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 68 of 82

min elli20% · Last minute

min elli

Bareboat

6 berths2 cabins10 m2011
from
€600
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Carry On

Carry On

Bareboat

5 berths2 cabins10 m2011
from
€1,450
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Cosma

Cosma

Bareboat

6 berths2 cabins10 m2015
from
€850
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Ribellina

Ribellina

Bareboat

5 berths2 cabins10 m2013
from
€1,300
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Kiki Kiss

Kiki Kiss

Bareboat

6 berths2 cabins10 m2013
from
€1,100
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Kalliste

Kalliste

Bareboat

6 berths2 cabins10 m2010
from
€1,240
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Paola

Paola

Bareboat

5 berths2 cabins10 m2012
from
€1,048
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Marie

Marie

Bareboat

5 berths2 cabins10 m2018
from
€1,400
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Antonija

Antonija

Bareboat

5 berths2 cabins10 m2019
from
€1,450
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Naya

Naya

Bareboat

5 berths2 cabins10 m2019
from
€2,600
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Mara

Mara

Bareboat

5 berths2 cabins10 m2023
from
€2,600
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Anastasia

Anastasia

Bareboat

5 berths2 cabins10 m2025
from
€1,500
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SheShe

SheShe

Bareboat

7 berths3 cabins10 m2015
from
€950
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Gemma

Gemma

Bareboat

7 berths3 cabins10 m2016
from
€1,200
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Cherie Bibi

Cherie Bibi

Bareboat

6 berths3 cabins10 m2016
from
€1,910
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Siberia

Siberia

Bareboat

7 berths3 cabins10 m2015
from
€1,000
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Cha - Cha

Cha - Cha

Bareboat

8 berths3 cabins10 m2017
from
€1,530
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Popeye

Popeye

Bareboat

7 berths3 cabins10 m2017
from
€1,200
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Romana

Romana

Bareboat

7 berths3 cabins10 m2017
from
€1,200
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Sarita

Sarita

Bareboat

6 berths3 cabins10 m2016
from
€2,100
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Castor20% · Last minute

Castor

Bareboat

8 berths3 cabins10 m2019
from
€1,400
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Nana

Nana

Bareboat

8 berths3 cabins10 m2019
from
€1,100
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Afrodite

Afrodite

Bareboat

8 berths3 cabins10 m2017
from
€1,500
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Pelias

Pelias

Bareboat

8 berths3 cabins10 m2017
from
€1,500
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Pelti

Pelti

Bareboat

8 berths3 cabins10 m2017
from
€1,500
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Kora

Kora

Bareboat

6 berths3 cabins10 m2015
from
€1,160
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Nara

Nara

Bareboat

8 berths3 cabins10 m2022
from
€850
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Nala

Nala

Bareboat

6 berths3 cabins10 m2018
from
€1,600
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Sweet Elli20% · Last minute

Sweet Elli

Bareboat

6 berths3 cabins10 m2022
from
€1,170
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gemelli20% · Last minute

gemelli

Bareboat

6 berths3 cabins10 m2023
from
€1,210
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true elli20% · Last minute

true elli

Bareboat

6 berths3 cabins10 m2023
from
€1,210
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Ana

Ana

Bareboat

8 berths3 cabins10 m2023
from
€1,500
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Bliss

Bliss

Bareboat

7 berths3 cabins10 m2016
from
€1,910
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Novara

Novara

Bareboat

6 berths3 cabins10 m2023
from
€1,500
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petit elli20% · Last minute

petit elli

Bareboat

6 berths3 cabins10 m2023
from
€1,210
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Joy Division

Joy Division

Bareboat

8 berths3 cabins10 m2024
from
€1,500
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White Feather

White Feather

Bareboat

8 berths3 cabins10 m2024
from
€1,500
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Why Not

Why Not

Bareboat

8 berths3 cabins10 m2024
from
€1,500
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Nara

Nara

Bareboat

8 berths3 cabins10 m2022
from
€850
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SheShe

SheShe

Bareboat

7 berths3 cabins10 m2015
from
€950
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Zatara

Zatara

Bareboat

8 berths3 cabins10 m2024
from
€1,320
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Horizonte

Horizonte

Bareboat

6 berths3 cabins10 m2016
from
€1,800
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Serineh

Serineh

Bareboat

6 berths3 cabins10 m2025
from
€1,500
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Freeway

Freeway

Bareboat

6 berths3 cabins10 m2025
from
€1,500
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DNA

DNA

Bareboat

6 berths3 cabins10 m2018
from
€1,500
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Grape

Grape

Bareboat

8 berths3 cabins10 m2018
from
€1,100
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Estrella

Estrella

Bareboat

8 berths3 cabins10 m2021
from
€1,300
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Off The Clock

Off The Clock

Bareboat

6 berths3 cabins10 m2020
from
€475
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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.