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 40 of 82

Sea Cloud 3

Sea Cloud 3

Bareboat

10 berths4 cabins14 m2020
from
€1,100
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AirTime 2

AirTime 2

Bareboat

10 berths4 cabins14 m2020
from
€1,100
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AirTime 3

AirTime 3

Bareboat

10 berths4 cabins14 m2020
from
€1,100
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Enya

Enya

Bareboat

10 berths4 cabins14 m2020
from
€2,000
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Thetis

Thetis

Bareboat

10 berths4 cabins14 m2020
from
€2,500
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Sax III

Sax III

Bareboat

10 berths4 cabins14 m2021
from
€2,050
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Kristi

Kristi

Bareboat

10 berths4 cabins14 m2021
from
€1,650
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Tatiana

Tatiana

Bareboat

10 berths4 cabins14 m2021
from
€1,650
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Vikki

Vikki

Bareboat

10 berths4 cabins14 m2021
from
€1,650
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Corgi

Corgi

Bareboat

10 berths4 cabins14 m2021
from
€2,960
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Sokol30% · Last minute

Sokol

Bareboat

10 berths4 cabins14 m2021
from
€1,540
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Lan

Lan

Bareboat

10 berths4 cabins14 m2021
from
€1,900
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Alina

Alina

Bareboat

10 berths4 cabins14 m2021
from
€2,100
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Linea Uno

Linea Uno

Bareboat

10 berths4 cabins14 m2021
from
€1,900
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Albatros30% · Last minute

Albatros

Bareboat

10 berths4 cabins14 m2021
from
€950
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Tattoo

Tattoo

Bareboat

10 berths4 cabins14 m2022
from
€1,100
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Ciao Ragazza

Ciao Ragazza

Bareboat

10 berths4 cabins14 m2022
from
€1,850
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Marita

Marita

Bareboat

10 berths4 cabins14 m2022
from
€2,050
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Flamingo30% · Last minute

Flamingo

Bareboat

10 berths4 cabins14 m2022
from
€265
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Pasithea

Pasithea

Bareboat

10 berths4 cabins14 m2022
from
€1,870
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Jackpot

Jackpot

Bareboat

10 berths4 cabins14 m2022
from
€2,240
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Luna

Luna

Bareboat

10 berths4 cabins14 m2022
from
€2,355
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Seraphim

Seraphim

Bareboat

8 berths3 cabins14 m2020
from
€1,250
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Moon Pearl

Moon Pearl

Bareboat

10 berths4 cabins14 m2023
from
€2,240
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Zeba30% · Last minute

Zeba

Bareboat

10 berths4 cabins14 m2023
from
€265
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Fjaka

Fjaka

Bareboat

10 berths4 cabins14 m2023
from
€2,240
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Simply the Best

Simply the Best

Bareboat

10 berths4 cabins14 m2023
from
€1,990
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Sea Cloud 3

Sea Cloud 3

Bareboat

10 berths4 cabins14 m2020
from
€1,100
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AirTime 3

AirTime 3

Bareboat

10 berths4 cabins14 m2020
from
€1,100
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AirTime 2

AirTime 2

Bareboat

10 berths4 cabins14 m2020
from
€1,100
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Tattoo

Tattoo

Bareboat

10 berths4 cabins14 m2022
from
€1,100
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Top Gun

Top Gun

Bareboat

10 berths4 cabins14 m2020
from
€2,090
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Lena

Lena

Bareboat

10 berths4 cabins14 m2020
from
€1,100
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Lena

Lena

Bareboat

10 berths4 cabins14 m2020
from
€1,100
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Josi

Josi

Bareboat

11 berths4 cabins14 m2022
from
€2,350
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HMS Magnolia

HMS Magnolia

Bareboat

10 berths4 cabins14 m2022
from
€2,900
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Bad Buoy

Bad Buoy

Bareboat

10 berths4 cabins14 m2021
from
€775
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Lara

Lara

Bareboat

10 berths4 cabins14 m2022
from
€860
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Lillemor II

Lillemor II

Bareboat

10 berths4 cabins14 m2023
from
€775
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Ziggy

Ziggy

Bareboat

10 berths4 cabins14 m2022
from
€775
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Viki

Viki

Bareboat

10 berths4 cabins14 m2022
from
€1,700
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Ianira

Ianira

Bareboat

8 berths3 cabins14 m2021
from
€2,200
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Urshy

Urshy

Bareboat

8 berths3 cabins14 m2022
from
€2,240
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Polaris

Polaris

Bareboat

8 berths3 cabins14 m2023
from
€1,700
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Soleos

Soleos

Bareboat

8 berths3 cabins14 m2022
from
€2,145
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Moonlight

Moonlight

Bareboat

8 berths3 cabins14 m2022
from
€830
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Oxygen

Oxygen

Bareboat

8 berths3 cabins14 m2023
from
€890
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Starlight

Starlight

Bareboat

8 berths3 cabins14 m2023
from
€2,200
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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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New sailors, beginners or seasoned skippers — tell us when, where, and how many. we send three real options the same day. No spam, no fluff, no commitment.

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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.