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 39 of 82

Plankton

Plankton

Bareboat

8 berths3 cabins12 m2020
from
€1,150
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Estela

Estela

Bareboat

8 berths3 cabins12 m2020
from
€1,150
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AirTime 1

AirTime 1

Bareboat

8 berths3 cabins12 m2020
from
€1,150
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Funky

Funky

Bareboat

8 berths3 cabins12 m2020
from
€1,900
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Best Secret

Best Secret

Bareboat

8 berths3 cabins12 m2022
from
€1,900
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Tamikaya

Tamikaya

Bareboat

8 berths3 cabins12 m2020
from
€1,700
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Pixi

Pixi

Bareboat

8 berths3 cabins12 m2023
from
€883
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Olelole

Olelole

Bareboat

6 berths3 cabins12 m2022
from
€1,650
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Micky

Micky

Bareboat

6 berths3 cabins12 m2022
from
€1,650
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California

California

Bareboat

10 berths4 cabins14 m2016
from
€1,800
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Lasta30% · Last minute

Lasta

Bareboat

10 berths4 cabins14 m2017
from
€250
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Tightrope

Tightrope

Bareboat

10 berths4 cabins14 m2017
from
€1,000
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Bine

Bine

Bareboat

10 berths4 cabins14 m2017
from
€1,850
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High AS

High AS

Bareboat

10 berths4 cabins14 m2017
from
€2,360
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Indiana

Indiana

Bareboat

10 berths4 cabins14 m2018
from
€1,400
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Vanja

Vanja

Bareboat

10 berths4 cabins14 m2018
from
€1,850
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Anita

Anita

Bareboat

10 berths4 cabins14 m2018
from
€1,830
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Popaj

Popaj

Bareboat

10 berths4 cabins14 m2018
from
€1,700
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Aciano

Aciano

Bareboat

10 berths4 cabins14 m2019
from
€1,850
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Hotspot

Hotspot

Bareboat

10 berths4 cabins14 m2019
from
€1,700
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Adelyna

Adelyna

Bareboat

10 berths4 cabins14 m2018
from
€1,900
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Amiya

Amiya

Bareboat

10 berths4 cabins14 m2018
from
€1,900
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Princess Tena

Princess Tena

Bareboat

10 berths4 cabins14 m2017
from
€1,600
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Skyfall

Skyfall

Bareboat

10 berths4 cabins14 m2016
from
€2,000
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No Limits

No Limits

Bareboat

10 berths4 cabins14 m2019
from
€1,300
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Ibiss

Ibiss

Bareboat

10 berths4 cabins14 m2018
from
€1,220
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Kaminari

Kaminari

Bareboat

10 berths4 cabins14 m2019
from
€1,100
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Heidi

Heidi

Bareboat

10 berths4 cabins14 m2016
from
€1,000
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Tightrope

Tightrope

Bareboat

10 berths4 cabins14 m2017
from
€1,000
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Lion

Lion

Bareboat

10 berths4 cabins14 m2015
from
€1,950
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Star

Star

Bareboat

10 berths4 cabins14 m2016
from
€2,000
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Heidi

Heidi

Bareboat

10 berths4 cabins14 m2016
from
€1,000
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Kaminari

Kaminari

Bareboat

10 berths4 cabins14 m2019
from
€1,100
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Elysium

Elysium

Bareboat

10 berths4 cabins14 m2017
from
€1,700
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Six Friends

Six Friends

Bareboat

10 berths4 cabins14 m2017
from
€1,100
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Six Friends

Six Friends

Bareboat

10 berths4 cabins14 m2017
from
€1,100
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Midnight

Midnight

Bareboat

10 berths4 cabins14 m2017
from
€699
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Vera

Vera

Bareboat

10 berths4 cabins14 m2019
from
€1,537
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Jasmin

Jasmin

Bareboat

10 berths4 cabins14 m2019
from
€1,537
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Alkistis

Alkistis

Bareboat

10 berths4 cabins14 m2015
from
€1,500
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Baby Boo

Baby Boo

Bareboat

10 berths4 cabins14 m2015
from
€1,497
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Jola

Jola

Bareboat

10 berths4 cabins14 m2019
from
€1,750
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Anaya

Anaya

Bareboat

10 berths4 cabins14 m2020
from
€2,090
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Anastasia

Anastasia

Bareboat

10 berths4 cabins14 m2020
from
€1,650
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Eva

Eva

Bareboat

10 berths4 cabins14 m2020
from
€1,650
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Carolina

Carolina

Bareboat

10 berths4 cabins14 m2020
from
€1,650
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Diana

Diana

Bareboat

10 berths4 cabins14 m2020
from
€1,650
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Josephine

Josephine

Bareboat

10 berths4 cabins14 m2020
from
€2,000
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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.