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 IslandsSarah and I have just finished sailing from Mykonos to Santorini with Fotis. This was an amazing experience and Fotis was a fantastic skipper who had a wealth of knowledge about sailing and the islands we were sailing through. Would 100% recommend and we are already missing life on board with him! Justin and Sarah
Sail Greece: Mykonos to SantoriniMy week on KODA Sail was a 25 year old female solo traveller was absolutely excellent! Chris and the team had thought of absolutely everything to ensure the week was one where we didn’t have to lift a finger or form a thought if we didn’t want to. The optional extras were all fantastic, the food aboard the Casanova was delicious, Chris’ local recommendations were thoughtful and scrumptious, the itinerary was the perfect mix of jam packed but also plenty of down time. Also a huge shout out to the whole Casanova crew for their professionalism and problem solving when faced with any issues - could not recommend KODA Sail more. Best holiday ever!!!!!
CROATIA SAIL - Split to Dubrovnik (The Southern Discovery)
Our traveler's Moments
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- 1-Week Sailing Yoga & SUP in the Saronic or/and Cycladic Islands ACCORDING WEATHER CONDITIONS. BREAKFAST & LIGHT LUNCHES INCLUDED.

- Med Sailing in Croatia (from Dubrovnik to Split)

- CROATIA SAIL - Split to Dubrovnik (The Southern Discovery)

- Sail Split to Dubrovnik / Premier Boat

- Sailing Greece - Mykonos to Santorini

- Sailing Greece - Athens to Mykonos

- Greece Sailing Adventure: Kefalonia to Corfu

- Croatia Sailing Adventure: Dubrovnik to Split

- Croatia Island Sail (Plus)

- CROATIA SAIL - Split to Split (The Dalmatian Voyager)

- Corfu Sailing Tour

10 best Sailing Mediterranean tour packages
Compiled by

MelissaMediterranean travel expert at TourRadar
- Greece Sailing Adventure: Cyclades Islands
- Sail Greece: Mykonos to Santorini
- CROATIA SAIL - Split to Dubrovnik (The Southern Discovery)
- Sailing Croatia Catamaran Cruise: Dubrovnik, Ston, Korcula Mljet, Lastovo and islands
- Cyclades Luxury Sailing Adventure (Catamaran)
- Med Sailing in Croatia (from Dubrovnik to Split)
- Sail Croatian Islands; Dubrovnik to Split in 8 Days
- Luxury Sailing & Archaeology adventure 8days
- Sail Greece: Santorini to Mykonos
- Sailing Greece - Santorini to Santorini
Greece Sailing Adventure: Cyclades Islands
“Lots of time spent on the boat, beautiful swimming spots and a great way to spend a short time at lots of islands.”
Shannah, traveled in August
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, Oia, Ios, Amorgos, Katapola, Koufonisia, Iraklia, Schoinousa, Naxos, SyrosSee all destinations Age Range Ages 15+ Operator Intrepid Travel From $2,848
19% Off- US$2,304+$128 local payments
Sail Greece: Mykonos to Santorini
“The trip was fantastic - we saw some amazing places, had a really good mix of activities and even got a chance to try sailing.”
Lily, 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, Ermoupouli, Naxos, Chora, Koufonisia, Iraklia, Schoinousa, Amorgos, KatapolaSee all destinations Age Range Ages 15+ Operator Intrepid Travel From $2,087
19% Off- US$1,693+$117 local payments
CROATIA SAIL - Split to Dubrovnik (The Southern Discovery)
“This was an amazing experience from day 1. The rooms are exactly as shown and all you need for the sail - comfy beds and working A/C.”
Damien, traveled in August
Cruise the Mediterranean's crystal waters on an A+ category vessel with private en-suite cabins and sundeck lounging. Zlatni Rat beach, Hvar's historic quarter, and Mljet's National Park highlight the journey, accompanied by freshly prepared Croatian cuisine and daily swim stops.
Duration 8 days Destinations Split, Bol, Hvar Island, Makarska, Korcula Island, Mljet Island, Dubrovnik Age Range Ages 25-40 Operator Koda Sail From
19% Off- US$1,691+$122 local payments
Sailing Croatia Catamaran Cruise: Dubrovnik, Ston, Korcula Mljet, Lastovo and islands
“Mljet National Park is a must-see! The catamaran cruise in Croatia was one of the best experiences I had.”
Peter, traveled in September
Duration 8 days Destinations Dubrovnik, Ston, Korčula, Lastovo, Mljet Island, Sipan Island Age Range Ages 18+ Operator Sailing Adriatic From $2,041
20% Off- US$1,633+$408 local payments
Cyclades Luxury Sailing Adventure (Catamaran)
“We loved the standup paddle boarding and snorkeling.”
Catherine, traveled in June
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$2,893
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
20% Off- US$1,738
Sail Croatian Islands; Dubrovnik to Split in 8 Days
“The atmosphere was relaxed and fun.”
Dario, traveled in March
Duration 8 days Destinations Dubrovnik, Slano, Mljet, Korčula, Vis, Hvar Island, Bol, Pucisca, Omis, Split Age Range All Ages Welcome Operator Choose Balkans From
20% Off- US$1,943
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."






























