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 76 of 82

Loleta

Loleta

Bareboat

8 berths4 cabins13 m2020
from
€2,230
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Ondeck

Ondeck

Bareboat

10 berths4 cabins13 m2019
from
€1,900
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Tolinho

Tolinho

Bareboat

8 berths4 cabins13 m2020
from
€1,900
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Soulmates

Soulmates

Bareboat

10 berths4 cabins13 m2020
from
€2,400
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Mike Charlie

Mike Charlie

Bareboat

8 berths4 cabins13 m2020
from
€1,900
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Eleni

Eleni

Bareboat

10 berths4 cabins13 m2021
from
€2,500
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Lornia

Lornia

Bareboat

8 berths4 cabins13 m2020
from
€3,000
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Anda

Anda

Bareboat

8 berths4 cabins13 m2020
from
€3,000
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Dory

Dory

Bareboat

8 berths4 cabins13 m2021
from
€1,900
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Nymeria

Nymeria

Bareboat

10 berths4 cabins13 m2021
from
€1,900
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Uri

Uri

Bareboat

9 berths4 cabins13 m2022
from
€2,100
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Suncity 4

Suncity 4

Bareboat

8 berths4 cabins13 m2021
from
€2,850
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Uccelli20% · Last minute

Uccelli

Bareboat

10 berths4 cabins13 m2022
from
€1,430
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Almyra 440

Almyra 440

Bareboat

10 berths4 cabins13 m2021
from
€2,600
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Amorgos

Amorgos

Bareboat

10 berths4 cabins13 m2021
from
€2,600
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Apostolis

Apostolis

Bareboat

10 berths4 cabins13 m2020
from
€2,600
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Armonia

Armonia

Bareboat

10 berths4 cabins13 m2021
from
€2,600
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Endeavour

Endeavour

Bareboat

10 berths4 cabins13 m2020
from
€2,600
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Eros

Eros

Bareboat

10 berths4 cabins13 m2019
from
€2,600
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Homesick George

Homesick George

Bareboat

10 berths4 cabins13 m2019
from
€2,600
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Monolith

Monolith

Bareboat

10 berths4 cabins13 m2019
from
€2,600
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Nimertis

Nimertis

Bareboat

10 berths4 cabins13 m2021
from
€2,600
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Orfeas

Orfeas

Bareboat

10 berths4 cabins13 m2022
from
€2,800
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Thivi

Thivi

Bareboat

10 berths4 cabins13 m2019
from
€2,600
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Tommy

Tommy

Bareboat

10 berths4 cabins13 m2020
from
€2,600
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Trinity

Trinity

Bareboat

8 berths4 cabins13 m2023
from
€3,150
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Esperos

Esperos

Bareboat

8 berths4 cabins13 m2022
from
€2,100
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Thousand Sunny

Thousand Sunny

Bareboat

10 berths4 cabins13 m2022
from
€2,800
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Soyka30% · Last minute

Soyka

Bareboat

10 berths4 cabins13 m2023
from
€265
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Vela

Vela

Bareboat

10 berths4 cabins13 m2023
from
€1,663
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Susanna

Susanna

Bareboat

10 berths4 cabins13 m2023
from
€2,680
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Pullan

Pullan

Bareboat

10 berths4 cabins13 m2023
from
€2,680
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Ecstasea

Ecstasea

Bareboat

8 berths4 cabins13 m2023
from
€1,955
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Ocean Song

Ocean Song

Bareboat

10 berths4 cabins13 m2018
from
€1,700
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free elli20% · Last minute

free elli

Bareboat

9 berths4 cabins13 m2023
from
€2,210
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White Rabbit

White Rabbit

Bareboat

8 berths4 cabins13 m2023
from
€3,150
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Dream On

Dream On

Bareboat

9 berths4 cabins13 m2020
from
€2,500
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Irini

Irini

Bareboat

8 berths4 cabins13 m2018
from
€1,700
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Ecstasea

Ecstasea

Bareboat

8 berths4 cabins13 m2023
from
€2,300
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Deep Water

Deep Water

Bareboat

10 berths4 cabins13 m2019
from
€1,700
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Sea Friends

Sea Friends

Bareboat

8 berths4 cabins13 m2023
from
€3,200
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Ikalos

Ikalos

Bareboat

10 berths4 cabins13 m2020
from
€2,090
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JOLLY ROGER

JOLLY ROGER

Bareboat

8 berths4 cabins13 m2023
from
€2,100
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Olympia

Olympia

Bareboat

10 berths4 cabins13 m2020
from
€2,000
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Aeolos

Aeolos

Bareboat

10 berths4 cabins13 m2023
from
€2,800
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Crane

Crane

Bareboat

10 berths4 cabins13 m2023
from
€2,800
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Asteri

Asteri

Bareboat

10 berths4 cabins13 m2023
from
€2,600
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Georgia

Georgia

Bareboat

10 berths4 cabins13 m2018
from
€2,300
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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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