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 30 of 82

Full Moon

Full Moon

Bareboat

10 berths4 cabins14 m2024
from
€1,400
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Dama

Dama

Bareboat

10 berths4 cabins14 m2024
from
€3,300
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Fortissimo

Fortissimo

Bareboat

10 berths4 cabins14 m2025
from
€2,200
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Presto

Presto

Bareboat

10 berths4 cabins14 m2025
from
€2,200
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Adagio

Adagio

Bareboat

10 berths4 cabins14 m2025
from
€2,200
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Furioso

Furioso

Bareboat

10 berths4 cabins14 m2025
from
€2,200
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Virtuoso

Virtuoso

Bareboat

10 berths4 cabins14 m2025
from
€2,200
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One Heart

One Heart

Bareboat

10 berths4 cabins14 m2025
from
€2,400
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Jazz

Jazz

Bareboat

10 berths4 cabins14 m2025
from
€1,500
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Blues

Blues

Bareboat

10 berths4 cabins14 m2025
from
€1,500
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Funk

Funk

Bareboat

10 berths4 cabins14 m2025
from
€1,500
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Soul

Soul

Bareboat

10 berths4 cabins14 m2025
from
€1,500
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Alfasyr

Alfasyr

Bareboat

8 berths4 cabins14 m2024
from
€3,200
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Payidar

Payidar

Bareboat

8 berths4 cabins14 m2025
from
€2,200
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Faidra25% · Last minute

Faidra

Bareboat

8 berths4 cabins14 m2026
from
€3,180
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Diomede

Diomede

Bareboat

10 berths4 cabins14 m2025
from
€3,850
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Happy AS

Happy AS

Bareboat

10 berths4 cabins14 m2004
from
€1,680
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Jonathan Pink

Jonathan Pink

Bareboat

9 berths4 cabins14 m2004
from
€1,600
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Maroussa

Maroussa

Bareboat

10 berths4 cabins14 m2015
from
€2,100
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Grace

Grace

Bareboat

8 berths4 cabins14 m2015
from
€2,350
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Pasja

Pasja

Bareboat

7 berths4 cabins14 m1998
from
€5,890
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Get Lucky

Get Lucky

Bareboat

10 berths4 cabins14 m2016
from
€2,250
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4 You

4 You

Bareboat

10 berths4 cabins14 m2016
from
€900
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Asia

Asia

Bareboat

10 berths4 cabins14 m2016
from
€2,540
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Neptune Planet

Neptune Planet

Bareboat

10 berths4 cabins14 m2016
from
€2,080
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Almar

Almar

Bareboat

10 berths4 cabins14 m2017
from
€2,500
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Carina

Carina

Bareboat

10 berths4 cabins14 m2017
from
€1,000
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Chuck

Chuck

Bareboat

10 berths4 cabins14 m2017
from
€1,000
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Santa Rosa

Santa Rosa

Bareboat

10 berths4 cabins14 m2017
from
€1,000
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Alba 1

Alba 1

Bareboat

10 berths4 cabins14 m2017
from
€2,500
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Fun Planet

Fun Planet

Bareboat

10 berths4 cabins14 m2017
from
€2,180
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Eva

Eva

Bareboat

10 berths4 cabins14 m2017
from
€1,700
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Podere Sapaio

Podere Sapaio

Bareboat

9 berths4 cabins14 m2017
from
€3,000
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Pinacolada

Pinacolada

Bareboat

10 berths4 cabins14 m2017
from
€2,100
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Sulaco

Sulaco

Bareboat

10 berths4 cabins14 m2017
price on enquiry
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Esra15% · Last minute

Esra

Bareboat

10 berths4 cabins14 m2018
from
€1,552
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Ocean Tango

Ocean Tango

Bareboat

10 berths4 cabins14 m2018
from
€1,000
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Horido

Horido

Bareboat

10 berths4 cabins14 m2018
from
€1,000
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Private dancer II

Private dancer II

Bareboat

10 berths4 cabins14 m2018
from
€2,500
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Vaiana

Vaiana

Bareboat

10 berths4 cabins14 m2018
from
€3,350
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Divna15% · Last minute

Divna

Bareboat

10 berths4 cabins14 m2018
from
€1,552
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Alegro

Alegro

Bareboat

10 berths4 cabins14 m2018
from
€2,200
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Lola

Lola

Bareboat

10 berths4 cabins14 m2018
from
€1,880
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Mincipesa

Mincipesa

Bareboat

10 berths4 cabins14 m2019
from
€1,100
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Vanilla Sky

Vanilla Sky

Bareboat

10 berths4 cabins14 m2019
from
€1,650
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Summer Planet

Summer Planet

Bareboat

10 berths4 cabins14 m2019
from
€2,300
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Fivek

Fivek

Bareboat

10 berths4 cabins14 m2019
from
€2,700
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Odysseas

Odysseas

Bareboat

10 berths4 cabins14 m2019
from
€3,350
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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.