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

MelissaMediterranean travel expert at TourRadar
- Sail Croatia and Explore Montenegro
- Greece Sailing Adventure: Cyclades Islands
- Sail Greece: Santorini to Mykonos
- Sailing Italy to Croatia
- Sailing Split (Premium) - 8 days
- Sailing Split (Premium Plus) - 8 days
- Cyclades Luxury Sailing Adventure (Catamaran)
- Blue Escape in Turkey: 5 Days Sailing Tour from Gocek to Fethiye
- Sail Greece: Mykonos to Santorini
- Sailing Greece - Santorini to Santorini
No departure dates availableDuration 15 days Destinations Croatia, Montenegro, Albania Age Range Ages 12+ Operator G Adventures Greece Sailing Adventure: Cyclades Islands
20 Reviews by TourRadar travelers“The natural beauty of Greek Islands and amazing local experiences offered us friendship and camaraderie.”
Simon, traveled in May
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, Oia, Amorgos, Katapola, Cyclades, Koufonisia, Iraklia, Naxos, SyrosSee all destinations Age Range Ages 15+ Operator Intrepid Travel From
- US$2,840+$128 local payments
Sail Greece: Santorini to Mykonos
1 Review by TourRadar travelers“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$2,015+$116 local payments
Sailing Italy to Croatia
1 Review by TourRadar travelers“The trip could not have been bettered. Just the right number of other passengers, no-one smoked.”
Kathy, traveled in September
From Venice's canals, a 52-foot yacht charts a course through the Gulf of Trieste to Slovenia's historic ports. The journey continues along Croatia's Istrian peninsula and the secluded Kvarner islands before reaching ancient Zadar.
Duration 10 days Destinations Venice, Grado, Rovinj, Pula, Losinj Island, Dugi Island, Molat Island, Zadar Age Range Ages 16+ Operator G Adventures From
- US$2,079
Cyclades Luxury Sailing Adventure (Catamaran)
3 Reviews by TourRadar travelers“The views were unbeatable, and everything was smoothly run!”
Marley, traveled in July
Luxury catamaran cruising through Cyclades waters awaits. Admire Milos's volcanic coastline, relax at Polyegos's untouched beaches, and soak in Kythnos's thermal springs. Professional skipper leads 209-nautical-mile route with daily swimming stops.
Duration 8 days Destinations Athens, Sounio, Serifos, Kimolos, Polyaigos, Milos, Sifnos, Kythnos Age Range All Ages Welcome Operator Trails Beyond From
20% Off- US$2,841
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 Ages 8+ Operator Tour Altinkum Travel From
20% Off- US$990
Sail Greece: Mykonos to Santorini
15 Reviews by TourRadar travelers“Booking was easy and the Intrepid booking staff were helpful and efficient. The trip itself was great.”
Amy, 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, Syros, Naxos, Amorgos, Ios, Santorini Age Range Ages 15+ Operator Intrepid Travel From
20% Off- US$2,110+$116 local payments
Sailing Greece - Santorini to Santorini
30 Reviews by TourRadar travelers“Excellent tour, great skipper, Marios and great group participation. Though travelling alone, I never felt left out.”
Liam, traveled in June
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
20% Off- US$2,349
What people love about Sailing Tours in Mediterranean
- Greece Sailing Adventure: Cyclades Islands
captain of Intrepid Sailboat was incredible
- Sailing Split (Premium Plus) - 8 days
We really enjoyed our cruise. The staff were friendly and helpful. It was well organised & everything explained each day. Plenty of food & catered for everyone. The last couple of days the tour was at full capacity & the dining area felt a bit crowded.
- Cyclades Luxury Sailing Adventure (Catamaran)
It was an awesome experience! Having done something similar in Croatia, we were hoping this tour would have more planned excursions at each island stop (or at some of them; eg a walk to a historic site or bike rides at a given island etc), and instead the structure was that we’d get somewhere and then be free to sunbathe, wander the small town, get food on our own. Also great, but much more oriented to a very laid back, nearly zero activity sort of vacation. The crew was amazing, the boat was great, the views were unbeatable, and everything was smoothly run!
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."





















