Sailaway Charters
Yacht types · Sailboats — Sail a monohull.
The traditional yacht.

Yacht types · Sailboats

Sail a monohull.
The traditional yacht.

Heels under sail, slices through chop, sails close to the wind. The original way to cross a sea.

32 – 58 ftSleeps 4 – 10

Live fleet

Sailboats ready to sail.

3,932 yachts · page 71 of 82

Marie20% · Last minute

Marie

Bareboat

6 berths3 cabins12 m2019
from
€1,490
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MoElli20% · Last minute

MoElli

Bareboat

8 berths3 cabins12 m2020
from
€1,560
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Carelli

Carelli

Bareboat

6 berths2 cabins12 m2019
from
€2,700
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Agios Georgios

Agios Georgios

Bareboat

8 berths3 cabins12 m2016
from
€2,250
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My Pearl20% · Last minute

My Pearl

Bareboat

8 berths3 cabins12 m2017
from
€950
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živjelli20% · Last minute

živjelli

Bareboat

8 berths3 cabins12 m2017
from
€950
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Imagine20% · Last minute

Imagine

Bareboat

8 berths3 cabins12 m2017
from
€950
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Tequila Sunrise20% · Last minute

Tequila Sunrise

Bareboat

8 berths3 cabins12 m2017
from
€950
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Sun elli20% · Last minute

Sun elli

Bareboat

6 berths3 cabins12 m2017
from
€1,190
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Sound of Silence20% · Last minute

Sound of Silence

Bareboat

8 berths3 cabins12 m2017
from
€1,290
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Emilina20% · Last minute

Emilina

Bareboat

8 berths3 cabins12 m2018
price on enquiry
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Islanders

Islanders

Bareboat

6 berths3 cabins12 m2018
from
€850
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Islanders

Islanders

Bareboat

6 berths3 cabins12 m2018
from
€850
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Freddie

Freddie

Bareboat

9 berths3 cabins12 m2019
from
€1,200
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Zappa

Zappa

Bareboat

9 berths3 cabins12 m2019
from
€1,200
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Cash

Cash

Bareboat

9 berths3 cabins12 m2019
from
€1,200
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Max

Max

Bareboat

8 berths3 cabins12 m2018
from
€1,548
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Lioba

Lioba

Bareboat

8 berths3 cabins12 m2018
from
€1,548
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Freiheit

Freiheit

Bareboat

8 berths3 cabins12 m2019
from
€1,548
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Eol

Eol

Bareboat

8 berths3 cabins12 m2018
from
€1,200
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Tara

Tara

Bareboat

5 berths2 cabins12 m2019
from
€1,500
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CarElli20% · Last minute

CarElli

Bareboat

4 berths2 cabins12 m2019
from
€1,490
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Cabiria

Cabiria

Bareboat

8 berths3 cabins12 m2008
from
€1,700
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Nomad

Nomad

Bareboat

8 berths3 cabins12 m2008
from
€1,240
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Panic

Panic

Bareboat

8 berths3 cabins12 m2002
from
€1,725
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Moulin Rouge

Moulin Rouge

Bareboat

6 berths3 cabins12 m2002
from
€1,248
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Evina

Evina

Bareboat

6 berths3 cabins12 m2002
from
€1,100
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Evina

Evina

Bareboat

6 berths3 cabins12 m2002
from
€935
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Azure

Azure

Bareboat

8 berths3 cabins12 m2005
from
€1,550
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Traveller

Traveller

Bareboat

6 berths3 cabins12 m2013
from
€250
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Oreia20% · Last minute

Oreia

Bareboat

8 berths3 cabins12 m2011
from
€1,390
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Piedanlo

Piedanlo

Bareboat

8 berths3 cabins12 m2013
from
€1,900
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Traveller

Traveller

Bareboat

8 berths3 cabins12 m2013
from
€1,300
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Amersa

Amersa

Bareboat

8 berths3 cabins12 m2015
from
€1,900
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Telchinis

Telchinis

Bareboat

8 berths3 cabins12 m2011
from
€1,350
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Korinne

Korinne

Bareboat

8 berths3 cabins12 m2012
from
€2,950
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Cavalier

Cavalier

Bareboat

6 berths3 cabins12 m2014
from
€2,375
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Rocky

Rocky

Bareboat

6 berths3 cabins12 m2013
from
€1,648
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Shinju

Shinju

Bareboat

6 berths3 cabins12 m2013
from
€1,648
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Eternity

Eternity

Bareboat

7 berths3 cabins12 m2015
from
€1,350
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Cecile

Cecile

Bareboat

8 berths3 cabins12 m2015
from
€2,000
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Sora

Sora

Bareboat

8 berths3 cabins12 m2012
from
€1,900
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Veterano

Veterano

Bareboat

8 berths3 cabins12 m2015
from
€1,648
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Telchinis

Telchinis

Bareboat

8 berths3 cabins12 m2011
from
€1,350
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FourTwo

FourTwo

Bareboat

6 berths3 cabins12 m2013
from
€1,650
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Signum Bravo

Signum Bravo

Bareboat

8 berths3 cabins12 m2019
from
€2,570
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Emotion

Emotion

Bareboat

8 berths3 cabins12 m2019
from
€1,950
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Sea Breeze

Sea Breeze

Bareboat

8 berths3 cabins12 m2019
from
€2,690
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Sailboat questions

Asked and answered.

How much will I heel under sail?
10-20° on a beam reach is normal. Off the wind it's almost flat. Upwind in 25 kts it can hit 30°, but most charter sailing is reaching in 10-18 kts where the heel is part of the experience, not a problem.
Are sailboats hard for non-sailors?
Not really. The crew can stay in the cockpit (or below) while the skipper sails. The deck angle takes a day to get used to. Most crews find sailboats more 'real' than catamarans by Wednesday.
What size sailboat do I need for 4 people?
38-42 ft. 38 ft is two cabins + saloon (tight but works), 42 ft is three cabins (comfortable). Anything over 45 ft is over-spec for 4 unless you want extra space.
Can a sailboat go anywhere a catamaran can?
Almost. The deeper draft (1.8 m vs 1.2 m) keeps you out of a handful of very shallow bays — Vis (Stončica), some Greek harbours. 95% of anchorages are fine for both.
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Quick inquiry

Get three sailboat options from the team.

Tell us roughly when, where, and how many. we'll send three sailboat options the same day — three boats, three prices, the trade-offs.

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New sailors, beginners or seasoned skippers — tell us when, where, and how many. we send three real options the same day. No spam, no fluff, no commitment.

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Yacht under sail at sunset

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Get three real options.

Tell us roughly when and where. we'll send three real boats, three prices, the trade-offs — usually within the hour.