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 48 of 82

Balena - OW

Balena - OW

Bareboat

10 berths4 cabins15 m2025
from
€2,080
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Captain K

Captain K

Bareboat

10 berths4 cabins15 m2025
from
€2,500
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Okeanida

Okeanida

Bareboat

8 berths4 cabins15 m2025
from
€4,300
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L'after

L'after

Bareboat

10 berths4 cabins15 m2025
from
€3,100
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Doris

Doris

Bareboat

8 berths4 cabins15 m2022
from
€2,880
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Antares

Antares

Bareboat

10 berths4 cabins15 m2026
from
€3,400
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Solace - OW

Solace - OW

Bareboat

10 berths4 cabins15 m2026
from
€1,920
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Stargirl - OW

Stargirl - OW

Bareboat

10 berths4 cabins15 m2026
from
€2,220
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I'm Alone

I'm Alone

Bareboat

10 berths4 cabins15 m2024
from
€2,100
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Vingilot - OW

Vingilot - OW

Bareboat

10 berths4 cabins15 m2025
from
€2,300
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Vingilot - OW

Vingilot - OW

Bareboat

10 berths4 cabins15 m2025
from
€2,300
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Astan

Astan

Bareboat

8 berths4 cabins15 m2024
from
€3,590
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Blue Bonnet af Lovnas - OW

Blue Bonnet af Lovnas - OW

Bareboat

11 berths4 cabins15 m2018
from
€1,480
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Kimi

Kimi

Bareboat

12 berths5 cabins15 m2015
from
€2,400
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Anse

Anse

Bareboat

12 berths5 cabins15 m2018
from
€3,500
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Amarone20% · Last minute

Amarone

Bareboat

11 berths5 cabins15 m2017
from
€1,800
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Evelyn

Evelyn

Bareboat

9 berths4 cabins16 m2022
from
€2,790
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Bright Future

Bright Future

Bareboat

7 berths3 cabins16 m2024
from
€2,890
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Phaedra

Phaedra

Bareboat

10 berths4 cabins16 m2020
from
€3,500
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Charlabelle - OW

Charlabelle - OW

Bareboat

11 berths4 cabins16 m2023
from
€2,220
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Alian

Alian

Bareboat

13 berths5 cabins16 m2019
from
€3,600
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Uptown Girl

Uptown Girl

Bareboat

13 berths5 cabins16 m2019
from
€1,720
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Supernatural

Supernatural

Bareboat

13 berths5 cabins16 m2019
from
€1,880
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Golden Box

Golden Box

Bareboat

13 berths5 cabins16 m2019
from
€2,020
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Attraction

Attraction

Bareboat

13 berths5 cabins16 m2019
from
€1,980
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Pegasus

Pegasus

Bareboat

12 berths5 cabins16 m2019
from
€1,990
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Hamam

Hamam

Bareboat

11 berths5 cabins16 m2019
from
€3,560
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El Grande

El Grande

Bareboat

11 berths5 cabins16 m2019
from
€2,600
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Poseidon

Poseidon

Bareboat

12 berths5 cabins16 m2020
from
€1,990
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Cosmopolitan

Cosmopolitan

Bareboat

13 berths5 cabins16 m2020
from
€1,880
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Khaleesi

Khaleesi

Bareboat

13 berths5 cabins16 m2020
from
€2,020
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Artemis

Artemis

Bareboat

13 berths5 cabins16 m2020
from
€2,800
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Apollo

Apollo

Bareboat

13 berths5 cabins16 m2020
from
€2,800
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Licence to Chill

Licence to Chill

Bareboat

13 berths5 cabins16 m2021
from
€2,120
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Ladies G

Ladies G

Bareboat

12 berths5 cabins16 m2023
from
€3,410
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Adriatiq Scum

Adriatiq Scum

Bareboat

12 berths5 cabins16 m2023
from
€3,410
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Big Blue

Big Blue

Bareboat

12 berths5 cabins16 m2020
from
€2,253
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Big Blue

Big Blue

Bareboat

12 berths6 cabins16 m2020
from
€2,690
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Moby Dick

Moby Dick

Bareboat

13 berths5 cabins16 m2022
from
€2,775
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Charles

Charles

Bareboat

13 berths5 cabins16 m2023
from
€2,850
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Medusa II

Medusa II

Bareboat

12 berths5 cabins16 m2021
from
€2,900
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Neraida

Neraida

Bareboat

12 berths5 cabins16 m2024
from
€3,300
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Box of Chocolate

Box of Chocolate

Bareboat

12 berths5 cabins16 m2025
from
€3,300
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Atena

Atena

Bareboat

11 berths5 cabins16 m2025
from
€4,060
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Quantum Wave

Quantum Wave

Bareboat

12 berths5 cabins16 m2021
from
€2,500
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Aktea

Aktea

Bareboat

12 berths5 cabins16 m2019
from
€3,700
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Poseidon

Poseidon

Bareboat

12 berths5 cabins16 m2020
from
€2,500
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Hugo

Hugo

Bareboat

12 berths5 cabins16 m2022
from
€3,300
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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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Tell us roughly when and where. we'll send three real boats, three prices, the trade-offs — usually within the hour.