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 49 of 82

Big  Blue

Big Blue

Bareboat

12 berths5 cabins16 m2020
from
€3,700
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Frizzante20% · Last minute

Frizzante

Bareboat

11 berths5 cabins16 m2025
from
€2,500
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Ocean Phoenix - OW

Ocean Phoenix - OW

Bareboat

9 berths3 cabins16 m2024
from
€2,440
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El Hana

El Hana

Bareboat

8 berths3 cabins16 m2026
from
€3,500
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Darling - OW

Darling - OW

Bareboat

11 berths4 cabins16 m2024
from
€3,980
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Tropea - OW

Tropea - OW

Bareboat

11 berths4 cabins16 m2024
from
€2,760
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Alma - OW

Alma - OW

Bareboat

11 berths4 cabins16 m2024
from
€3,020
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Amber - OW

Amber - OW

Bareboat

11 berths4 cabins16 m2025
from
€3,020
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Illusion - OW

Illusion - OW

Bareboat

11 berths4 cabins16 m2026
from
€2,620
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Hype

Hype

Bareboat

13 berths5 cabins16 m2023
from
€2,440
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Vivid

Vivid

Bareboat

13 berths5 cabins16 m2024
from
€3,020
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Kille

Kille

Bareboat

11 berths5 cabins16 m2024
from
€4,520
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Balance

Balance

Bareboat

13 berths5 cabins16 m2025
from
€2,620
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Apollonis

Apollonis

Bareboat

10 berths4 cabins16 m2008
price on enquiry
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Maravillosa

Maravillosa

Bareboat

11 berths4 cabins16 m2011
from
€1,300
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Joy

Joy

Bareboat

9 berths4 cabins16 m2018
from
€3,500
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Lady Ardea

Lady Ardea

Bareboat

11 berths4 cabins16 m2020
from
€3,300
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Mila Felice

Mila Felice

Bareboat

9 berths4 cabins16 m2019
from
€3,295
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Air King

Air King

Bareboat

12 berths5 cabins16 m2018
from
€1,550
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Moje

Moje

Bareboat

12 berths5 cabins16 m2018
from
€2,000
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Simply The Best

Simply The Best

Bareboat

13 berths5 cabins16 m2018
from
€2,420
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Stargazing

Stargazing

Bareboat

13 berths5 cabins16 m2020
from
€2,320
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Playa

Playa

Bareboat

11 berths5 cabins16 m2023
from
€4,980
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Adele

Adele

Bareboat

12 berths5 cabins16 m2022
from
€3,200
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Janna

Janna

Bareboat

10 berths5 cabins16 m2021
from
€5,280
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Vidar

Vidar

Bareboat

9 berths3 cabins17 m2015
from
€2,550
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Star Princess

Star Princess

Bareboat

12 berths5 cabins17 m2016
from
€2,380
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Amethyst

Amethyst

Bareboat

11 berths5 cabins17 m2014
from
€3,270
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Amadea

Amadea

Bareboat

9 berths3 cabins17 m2020
from
€5,600
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Joanna

Joanna

Bareboat

9 berths3 cabins17 m2023
from
€7,950
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Oceanelle

Oceanelle

Bareboat

9 berths3 cabins17 m2024
from
€4,260
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Constanta

Constanta

Bareboat

11 berths4 cabins17 m2023
from
€4,350
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Mischief 2.0

Mischief 2.0

Bareboat

12 berths4 cabins17 m2022
from
€3,690
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Mivasa

Mivasa

Bareboat

13 berths5 cabins17 m2020
from
€4,120
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Jasmine

Jasmine

Bareboat

13 berths5 cabins17 m2017
from
€2,250
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Hot Stuff

Hot Stuff

Bareboat

13 berths5 cabins17 m2022
from
€4,520
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Eywa

Eywa

Bareboat

13 berths5 cabins17 m2024
from
€4,720
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Citrus

Citrus

Bareboat

13 berths5 cabins17 m2025
from
€4,960
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Volare

Volare

Bareboat

12 berths4 cabins18 m2025
from
€5,540
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Art H

Art H

Bareboat

11 berths4 cabins18 m2026
from
€5,440
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Bellissima

Bellissima

Bareboat

6 berths2 cabins11 m2024
from
€3,300
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Marche Ou Reve

Marche Ou Reve

Bareboat

4 berths2 cabins11 m2019
from
€1,500
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FLOW Yacht Club

FLOW Yacht Club

Bareboat

7 m2017
from
€180
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Sogno di Mare

Sogno di Mare

Bareboat

6 berths3 cabins15 m2022
from
€3,500
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Aybalam

Aybalam

Bareboat

7 berths3 cabins16 m2014
from
€5,600
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Trinity20% · Last minute

Trinity

Bareboat

11 berths4 cabins16 m2013
from
€4,000
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Keep Calm

Keep Calm

Bareboat

8 berths4 cabins16 m2012
from
€1,650
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Anita

Anita

Bareboat

11 berths5 cabins16 m2011
from
€3,000
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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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Quick inquiry

Get three sailboat options from the team.

Tell us roughly when, where, and how many. we'll send three sailboat options the same day — three boats, three prices, the trade-offs.

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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

Free quote

Get three real options.

Tell us roughly when and where. we'll send three real boats, three prices, the trade-offs — usually within the hour.