Sailing Tours & Trips in Mediterranean
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10 best Sailing Mediterranean tour packages
Compiled by

MelissaMediterranean travel expert at TourRadar
- Sailing Greece - Mykonos to Santorini
- Blue Escape in Turkey: 5 Days Sailing Tour from Gocek to Fethiye
- Greece Sailing Adventure: Cyclades Islands
- Sail Greece: Mykonos to Santorini
- Croatia Island Sail (Premium)
- Croatia Island Sail
- Croatia Sailing Adventure - 8 days
- Sailing Greece - Santorini to Santorini
- Sailing Greece - Mykonos to Mykonos
- Sailing Greece - Santorini to Mykonos
Sailing Greece - Mykonos to Santorini
50 Reviews by TourRadar travelers“Best experience of my life. I would recommend this trip to anyone and everyone.”
Rebekah, traveled in September
A 57-foot yacht provides the perfect platform for Mediterranean navigation between Mykonos and Santorini. The skipper shares sailing expertise while visiting ancient temples, Venetian ruins, and traditional villages.
Duration 8 days Destinations Mykonos, Naxos, Paros, Antiparos, Ios, Sifnos, Folegandros, Santorini Age Range 18 to 99 year olds Operator G Adventures From
- NZ$2,039
Blue Escape in Turkey: 5 Days Sailing Tour from Gocek to Fethiye
2 Reviews by TourRadar travelers“Great experience lovely food lovely people.”
Eva, traveled in August
Crystal-clear Mediterranean waters stretch from Gocek to Fethiye, offering hidden coves and ancient ruins. The expert crew guides swimming at Tershane Island and tours of historic Gemiler Island. Comfortable berth cabin accommodation provides perfect blend of relaxation and adventure.
Duration 5 days Destinations Gocek, Fethiye Age Range 8 to 80 year olds Operator Tour Altinkum Travel From $1,285
10% Off- NZ$1,157You save $128
Greece Sailing Adventure: Cyclades Islands
18 Reviews by TourRadar travelers“This was on my bucket list and it has exceeded my expectations, loved every minute of it.”
Deborah, traveled in June
A 54-56ft yacht glides through Mediterranean waters, revealing hidden coves and vibrant harbors. Routes stretch from Santorini's caldera to Mykonos' coastline, featuring swim stops at secluded beaches like Paradisi and Gaidharos Bay.
Duration 10 days Destinations Santorini, Ios, Amorgos, Cyclades, Naxos, Syros, Mykonos, Sifnos, Folegandros Age Range 15 to 99 year olds Operator Intrepid Travel From $3,775
25% Off- NZ$2,831+$211 local paymentsYou save $944
Sail Greece: Mykonos to Santorini
14 Reviews by TourRadar travelers“I would definitely do another sailing trip with Intrepid especially if Rita was at the helm!”
Tracy, traveled in May
Crystal waters carry the 54-56ft yacht from Mykonos to Santorini. The route includes secluded Gaidharos bay, traditional fishing villages in Small Cyclades, and iconic ports like Katapola in Amorgos.
Duration 8 days Destinations Mykonos, Naxos, Syros, Cyclades, Amorgos, Ios, Santorini Age Range 15 to 99 year olds Operator Intrepid Travel From $2,730
20% Off- NZ$2,184+$191 local paymentsYou save $546
Ancient harbors and historic walls connect Split to Dubrovnik across the Mediterranean. The route features Hvar's Spanish Fortress, Korčula's Venetian architecture, and Trstenik's wineries. Seven nights aboard with ensuite cabins and expert crew.
Duration 8 days Destinations Split, Hvar Island, Korcula Island, Dubrovnik, Trstenik, Makarska Age Range 18 to 35 year olds Operator Contiki From $2,475
13% Off- NZ$2,150You save $325
Croatia Sailing Adventure - 8 days
1 Review by TourRadar travelers“Amazing trip! Beautiful places and great crew.”
Anna, traveled in August
Split to Dubrovnik reveals Mediterranean treasures aboard a traditional ship. Ports of call include Hvar's jet-set harbor, Mljet's emerald lakes, and Korcula's medieval streets, with daily swim stops and 3-course lunches.
Duration 8 days Destinations Split, Stari Grad, Hvar Island, Mljet Island, Dubrovnik, Korcula Island, Makarska, Omis Age Range 18 to 35 year olds Operator On The Go Tours From $2,365
35% Off- NZ$1,537You save $827
Sailing Greece - Santorini to Santorini
30 Reviews by TourRadar travelers“Best holiday of my life. Nick really gave us a great love for sailing.”
Brian, traveled in December
A 57-foot yacht provides intimate Mediterranean adventures through crystal-clear waters and ancient harbors. The route includes Magganari Beach, Homer's tomb on Ios, and Mykonos' Little Venice, perfect for groups of 8.
Duration 10 days Destinations Santorini, Ios, Naxos, Mykonos, Syros, Paros, Sifnos, Folegandros Age Range 16 to 70 year olds Operator G Adventures From $3,619
17% Off- NZ$3,004You save $615
Sailing Greece - Mykonos to Mykonos
44 Reviews by TourRadar travelers“Very respectful, knowledgeable and helpful. Was a pleasure traveling under his guidance.”
Laura, traveled in September
The 56-ft yacht sails Cyclades waters from Mykonos' windmills to Santorini's caldera. The voyage reveals hidden coves near Folegandros and ancient ruins in Paros, combining nautical skills with cultural discoveries.
Duration 10 days Destinations Mykonos, Syros, Paros, Folegandros, Santorini, Ios, Naxos Age Range 16 to 70 year olds Operator G Adventures From $3,139
17% Off- NZ$2,605You save $533
Sailing Greece - Santorini to Mykonos
20 Reviews by TourRadar travelers“The sailing was an incredible experience and the best way to see Greece in my opinion. I also met some phenomenal people who have now become travel friends.”
Leigh, traveled in May
A 57-ft yacht charts course from Santorini to Mykonos across Mediterranean waters. Sailors develop skills while visiting Folegandros's secluded coves and Antiparos's caves, with evenings spent in charming Cyclades ports.
Duration 8 days Destinations Santorini, Folegandros, Sifnos, Ios, Antiparos, Paros, Naxos, Mykonos Age Range 16 to 70 year olds Operator G Adventures From
17% Off- NZ$2,039
What people love about Sailing Tours in Mediterranean
- Sailing Greece - Santorini to Santorini
An open mind and adventurous spirit are needed for this trip. If you have that and love the sea, this is a trip of a lifetime. This isn't a luxury sailing trip, this is real sailing, with cramped accommodations. But you get to be outside, sailing and exploring the islands, eating the best meals, and swimming in beautiful private bays.
- Greece Sailing Adventure: Cyclades Islands
captain of Intrepid Sailboat was incredible
- Sail Greece: Mykonos to Santorini
Fantastic trip! Highly recommend
What our customers ask about Sailing Tours & Trips in Mediterranean
What are the typical sailing routes and destinations covered?
Mediterranean sailing tours connect many of Europe's most well-known coastal destinations. Popular routes weave through the Greek Cyclades linking Santorini Mykonos and Naxos. The Dalmatian Coast route covers Croatian highlights from Split to Dubrovnik with stops in Hvar. Along Italy's coastline boats navigate the waters between Capri Positano and the Amalfi Coast. A typical Santorini departure might include time at Ios Island's Manganari beach a visit to Naxos's Temple of Dimitra and exploration of Mykonos's narrow streets. As one TourRadar traveler noted: "Each island offered something unique - from the beach clubs of Hvar to the historic walls of Dubrovnik."
What is the best time of year to book a Mediterranean sailing tour?
The Mediterranean's sailing calendar peaks from May through September. Each region offers distinct conditions. Croatia's Dalmatian Coast sees ideal conditions in July and August with warm water and reliable winds. The Greek Cyclades work best in June and September when the strong Meltemi winds ease. Water temperatures stay comfortable at 75-85°F (24-29°C) perfect for swimming at spots like Hvar's coves or Santorini's beaches. One TourRadar traveler shared their experience: "We got really lucky with weather so we were able to visit 7 islands in 7 days but it never felt rushed!"
What kind of activities are available during port stops?
Each stop brings opportunities for both cultural and water-based activities. Visitors can walk Dubrovnik's UNESCO-listed walls paddle through Hvar's hidden coves or taste wines in Croatian villages like Trstenik. Greek itineraries often include visits to Delos's ancient sites beach time on Naxos and evening views from Santorini. Most tours blend scheduled activities with free time. A TourRadar traveler confirms: "Highlights included our daily swims cycling around Mljet National Park and wine tasting in Trstenik."
How rough are the waters during Mediterranean sailing tours?
From May to September the Mediterranean tends to offer stable sailing conditions. Croatia's Adriatic waters usually stay calm while Greece's Cyclades can get choppy from Meltemi winds particularly in July and August. Modern boats come equipped with stabilization systems and experienced captains plan routes around weather patterns. According to one TourRadar traveler: "We had perfect sailing conditions with calm mornings for swimming and afternoon breezes for sailing between islands like Mykonos and Ios."
What kind of meals are provided on Mediterranean sailing tours?
Food service typically follows a split format. Most tours provide on-board breakfast and lunch through a shared food fund (usually 60-80 USD weekly per person). Dinners happen at local restaurants in port towns. Along the Amalfi Coast this might mean fresh seafood at Capri's Marina Piccola or pasta at family-run establishments. A G Adventures guest reported: "The food kitty system worked well for breakfasts and lunches while evenings gave us the chance to explore amazing local restaurants."
How many people typically share a sailing vessel on Mediterranean tours?
Boats usually carry between 8 and 12 passengers. G Adventures uses 16m yachts with 4 twin/double cabins and 3 shared bathrooms. Larger operators like Emerald Cruises run bigger vessels for more guests. The intimate setting allows for both social time and quiet moments as confirmed by a TourRadar traveler: "The group size was perfect we had an AWESOME group and there was plenty of space to socialize or find quiet time."