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 16 of 82

Sail Vega

Sail Vega

Bareboat

8 berths4 cabins14 m2014
from
€1,725
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Orsalia

Orsalia

Bareboat

10 berths4 cabins14 m2019
from
€2,800
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Palolem

Palolem

Bareboat

8 berths4 cabins14 m2020
from
€3,150
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Santiago

Santiago

Bareboat

8 berths4 cabins14 m2020
from
€3,090
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Irene

Irene

Bareboat

10 berths4 cabins14 m2020
from
€2,080
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Optima Prime

Optima Prime

Bareboat

9 berths4 cabins14 m2017
from
€2,480
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Amsterdam

Amsterdam

Bareboat

8 berths4 cabins14 m2020
from
€2,890
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Sail Deneb

Sail Deneb

Bareboat

8 berths4 cabins14 m2021
from
€2,250
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Barcelona

Barcelona

Bareboat

8 berths4 cabins14 m2021
from
€2,990
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Istanbul

Istanbul

Bareboat

8 berths4 cabins14 m2021
from
€2,990
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Zulu

Zulu

Bareboat

8 berths4 cabins14 m2015
from
€2,900
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Nereus

Nereus

Bareboat

9 berths4 cabins14 m2017
from
€1,900
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Topcu

Topcu

Bareboat

8 berths4 cabins14 m2021
from
€2,300
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Leonidas II

Leonidas II

Bareboat

9 berths4 cabins14 m2019
from
€1,500
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Galeb30% · Last minute

Galeb

Bareboat

10 berths4 cabins14 m2021
from
€265
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Kassandra

Kassandra

Bareboat

9 berths4 cabins14 m2017
from
€3,000
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Panda IV

Panda IV

Bareboat

9 berths4 cabins14 m2022
from
€1,700
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Noelle

Noelle

Bareboat

9 berths4 cabins14 m2022
from
€1,700
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Amazing Grace15% · Last minute

Amazing Grace

Bareboat

9 berths4 cabins14 m2022
from
€1,746
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Sail Betelgeuse

Sail Betelgeuse

Bareboat

8 berths4 cabins14 m2022
from
€2,575
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Tess Point

Tess Point

Bareboat

9 berths4 cabins14 m2022
from
€2,100
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Batukaan

Batukaan

Bareboat

8 berths4 cabins14 m2022
from
€2,500
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Just Be

Just Be

Bareboat

9 berths4 cabins14 m2022
from
€3,600
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Classy

Classy

Bareboat

8 berths4 cabins14 m2022
from
€3,610
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First Step

First Step

Bareboat

8 berths4 cabins14 m2022
from
€4,000
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Kalev

Kalev

Bareboat

9 berths4 cabins14 m2018
from
€1,800
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Coco

Coco

Bareboat

8 berths4 cabins14 m2022
from
€2,750
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Summer Jazz

Summer Jazz

Bareboat

9 berths4 cabins14 m2023
from
€2,100
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Orion

Orion

Bareboat

8 berths4 cabins14 m2023
from
€4,000
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White Cloud

White Cloud

Bareboat

8 berths4 cabins14 m2023
from
€3,300
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Borgo Erizzo

Borgo Erizzo

Bareboat

9 berths4 cabins14 m2023
from
€2,000
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Spring Dolphin

Spring Dolphin

Bareboat

9 berths4 cabins14 m2023
from
€2,310
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Sunny Point

Sunny Point

Bareboat

9 berths4 cabins14 m2023
from
€2,310
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Sail Leo

Sail Leo

Bareboat

8 berths4 cabins14 m2023
from
€2,825
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Chagla

Chagla

Bareboat

8 berths4 cabins14 m2023
from
€2,600
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Northberry Blu

Northberry Blu

Bareboat

8 berths4 cabins14 m2023
from
€2,600
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Miber Mars

Miber Mars

Bareboat

8 berths4 cabins14 m2023
from
€1,938
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Miber Yigit

Miber Yigit

Bareboat

8 berths4 cabins14 m2023
from
€1,798
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Sunset Breeze

Sunset Breeze

Bareboat

9 berths3 cabins14 m2023
from
€2,100
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Rea

Rea

Bareboat

9 berths4 cabins14 m2015
from
€2,450
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Alma Libre IV

Alma Libre IV

Bareboat

10 berths4 cabins14 m2019
from
€1,890
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Nefeli

Nefeli

Bareboat

9 berths4 cabins14 m2021
from
€2,360
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Renee

Renee

Bareboat

10 berths4 cabins14 m2021
from
€2,360
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Sea Wonder II

Sea Wonder II

Bareboat

10 berths4 cabins14 m2021
from
€2,180
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Leonidas

Leonidas

Bareboat

9 berths4 cabins14 m2017
from
€2,000
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H2O

H2O

Bareboat

9 berths4 cabins14 m2017
from
€1,925
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Jenga

Jenga

Bareboat

8 berths4 cabins14 m2024
from
€3,900
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Mojito

Mojito

Bareboat

8 berths4 cabins14 m2016
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.