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.

3,932 yachts · page 20 of 82

Firewall

Firewall

Bareboat

12 berths5 cabins16 m2014
from
€2,137
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Vela Tonka

Vela Tonka

Bareboat

11 berths5 cabins16 m2018
from
€2,300
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Navarino

Navarino

Bareboat

12 berths5 cabins16 m2016
from
€3,400
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Summer Smile

Summer Smile

Bareboat

11 berths5 cabins16 m2017
from
€2,250
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Nata

Nata

Bareboat

10 berths5 cabins16 m2015
from
€1,700
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Lui

Lui

Bareboat

11 berths5 cabins16 m2018
from
€2,700
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okkio che ti vedo

okkio che ti vedo

Bareboat

11 berths5 cabins16 m2017
from
€3,100
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Thalassa

Thalassa

Bareboat

12 berths5 cabins16 m2019
from
€3,400
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Elpida

Elpida

Bareboat

12 berths5 cabins16 m2019
from
€2,780
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Fantasia

Fantasia

Bareboat

12 berths5 cabins16 m2016
from
€2,620
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Prince John

Prince John

Bareboat

10 berths5 cabins16 m2019
from
€2,000
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Prince Nikolaos

Prince Nikolaos

Bareboat

10 berths5 cabins16 m2019
from
€1,900
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Ivolga30% · Last minute

Ivolga

Bareboat

12 berths5 cabins16 m2020
from
€285
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Bonnytta

Bonnytta

Bareboat

11 berths5 cabins16 m2020
from
€2,300
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Bamboo

Bamboo

Bareboat

10 berths5 cabins16 m2021
from
€3,600
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Marie

Marie

Bareboat

11 berths5 cabins16 m2021
from
€3,090
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Locura

Locura

Bareboat

10 berths5 cabins16 m2015
from
€2,900
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Callisti

Callisti

Bareboat

12 berths5 cabins16 m2016
from
€3,400
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Alissa20% · Last minute

Alissa

Bareboat

10 berths5 cabins16 m2016
from
€2,080
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Seawalker

Seawalker

Bareboat

10 berths5 cabins16 m2022
from
€3,590
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Sea Wonder

Sea Wonder

Bareboat

10 berths5 cabins16 m2018
from
€2,800
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Mango

Mango

Bareboat

10 berths5 cabins16 m2015
from
€2,750
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Sea Wonder I

Sea Wonder I

Bareboat

10 berths5 cabins16 m2018
from
€2,420
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Alma Libre III

Alma Libre III

Bareboat

11 berths5 cabins16 m2018
from
€2,260
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Morillon20% · Last minute

Morillon

Bareboat

12 berths5 cabins16 m2017
from
€1,800
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Oreo

Oreo

Bareboat

10 berths5 cabins16 m2016
from
€2,560
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Alice

Alice

Bareboat

10 berths5 cabins16 m2016
from
€2,637
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Prince Nikolaos

Prince Nikolaos

Bareboat

10 berths5 cabins16 m2019
from
€1,620
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Prince John

Prince John

Bareboat

10 berths5 cabins16 m2019
from
€1,620
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Philoctetes

Philoctetes

Bareboat

10 berths5 cabins16 m2015
from
€2,240
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Roxane

Roxane

Bareboat

10 berths5 cabins16 m2015
from
€2,830
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Salvia

Salvia

Bareboat

10 berths5 cabins16 m2019
from
€4,300
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Pandora

Pandora

Bareboat

10 berths5 cabins16 m2016
from
€2,240
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Jumbo

Jumbo

Bareboat

10 berths5 cabins16 m2015
from
€2,748
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Tramuntana

Tramuntana

Bareboat

11 berths5 cabins16 m2014
from
€1,250
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Tramuntana

Tramuntana

Bareboat

11 berths5 cabins16 m2014
from
€1,250
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Soleado

Soleado

Bareboat

12 berths5 cabins16 m2019
from
€2,214
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Petra 2

Petra 2

Bareboat

12 berths5 cabins16 m2015
from
€2,590
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Gin Tonic

Gin Tonic

Bareboat

10 berths5 cabins16 m2015
from
€4,300
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Sea Wonder I

Sea Wonder I

Bareboat

10 berths5 cabins16 m2018
from
€4,300
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Ivana

Ivana

Bareboat

11 berths5 cabins16 m2018
from
€2,290
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Lina

Lina

Bareboat

11 berths5 cabins16 m2019
from
€2,050
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Apollon

Apollon

Bareboat

11 berths5 cabins16 m2018
from
€1,900
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Papaya

Papaya

Bareboat

10 berths5 cabins16 m2019
from
€2,000
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Jozefina

Jozefina

Bareboat

12 berths5 cabins16 m2018
from
€2,350
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Zoilo

Zoilo

Bareboat

11 berths5 cabins16 m2017
from
€2,400
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Sveti Ante

Sveti Ante

Bareboat

11 berths5 cabins16 m2015
from
€2,400
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Pevero

Pevero

Bareboat

10 berths5 cabins16 m2017
from
€3,157
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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.