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

MelissaMediterranean travel expert at TourRadar
- Croatia Island Sail (8 Days)
- Sailing Greece - Santorini to Santorini
- Croatia Island Sail (Premium, 8 Days)
- Blue Escape in Turkey: 5 Days Sailing Tour from Gocek to Fethiye
- Greece Sailing Adventure: Cyclades Islands
- Sail Greece: Mykonos to Santorini
- Med Sailing in Croatia (from Split to Dubrovnik)
- Sailing Greece - Mykonos to Mykonos
- Sailing Croatia - Dubrovnik to Split
- Dalmatian Coast & Montenegro Sailing
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 $1,689
13% Off- US$1,467You save $222
Sailing Greece - Santorini to Santorini
30 Reviews by TourRadar travelers“The overall Adventure is totally worth it! Best part of this Tour was the outstanding leadership.”
Joan, traveled in May
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
13% Off- US$1,999
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 $728
10% Off- US$656You save $72
Greece Sailing Adventure: Cyclades Islands
18 Reviews by TourRadar travelers“Great way to see and experience the cyclades.”
Kornelia, traveled in September
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
10% Off- US$2,575+$119 local payments
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 $1,870
20% Off- US$1,496+$108 local paymentsYou save $374
Med Sailing in Croatia (from Split to Dubrovnik)
5 Reviews by TourRadar travelers“The boat was clean and nicely maintained, everything worked flawlessly.”
Marc, traveled in August
The Oceanis 48 yacht cuts through crystal-clear Adriatic waters. Highlights include Hvar's Hula Hula bar, Vis's Blue Caves, and Mljet's saltwater lakes with professional crew support.
Duration 8 days Destinations Split, Brac, Hvar Island, Vis, Korcula Island, Pomena, Mljet Island, Dubrovnik Age Range 18 to 80 year olds Operator Med Sailing Holidays From
20% Off- US$1,403
Sailing Greece - Mykonos to Mykonos
44 Reviews by TourRadar travelers“Great experience & perfect way to discover Islands of Greece. For sure, that was not my last sailing trip.”
Florían, traveled in May
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 $2,199
15% Off- US$1,869You save $329
Sailing Croatia - Dubrovnik to Split
22 Reviews by TourRadar travelers“I cannot think of a better way to see Croatia than by boat. It will be the highlight of my trip that hasn't ended yet.”
jan, traveled in June
A 17m yacht takes you through the Mediterranean's crystal waters to hidden coves around Mljet and Korčula. The route winds through Hvar's Pakleni Islands and Brač's Golden Horn beach, offering the perfect blend of adventure and relaxed Mediterranean sailing.
Duration 8 days Destinations Dubrovnik, Mljet Island, Korcula Island, Ploce, Hvar Island, Brac, Split Age Range 16 to 90 year olds Operator G Adventures From $1,949
40% Off- US$1,169You save $779
Dalmatian Coast & Montenegro Sailing
8 Reviews by TourRadar travelers“This is my 9th trip with gadventures and by far my favorite. Loved everything about it!”
Michelle, traveled in May
Crystal-clear waters guide the 16m yacht through hidden coves from Split to Dubrovnik. The route includes UNESCO-listed Kotor, Budva's beaches, and snorkeling in Bigovo's pristine waters. Fifteen days of sailing adventure connects 7 stunning ports.
Duration 15 days Destinations Split, Dubrovnik, Cavtat, Herceg Novi, Budva, Kotor, Tivat Age Range 16 to 90 year olds Operator G Adventures From $4,099
15% Off- US$3,484You save $614
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
My daughter and I just got back from sailing around 9 greek islands starting in Santorini n finishing there. The whole experience was sensational and I highly recommend it. The group got on really well we had a blast of a time. The Skipper Antonios was totally awesome in assuring our safety n explaining the different parts of the yatch n he gave us an opportunity to sail the boat I totally loved sailing the boat what an experience it was. Ill never forget the deep blue sea i was mesmorised by the colour. Antonios did great job at telling us about the islands n where to catch the bus if we wanted n guided us in best way possible. I loved everything about this holiday the only downfall was how tiny the cabins were pretty tight n squishy but we survived, we were there for 3wks but it felt like 3 months in a fantabulous way. Will definately do it again 1 day. Love love loved it. Cat and Bonnie xo
- Croatia Island Sail (Premium, 8 Days)
The itinerary for the trip was well set out it had a great balance of free time add ons provided through contiki and also enough of our own free time to do what we wanted ourselves. Demi our trip manager was amazing with such a positive attitude it made any anxious solo traveller feel right at home and welcomed into such a warm environment. Also on board the Dionis ship the crew were outstanding from the food to the bar it was impeccable and definitely great value for money.
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."