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 35 of 82

Agnese

Agnese

Bareboat

15 berths6 cabins16 m2023
from
€4,300
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Gryffindor

Gryffindor

Bareboat

13 berths6 cabins16 m2020
from
€2,150
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Albus

Albus

Bareboat

15 berths6 cabins16 m2021
from
€3,800
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Anna III

Anna III

Bareboat

14 berths6 cabins16 m2022
from
€1,470
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Johanna

Johanna

Bareboat

14 berths6 cabins16 m2022
from
€2,000
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Sonja

Sonja

Bareboat

14 berths6 cabins16 m2020
from
€1,037
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Venus

Venus

Bareboat

10 berths3 cabins16 m2021
from
€4,650
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Dimpa

Dimpa

Bareboat

7 berths3 cabins16 m2021
from
€3,500
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Cholita

Cholita

Bareboat

9 berths3 cabins16 m2022
from
€5,800
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Vita

Vita

Bareboat

10 berths4 cabins16 m2021
from
€4,800
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Sofia

Sofia

Bareboat

11 berths4 cabins16 m2022
from
€3,550
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Hermes

Hermes

Bareboat

11 berths4 cabins16 m2022
from
€3,550
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Fat Bottom Girl

Fat Bottom Girl

Bareboat

9 berths4 cabins16 m2021
from
€6,300
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Rhamnus

Rhamnus

Bareboat

9 berths4 cabins16 m2023
from
€2,130
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Gringott

Gringott

Bareboat

9 berths4 cabins16 m2021
from
€2,060
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Ionian Blue

Ionian Blue

Bareboat

11 berths4 cabins16 m2024
from
€3,550
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Liliana Bella

Liliana Bella

Bareboat

9 berths4 cabins16 m2021
from
€6,200
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Steel Away

Steel Away

Bareboat

8 berths4 cabins16 m2022
from
€5,700
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Dream Big

Dream Big

Bareboat

8 berths4 cabins16 m2024
from
€5,700
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Pura Vida

Pura Vida

Bareboat

8 berths4 cabins16 m2022
from
€5,800
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Anema

Anema

Bareboat

13 berths5 cabins16 m2021
from
€3,550
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Wish Planet

Wish Planet

Bareboat

13 berths5 cabins16 m2022
from
€3,810
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Allegro

Allegro

Bareboat

13 berths5 cabins16 m2023
from
€2,950
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Rondo

Rondo

Bareboat

13 berths5 cabins16 m2023
from
€2,950
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Grande Sofia

Grande Sofia

Bareboat

12 berths5 cabins16 m2023
from
€3,550
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Asperula

Asperula

Bareboat

11 berths5 cabins16 m2022
from
€2,110
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Edvige

Edvige

Bareboat

11 berths5 cabins16 m2021
from
€2,140
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SPLASH

SPLASH

Bareboat

11 berths5 cabins16 m2023
from
€4,200
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Blue Therapy

Blue Therapy

Bareboat

13 berths5 cabins16 m2024
from
€2,700
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Olimpia

Olimpia

Bareboat

13 berths5 cabins16 m2025
from
€4,580
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Atua

Atua

Bareboat

12 berths5 cabins16 m2023
from
€4,500
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Princess Leia

Princess Leia

Bareboat

12 berths5 cabins16 m2021
from
€3,500
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Taddarita

Taddarita

Bareboat

13 berths5 cabins16 m2025
from
€5,250
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Saro

Saro

Bareboat

13 berths5 cabins16 m2023
from
€5,250
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Suzie Q

Suzie Q

Bareboat

13 berths5 cabins16 m2025
from
€2,925
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Tano

Tano

Bareboat

13 berths5 cabins16 m2024
from
€5,500
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Skadi

Skadi

Bareboat

14 berths6 cabins16 m2022
from
€1,050
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Kasper

Kasper

Bareboat

14 berths6 cabins16 m2023
from
€1,450
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Dreamweaver

Dreamweaver

Bareboat

15 berths6 cabins16 m2024
from
€1,450
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Graceful Dancer

Graceful Dancer

Bareboat

13 berths6 cabins16 m2024
from
€1,450
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Astrid

Astrid

Bareboat

14 berths6 cabins16 m2022
from
€1,000
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Violante

Violante

Bareboat

15 berths6 cabins17 m2026
from
€4,540
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Aphrodite

Aphrodite

Bareboat

14 berths6 cabins17 m2026
from
€1,200
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Seraphine

Seraphine

Bareboat

14 berths6 cabins17 m2026
from
€1,200
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Petrovich

Petrovich

Bareboat

11 berths4 cabins17 m2016
from
€3,140
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Altamira

Altamira

Bareboat

10 berths6 cabins17 m2020
from
€6,050
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Euphoria Planet

Euphoria Planet

Bareboat

11 berths4 cabins17 m2022
from
€3,440
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POSEIDON

POSEIDON

Bareboat

11 berths4 cabins17 m2022
from
€6,290
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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.