Paros, Antiparos, Ios, Sifnos, Folegandros, Santorini+3 more
- Group size
- Max 8
- age range
- 16 to 70 year olds
- Regions
- Greek Islands, Aegean Islands, Cyclades Greece, Athens Santorini & Mykonos+3 more
- Travel style
- Family, Sailboat, Discovery+1 more
- operator
- G Adventures
Download brochure-15%- Tour length
- 15 days
- From $2,749
- US$2,337
Sign up to save $459
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"We had a lovely time and Petros made everything extra special. His knowledge of the..."
Western Cyclades & Santorini Sailing Week"Just absolutely unbelievable. Was the trip of a lifetime! I’ve never had such fun...."
Med Sailing in Greece"Amazing week, the good weather helped, Alex was the best sort of captain, eager to..."
Sail the Greek Cyclades