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 63 of 82

Tide Of Your Life

Tide Of Your Life

Bareboat

12 berths5 cabins15 m2026
from
€1,950
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Offline

Offline

Bareboat

10 berths5 cabins15 m2026
from
€2,600
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Kos 47.1

Kos 47.1

Bareboat

10 berths5 cabins15 m2026
from
€2,300
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Tundra

Tundra

Crewed

6 berths3 cabins15 m2014
from
€240
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Gold One

Gold One

Bareboat

10 berths4 cabins15 m2016
from
€2,100
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Flou

Flou

Bareboat

10 berths4 cabins15 m2018
from
€1,250
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J Dog

J Dog

Bareboat

10 berths4 cabins15 m2017
from
€5,050
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Jazz

Jazz

Bareboat

10 berths4 cabins15 m2014
from
€2,300
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Flou

Flou

Bareboat

10 berths4 cabins15 m2018
from
€1,250
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Ultra Dubrovnik

Ultra Dubrovnik

Bareboat

11 berths5 cabins15 m2015
from
€1,250
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Jimmy's

Jimmy's

Bareboat

10 berths5 cabins15 m2014
from
€2,200
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Annita

Annita

Bareboat

10 berths5 cabins15 m2015
from
€2,200
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Filomena

Filomena

Bareboat

11 berths5 cabins15 m2014
from
€2,440
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Anthea

Anthea

Bareboat

12 berths5 cabins15 m2015
from
€2,800
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Mars Planet

Mars Planet

Bareboat

12 berths5 cabins15 m2015
from
€2,500
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Butterfly

Butterfly

Bareboat

12 berths5 cabins15 m2015
from
€2,600
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O48-15

O48-15

Bareboat

10 berths5 cabins15 m2015
from
€2,330
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San Clemente

San Clemente

Bareboat

12 berths5 cabins15 m2017
from
€2,390
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Pherousa

Pherousa

Bareboat

10 berths5 cabins15 m2015
from
€2,200
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Pherousa

Pherousa

Bareboat

10 berths5 cabins15 m2015
from
€3,000
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Joy

Joy

Bareboat

10 berths5 cabins15 m2016
from
€3,200
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Joy

Joy

Bareboat

10 berths5 cabins15 m2016
from
€2,310
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Joy

Joy

Bareboat

10 berths5 cabins15 m2016
from
€3,000
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Invictus

Invictus

Bareboat

10 berths5 cabins15 m2015
from
€2,100
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Alisa

Alisa

Bareboat

10 berths5 cabins15 m2015
from
€1,533
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Athena

Athena

Bareboat

10 berths5 cabins15 m2013
from
€2,850
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Franziska

Franziska

Bareboat

12 berths5 cabins15 m2016
from
€3,100
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Marilyn

Marilyn

Bareboat

12 berths5 cabins15 m2018
from
€3,100
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San Marco

San Marco

Bareboat

12 berths5 cabins15 m2018
from
€2,900
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Summer Dream

Summer Dream

Bareboat

12 berths5 cabins15 m2017
from
€2,600
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Cheeky Lady

Cheeky Lady

Bareboat

11 berths5 cabins15 m2015
from
€2,590
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Skiron

Skiron

Bareboat

10 berths5 cabins15 m2015
from
€3,000
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Blues

Blues

Bareboat

12 berths5 cabins15 m2014
from
€2,300
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Ultra Dubrovnik

Ultra Dubrovnik

Bareboat

11 berths5 cabins15 m2015
from
€1,250
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Dima I

Dima I

Bareboat

10 berths5 cabins15 m2017
from
€2,100
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Vanessa M

Vanessa M

Bareboat

10 berths4 cabins15 m2011
from
€3,200
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Vanessa M

Vanessa M

Bareboat

10 berths4 cabins15 m2011
from
€2,700
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Calypso

Calypso

Bareboat

7 berths3 cabins15 m2007
from
€6,650
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Promise

Promise

Bareboat

10 berths4 cabins15 m2011
from
€2,200
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Seladon II

Seladon II

Bareboat

11 berths5 cabins15 m2010
from
€2,500
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Sueno

Sueno

Bareboat

12 berths5 cabins15 m2010
from
€2,495
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La Stella

La Stella

Bareboat

13 berths5 cabins15 m2012
from
€1,800
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Sueno

Sueno

Bareboat

11 berths5 cabins15 m2010
from
€3,100
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Mississippi

Mississippi

Bareboat

12 berths5 cabins15 m2012
from
€1,800
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Kos 51.1

Kos 51.1

Bareboat

11 berths5 cabins16 m2018
from
€3,250
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Thano

Thano

Bareboat

11 berths5 cabins16 m2018
from
€3,250
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Aeolian Muse

Aeolian Muse

Bareboat

11 berths4 cabins16 m2019
from
€3,000
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Grey Goose

Grey Goose

Bareboat

11 berths4 cabins16 m2019
from
€3,300
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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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Yacht under sail at sunset

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