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 29 of 82

Blue Moon II

Blue Moon II

Bareboat

8 berths4 cabins13 m2020
from
€2,100
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Blue Moon I

Blue Moon I

Bareboat

8 berths4 cabins13 m2020
from
€2,100
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Magdalena

Magdalena

Bareboat

10 berths4 cabins13 m2020
from
€2,600
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Bibi20% · Last minute

Bibi

Bareboat

10 berths4 cabins13 m2019
from
€1,600
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Thor

Thor

Bareboat

10 berths4 cabins13 m2021
from
€1,100
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Sweetest taboo

Sweetest taboo

Bareboat

10 berths4 cabins13 m2021
from
€2,600
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Tahiri - bareboat

Tahiri - bareboat

Bareboat

10 berths4 cabins13 m2021
from
€3,500
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Sandra

Sandra

Bareboat

8 berths4 cabins13 m2022
from
€2,000
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Sweet

Sweet

Bareboat

8 berths4 cabins13 m2022
from
€2,850
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Esperanza

Esperanza

Bareboat

8 berths4 cabins13 m2022
from
€2,390
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Isabella

Isabella

Bareboat

8 berths4 cabins13 m2022
from
€2,390
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Kaja

Kaja

Bareboat

10 berths4 cabins13 m2023
from
€1,700
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Freya

Freya

Bareboat

10 berths4 cabins13 m2023
from
€3,050
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Nima XI

Nima XI

Bareboat

8 berths4 cabins13 m2021
from
€2,200
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Calypso

Calypso

Bareboat

10 berths4 cabins13 m2023
from
€2,100
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Trinity

Trinity

Bareboat

10 berths4 cabins13 m2023
from
€2,100
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Pyxis

Pyxis

Bareboat

10 berths4 cabins13 m2020
from
€2,200
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Julianna

Julianna

Bareboat

10 berths4 cabins13 m2023
from
€2,400
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Ithaki

Ithaki

Bareboat

10 berths4 cabins13 m2024
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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Kummsal

Kummsal

Bareboat

8 berths4 cabins13 m2021
from
€2,850
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Akira

Akira

Bareboat

10 berths4 cabins13 m2022
from
€3,200
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Pepsi

Pepsi

Bareboat

10 berths4 cabins13 m2024
from
€3,200
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Ventotene

Ventotene

Bareboat

10 berths4 cabins13 m2024
from
€3,200
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Levan

Levan

Bareboat

10 berths4 cabins13 m2019
from
€1,600
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Fiodena

Fiodena

Bareboat

10 berths4 cabins13 m2019
from
€2,950
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Ilio

Ilio

Bareboat

10 berths4 cabins13 m2024
from
€3,500
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Malime

Malime

Bareboat

10 berths4 cabins13 m2021
from
€3,200
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Lana V

Lana V

Bareboat

10 berths4 cabins13 m2019
from
€1,485
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Echo I

Echo I

Bareboat

10 berths4 cabins13 m2020
from
€1,800
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Echo II

Echo II

Bareboat

10 berths4 cabins13 m2020
from
€1,800
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Mojito Sunrise

Mojito Sunrise

Bareboat

10 berths4 cabins13 m2019
from
€2,400
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Horu

Horu

Bareboat

8 berths3 cabins14 m2025
from
€2,500
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Bossa Nova

Bossa Nova

Bareboat

8 berths3 cabins14 m2025
from
€1,900
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Vera

Vera

Bareboat

8 berths3 cabins14 m2025
from
€3,300
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Gimme! Gimme!

Gimme! Gimme!

Bareboat

6 berths3 cabins14 m2026
from
€3,000
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Junior Mary 2

Junior Mary 2

Bareboat

8 berths3 cabins14 m2026
from
€2,600
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Amaco

Amaco

Bareboat

8 berths3 cabins14 m2025
from
€3,000
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Smack5% · Last minute

Smack

Bareboat

8 berths3 cabins14 m2026
from
€2,900
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Experience 2

Experience 2

Bareboat

8 berths3 cabins14 m2026
from
€2,500
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Astrae

Astrae

Bareboat

8 berths3 cabins14 m2025
from
€2,750
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Bosco

Bosco

Bareboat

8 berths3 cabins14 m2025
from
€2,750
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I Have A Dream

I Have A Dream

Bareboat

6 berths3 cabins14 m2025
from
€2,750
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Betty

Betty

Bareboat

6 berths3 cabins14 m2023
from
€4,900
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Leitmotiv II

Leitmotiv II

Bareboat

8 berths3 cabins14 m2005
from
€1,860
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Timeless

Timeless

Bareboat

10 berths4 cabins14 m2024
from
€1,400
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Scooby Doo

Scooby Doo

Bareboat

9 berths4 cabins14 m2024
from
€1,400
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Scooby Doo

Scooby Doo

Bareboat

9 berths4 cabins14 m2024
from
€1,400
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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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Get three sailboat options from the team.

Tell us roughly when, where, and how many. we'll send three sailboat options the same day — three boats, three prices, the trade-offs.

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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

Free quote

Get three real options.

Tell us roughly when and where. we'll send three real boats, three prices, the trade-offs — usually within the hour.