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 44 of 82

Brukus

Brukus

Bareboat

8 berths3 cabins11 m2019
from
€1,020
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Fany

Fany

Bareboat

8 berths3 cabins11 m2020
from
€1,400
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Sweet Summer

Sweet Summer

Bareboat

8 berths3 cabins11 m2021
from
€1,080
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Jolana

Jolana

Bareboat

8 berths3 cabins11 m2019
from
€1,040
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Chablis20% · Last minute

Chablis

Bareboat

8 berths3 cabins11 m2020
from
€1,200
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Smiley

Smiley

Bareboat

8 berths3 cabins11 m2023
from
€1,220
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Atlas

Atlas

Bareboat

7 berths3 cabins11 m2021
from
€2,290
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Barcelona

Barcelona

Bareboat

8 berths3 cabins11 m2023
from
€1,180
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Calypso

Calypso

Bareboat

7 berths3 cabins11 m2022
from
€1,990
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Tecla

Tecla

Bareboat

7 berths3 cabins11 m2023
from
€2,320
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Medusa III

Medusa III

Bareboat

7 berths3 cabins11 m2022
from
€1,500
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FuFu

FuFu

Bareboat

8 berths3 cabins11 m2023
from
€2,090
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Lady Marga

Lady Marga

Bareboat

6 berths3 cabins11 m2022
from
€2,200
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Odyssee

Odyssee

Bareboat

8 berths3 cabins11 m2025
from
€2,750
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Pixtin

Pixtin

Bareboat

6 berths3 cabins11 m2021
from
€2,200
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Flyer Of Lorne

Flyer Of Lorne

Bareboat

8 berths3 cabins12 m2006
from
€1,550
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Aeolus

Aeolus

Bareboat

8 berths3 cabins12 m2007
from
€1,550
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Mara20% · Last minute

Mara

Bareboat

7 berths3 cabins12 m2011
from
€1,250
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Bela

Bela

Bareboat

8 berths3 cabins13 m2024
from
€1,320
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La Brisa

La Brisa

Bareboat

8 berths3 cabins13 m2024
from
€1,440
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Demirs

Demirs

Bareboat

6 berths3 cabins13 m2024
from
€2,220
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Taja

Taja

Bareboat

8 berths3 cabins13 m2025
from
€1,860
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Señorita

Señorita

Bareboat

8 berths3 cabins13 m2025
from
€1,420
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Cleo

Cleo

Bareboat

8 berths3 cabins13 m2025
from
€1,320
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Sundance

Sundance

Bareboat

8 berths3 cabins13 m2025
from
€1,320
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Capi'10

Capi'10

Bareboat

8 berths3 cabins13 m2024
from
€2,100
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Marius

Marius

Bareboat

8 berths3 cabins13 m2025
from
€1,850
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Al Dente

Al Dente

Bareboat

8 berths3 cabins13 m2025
from
€2,000
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Spark

Spark

Bareboat

8 berths3 cabins13 m2026
from
€1,220
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Catch me if you can

Catch me if you can

Bareboat

8 berths3 cabins13 m2026
from
€1,440
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Deep Blue

Deep Blue

Bareboat

8 berths3 cabins12 m2014
from
€1,700
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Kuro Siwo

Kuro Siwo

Bareboat

6 berths3 cabins12 m2017
from
€1,700
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Vega

Vega

Bareboat

8 berths3 cabins12 m2017
from
€1,450
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take a break

take a break

Bareboat

8 berths3 cabins12 m2017
from
€1,140
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Luna

Luna

Bareboat

8 berths3 cabins12 m2017
from
€1,080
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Natali

Natali

Bareboat

8 berths3 cabins12 m2016
from
€1,020
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Talia

Talia

Bareboat

8 berths3 cabins12 m2017
from
€2,270
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Pretty Woman

Pretty Woman

Bareboat

8 berths3 cabins12 m2018
from
€1,120
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Ivy15% · Last minute

Ivy

Bareboat

8 berths3 cabins12 m2015
from
€1,067
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Escape

Escape

Bareboat

6 berths3 cabins12 m2016
from
€1,798
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Mickey

Mickey

Bareboat

8 berths3 cabins12 m2016
from
€1,990
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Eva

Eva

Bareboat

8 berths3 cabins12 m2018
from
€1,650
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Azur

Azur

Bareboat

8 berths3 cabins12 m2019
from
€1,800
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Vivien

Vivien

Bareboat

8 berths3 cabins12 m2019
from
€1,220
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Blue Eagle

Blue Eagle

Bareboat

8 berths3 cabins12 m2019
from
€1,120
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Shrimp

Shrimp

Bareboat

8 berths3 cabins12 m2020
from
€1,700
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Pollux

Pollux

Bareboat

8 berths3 cabins12 m2020
from
€1,180
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Leia

Leia

Bareboat

8 berths3 cabins12 m2020
from
€1,160
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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.