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 31 of 82

Ceto

Ceto

Bareboat

10 berths4 cabins14 m2019
from
€2,700
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Joanne

Joanne

Bareboat

10 berths4 cabins14 m2019
from
€2,950
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Lisabet

Lisabet

Bareboat

10 berths4 cabins14 m2018
from
€1,850
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Madicken

Madicken

Bareboat

10 berths4 cabins14 m2018
from
€1,850
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Katajina

Katajina

Bareboat

10 berths4 cabins14 m2020
from
€2,050
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Nadine

Nadine

Bareboat

10 berths4 cabins14 m2020
from
€2,050
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Rubato

Rubato

Bareboat

10 berths4 cabins14 m2020
from
€1,800
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Amigo

Amigo

Bareboat

10 berths4 cabins14 m2020
from
€2,430
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Familia

Familia

Bareboat

9 berths4 cabins14 m2020
from
€1,906
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Adventure Planet

Adventure Planet

Bareboat

10 berths4 cabins14 m2020
from
€2,380
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Wonder Planet

Wonder Planet

Bareboat

10 berths4 cabins14 m2020
from
€2,400
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Sylke

Sylke

Bareboat

10 berths4 cabins14 m2020
from
€400
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Elsa

Elsa

Bareboat

10 berths4 cabins14 m2019
from
€1,800
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Petra

Petra

Bareboat

10 berths4 cabins14 m2020
from
€2,500
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Mania Planet

Mania Planet

Bareboat

10 berths4 cabins14 m2021
from
€2,500
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Discovery Planet

Discovery Planet

Bareboat

10 berths4 cabins14 m2021
from
€2,380
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Aruna

Aruna

Bareboat

10 berths4 cabins14 m2017
from
€2,000
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Alila III15% · Last minute

Alila III

Bareboat

10 berths4 cabins14 m2017
from
€1,550
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Harvey

Harvey

Bareboat

10 berths4 cabins14 m2017
from
€2,000
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Vanilla

Vanilla

Bareboat

8 berths4 cabins14 m2020
from
€2,200
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Kosmopolitan

Kosmopolitan

Bareboat

10 berths4 cabins14 m2019
from
€2,000
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Dream Weaver

Dream Weaver

Bareboat

8 berths4 cabins14 m2020
from
€2,200
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Dioni

Dioni

Bareboat

10 berths4 cabins14 m2020
from
€3,600
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Athi Available

Athi

Bareboat

8 berths4 cabins14 m2017
from
€2,200
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Erco

Erco

Bareboat

10 berths4 cabins14 m2017
from
€2,000
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Mincipesa

Mincipesa

Bareboat

10 berths4 cabins14 m2019
from
€1,100
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Aquilo

Aquilo

Bareboat

10 berths4 cabins14 m2016
from
€3,200
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Diego

Diego

Bareboat

10 berths4 cabins14 m2018
from
€3,200
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Despoina

Despoina

Bareboat

10 berths4 cabins14 m2020
from
€2,200
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Carpe Diem

Carpe Diem

Bareboat

8 berths4 cabins14 m2020
from
€2,200
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Cygnus

Cygnus

Bareboat

10 berths4 cabins14 m2018
from
€3,200
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Good Luck

Good Luck

Bareboat

10 berths4 cabins14 m2018
from
€1,000
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Nearchos

Nearchos

Bareboat

10 berths4 cabins14 m2019
from
€3,200
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Zenith

Zenith

Bareboat

10 berths4 cabins14 m2019
from
€2,800
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Millennium Falcon

Millennium Falcon

Bareboat

10 berths4 cabins14 m2019
from
€2,200
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Ava

Ava

Bareboat

10 berths4 cabins14 m2020
from
€1,900
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Daiquiri

Daiquiri

Bareboat

10 berths4 cabins14 m2018
from
€2,750
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Pinacolada

Pinacolada

Bareboat

10 berths4 cabins14 m2017
from
€2,200
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Ritmico

Ritmico

Bareboat

9 berths4 cabins14 m2018
from
€2,000
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Avalon II

Avalon II

Bareboat

8 berths3 cabins14 m2017
from
€2,400
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Malin

Malin

Bareboat

8 berths3 cabins14 m2018
from
€1,950
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Fantasea

Fantasea

Bareboat

6 berths3 cabins14 m2018
from
€2,000
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Siri

Siri

Bareboat

8 berths3 cabins14 m2016
from
€1,100
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Fantasea

Fantasea

Bareboat

6 berths3 cabins14 m2018
from
€1,700
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Tequila Night

Tequila Night

Bareboat

8 berths3 cabins14 m2020
from
€2,850
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Ibis30% · Last minute

Ibis

Bareboat

12 berths5 cabins14 m2019
from
€950
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Fish N'Chips

Fish N'Chips

Bareboat

12 berths5 cabins14 m2019
from
€1,650
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Salted Caramel

Salted Caramel

Bareboat

12 berths5 cabins14 m2019
from
€1,650
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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.