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 5 of 82

Tatyana

Tatyana

Bareboat

8 berths3 cabins12 m2022
from
€1,200
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Ivana

Ivana

Bareboat

8 berths3 cabins12 m2024
from
€1,600
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Zen

Zen

Bareboat

8 berths3 cabins12 m2024
from
€1,820
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Siroco

Siroco

Bareboat

8 berths3 cabins12 m2024
from
€2,240
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Horizon

Horizon

Bareboat

8 berths3 cabins12 m2023
from
€1,900
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Coco

Coco

Bareboat

7 berths3 cabins12 m2023
from
€1,500
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Aurora

Aurora

Bareboat

8 berths3 cabins12 m2024
from
€2,500
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Juju

Juju

Bareboat

6 berths3 cabins12 m2024
from
€2,300
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Leopard

Leopard

Bareboat

8 berths3 cabins12 m2023
from
€2,160
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Sail Scorpius

Sail Scorpius

Bareboat

6 berths3 cabins12 m2024
from
€1,975
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Maia

Maia

Bareboat

8 berths3 cabins12 m2024
from
€2,800
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Aeolus

Aeolus

Bareboat

8 berths3 cabins12 m2022
from
€1,810
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Sorores

Sorores

Bareboat

6 berths3 cabins12 m2024
from
€3,240
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Avra

Avra

Bareboat

8 berths3 cabins12 m2023
from
€2,180
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Harmonia

Harmonia

Bareboat

8 berths3 cabins12 m2024
from
€2,180
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Summertime

Summertime

Bareboat

7 berths3 cabins12 m2024
from
€1,800
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Levente

Levente

Bareboat

8 berths3 cabins12 m2024
from
€900
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Gala

Gala

Bareboat

8 berths3 cabins12 m2023
from
€1,900
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Palma

Palma

Bareboat

8 berths3 cabins12 m2023
from
€900
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Moana

Moana

Bareboat

8 berths3 cabins12 m2024
from
€1,900
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Gala

Gala

Bareboat

8 berths3 cabins12 m2023
from
€1,900
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Palma

Palma

Bareboat

8 berths3 cabins12 m2023
from
€900
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Ulysse 1

Ulysse 1

Bareboat

8 berths3 cabins12 m2024
from
€2,750
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Selene

Selene

Bareboat

6 berths3 cabins12 m2024
from
€1,990
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Maia

Maia

Bareboat

8 berths3 cabins12 m2024
from
€2,440
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Roscana

Roscana

Bareboat

8 berths3 cabins12 m2024
from
€2,750
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Alara 3

Alara 3

Bareboat

6 berths3 cabins12 m2025
from
€2,900
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Blackberry

Blackberry

Bareboat

8 berths3 cabins12 m2025
from
€2,010
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Nayjara II

Nayjara II

Bareboat

7 berths3 cabins12 m2024
from
€3,000
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Silver VII

Silver VII

Bareboat

6 berths3 cabins12 m2022
from
€2,800
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Kalispera

Kalispera

Bareboat

6 berths3 cabins12 m2022
from
€2,800
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Christos

Christos

Bareboat

8 berths3 cabins12 m2025
from
€1,700
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Marijana

Marijana

Bareboat

7 berths3 cabins12 m2024
from
€1,700
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Ostwind II

Ostwind II

Bareboat

8 berths3 cabins12 m2023
from
€4,000
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7 Iles

7 Iles

Bareboat

8 berths3 cabins12 m2025
from
€2,750
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Balarina

Balarina

Bareboat

6 berths3 cabins12 m2023
from
€2,800
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Blackberry

Blackberry

Bareboat

8 berths3 cabins12 m2025
from
€3,343
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Seaduction

Seaduction

Bareboat

7 berths3 cabins12 m2021
from
€1,600
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Onyx

Onyx

Bareboat

8 berths3 cabins12 m2025
from
€1,550
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Atlanta

Atlanta

Bareboat

7 berths3 cabins12 m2023
from
€2,000
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Sakura J

Sakura J

Bareboat

8 berths3 cabins12 m2022
from
€2,675
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Blue Eyes

Blue Eyes

Bareboat

6 berths3 cabins12 m2024
from
€2,700
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Maia

Maia

Bareboat

8 berths3 cabins12 m2024
from
€2,062
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Oktana

Oktana

Bareboat

8 berths3 cabins12 m2023
from
€2,062
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Tanguera

Tanguera

Bareboat

6 berths3 cabins14 m2022
from
€3,100
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Efix

Efix

Bareboat

8 berths3 cabins14 m2024
from
€3,252
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Galini

Galini

Bareboat

8 berths3 cabins14 m2023
from
€1,850
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Galini

Galini

Bareboat

8 berths3 cabins14 m2023
from
€2,350
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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.