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

MelissaMediterranean travel expert at TourRadar
- Greece Sailing Adventure: Cyclades Islands
- Sail Greece: Mykonos to Santorini
- Sailing Greece - Santorini to Santorini
- Croatia Island Sail (Plus)
- Sailing Split Premium Plus - 8 days
- Croatia Sailing Adventure - 8 days
- Sailing Croatia Catamaran Cruise: Mljet, Korcula and Dubrovnik
- Croatia Sailing Adventure: Dubrovnik to Split (10 destinations)
- Amalfi Coast Sailing Adventure (8 destinations)
- Sail Greece: Santorini to Mykonos
Greece Sailing Adventure: Cyclades Islands
18 Reviews by TourRadar travelers“Amazing Tour with an amazing skipper.”
Kaja, 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, Amorgos, Cyclades, Naxos, Syros, Mykonos, Sifnos, Folegandros Age Range Ages 15+ Operator Intrepid Travel From $3,760
10% Off- NZ$3,384+$221 local paymentsYou save $376
Sail Greece: Mykonos to Santorini
15 Reviews by TourRadar travelers“We had an excellent professional friendly delightful experience of a life time...we will never forget.”
Maureen, 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 Ages 15+ Operator Intrepid Travel From $2,935
25% Off- NZ$2,201+$200 local paymentsYou save $734
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 Ages 16+ Operator G Adventures From
25% Off- NZ$2,999
Croatia Island Sail (Plus)
38 Reviews by TourRadar travelers“She created a family atmosphere and I couldn't have asked for anything more in a tour manager.”
Brooke, traveled in May
A premium vessel with air-conditioned cabins awaits on the Mediterranean. The route includes Dubrovnik's UNESCO walls, kayaking in crystal waters, Hvar's Spanish Fortress, and wine tasting in Trstenik. Seven nights with half-board meals and expert Trip Manager included.
Duration 8 days Destinations Split, Korcula Island, Korčula, Dubrovnik, Trstenik, Makarska Age Range Ages 18-35 Operator Contiki From
25% Off- NZ$2,365
Croatia Sailing Adventure - 8 days
3 Reviews by TourRadar travelers“The weather was less than ideal, and our initial boat had some issues - but it happens :) We still all had a great time cruising Croatia.”
Andrea, traveled in May
Split to Dubrovnik reveals Mediterranean treasures aboard a traditional ship. Ports of call include Hvar's jet-set harbor, Mljet's emerald lakes, and Korcula's medieval streets, with daily swim stops and 3-course lunches.
Duration 8 days Destinations Split, Stari Grad, Hvar Island, Mljet Island, Dubrovnik, Korcula Island, Makarska, Omis Age Range Ages 18-35 Operator On The Go Tours From $2,775
40% Off- NZ$1,665You save $1,110
Sailing Croatia Catamaran Cruise: Mljet, Korcula and Dubrovnik
1 Review by TourRadar travelers“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 Slano, Pomena, Korčula, Mljet Island, Dubrovnik, Sipan Island Age Range Ages 30+ Operator Sailing Adriatic From $3,007
20% Off- NZ$2,406+$601 local paymentsYou save $601
Croatia Sailing Adventure: Dubrovnik to Split (10 destinations)
17 Reviews by TourRadar travelers“Beautiful coastal towns visited, wonderful experience.”
Diego, 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, Kolocep Island, Lopud Island, Sipan Island, Mljet Island, Korcula Island, Vis, Hvar Island, Brac, Split Age Range Ages 15+ Operator Intrepid Travel From
20% Off- NZ$2,615
Amalfi Coast Sailing Adventure (8 destinations)
8 Reviews by TourRadar travelers“A great week, thanks.”
Michael, traveled in August
A 48-52ft yacht takes you through secluded bays between Procida and Amalfi. Passengers learn sailing fundamentals while exploring the Sirenusas archipelago and hidden swimming spots, spending seven nights at sea from Ischia to Capri.
Duration 7 days Destinations Procida, Ischia, Sorrento, Pompeii, Amalfi, Capri, Forio Age Range Ages 15+ Operator Intrepid Travel From
20% Off- NZ$3,875+$180 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, Cyclades, Amorgos, Naxos, Syros, Mykonos Age Range Ages 15+ Operator Intrepid Travel From
20% Off- NZ$2,425+$200 local payments
What people love about Sailing Tours in Mediterranean
- Greece Sailing Adventure: Cyclades Islands
captain of Intrepid Sailboat was incredible
- 1-Week Sailing Yoga & SUP in the Saronic or/and Cycladic Islands
Best vacation I've been on, good crew, great sailing.
- Sailing Greece - Santorini to Santorini
Sailing the Greek Islands was an amazing experience. I had been to Greece several times, but had never sailed from island to island. I felt as if I were seeing Greece for the first time. Our guide was awesome and the group was made up of the coolest people you could ever meet!
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."