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 64 of 82

Mamakita

Mamakita

Bareboat

9 berths4 cabins16 m2020
from
€2,500
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Full Moon

Full Moon

Bareboat

12 berths5 cabins16 m2019
from
€2,300
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Nireas

Nireas

Bareboat

10 berths4 cabins16 m2020
from
€2,500
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Panda II

Panda II

Bareboat

12 berths5 cabins16 m2022
from
€2,800
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Obelix

Obelix

Bareboat

11 berths5 cabins16 m2022
from
€2,600
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Living in sea

Living in sea

Bareboat

10 berths4 cabins16 m2022
from
€2,700
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Bambi

Bambi

Bareboat

11 berths5 cabins16 m2022
from
€2,600
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Flipper

Flipper

Bareboat

12 berths5 cabins16 m2023
from
€3,900
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Demilia Star

Demilia Star

Bareboat

10 berths4 cabins16 m2020
from
€2,500
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Dune

Dune

Bareboat

13 berths5 cabins16 m2024
from
€2,800
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Sunday Girl

Sunday Girl

Bareboat

10 berths4 cabins16 m2024
from
€1,499
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Amelia

Amelia

Bareboat

11 berths5 cabins16 m2018
from
€2,690
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Sea Eagle II

Sea Eagle II

Bareboat

12 berths6 cabins16 m2023
from
€4,369
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Cloudy Bay

Cloudy Bay

Bareboat

9 berths3 cabins16 m2020
from
€3,300
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Marny

Marny

Bareboat

9 berths3 cabins16 m2026
from
€2,800
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My Way

My Way

Bareboat

11 berths4 cabins16 m2022
from
€3,250
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Myrdia

Myrdia

Bareboat

10 berths4 cabins16 m2018
from
€2,500
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Shine

Shine

Bareboat

12 berths6 cabins16 m2019
from
€2,425
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Antonios

Antonios

Bareboat

12 berths5 cabins16 m2019
from
€2,250
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Famiglia

Famiglia

Bareboat

12 berths5 cabins16 m2019
from
€3,200
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Calypso

Calypso

Bareboat

12 berths5 cabins16 m2019
from
€2,700
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Brando

Brando

Bareboat

11 berths5 cabins16 m2019
from
€3,800
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Viennastar

Viennastar

Bareboat

11 berths5 cabins16 m2019
from
€2,700
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Jupiter

Jupiter

Bareboat

12 berths5 cabins16 m2020
from
€1,700
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Air 1

Air 1

Bareboat

12 berths5 cabins16 m2020
from
€1,700
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Pearl Dreams

Pearl Dreams

Bareboat

12 berths5 cabins16 m2020
from
€3,000
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Babakita

Babakita

Bareboat

11 berths5 cabins16 m2020
from
€2,500
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Elise

Elise

Bareboat

13 berths5 cabins16 m2020
from
€4,550
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Salt Water

Salt Water

Bareboat

11 berths5 cabins16 m2020
from
€3,200
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Jack

Jack

Bareboat

13 berths5 cabins16 m2021
from
€3,760
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Infinity

Infinity

Bareboat

12 berths5 cabins16 m2020
from
€3,500
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Cuba Libre

Cuba Libre

Bareboat

11 berths5 cabins16 m2021
from
€2,500
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Orion

Orion

Bareboat

12 berths5 cabins16 m2021
from
€2,500
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Freyja

Freyja

Bareboat

11 berths5 cabins16 m2020
from
€2,500
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Yria

Yria

Bareboat

11 berths5 cabins16 m2022
from
€2,700
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Carpe Diem

Carpe Diem

Bareboat

11 berths5 cabins16 m2022
from
€2,700
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Escape

Escape

Bareboat

13 berths5 cabins16 m2022
from
€2,700
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Tsuki

Tsuki

Bareboat

12 berths5 cabins16 m2020
from
€3,600
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Elettra

Elettra

Bareboat

13 berths5 cabins16 m2022
from
€3,070
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Orsa 4

Orsa 4

Bareboat

13 berths5 cabins16 m2022
from
€4,010
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Lara

Lara

Bareboat

13 berths5 cabins16 m2022
from
€3,970
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Reboot

Reboot

Bareboat

13 berths5 cabins16 m2022
from
€3,250
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Black Swan

Black Swan

Bareboat

11 berths5 cabins16 m2019
from
€3,200
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Anna

Anna

Bareboat

12 berths5 cabins16 m2020
from
€3,000
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Annezia Star

Annezia Star

Bareboat

13 berths5 cabins16 m2022
from
€2,700
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O. P

O. P

Bareboat

12 berths5 cabins16 m2018
from
€3,800
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South Point

South Point

Bareboat

12 berths5 cabins16 m2018
from
€3,100
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Mighty M

Mighty M

Bareboat

13 berths5 cabins16 m2023
from
€2,800
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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.