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 7 of 82

Payetra

Payetra

Bareboat

9 berths4 cabins15 m2025
from
€2,200
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Azzurra

Azzurra

Bareboat

10 berths4 cabins15 m2026
from
€2,160
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Jason

Jason

Bareboat

10 berths5 cabins15 m2024
from
€2,300
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Arke

Arke

Bareboat

10 berths5 cabins15 m2025
from
€2,990
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Iris

Iris

Bareboat

10 berths5 cabins15 m2024
from
€2,990
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Lady Andaman

Lady Andaman

Bareboat

10 berths5 cabins15 m2024
from
€3,602
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Princess Laura

Princess Laura

Bareboat

12 berths5 cabins15 m2025
from
€2,700
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Rib Eye

Rib Eye

Bareboat

12 berths5 cabins15 m2025
from
€3,080
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Sueno

Sueno

Bareboat

10 berths5 cabins15 m2025
from
€3,390
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Kebifaiv

Kebifaiv

Bareboat

10 berths5 cabins15 m2024
from
€2,500
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Kebifaiv

Kebifaiv

Bareboat

8 berths5 cabins15 m2024
from
€3,000
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461 Ocean Boulevard

461 Ocean Boulevard

Bareboat

12 berths5 cabins15 m2025
from
€2,700
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Elli

Elli

Bareboat

12 berths5 cabins16 m2020
from
€3,950
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Lady Flora 3

Lady Flora 3

Bareboat

11 berths5 cabins16 m2019
from
€2,800
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B-Line

B-Line

Bareboat

11 berths5 cabins16 m2023
from
€4,700
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Malena

Malena

Bareboat

12 berths5 cabins16 m2023
from
€4,000
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El Presidente

El Presidente

Bareboat

10 berths5 cabins16 m2024
from
€4,100
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Roza Deflores 2

Roza Deflores 2

Bareboat

12 berths5 cabins16 m2024
from
€3,000
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Amaltheia

Amaltheia

Bareboat

11 berths5 cabins16 m2020
from
€4,450
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Big Blue

Big Blue

Bareboat

12 berths5 cabins16 m2024
from
€3,000
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Size Matters15% · Last minute

Size Matters

Bareboat

11 berths5 cabins16 m2022
from
€2,539
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Hangover15% · Last minute

Hangover

Bareboat

11 berths5 cabins16 m2024
from
€2,799
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Ciao Bella15% · Last minute

Ciao Bella

Bareboat

11 berths5 cabins16 m2024
from
€2,799
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Shala

Shala

Bareboat

8 berths3 cabins15 m2023
from
€2,900
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Dragonfly

Dragonfly

Bareboat

6 berths3 cabins15 m2023
from
€2,565
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Naltoya

Naltoya

Bareboat

11 berths4 cabins15 m2023
from
€2,400
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Xenia

Xenia

Bareboat

10 berths5 cabins15 m2020
from
€3,000
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Mathilda

Mathilda

Bareboat

11 berths5 cabins15 m2024
from
€2,100
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Sea Queen

Sea Queen

Bareboat

12 berths5 cabins15 m2025
from
€2,050
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Sea Queen

Sea Queen

Bareboat

12 berths5 cabins15 m2025
from
€2,050
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BE Luxe

BE Luxe

Bareboat

10 berths3 cabins17 m2017
from
€2,500
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Promitheas

Promitheas

Bareboat

10 berths4 cabins17 m2021
from
€4,500
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Elli

Elli

Bareboat

12 berths4 cabins17 m2020
from
€2,900
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Ghost

Ghost

Bareboat

9 berths4 cabins17 m2022
from
€6,250
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Olimp

Olimp

Bareboat

12 berths5 cabins17 m2024
from
€4,300
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Seacret

Seacret

Bareboat

12 berths5 cabins17 m2020
from
€3,672
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Blue Beyond

Blue Beyond

Bareboat

12 berths5 cabins17 m2018
from
€4,300
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Mina

Mina

Bareboat

12 berths5 cabins17 m2024
from
€3,950
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Sax10% · Last minute Available

Sax

Bareboat

6 berths2 cabins10 m2014
from
€800
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Nici

Nici

Bareboat

4 berths2 cabins10 m2011
from
€900
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Anemos

Anemos

Bareboat

5 berths2 cabins10 m2011
from
€1,150
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Big Kahuna

Big Kahuna

Bareboat

4 berths2 cabins10 m2011
from
€1,850
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Star Chiara

Star Chiara

Bareboat

5 berths2 cabins10 m2012
from
€855
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Homeoffice

Homeoffice

Bareboat

5 berths2 cabins10 m2013
from
€900
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Chiara

Chiara

Bareboat

6 berths2 cabins10 m2013
from
€1,100
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Mirella

Mirella

Bareboat

6 berths2 cabins10 m2013
from
€1,100
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Ami

Ami

Bareboat

6 berths2 cabins10 m2013
from
€1,040
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Dolce Vita

Dolce Vita

Bareboat

5 berths2 cabins10 m2016
from
€850
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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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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

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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.