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 28 of 82

Tian

Tian

Bareboat

8 berths4 cabins13 m2022
from
€2,850
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Triumph

Triumph

Bareboat

10 berths4 cabins13 m2022
from
€1,930
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Noah

Noah

Bareboat

10 berths4 cabins13 m2022
from
€3,160
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Hierax

Hierax

Bareboat

8 berths4 cabins13 m2022
from
€2,100
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Kostas

Kostas

Bareboat

8 berths4 cabins13 m2022
from
€1,800
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Hoosier Lady

Hoosier Lady

Bareboat

8 berths4 cabins13 m2021
from
€4,300
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Whisky

Whisky

Bareboat

10 berths4 cabins13 m2023
from
€1,950
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First Love

First Love

Bareboat

8 berths4 cabins13 m2023
from
€1,880
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Billywig

Billywig

Bareboat

8 berths4 cabins13 m2020
from
€1,200
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Thymus

Thymus

Bareboat

8 berths4 cabins13 m2023
from
€1,340
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Penelope

Penelope

Bareboat

6 berths3 cabins13 m2023
from
€4,300
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Armonia

Armonia

Bareboat

8 berths4 cabins13 m2023
from
€2,100
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Brahms

Brahms

Bareboat

8 berths4 cabins13 m2023
from
€3,500
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Dancer

Dancer

Bareboat

6 berths3 cabins13 m2024
from
€4,700
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Catacea

Catacea

Bareboat

10 berths4 cabins13 m2020
from
€2,550
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Kairos

Kairos

Bareboat

10 berths4 cabins13 m2024
from
€2,700
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Alma Libre X

Alma Libre X

Bareboat

10 berths4 cabins13 m2024
from
€2,100
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Nima Xi

Nima Xi

Bareboat

8 berths4 cabins13 m2021
from
€1,800
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Scarlet

Scarlet

Bareboat

8 berths4 cabins13 m2022
from
€3,000
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Hermione

Hermione

Bareboat

8 berths4 cabins13 m2019
from
€2,500
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Ocean Whisper

Ocean Whisper

Bareboat

10 berths4 cabins13 m2020
from
€2,640
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San Luis Blues

San Luis Blues

Bareboat

10 berths4 cabins13 m2023
from
€3,282
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Etosha

Etosha

Bareboat

8 berths4 cabins13 m2022
from
€2,610
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Ocean Whisper

Ocean Whisper

Bareboat

10 berths4 cabins13 m2020
from
€3,300
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Bloody Mary

Bloody Mary

Bareboat

8 berths3 cabins13 m2021
from
€2,000
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Seeadler

Seeadler

Bareboat

8 berths3 cabins13 m2022
from
€1,150
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Opportune Moment

Opportune Moment

Bareboat

6 berths3 cabins13 m2021
from
€5,199
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Feeling Good

Feeling Good

Bareboat

8 berths3 cabins13 m2022
from
€2,500
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Andream

Andream

Bareboat

6 berths3 cabins13 m2022
from
€1,250
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Sunshine Daydream

Sunshine Daydream

Bareboat

6 berths3 cabins13 m2023
from
€4,700
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Si Puo Fare

Si Puo Fare

Bareboat

8 berths3 cabins13 m2023
from
€2,250
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Enki

Enki

Bareboat

6 berths3 cabins13 m2022
from
€2,500
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Lucie5% · Last minute

Lucie

Bareboat

8 berths3 cabins13 m2023
from
€2,700
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Chipon

Chipon

Bareboat

8 berths3 cabins13 m2023
from
€2,900
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Bloody Mary

Bloody Mary

Bareboat

8 berths3 cabins13 m2021
from
€2,100
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Sea Cloud 1

Sea Cloud 1

Bareboat

10 berths4 cabins13 m2019
from
€1,200
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Adriatic Office

Adriatic Office

Bareboat

10 berths4 cabins13 m2019
from
€1,100
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Friendship

Friendship

Bareboat

10 berths4 cabins13 m2019
from
€1,100
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Good Friends

Good Friends

Bareboat

10 berths4 cabins13 m2019
from
€1,100
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Air Princess

Air Princess

Bareboat

10 berths4 cabins13 m2019
from
€1,100
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Vivo

Vivo

Bareboat

10 berths4 cabins13 m2019
from
€1,800
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Moderato

Moderato

Bareboat

10 berths4 cabins13 m2019
from
€1,800
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Lento

Lento

Bareboat

10 berths4 cabins13 m2020
from
€1,800
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Largo

Largo

Bareboat

10 berths4 cabins13 m2020
from
€1,800
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Calando

Calando

Bareboat

10 berths4 cabins13 m2020
from
€1,800
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Amoroso

Amoroso

Bareboat

10 berths4 cabins13 m2020
from
€1,800
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Grazioso

Grazioso

Bareboat

10 berths4 cabins13 m2020
from
€1,800
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Nikolas-Aegeas

Nikolas-Aegeas

Bareboat

8 berths4 cabins13 m2020
from
€2,100
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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.