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 60 of 82

Princess Mia

Princess Mia

Bareboat

12 berths5 cabins15 m2020
from
€1,550
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Whisper

Whisper

Bareboat

12 berths5 cabins15 m2020
from
€2,700
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Vienna Princess

Vienna Princess

Bareboat

12 berths5 cabins15 m2020
from
€2,100
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Kalmi

Kalmi

Bareboat

10 berths5 cabins15 m2020
from
€3,780
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Everest

Everest

Bareboat

10 berths5 cabins15 m2021
from
€2,600
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Kos 46.7

Kos 46.7

Bareboat

10 berths5 cabins15 m2020
from
€2,200
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Kos 46.8

Kos 46.8

Bareboat

10 berths5 cabins15 m2020
from
€2,200
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Rebekka Blue

Rebekka Blue

Bareboat

10 berths5 cabins15 m2020
from
€2,300
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Bar-Bar

Bar-Bar

Bareboat

10 berths5 cabins15 m2020
from
€2,240
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Speechless

Speechless

Bareboat

12 berths5 cabins15 m2020
from
€1,800
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Athanasia

Athanasia

Bareboat

10 berths5 cabins15 m2020
from
€3,780
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Luna

Luna

Bareboat

12 berths5 cabins15 m2021
from
€3,190
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Emma

Emma

Bareboat

12 berths5 cabins15 m2021
from
€3,190
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Paradisea

Paradisea

Bareboat

10 berths5 cabins15 m2021
from
€2,300
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Zoe

Zoe

Bareboat

12 berths5 cabins15 m2022
from
€3,250
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Mary Too

Mary Too

Bareboat

12 berths5 cabins15 m2022
from
€3,780
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Nora

Nora

Bareboat

12 berths5 cabins15 m2022
from
€2,600
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Ludi

Ludi

Bareboat

12 berths5 cabins15 m2022
from
€2,600
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Evi

Evi

Bareboat

10 berths5 cabins15 m2022
from
€2,300
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Kos 46.9

Kos 46.9

Bareboat

10 berths5 cabins15 m2022
from
€2,600
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Chrisel

Chrisel

Bareboat

10 berths5 cabins15 m2020
from
€2,280
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Dream

Dream

Bareboat

10 berths5 cabins15 m2023
from
€2,200
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Joy's Grace

Joy's Grace

Bareboat

10 berths5 cabins15 m2020
from
€1,582
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Summer Spirit

Summer Spirit

Bareboat

12 berths5 cabins15 m2023
from
€2,400
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BreezY

BreezY

Bareboat

12 berths5 cabins15 m2023
from
€3,860
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Gkilia Mare

Gkilia Mare

Bareboat

10 berths5 cabins15 m2023
from
€2,300
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Ilia

Ilia

Bareboat

10 berths5 cabins15 m2022
from
€2,526
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Ostria

Ostria

Bareboat

10 berths5 cabins15 m2019
from
€2,700
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Marilyn

Marilyn

Bareboat

10 berths5 cabins15 m2019
from
€1,485
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Larimar

Larimar

Bareboat

10 berths5 cabins15 m2023
from
€3,780
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Ivy

Ivy

Bareboat

12 berths5 cabins15 m2024
from
€1,900
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Ostria

Ostria

Bareboat

10 berths5 cabins15 m2019
from
€2,190
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Arianna

Arianna

Bareboat

12 berths5 cabins15 m2024
from
€3,190
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Dommie

Dommie

Bareboat

12 berths5 cabins15 m2024
from
€1,900
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Bellagio

Bellagio

Bareboat

10 berths5 cabins15 m2024
from
€2,900
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Lella Belle

Lella Belle

Bareboat

10 berths5 cabins15 m2024
from
€2,200
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Bumblebee

Bumblebee

Bareboat

12 berths5 cabins15 m2024
from
€1,850
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Amorino

Amorino

Bareboat

12 berths5 cabins15 m2024
from
€3,400
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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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Namaka

Namaka

Bareboat

12 berths5 cabins15 m2021
from
€3,000
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Valvento

Valvento

Bareboat

12 berths5 cabins15 m2023
from
€3,100
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Amore di Mare

Amore di Mare

Bareboat

12 berths5 cabins15 m2022
from
€1,653
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Vento di Mare

Vento di Mare

Bareboat

10 berths5 cabins15 m2021
from
€1,618
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Pura Vida

Pura Vida

Bareboat

12 berths5 cabins15 m2023
from
€1,740
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Capriccio

Capriccio

Bareboat

10 berths5 cabins15 m2020
from
€2,700
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Sail Away

Sail Away

Bareboat

10 berths5 cabins15 m2019
from
€2,700
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Chrisel

Chrisel

Bareboat

10 berths5 cabins15 m2020
price on enquiry
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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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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

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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.