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 72 of 82

Aquaholic

Aquaholic

Bareboat

8 berths3 cabins12 m2019
from
€2,000
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Aris25% · Last minute

Aris

Bareboat

6 berths3 cabins12 m2020
from
€2,460
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Elcano

Elcano

Bareboat

6 berths3 cabins12 m2020
from
€1,850
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Lara

Lara

Bareboat

8 berths3 cabins12 m2020
from
€1,650
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Locean

Locean

Bareboat

6 berths3 cabins12 m2021
from
€1,850
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Geva X

Geva X

Bareboat

6 berths3 cabins12 m2020
from
€1,900
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Sea Tamer

Sea Tamer

Bareboat

8 berths3 cabins12 m2020
from
€2,000
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Chimera

Chimera

Bareboat

8 berths3 cabins12 m2021
from
€1,850
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Borgeri

Borgeri

Bareboat

8 berths3 cabins12 m2021
from
€2,600
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Sea Whisper

Sea Whisper

Bareboat

6 berths3 cabins12 m2021
from
€1,900
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Nami

Nami

Bareboat

8 berths3 cabins12 m2021
from
€1,900
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Diona

Diona

Bareboat

8 berths3 cabins12 m2021
from
€1,471
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Deba

Deba

Bareboat

8 berths3 cabins12 m2021
from
€2,570
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Rea

Rea

Bareboat

8 berths3 cabins12 m2022
from
€1,501
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Vague

Vague

Bareboat

8 berths3 cabins12 m2021
from
€2,424
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Aloha

Aloha

Bareboat

8 berths3 cabins12 m2022
from
€2,900
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Evelyne

Evelyne

Bareboat

7 berths3 cabins12 m2022
from
€1,700
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Marianna

Marianna

Bareboat

8 berths3 cabins12 m2022
from
€2,500
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Aella

Aella

Bareboat

8 berths3 cabins12 m2022
from
€1,900
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Suncity 3

Suncity 3

Bareboat

6 berths3 cabins12 m2021
from
€2,500
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Shaken Not Stirred

Shaken Not Stirred

Bareboat

8 berths3 cabins12 m2022
from
€2,570
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Feel The Magic

Feel The Magic

Bareboat

6 berths3 cabins12 m2022
from
€2,650
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Anassa

Anassa

Bareboat

8 berths3 cabins12 m2020
from
€2,050
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Barracuda

Barracuda

Bareboat

8 berths3 cabins12 m2022
from
€2,300
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Della Grazia

Della Grazia

Bareboat

8 berths3 cabins12 m2021
from
€2,050
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High Time

High Time

Bareboat

8 berths3 cabins12 m2021
from
€2,050
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Kallisto

Kallisto

Bareboat

8 berths3 cabins12 m2019
from
€2,050
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Konstantinos

Konstantinos

Bareboat

8 berths3 cabins12 m2020
from
€2,050
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Salty

Salty

Bareboat

8 berths3 cabins12 m2020
from
€2,050
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Sylphie

Sylphie

Bareboat

8 berths3 cabins12 m2020
from
€2,050
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Tento

Tento

Bareboat

8 berths3 cabins12 m2021
from
€2,050
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Thalia

Thalia

Bareboat

8 berths3 cabins12 m2022
from
€2,570
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Wind Kiss

Wind Kiss

Bareboat

8 berths3 cabins12 m2022
from
€2,570
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Artemis

Artemis

Bareboat

8 berths3 cabins12 m2022
from
€2,500
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Freya

Freya

Bareboat

8 berths3 cabins12 m2023
from
€1,532
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Baghera

Baghera

Bareboat

8 berths3 cabins12 m2023
from
€1,850
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Marelli20% · Last minute

Marelli

Bareboat

8 berths3 cabins12 m2023
from
€1,360
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Laertes

Laertes

Bareboat

8 berths3 cabins12 m2023
from
€2,300
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Star Rene

Star Rene

Bareboat

8 berths3 cabins12 m2023
from
€2,300
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Pangeo

Pangeo

Bareboat

8 berths3 cabins12 m2023
from
€2,300
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Liliane

Liliane

Bareboat

8 berths3 cabins12 m2023
from
€2,300
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Milla

Milla

Bareboat

7 berths3 cabins12 m2023
from
€1,800
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Kingfisher

Kingfisher

Bareboat

7 berths3 cabins12 m2023
from
€1,800
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Sky Kiss

Sky Kiss

Bareboat

8 berths3 cabins12 m2021
from
€2,570
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Lucia

Lucia

Bareboat

8 berths3 cabins12 m2023
from
€2,250
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First Date

First Date

Bareboat

6 berths3 cabins12 m2023
from
€1,500
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Pnoe

Pnoe

Bareboat

6 berths3 cabins12 m2023
from
€1,900
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Alma Libre VI

Alma Libre VI

Bareboat

8 berths3 cabins12 m2020
from
€1,640
View →

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.