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 61 of 82

Circe

Circe

Bareboat

12 berths5 cabins15 m2025
from
€3,470
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Bar-Bar

Bar-Bar

Bareboat

10 berths5 cabins15 m2020
from
€3,780
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Liberty

Liberty

Bareboat

12 berths5 cabins15 m2022
from
€2,300
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Dancing Queen

Dancing Queen

Bareboat

12 berths5 cabins15 m2019
from
€1,700
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Enjoyablue

Enjoyablue

Bareboat

10 berths5 cabins15 m2020
from
€1,000
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Athena 5

Athena 5

Bareboat

10 berths5 cabins15 m2023
from
€3,000
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Okiroi

Okiroi

Bareboat

10 berths5 cabins15 m2020
from
€2,300
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Luna

Luna

Bareboat

10 berths5 cabins15 m2025
from
€2,300
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Ariel

Ariel

Bareboat

12 berths5 cabins15 m2024
from
€1,850
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Blue sky

Blue sky

Bareboat

12 berths5 cabins15 m2024
from
€1,850
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Bumblebee

Bumblebee

Bareboat

12 berths5 cabins15 m2024
from
€1,850
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Dommie

Dommie

Bareboat

12 berths5 cabins15 m2024
from
€1,900
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Ivy

Ivy

Bareboat

12 berths5 cabins15 m2024
from
€1,900
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Princess Mia

Princess Mia

Bareboat

12 berths5 cabins15 m2020
from
€1,550
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Summer Spirit

Summer Spirit

Bareboat

12 berths5 cabins15 m2023
from
€2,400
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Eros

Eros

Bareboat

10 berths5 cabins15 m2025
from
€2,300
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Tria

Tria

Bareboat

12 berths5 cabins15 m2025
from
€2,300
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Paula

Paula

Bareboat

12 berths5 cabins15 m2026
from
€3,400
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Brisnik

Brisnik

Bareboat

12 berths5 cabins15 m2026
from
€2,300
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Layla

Layla

Bareboat

12 berths5 cabins15 m2021
from
€3,800
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Folie Douce

Folie Douce

Bareboat

12 berths5 cabins15 m2023
from
€3,590
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Cookie

Cookie

Bareboat

10 berths5 cabins15 m2024
from
€3,500
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Bieckert20% · Last minute

Bieckert

Bareboat

12 berths5 cabins15 m2025
from
€2,890
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My Course

My Course

Bareboat

8 berths3 cabins15 m2020
from
€1,500
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Air 2

Air 2

Bareboat

8 berths3 cabins15 m2020
from
€1,500
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wunderbar

wunderbar

Bareboat

6 berths3 cabins15 m2020
from
€3,100
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Thetis

Thetis

Bareboat

8 berths3 cabins15 m2023
from
€3,300
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Kebiwan

Kebiwan

Bareboat

6 berths3 cabins15 m2021
from
€2,500
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Pebbles

Pebbles

Bareboat

8 berths3 cabins15 m2025
from
€2,300
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Family Spirit

Family Spirit

Bareboat

8 berths3 cabins15 m2020
from
€2,440
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Anse Soleil

Anse Soleil

Bareboat

6 berths3 cabins15 m2023
from
€1,700
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Kebiwan

Kebiwan

Bareboat

8 berths3 cabins15 m2021
from
€3,780
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Andiamo

Andiamo

Bareboat

11 berths4 cabins15 m2020
from
€3,300
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Esperanza

Esperanza

Bareboat

12 berths5 cabins15 m2021
from
€3,150
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Almyra

Almyra

Bareboat

10 berths4 cabins15 m2019
from
€2,300
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Ellaida

Ellaida

Bareboat

10 berths4 cabins15 m2019
from
€2,800
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Antonela M

Antonela M

Bareboat

10 berths4 cabins15 m2019
from
€3,041
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Auf Kurs

Auf Kurs

Bareboat

10 berths4 cabins15 m2020
from
€1,100
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Ladybug

Ladybug

Bareboat

10 berths4 cabins15 m2020
from
€1,100
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Lambda

Lambda

Bareboat

10 berths4 cabins15 m2020
from
€1,100
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Sasool

Sasool

Bareboat

10 berths4 cabins15 m2020
from
€1,100
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Anne

Anne

Bareboat

10 berths4 cabins15 m2020
from
€1,100
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Saturn

Saturn

Bareboat

10 berths4 cabins15 m2020
from
€1,100
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Arabella

Arabella

Bareboat

10 berths4 cabins15 m2020
from
€1,100
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Sail Delta

Sail Delta

Bareboat

8 berths4 cabins15 m2020
from
€2,500
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July

July

Bareboat

8 berths4 cabins15 m2020
from
€2,320
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Aeolian Melody

Aeolian Melody

Bareboat

10 berths4 cabins15 m2021
from
€2,600
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Nalu

Nalu

Bareboat

10 berths4 cabins15 m2020
from
€1,250
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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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New sailors, beginners or seasoned skippers — tell us when, where, and how many. we send three real options the same day. No spam, no fluff, no commitment.

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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.