Sailing Tours & Trips in Mediterranean
Picture yourself sailing around the Mediterranean, taking in Croatia and Montenegro to name just two. Check out Diocletian's Palace in Split, Korčula (which claims to be Marco Polo's birthplace), and Montenegro's Bay of Kotor with its fjord-like vibes. Head to Podgorica, and enjoy Budva's beaches. So much to see, so little time!
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They can't do much better than our trip with Jiorgos
Greece Sailing Adventure: Cyclades IslandsWe had a great time meeting lots of new friends who all got on from many nationalities. At a restaurant one evening another group asked if we were a family which is how we ended up but without the disputes! Our skipper, Rita displayed wonderful leadership & sailing skills telling many interesting stories. Twice we has difficult dockings in strong crosswinds & other boats were messing it up big time but Rita nailed it both times & I was informed she received applause at Mykonos from the people on the dock. She also spent lot of time producing a video of our trip that she gave to us all. If your other CEO’s are half as good as her you have a very good team. Please note that you may only use my first name publically for this review, Peter!
Sail Greece: Santorini to MykonosSuperb trip with fun hilarious skipper. Good group. Lots of nice islands and swim stops. One day with strong winds. Strong winds can happen in cyclades July and August, so if you get seasick easily avoid these months. Of the year but definitely do the trip.
Sailing Greece - Santorini to Santorini
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10 best Sailing Mediterranean tour packages
Compiled by

MelissaMediterranean travel expert at TourRadar
- Greece Sailing Adventure: Cyclades Islands
- Sail Greece: Santorini to Mykonos
- Sailing Greece - Santorini to Santorini
- Sailing Greece - Mykonos to Mykonos
- 15-Day Private, Premium Tour of TURKEY | Gulet Sailing, Serenity & VIP Road Trip | May to October | by ANGELS VACATIONS
- Med Sailing in Croatia (from Split to Dubrovnik)
- Med Sailing in Croatia (from Dubrovnik to Split)
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Greece Sailing Adventure: Cyclades Islands
“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, Thera, Firostefani, Oia, Ios, Amorgos, Katapola, Koufonisia, Iraklia, SchoinousaSee all destinations Age Range Ages 15+ Operator Intrepid Travel From
- US$2,883+$124 local payments
Sail Greece: Santorini to Mykonos
“We had a great time meeting lots of new friends who all got on from many nationalities. Without the disputes!”
Peter, traveled in September
A 56ft yacht sails from Santorini's dramatic cliffs to Mykonos's bustling harbor. Professional skippers guide you through the region's most scenic routes, stopping at hidden coves and historic ports over 8 unforgettable days.
Duration 8 days Destinations Santorini, Ios, Amorgos, Koufonisia, Iraklia, Naxos, Syros, Mykonos Age Range Ages 15+ Operator Intrepid Travel From
- US$2,112+$113 local payments
Sailing Greece - Santorini to Santorini
“This was by far one of the top holiday experiences of my life. I will 100% go on another G adventure.”
Aislinn, 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 Ages 16+ Operator G Adventures From
- US$2,549
Sailing Greece - Mykonos to Mykonos
“The 2nd Sailing Trip with G was just outstanding!”
Dario, traveled in June
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 Ages 16+ Operator G Adventures From
- US$2,499
Med Sailing in Croatia (from Split to Dubrovnik)
“explored the scenery and the beauty of the Adriatic Sea and all the islands around the coast.”
Raj, traveled in June
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 Ages 18+ Operator Med Sailing Holidays From
5% Off- US$1,565
Med Sailing in Croatia (from Dubrovnik to Split)
“Incredible experience. We have booked to go again next year.”
An Oceanis 48 yacht carries you through the Mediterranean's clearest waters. Hvar's iconic Hula Hula bar, Vis's famous caves, and cycling through Mljet National Park highlight the journey. Fresh meals accompany discoveries of hidden bays and authentic konoba restaurants.
Duration 8 days Destinations Dubrovnik, Mljet Island, Pomena, Korcula Island, Vis, Hvar Island, Maslinica, Split Age Range Ages 18+ Operator Med Sailing Holidays From
5% Off- US$1,677
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."































