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
- Blue Escape in Turkey: 5 Days Sailing Tour from Gocek to Fethiye
- CROATIA SAIL - Split to Split (The Dalmatian Voyager)
- Blue Escape in Turkey: 8 Days Sailing Tour from Fethiye
- Sail Split to Dubrovnik / Premier Boat
- Sailing Split Premium - 8 days
- Turkish Sailing
- Delicious Amalfi Coast - Luxury Sailing Catamaran ALL INCLUSIVE
Greece Sailing Adventure: Cyclades Islands
18 Reviews by TourRadar travelers“I've already gotten a few friends to use Intrepid as well. There are many groups to choose from and I've found you to be the best by far.”
Carmen, 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 $3,955
25% Off- NZ$2,966+$213 local paymentsYou save $989
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
20% Off- NZ$2,348+$194 local paymentsYou save $587
Sailing Greece - Santorini to Santorini
30 Reviews by TourRadar travelers“Wonderful trip with wonderful crew!”
Sarah, traveled in July
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 $2,999
25% Off- NZ$2,249You save $750
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
25% Off- NZ$1,298
CROATIA SAIL - Split to Split (The Dalmatian Voyager)
509 Reviews by TourRadar travelers“We had 3 course meal on board everyday and it was always delicious. I would definitely recommend Koda Sails.”
Luxury A+ vessel provides private en-suite cabins for Mediterranean exploration. Daily swimming in secluded coves, UNESCO sites in Split and Dubrovnik, and sunset cocktails at historic fortresses create perfect balance of adventure and comfort for ages 25+.
Duration 8 days Destinations Split, Bol, Hvar Island, Mljet Island, Dubrovnik, Korcula Island, Makarska Age Range Ages 25-40 Operator Koda Sail From
25% Off- NZ$2,712+$194 local payments
Turkish Mediterranean coast unfolds aboard a traditional vessel, revealing hidden gems like Tersane Island and Boncuklu Cove. The crew leads snorkeling in Kleopatra Hamam's crystal waters and sunset viewing at Gemiler Island. Eight days of coastal wonders include stops at secluded swimming spots.
Duration 8 days Destinations Fethiye, Gocek Age Range Ages 8+ Operator Tour Altinkum Travel From
25% Off- NZ$1,550
Sail Split to Dubrovnik / Premier Boat
18 Reviews by TourRadar travelers“The food was a highlight, each lunch better than the last - and that was before we had our BBQ feast.”
Danielle, traveled in September
The M/S Morena glides through Mediterranean crystal waters, anchoring at secluded bays and historic ports. Take in Hvar's lavender fields, Korcula's olive groves, and Dubrovnik's ancient harbor. Daily swim stops, local wine tastings, and fresh seafood lunches await.
Duration 8 days Destinations Split, Omis, Makarska, Hvar Island, Korcula Island, Mljet Island, Dubrovnik Age Range Ages 18-59 Operator Travel Talk From $3,134
57% Off- NZ$1,343You save $1,791
Turkish Sailing
4 Reviews by TourRadar travelers“I was shocked that the cook could create such amazing and flavorful food on the limited space on the boat. It was also really nice that all meals were included.”
Norah, traveled in May
Traditional gulet accommodation carries you from Bodrum through hidden bays and ancient harbors. The journey features Ölüdeniz's blue lagoon, St Nicholas Island's ruins, and daily swimming in secluded coves, complemented by 20 authentic meals.
Duration 8 days Destinations Bodrum, Orak Island, Cokertme, Seven Islands, Sedir Island, Kisebuku Age Range Ages 18-35 Operator Contiki From $1,995
10% Off- NZ$1,796+$170 upfront costsYou save $199
Delicious Amalfi Coast - Luxury Sailing Catamaran ALL INCLUSIVE
1 Review by TourRadar travelers“This is a great opportunity to discover the Amalfi coast in great company. He will make you feel like home even on the other side of the world!”
Barney, traveled in September
A luxury 43ft catamaran carries you through Mediterranean waters, past hidden caves and secluded bays. Professional crew guides through Gulf of Naples highlights while offering sailing instruction. Modern amenities and spacious outdoor areas ensure optimal comfort.
Duration 7 days Destinations Castellammare di Stabia, Procida, Ischia, Capri, Positano, Amalfi, Sorrento, Pompeii Age Range All Ages Welcome Operated in English, Italian Operator Sail And Experience From
10% Off- NZ$10,171+$969 local payments
What people love about Sailing Tours in Mediterranean
- Sailing Greece - Santorini to Santorini
An open mind and adventurous spirit are needed for this trip. If you have that and love the sea, this is a trip of a lifetime. This isn't a luxury sailing trip, this is real sailing, with cramped accommodations. But you get to be outside, sailing and exploring the islands, eating the best meals, and swimming in beautiful private bays.
- CROATIA SAIL - Split to Split (The Dalmatian Voyager)
best week, great food, epic staff, and Croatia is one of the most beautiful places I've ever visited. Eat, swim, party, repeat!
- Sailing Split Premium - 8 days
The boat was very comfortable, with a 3:1 ratio of passengers (just 18 of us) to crew, all native Croatians and all delightful and attentive. Because the boat was small, we could put in for our daily swim in hidden coves that the big cruise ships can’t go near. Breakfast and lunch were provided daily, and the food was wholesome, tasty, and abundant. The itinerary—Split/Dubrovnik/Split, with overnight stops at different islands each way—was logical, and the tour manager on board gave us an engaging introduction to maritime Dalmatia along the way. The trip was perfect for us.
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."