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 53 of 82

Beleza

Beleza

Bareboat

8 berths3 cabins11 m2010
from
€1,560
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Agios

Agios

Bareboat

8 berths3 cabins12 m2024
from
€1,550
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Breeze

Breeze

Bareboat

8 berths3 cabins12 m2024
from
€850
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Uraz

Uraz

Bareboat

6 berths3 cabins12 m2024
from
€1,400
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First Dream

First Dream

Bareboat

6 berths3 cabins12 m2024
from
€1,380
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Katja

Katja

Bareboat

8 berths3 cabins12 m2025
from
€1,550
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Mercator

Mercator

Bareboat

6 berths3 cabins12 m2025
from
€2,200
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Breeze

Breeze

Bareboat

8 berths3 cabins12 m2024
from
€850
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Aura

Aura

Bareboat

8 berths3 cabins12 m2017
from
€1,320
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Missy

Missy

Bareboat

8 berths3 cabins12 m2017
from
€2,190
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Luce

Luce

Bareboat

8 berths3 cabins12 m2017
from
€850
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Dama

Dama

Bareboat

8 berths3 cabins12 m2018
from
€1,200
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Philyra

Philyra

Bareboat

8 berths3 cabins12 m2018
from
€1,850
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Bellona

Bellona

Bareboat

8 berths3 cabins12 m2018
from
€1,750
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Anima Maris II

Anima Maris II

Bareboat

8 berths3 cabins12 m2018
from
€1,450
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Anima Maris III

Anima Maris III

Bareboat

8 berths3 cabins12 m2018
from
€1,450
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Elisa

Elisa

Bareboat

8 berths3 cabins12 m2018
from
€1,750
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Pleasure

Pleasure

Bareboat

8 berths3 cabins12 m2018
from
€1,530
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Obsession

Obsession

Bareboat

8 berths3 cabins12 m2018
from
€1,530
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Elsa

Elsa

Bareboat

8 berths3 cabins12 m2018
from
€1,320
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Ariela

Ariela

Bareboat

8 berths3 cabins12 m2018
from
€1,320
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Bordeaux20% · Last minute

Bordeaux

Bareboat

8 berths3 cabins12 m2019
from
€1,200
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Majano

Majano

Bareboat

8 berths3 cabins12 m2019
from
€1,460
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Rania

Rania

Bareboat

8 berths3 cabins12 m2019
from
€2,200
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Cvita

Cvita

Bareboat

8 berths3 cabins12 m2019
from
€850
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Reya

Reya

Bareboat

8 berths3 cabins12 m2018
from
€1,200
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Tena

Tena

Bareboat

8 berths3 cabins12 m2021
from
€1,500
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Mici

Mici

Bareboat

8 berths3 cabins12 m2018
from
€1,320
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Aga

Aga

Bareboat

8 berths3 cabins12 m2019
from
€1,320
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La Rose

La Rose

Bareboat

8 berths3 cabins12 m2020
from
€1,390
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Gang of Four

Gang of Four

Bareboat

8 berths3 cabins12 m2018
from
€1,510
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New Order

New Order

Bareboat

8 berths3 cabins12 m2018
from
€1,510
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Nirvana

Nirvana

Bareboat

8 berths3 cabins12 m2018
from
€1,510
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Prodigy

Prodigy

Bareboat

8 berths3 cabins12 m2018
from
€1,510
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Simple Minds

Simple Minds

Bareboat

8 berths3 cabins12 m2018
from
€1,510
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Maja

Maja

Bareboat

8 berths3 cabins12 m2021
from
€1,500
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Flip

Flip

Bareboat

8 berths3 cabins12 m2021
from
€1,500
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The Boss

The Boss

Bareboat

8 berths3 cabins12 m2021
from
€2,200
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Mare Nostrum II

Mare Nostrum II

Bareboat

8 berths3 cabins12 m2018
from
€1,700
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Sailor Mercury

Sailor Mercury

Bareboat

8 berths3 cabins12 m2018
from
€850
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Sailor Jupiter

Sailor Jupiter

Bareboat

8 berths3 cabins12 m2018
from
€850
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Rosa Bella

Rosa Bella

Bareboat

6 berths3 cabins12 m2021
from
€2,290
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Sail Lyra

Sail Lyra

Bareboat

6 berths3 cabins12 m2022
from
€1,675
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Teodora

Teodora

Bareboat

8 berths3 cabins12 m2022
from
€1,850
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Dancefloor

Dancefloor

Bareboat

6 berths3 cabins12 m2023
from
€1,800
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Bellagio

Bellagio

Bareboat

8 berths3 cabins12 m2018
from
€1,370
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Stargazer

Stargazer

Bareboat

6 berths3 cabins12 m2023
from
€2,450
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Sail Bellatrix

Sail Bellatrix

Bareboat

6 berths3 cabins12 m2023
from
€1,800
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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.