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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Fiona • traveled in October, 2025
The actual trip was amazing. The skipper was very knowledgeable and safety conscious. You have to allow 2 days for adjusting to boat life.
Greece Sailing Adventure: Cyclades Islands - K
Kathy • traveled in October, 2024
I did a review for G Adventures a few hours ago.The trip could not have been bettered. Just the right number of other passengers, no-one smoked,.our captain was very professional, the boat was very clean, kitchen utensils were of good quality, the toilet/shower facilities at the marinas were first rate and it was traven experience I had not had before.
Sailing Italy to Croatia - A
Ann • traveled in June
Sandre was an excellent captain. The group was lovely. Pula and Isola were the highlights.
Sailing Croatia to Italy
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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 Italy to Croatia
- Sailing Croatia to Italy
- Sailing Split (Premium Plus) - 8 days
- Cyclades Luxury Sailing Adventure (Catamaran)
- Sail Greece: Mykonos to Santorini
- Sailing Croatia - Dubrovnik to Split
- Croatia Sailing Adventure: Dubrovnik to Split
- Sailing Greece - Santorini to Santorini
Greece Sailing Adventure: Cyclades Islands
20 Reviews by TourRadar travelers“Varied and interesting itinerary. Got the whole group to bond together really well.”
Stephen, 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 $2,079
25% Off- US$1,559You save $520
Sailing Croatia to Italy
2 Reviews by TourRadar travelers“Very early in the season so the weather wasn't stunning but had a fantastic time and met some great people.”
Matthew, traveled in April
A 16m yacht carries passengers from Zadar to Venice through pristine Mediterranean waters. The route includes Kvarner Gulf's secluded coves, Rovinj's seafood restaurants, and Pula's Roman heritage, with a professional skipper guiding through three countries' waters.
Duration 10 days Destinations Zadar, Molat Island, Dugi Island, Losinj Island, Rovinj, Pula, Grado, Venice Age Range Ages 16+ Operator G Adventures From $2,079
25% Off- US$1,559You save $520
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
45% Off- US$2,831
Sail Greece: Mykonos to Santorini
15 Reviews by TourRadar travelers“We had a great time on the boat. Made us feel very welcome and showed us all the relevant stuff.”
Lukas, traveled in June
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
45% Off- US$2,110+$116 local payments
Sailing Croatia - Dubrovnik to Split
23 Reviews by TourRadar travelers“Amazing trip 😍 would really recommend.”
joanne, traveled in July
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 Ages 16+ Operator G Adventures From $1,949
17% Off- US$1,618You save $331
Croatia Sailing Adventure: Dubrovnik to Split
17 Reviews by TourRadar travelers“The restaurant selections were outstanding. His local knowledge was a real bonus.”
Craig, traveled in May
A 48-52ft yacht serves as your gateway to Croatia's hidden coves and historic harbors. The itinerary features Mljet's emerald lakes, Korcula's medieval streets, and pristine swimming bays near Hvar, with expert navigation through ten stunning destinations.
Duration 8 days Destinations Dubrovnik, Mljet, Veliko Jezero, Korčula, Scedro, Vis, Solta, Maslinica, Trogir, Split Age Range Ages 15+ Operator Intrepid Travel From
17% Off- US$2,075
Sailing Greece - Santorini to Santorini
30 Reviews by TourRadar travelers“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 $2,349
25% Off- US$1,762You save $587
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."
































