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.

3,934 yachts · page 38 of 82

Lyra

Lyra

Bareboat

8 berths3 cabins12 m2017
from
€1,400
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Orca.I

Orca.I

Bareboat

8 berths3 cabins12 m2017
from
€1,680
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Hope E.

Hope E.

Bareboat

8 berths3 cabins12 m2017
from
€1,680
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Tino

Tino

Bareboat

8 berths3 cabins12 m2017
from
€1,595
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Stardust

Stardust

Bareboat

8 berths3 cabins12 m2017
from
€1,000
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Dos Bandidos

Dos Bandidos

Bareboat

8 berths3 cabins12 m2018
from
€1,050
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Danu

Danu

Bareboat

8 berths3 cabins12 m2019
from
€1,400
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Janina

Janina

Bareboat

8 berths3 cabins12 m2019
from
€800
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Anadea

Anadea

Bareboat

8 berths3 cabins12 m2017
from
€1,629
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Despacito

Despacito

Bareboat

8 berths3 cabins12 m2018
from
€1,696
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Maloi

Maloi

Bareboat

8 berths3 cabins12 m2018
from
€1,696
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Mona

Mona

Bareboat

8 berths3 cabins12 m2018
from
€1,696
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Fortiss

Fortiss

Bareboat

8 berths3 cabins12 m2019
from
€1,100
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Silente

Silente

Bareboat

8 berths3 cabins12 m2016
from
€2,350
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Iron man

Iron man

Bareboat

8 berths3 cabins12 m2019
from
€1,400
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Marco Polo

Marco Polo

Bareboat

8 berths3 cabins12 m2019
from
€1,705
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Hulk

Hulk

Bareboat

8 berths3 cabins12 m2019
from
€1,705
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Black Panther

Black Panther

Bareboat

8 berths3 cabins12 m2019
from
€1,705
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Tariq

Tariq

Bareboat

8 berths3 cabins12 m2018
from
€800
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Thor

Thor

Bareboat

8 berths3 cabins12 m2019
from
€1,370
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Desideria

Desideria

Bareboat

8 berths3 cabins12 m2017
from
€800
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Janina

Janina

Bareboat

8 berths3 cabins12 m2019
from
€800
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Laali

Laali

Bareboat

8 berths3 cabins12 m2016
from
€700
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Tariq

Tariq

Bareboat

8 berths3 cabins12 m2018
from
€800
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Happy

Happy

Bareboat

8 berths3 cabins12 m2019
from
€1,850
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Pasithea

Pasithea

Bareboat

8 berths3 cabins12 m2019
from
€800
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Desideria

Desideria

Bareboat

8 berths3 cabins12 m2017
from
€800
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Fides

Fides

Bareboat

8 berths3 cabins12 m2017
from
€1,550
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Google

Google

Bareboat

8 berths3 cabins12 m2018
from
€591
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Evita

Evita

Bareboat

8 berths3 cabins12 m2016
from
€1,680
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Val

Val

Bareboat

8 berths3 cabins12 m2017
from
€1,250
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Shamal

Shamal

Bareboat

8 berths3 cabins12 m2019
from
€850
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Shamal

Shamal

Bareboat

8 berths3 cabins12 m2019
from
€850
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Kate

Kate

Bareboat

8 berths3 cabins12 m2020
from
€1,100
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Plankton

Plankton

Bareboat

8 berths3 cabins12 m2020
from
€1,150
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AirTime 1

AirTime 1

Bareboat

8 berths3 cabins12 m2020
from
€1,150
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Baby Shark

Baby Shark

Bareboat

8 berths3 cabins12 m2020
from
€1,150
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Top Secret

Top Secret

Bareboat

8 berths3 cabins12 m2020
from
€1,450
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Valata

Valata

Bareboat

8 berths3 cabins12 m2022
from
€1,760
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Ciao Bella

Ciao Bella

Bareboat

8 berths3 cabins12 m2022
from
€1,950
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Tonka

Tonka

Bareboat

8 berths3 cabins12 m2022
from
€1,950
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Finola

Finola

Bareboat

8 berths3 cabins12 m2022
from
€1,500
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Oto

Oto

Bareboat

8 berths3 cabins12 m2022
from
€2,035
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Eliana

Eliana

Bareboat

8 berths3 cabins12 m2022
from
€1,760
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Sv. Nikola

Sv. Nikola

Bareboat

8 berths3 cabins12 m2023
from
€1,760
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Fuga

Fuga

Bareboat

8 berths3 cabins12 m2023
from
€1,890
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Kaya

Kaya

Bareboat

8 berths3 cabins12 m2023
from
€1,760
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Lady Blue

Lady Blue

Bareboat

8 berths3 cabins12 m2023
from
€1,550
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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.