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 54 of 82

Jana

Jana

Bareboat

8 berths3 cabins12 m2023
from
€1,350
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Triton 89

Triton 89

Bareboat

6 berths3 cabins12 m2022
from
€2,080
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Harmonia

Harmonia

Bareboat

8 berths3 cabins12 m2018
from
€2,000
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Gwada

Gwada

Bareboat

7 berths3 cabins12 m2023
from
€1,590
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Diana

Diana

Bareboat

8 berths3 cabins12 m2023
from
€1,550
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Lukas

Lukas

Bareboat

7 berths3 cabins12 m2023
from
€1,450
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Cocco

Cocco

Bareboat

8 berths3 cabins12 m2023
from
€1,750
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Delfino

Delfino

Bareboat

8 berths3 cabins12 m2019
from
€1,800
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Zeus

Zeus

Bareboat

8 berths3 cabins12 m2017
from
€1,850
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Sail Pride

Sail Pride

Bareboat

6 berths3 cabins12 m2024
from
€1,825
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Naima

Naima

Bareboat

8 berths3 cabins12 m2017
from
€2,100
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Ariele

Ariele

Bareboat

8 berths3 cabins12 m2018
from
€2,000
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Jasmine

Jasmine

Bareboat

8 berths3 cabins12 m2017
from
€2,000
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Hydra

Hydra

Bareboat

8 berths3 cabins12 m2018
price on enquiry
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Cvita

Cvita

Bareboat

8 berths3 cabins12 m2019
from
€850
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Luce

Luce

Bareboat

8 berths3 cabins12 m2017
from
€850
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Majano

Majano

Bareboat

8 berths3 cabins12 m2019
from
€1,460
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Sailor Jupiter

Sailor Jupiter

Bareboat

8 berths3 cabins12 m2018
from
€850
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Sailor Mercury

Sailor Mercury

Bareboat

8 berths3 cabins12 m2018
from
€850
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Teodora

Teodora

Bareboat

8 berths3 cabins12 m2022
from
€1,850
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Bohemian Rapsody20% · Last minute

Bohemian Rapsody

Bareboat

8 berths3 cabins12 m2019
from
€1,900
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Vita20% · Last minute

Vita

Bareboat

8 berths3 cabins12 m2022
from
€1,900
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Sea Wolf

Sea Wolf

Bareboat

7 berths3 cabins12 m2021
from
€2,320
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Summer Breeze 1

Summer Breeze 1

Bareboat

4 berths2 cabins12 m2019
from
€2,200
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Arun

Arun

Bareboat

6 berths2 cabins12 m2020
from
€2,700
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Tamara

Tamara

Bareboat

6 berths2 cabins12 m2023
from
€1,400
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Olli

Olli

Bareboat

8 berths3 cabins12 m2014
from
€1,400
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One

One

Bareboat

8 berths3 cabins12 m2016
from
€700
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Rusalka

Rusalka

Bareboat

8 berths3 cabins12 m2016
from
€700
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Solar

Solar

Bareboat

6 berths3 cabins12 m2015
from
€2,300
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Fede

Fede

Bareboat

8 berths3 cabins12 m2016
from
€1,240
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Arsen

Arsen

Bareboat

8 berths3 cabins12 m2016
from
€1,350
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Omega

Omega

Bareboat

8 berths3 cabins12 m2015
from
€1,200
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Ulysses

Ulysses

Bareboat

6 berths3 cabins12 m2014
from
€1,548
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Martine

Martine

Bareboat

8 berths3 cabins12 m2015
from
€1,300
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Monica

Monica

Bareboat

8 berths3 cabins12 m2016
from
€2,100
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Caroline

Caroline

Bareboat

8 berths3 cabins12 m2017
from
€2,000
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Epicteto

Epicteto

Bareboat

8 berths3 cabins12 m2016
from
€1,750
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Rusalka

Rusalka

Bareboat

8 berths3 cabins12 m2016
from
€700
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Kos 38.1

Kos 38.1

Bareboat

8 berths3 cabins12 m2015
from
€1,430
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Toscana

Toscana

Bareboat

8 berths3 cabins12 m2010
price on enquiry
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Arietta

Arietta

Bareboat

7 berths3 cabins12 m2011
from
€1,400
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Violet

Violet

Bareboat

6 berths3 cabins12 m2011
from
€1,250
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Arina

Arina

Bareboat

6 berths3 cabins12 m2008
from
€2,200
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Kos 40.1

Kos 40.1

Bareboat

8 berths4 cabins13 m2020
from
€1,900
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Poseidon

Poseidon

Bareboat

10 berths4 cabins13 m2021
from
€2,487
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Fots

Fots

Bareboat

10 berths4 cabins13 m2021
from
€2,800
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Magnum

Magnum

Bareboat

10 berths4 cabins13 m2021
from
€1,900
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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.