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 24 of 82

Vasco5% · Last minute

Vasco

Bareboat

4 berths2 cabins11 m2023
from
€1,800
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Momo

Momo

Bareboat

4 berths2 cabins11 m2024
from
€1,200
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Iulo

Iulo

Bareboat

4 berths2 cabins11 m2024
from
€1,750
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Affio

Affio

Bareboat

6 berths2 cabins11 m2026
from
€2,000
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Miss Daisy

Miss Daisy

Bareboat

4 berths2 cabins11 m2024
from
€4,500
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Horizon

Horizon

Bareboat

5 berths2 cabins11 m2023
from
€2,200
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Polygala

Polygala

Bareboat

6 berths3 cabins11 m2023
from
€900
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Rhapsody

Rhapsody

Bareboat

6 berths3 cabins11 m2024
from
€1,700
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Myriad’ V

Myriad’ V

Bareboat

6 berths3 cabins11 m2024
from
€1,600
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Marsel The Angel

Marsel The Angel

Bareboat

6 berths3 cabins11 m2024
from
€1,300
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Lumi

Lumi

Bareboat

8 berths3 cabins11 m2024
from
€850
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First Laugh

First Laugh

Bareboat

6 berths3 cabins11 m2024
from
€1,250
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Nessie

Nessie

Bareboat

8 berths3 cabins11 m2024
from
€850
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Viridis

Viridis

Bareboat

6 berths3 cabins11 m2024
from
€1,010
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Margaux

Margaux

Bareboat

7 berths3 cabins11 m2024
from
€1,600
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Spicy Rum

Spicy Rum

Bareboat

6 berths3 cabins11 m2024
from
€2,599
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Alma

Alma

Bareboat

8 berths3 cabins11 m2023
from
€1,440
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Nala

Nala

Bareboat

6 berths3 cabins11 m2025
from
€2,050
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Epicure5% · Last minute

Epicure

Bareboat

6 berths3 cabins11 m2023
from
€2,000
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Flavours of the sea5% · Last minute

Flavours of the sea

Bareboat

6 berths3 cabins11 m2025
from
€2,100
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Anima Grande

Anima Grande

Bareboat

6 berths3 cabins11 m2025
from
€2,380
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Island Girl

Island Girl

Bareboat

6 berths3 cabins11 m2023
from
€5,250
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Kalynea

Kalynea

Bareboat

8 berths3 cabins11 m2026
from
€2,113
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Skiona

Skiona

Bareboat

8 berths3 cabins11 m2026
from
€1,700
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Chouchou5% · Last minute

Chouchou

Bareboat

6 berths3 cabins11 m2025
from
€2,100
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Helios III

Helios III

Bareboat

6 berths3 cabins11 m2026
from
€1,600
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Evren

Evren

Bareboat

8 berths3 cabins11 m2026
from
€1,700
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JustIn

JustIn

Bareboat

8 berths3 cabins11 m2016
from
€1,200
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Siroko

Siroko

Bareboat

8 berths3 cabins11 m2016
from
€2,150
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Major Tom

Major Tom

Bareboat

8 berths3 cabins11 m2016
from
€2,000
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Louise

Louise

Bareboat

8 berths3 cabins11 m2015
from
€1,180
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Thelma

Thelma

Bareboat

8 berths3 cabins11 m2015
from
€1,180
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Lotta

Lotta

Bareboat

7 berths3 cabins11 m2017
from
€1,450
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Henry

Henry

Bareboat

7 berths3 cabins11 m2017
from
€1,350
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Medoc20% · Last minute

Medoc

Bareboat

8 berths3 cabins11 m2017
from
€1,050
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Diniva II

Diniva II

Bareboat

7 berths3 cabins11 m2016
from
€1,380
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Eftychia 3

Eftychia 3

Bareboat

7 berths3 cabins11 m2016
from
€1,150
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Prince Folegandros

Prince Folegandros

Bareboat

8 berths3 cabins11 m2015
from
€901
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Niké

Niké

Bareboat

8 berths3 cabins11 m2018
from
€800
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Morning Star

Morning Star

Bareboat

8 berths3 cabins11 m2018
from
€1,150
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Eftychia 4

Eftychia 4

Bareboat

7 berths3 cabins11 m2018
from
€1,350
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Delta

Delta

Bareboat

7 berths3 cabins11 m2018
from
€1,671
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Sun 382

Sun 382

Bareboat

7 berths3 cabins11 m2015
from
€1,310
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Kalliste

Kalliste

Bareboat

6 berths3 cabins11 m2017
from
€1,600
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Prince Folegandros

Prince Folegandros

Bareboat

7 berths3 cabins11 m2015
from
€1,080
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Niké

Niké

Bareboat

8 berths3 cabins11 m2018
from
€800
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Notus

Notus

Bareboat

8 berths3 cabins11 m2016
from
€1,900
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Shira

Shira

Bareboat

8 berths3 cabins11 m2018
from
€1,900
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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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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.