What is the typical group size on a sailing tour?

Most sailing tours keep it cozy with 8-10 people per yacht. In Greece, you'll be on a 57-foot yacht with 5 cabins, while Croatian boats have up to 8 cabins. A recent TourRadar traveler put it well: "Small groups, value for money, experienced and knowledgeable tour guides made for an amazing experience sailing through the Greek islands."

When is the best time to book a sailing tour?

Want the best weather? Go between May and September for Mediterranean sailing. Croatia and Montenegro tours run from April through October, while Greek trips stick to May through September. If you're headed to Halong Bay in Vietnam, book between October and March for nice temperatures and clear skies. The Mediterranean routes are busiest from July through September - that's when most boats are out on the water.

How much sailing versus port time can I expect?

You'll spend about 3-6 hours sailing each day, with plenty of time to explore ports in the afternoon and evening. If you're in Greece, you'll hop between big-name islands like Santorini and Mykonos, plus some smaller hidden gems in the Cyclades. Croatia and Montenegro tours mix coastal towns with quiet bays. One TourRadar traveler described it perfectly: "Perfect mix of sailing, swimming in hidden coves, and exploring charming port towns."

What meals are included during sailing trips?

Your trip usually includes all meals, cooked fresh by the boat's chef. In Croatia, you get 7 breakfasts, 7 lunches and 1 dinner, while Galapagos trips include all three meals every day. One TourRadar traveler raved about their Maldives experience: "The food prepared each day almost singlehandedly by the chef was also a highlight." You can expect lots of fresh seafood and local dishes. Just let them know about any dietary needs before you go.

What are the typical sleeping arrangements on sailing tours?

You'll share a cabin with 2-4 other people and usually share bathrooms too. In the Galapagos, the Yolita boat offers twin rooms with private bathrooms. Mediterranean boats, like those in Greece, typically have 3-4 double cabins. One TourRadar traveler noted: "The cabins were comfortable and clean, though space is limited as expected on a sailing vessel."

What destinations are most popular for sailing tours?

Greece's islands (especially the Cyclades and Saronic group), the Galapagos, and the Maldives top the list. Each place offers something different - Greece is great for mixing island visits with ancient history, the Galapagos is perfect for wildlife lovers, and the Maldives has amazing beaches and snorkeling spots. As one TourRadar traveler said: "The Saronic islands of Greece are absolutely stunning, with each day offering plenty of sun, beautiful swimming spots, and charming little ports."

Sailing Tours & Trips

10 best Sailing tour packages

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Sailing
Marmaris - Fethiye (7 Night Blue Cruise)
4.0 (2 reviews)
Duration
8 days
Destinations
Marmaris, Ekincik, Dalyan, Gocek, Tersane Island, Fethiye,Saklikent Gorge,Oludeniz,Yassica Adalari,Kumlubük+4 more
Age Range
Ages 10+
Operated in
English
Operator
Barbaros Yachting
From
US$1,150per person
+$58 local payments
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Sailing
Amalfi Coast by Luxury Sailing Boat - Walking with the Gods
5.0 (2 reviews)
"The boat was nice and clean. The itinerary was well planned so the trip was really relaxing and enjoyable."
Alexis, traveled in June
Duration
3 days
Destinations
Castellammare di Stabia, Capri, Amalfi, Positano, Sorrento
Age Range
All Ages Welcome
Country Region
Amalfi CoastSouth ItalyCampania+2 more
Operated in
English, Italian
Operator
Sail And Experience
From
US$3,833per person
+$290 local payments
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Price based on Private Double Room
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Sailing
Greece Sailing Adventure: Cyclades Islands
4.6 (21 reviews)
"Great way to see and experience the cyclades."
Kornelia, traveled in September
Duration
10 days
Destinations
Santorini, Oia, Ios, Amorgos, Katapola, Koufonisia, Iraklia,Schoinousa,Naxos,Syros,Ermoupouli,Mykonos,Sifnos,Folegandros+7 more
Age Range
Ages 15+
Islands
Greek IslandsAegean IslandsCyclades Greece+2 more
Operated in
English
Operator
Intrepid Travel
14% Off
From $2,848
US$2,440per person
+$128 local payments
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Sailing
Sail Greece: Santorini to Mykonos
5.0 (1 review)
"We had a great time meeting lots of new friends who all got on from many nationalities. Without the disputes!"
Peter, traveled in September
Duration
8 days
Destinations
Santorini, Ios, Amorgos, Koufonisia, Iraklia, Naxos, Syros,Mykonos+1 more
Age Range
Ages 15+
Islands
Greek IslandsAegean IslandsCyclades Greece+2 more
Operated in
English
Operator
Intrepid Travel
28% Off
From $2,102
US$1,507per person
+$116 local payments
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Sailing
4 Days Fethiye to Olympos
4.0 (1 review)
"The staff were great, the food was excellent and we had lots of fun."
Karolyn, traveled in May
Duration
4 days
Destinations
Fethiye, Gemile Island, Kas, Kekova, Olympus
Age Range
Ages 8+
Operated in
English
Operator
Turkey Escapades
28% Off
From
US$580per person
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Sailing
Sailing Croatia - Dubrovnik to Split
4.6 (23 reviews)
"Croatia is a beautiful place to explore, sailing down the Dalmatian Coast is an experience that I will never forget."
Megan, traveled in May
Duration
8 days
Destinations
Dubrovnik, Mljet Island, Korcula Island, Ploce,Hvar Island,Brac,Split+3 more
Age Range
Ages 16+
Ship
G Adventures Sailing Yacht
Regions
Dalmatia AdriaticCroatian Islands+1 more
Operated in
English
Operator
G Adventures
28% Off
From
US$1,999per person
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Sailing
Southern Pearls (Dubrovnik to Split) Premium Superior
5.0 (3 reviews)
"The ship was very clean and the food was delicious."
Katie, traveled in May
Duration
8 days
Destinations
Dubrovnik, Sipan Island, Slano, Mljet Island, Korčula,Biševo,Vis,Scedro,Hvar,Bol,Makarska,Pucisca,Split+8 more
Age Range
All Ages Welcome
Ships
Spalato MV Seagull MV Paradis MS Dream MV Majestic+3 ships
Regions
Dalmatia AdriaticCroatian Islands+1 more
Operated in
English
Operator
Katarina Line
28% Off
From
US$1,568per person
+$99 local payments
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Sailing
Turkey: Sail & Swim
Duration
8 days
Destinations
Fethiye, Oludeniz, Ekincik, Dalyan, Marmaris, Gocek
Age Range
Ages 18-32
Country Region
Western TurkeyAegean+1 more
Operated in
English
Operator
Topdeck
5% Off
From $1,269
US$1,206per person
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Sailing
Turquoise Blue - Fethiye/Kekova/Fethiye
4.0 (4 reviews)
"The food was excellent and plentiful. The boat saw so many pretty places."
Susan, traveled in October
Duration
8 days
Destinations
Fethiye, Oludeniz, St. Nicholas Island, Kas, Kekova, Simena,Demre,Kalkan+2 more
Age Range
Ages 12+
Operated in
English
Operator
Fez Travel
5% Off
From
US$865per person
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Sailing
Cyclades Luxury Sailing Adventure (Catamaran)
4.8 (4 reviews)
"We loved the standup paddle boarding and snorkeling."
Catherine, traveled in June
Duration
8 days
Destinations
Athens, Sounio, Serifos, Kimolos, Polyaigos, Milos, Sifnos,Kythnos+1 more
Age Range
All Ages Welcome
Islands
Greek IslandsCyclades Greece+1 more
Operated in
English
Operator
Trails Beyond
5% Off
From
US$2,881per person
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Sailing
Sailing Croatia 8 day -Split, Blue Lagoon, Vis, Hvar, Bol and Trogir
4.7 (3 reviews)
"The itinerary was perfect. Croatia is so beautiful, a must trip for anyone!!"
Robin, traveled in September
Duration
8 days
Destinations
Split, Stomorska, Hvar Island, Milna (Brac Island), Bol,Primosten,Vis,Biševo,Ciovo island,Trogir+5 more
Age Range
Ages 21+
Regions
Dalmatia AdriaticCroatian Islands+1 more
Operated in
English
Operator
Rhythm Travel Experience
30% Off
From $1,057
US$740per person
+$12 local payments
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Sailing
1-Week Sailing Yoga & SUP in the Saronic or/and Cycladic Islands ACCORDING WEATHER CONDITIONS. BREAKFAST & LIGHT LUNCHES INCLUDED.
4.9 (15 reviews)
"As a solo female traveler I was apprehensive about safety and can confirm that this was such a wonderful, safe, and fun experience."
Isabelle, traveled in August
Duration
8 days
Destinations
Athens, Aegina, Epidaurus, Poros, Methana, Ermioni, Agkistri,Hydra,Moni Island,Alimos+3 more
Age Range
Ages 18+
Regions
Mainland GreeceSaronic IslandsPeloponnese Islands+2 more
Operated in
English
Operator
Med Sun Yachts
30% Off
From
US$1,150per person
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Sailing
Croatia Sail Adventure
5.0 (116 reviews)
"Had an incredible time from the group leader to the tour as a whole"
Scott, traveled in June
Duration
10 days
Destinations
Split, Makarska, Mljet, Dubrovnik, Trstenik, Korčula,Hvar Island+1 more
Age Range
Ages 18-49
Regions
Dalmatia AdriaticCroatian Islands+1 more
Operated in
English
Operator
INTRO Travel
30% Off
From
US$2,524per person
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Sailing
Sailing Italy to Croatia
5.0 (1 review)
"The trip could not have been bettered. Just the right number of other passengers, no-one smoked."
Kathy, traveled in September
Duration
10 days
Destinations
Italy Slovenia Croatia
Age Range
Ages 16+
Country Region
Adriatic
Operated in
English
Operator
G Adventures
30% Off
From
US$2,179per person
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Sailing
Luxury Sailing & Archaeology adventure 8days
5.0 (1 review)
"Hands down best trip ever! Danae and Costas were very gracious hosts and passionate about sharing a unique side of Greece."
IreneMeyer, traveled in May
Duration
8 days
Destinations
Athens, Agkistri, Corinth, Mycenae, Palaia Epidavros,Epidaurus,Nafplion,Methana,Poros,Hydra,Aegina+6 more
Age Range
Ages 8+
Regions
Mainland GreecePeloponnese Islands+1 more
Operated in
English
Operator
Trails Beyond
30% Off
From
US$3,206per person
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Price based on Shared Room
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