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

250+ tours

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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
From
US$480per person
Price based on Shared Room
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$6-Day Tour Athens & Santorini Island to Discover Greece\'s Charm Tour$
$6-Day Tour Athens & Santorini Island to Discover Greece\'s Charm - 9 destinations$
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Sailing
6-Day Tour Athens & Santorini Island to Discover Greece's Charm
5.0 (19 reviews)
"The tour guides and drivers were all great."
Jennifer, traveled in November
Duration
6 days
Destinations
Athens, Santorini, Nea Kameni Island, Oia, Emporios,Perissa+1 more
Age Range
Ages 1-30
Regions
Greek IslandsAegean IslandsCyclades GreeceAthens Santorini & Mykonos+3 more
Operated in
English
Operator
Private Tours Greece
25% Off
From $2,350
US$1,762per person
Price based on Private Double Room
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Sailing
Marmaris - Fethiye (7 Night Blue Cruise)
4.0 (2 reviews)
Duration
8 days
Destinations
Marmaris, Kumlubük, Ekincik, Dalyan, Gocek, Tersane Island,Fethiye,Saklikent Gorge,Oludeniz,Yassica Adalari+4 more
Age Range
Ages 10+
Operated in
English
Operator
Barbaros Yachting
25% Off
From
US$1,247per person
+$57 local payments
Price based on Private Double Room
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Sailing
Greece Sailing Adventure: Cyclades Islands
4.6 (21 reviews)
"Amazing visits to the islands, each unique. The trip surpassed my expectations."
Susan, traveled in May
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
24% Off
From $2,564
US$1,955per person
+$126 local payments
Price based on Shared Room
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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
24% Off
From $2,102
US$1,606per person
+$114 local payments
Price based on Shared Room
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Sailing
Delicious Amalfi Coast - Luxury Sailing Catamaran ALL INCLUSIVE
5.0 (1 review)
"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
Duration
7 days
Destinations
Castellammare di Stabia, Procida, Ischia, Forio, Capri,Positano,Amalfi,Sorrento,Pompeii+4 more
Age Range
All Ages Welcome
Country Region
Amalfi CoastSouth ItalyCampania+2 more
Operated in
English, Italian
Operator
Sail And Experience
24% Off
From
US$8,580per person
+$343 local payments
Price based on Private Double Room
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Sailing
Philippines East
4.8 (131 reviews)
"Orty is a fantastic tour guide, helpful, approachable and always there for everyone and their needs."
victoria, traveled in December
Duration
8 days
Destinations
Moalboal, Badian, Cebu City, Boracay
Age Range
Ages 18-39
Islands
Cebu Island
Operated in
English
Operator
TruTravels
40% Off
From $1,250
US$750per person
Price based on Shared Room
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Sailing
Sail Phuket to Ko Phi Phi
4.7 (15 reviews)
"The information and the itinerary of the trip was accurate. The meet-up and drop off worked perfectly."
Amanda-Jayne, traveled in December
Duration
4 days
Destinations
Phuket, Krabi, Ko Phi Phi
Age Range
Ages 15+
Country Region
Southern Thailand
Operated in
English
Operator
Intrepid Travel
40% Off
From
US$1,100per person
Price based on Shared Room
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Sailing
Sail Greece: Mykonos to Santorini
4.5 (15 reviews)
"Having an organized trip and itinerary that is well researched."
Nicole, traveled in June
Duration
8 days
Destinations
Mykonos, Syros, Ermoupouli, Naxos, Ano Koufonisi Island,Iraklia,Schoinousa,Amorgos,Katapola,Chora,Ios,Santorini+7 more
Age Range
Ages 15+
Islands
Greek IslandsAegean IslandsCyclades Greece+2 more
Operated in
English
Operator
Intrepid Travel
28% Off
From $2,192
US$1,570per person
+$114 local payments
Price based on Shared Room
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Sailing
Sailing Croatia - Dubrovnik to Split
4.6 (23 reviews)
"Sailing with G-Adventures, having Marin as our Skipper and the 4 other passengers exceeded beyond my expectations."
Michelle, 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
Croatian IslandsDalmatiaAdriatic+2 more
Operated in
English
Operator
G Adventures
20% Off
From $1,949
US$1,559per person
Price based on Private Double Room
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Sailing
Green Coast: Rio, Paraty & Ilha Grande
5.0 (2 reviews)
"Excellent tour well appreciated"
Denis, traveled in April
Duration
11 days
Destinations
Rio de Janeiro, Paraty, Ilha Grande
Age Range
All Ages Welcome
Country Region
Mata Atlantica
Operated in
English, Portuguese,Spanish+1 more
Operator
ETours Brazil DMC
20% Off
From
US$1,610per person
Price based on Private Double Room
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Sailing
Explore Dubai & Abu Dhabi 4 Nights 5 Days
4.2 (13 reviews)
"We were able to explore majority of the tourist attractions within 3 full days. I get to do my own exploration of the city."
Josie, traveled in January
Duration
5 days
Destinations
Dubai, Abu Dhabi
Age Range
All Ages Welcome
Operated in
English
Operator
JTR Holidays
20% Off
From
US$635per person
Price based on Private Double Room
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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
20% Off
From
US$2,179per person
Price based on Private Double Room
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Sailing
Croatia Sail Adventure
5.0 (116 reviews)
"the trip itinerary was amazing with a good mix between chilling out on the boat and exploring Croatia."
Hannah, traveled in June
Duration
10 days
Destinations
Split, Makarska, Mljet, Dubrovnik, Trstenik, Korčula,Hvar Island+1 more
Age Range
Ages 18-49
Regions
Croatian IslandsDalmatiaAdriatic+2 more
Operated in
English
Operator
INTRO Travel
20% Off
From
US$2,524per person
Price based on Shared Room
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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
20% Off
From
US$2,969per person
Price based on Private Double Room
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