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 82 of 82

Ataraxia

Ataraxia

Bareboat

11 berths5 cabins16 m2020
from
€3,060
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Mayflower

Mayflower

Bareboat

12 berths5 cabins16 m2020
from
€3,600
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Aurora

Aurora

Bareboat

10 berths5 cabins16 m2016
from
€2,600
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Aquaholic

Aquaholic

Bareboat

12 berths5 cabins16 m2019
from
€3,000
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Aethra

Aethra

Bareboat

11 berths5 cabins16 m2020
from
€3,950
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Impavida

Impavida

Bareboat

11 berths5 cabins16 m2018
from
€3,750
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Misty

Misty

Bareboat

12 berths5 cabins16 m2019
from
€3,800
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Fiesta

Fiesta

Bareboat

11 berths5 cabins16 m2020
from
€2,800
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Bianca

Bianca

Bareboat

12 berths5 cabins16 m2017
from
€3,080
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Ciao Bao

Ciao Bao

Bareboat

12 berths5 cabins16 m2018
from
€1,950
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Juicy Lucy

Juicy Lucy

Bareboat

12 berths5 cabins16 m2020
from
€3,600
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Kalliroi

Kalliroi

Bareboat

12 berths5 cabins16 m2020
from
€3,600
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Panagia

Panagia

Bareboat

12 berths5 cabins16 m2020
from
€3,600
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Perro Blanco

Perro Blanco

Bareboat

12 berths5 cabins16 m2018
from
€4,900
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Unique I

Unique I

Bareboat

12 berths5 cabins16 m2020
from
€3,600
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Maistros

Maistros

Bareboat

12 berths5 cabins16 m2020
from
€3,600
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Giovanna

Giovanna

Bareboat

12 berths5 cabins16 m2017
from
€2,880
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Elise af Sweden

Elise af Sweden

Bareboat

12 berths5 cabins16 m2016
from
€2,000
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Freyja20% · Last minute

Freyja

Bareboat

12 berths5 cabins16 m2018
from
€2,100
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Hesiodos

Hesiodos

Bareboat

12 berths5 cabins15 m2000
from
€1,590
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Slow

Slow

Bareboat

8 berths4 cabins15 m2004
from
€1,200
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Windward Spirit

Windward Spirit

Crewed

8 berths4 cabins17 m2003
from
€6,000
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Felicita

Felicita

Bareboat

10 berths5 cabins17 m2005
from
€3,200
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Olivia Adriatica

Olivia Adriatica

Bareboat

8 berths3 cabins17 m2008
from
€4,800
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Veni

Veni

Bareboat

8 berths4 cabins17 m2007
from
€2,500
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Vika

Vika

Bareboat

10 berths4 cabins17 m2006
from
€2,200
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Karoline

Karoline

Bareboat

6 berths3 cabins12 m2012
from
€1,648
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eXess

eXess

Bareboat

6 berths3 cabins11 m2008
from
€1,598
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Areti

Areti

Bareboat

6 berths2 cabins12 m2022
from
€4,410
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Xara

Xara

Bareboat

7 berths3 cabins13 m2018
from
€2,200
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Cum Ventis

Cum Ventis

Bareboat

7 berths3 cabins13 m2018
from
€2,200
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Calliope

Calliope

Bareboat

8 berths3 cabins13 m2023
from
€4,860
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Ma Detox

Ma Detox

Bareboat

7 berths3 cabins13 m2021
from
€2,580
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Alive

Alive

Bareboat

6 berths3 cabins13 m2023
from
€4,148
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Kallisti

Kallisti

Bareboat

8 berths3 cabins13 m2026
from
€4,860
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Athena

Athena

Bareboat

8 berths3 cabins14 m2019
from
€5,230
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Sophia

Sophia

Bareboat

8 berths3 cabins14 m2019
from
€5,230
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Artemis

Artemis

Bareboat

8 berths3 cabins14 m2019
from
€5,230
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Lady X

Lady X

Bareboat

6 berths2 cabins10 m2018
from
€1,400
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Penelope

Penelope

Bareboat

8 berths3 cabins15 m2025
from
€9,660
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Gazelle

Gazelle

Bareboat

8 berths3 cabins13 m2020
from
€5,410
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Aqua Nomis

Aqua Nomis

Bareboat

6 berths3 cabins13 m2012
price on enquiry
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Pia

Pia

Bareboat

10 berths4 cabins12 m2008
from
€1,680
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Nadamas

Nadamas

Crewed

8 berths4 cabins24 m2022
from
€39,200
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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.