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 32 of 82

Barrique I20% · Last minute

Barrique I

Bareboat

12 berths5 cabins14 m2019
from
€1,700
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SunnyLife

SunnyLife

Bareboat

12 berths5 cabins14 m2019
from
€1,800
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Ane

Ane

Bareboat

12 berths5 cabins14 m2019
from
€2,200
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Abraxan

Abraxan

Bareboat

10 berths5 cabins14 m2019
from
€1,420
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Newt

Newt

Bareboat

10 berths5 cabins14 m2019
from
€1,500
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Vellamo

Vellamo

Bareboat

10 berths5 cabins14 m2020
from
€2,260
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Wilma

Wilma

Bareboat

12 berths5 cabins14 m2021
from
€530
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WindyLife

WindyLife

Bareboat

12 berths5 cabins14 m2019
from
€2,253
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Sea Splash

Sea Splash

Bareboat

12 berths5 cabins14 m2019
from
€819
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Tango I

Tango I

Bareboat

10 berths5 cabins14 m2019
from
€1,900
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Tango II

Tango II

Bareboat

10 berths5 cabins14 m2019
from
€1,900
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Mega

Mega

Bareboat

12 berths5 cabins14 m2019
from
€2,200
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Stargate

Stargate

Bareboat

8 berths3 cabins15 m2022
from
€1,150
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Jolie

Jolie

Bareboat

8 berths3 cabins15 m2022
from
€1,150
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Knot Online

Knot Online

Bareboat

6 berths3 cabins15 m2022
from
€5,100
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Unforgettable

Unforgettable

Bareboat

6 berths3 cabins15 m2022
from
€5,400
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Shandy Breeze

Shandy Breeze

Bareboat

6 berths3 cabins15 m2022
from
€5,100
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Euphoria

Euphoria

Bareboat

7 berths3 cabins15 m2022
from
€1,690
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Amber

Amber

Bareboat

8 berths3 cabins15 m2023
from
€1,600
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Energy

Energy

Bareboat

8 berths3 cabins15 m2024
from
€1,850
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Robin

Robin

Bareboat

6 berths3 cabins15 m2022
from
€3,800
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Discovery

Discovery

Bareboat

8 berths3 cabins15 m2024
from
€5,050
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Sarpico

Sarpico

Bareboat

7 berths3 cabins15 m2022
from
€3,000
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Andromaca

Andromaca

Bareboat

6 berths3 cabins15 m2025
from
€4,000
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Galeo5% · Last minute

Galeo

Bareboat

8 berths3 cabins15 m2024
from
€3,500
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Blue Mermaid

Blue Mermaid

Bareboat

11 berths4 cabins15 m2022
from
€2,600
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Optasia

Optasia

Bareboat

11 berths4 cabins15 m2022
from
€2,600
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Emphasis

Emphasis

Bareboat

10 berths4 cabins15 m2022
from
€4,200
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La Familia

La Familia

Bareboat

11 berths4 cabins15 m2023
from
€3,614
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Aqua Azzurro

Aqua Azzurro

Bareboat

11 berths4 cabins15 m2023
from
€2,600
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Luna

Luna

Bareboat

10 berths4 cabins15 m2022
from
€3,280
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Suha Bey

Suha Bey

Bareboat

9 berths4 cabins15 m2022
from
€3,400
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Imagine

Imagine

Bareboat

9 berths4 cabins15 m2023
from
€2,500
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Aegean Blue

Aegean Blue

Bareboat

11 berths4 cabins15 m2024
from
€2,600
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Aruba

Aruba

Bareboat

11 berths4 cabins15 m2022
from
€2,500
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Valchiria

Valchiria

Bareboat

11 berths4 cabins15 m2022
from
€3,300
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Dufour 470

Dufour 470

Bareboat

9 berths4 cabins15 m2024
from
€8,000
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Marco Polo

Marco Polo

Bareboat

9 berths4 cabins15 m2022
from
€4,200
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Alyss

Alyss

Bareboat

9 berths4 cabins15 m2025
from
€1,760
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She

She

Bareboat

11 berths4 cabins15 m2025
from
€1,000
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Scruscio du Mari

Scruscio du Mari

Bareboat

11 berths4 cabins15 m2025
from
€4,150
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Bedda Matri

Bedda Matri

Bareboat

11 berths4 cabins15 m2025
from
€4,150
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Briseide

Briseide

Bareboat

11 berths4 cabins15 m2023
from
€4,750
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Emma

Emma

Bareboat

9 berths4 cabins15 m2022
from
€3,600
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Mirasole

Mirasole

Bareboat

11 berths4 cabins15 m2024
from
€4,550
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M'arricrio

M'arricrio

Bareboat

11 berths4 cabins15 m2023
from
€4,000
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Chuck

Chuck

Bareboat

11 berths4 cabins15 m2024
from
€3,500
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Jeroboam

Jeroboam

Bareboat

11 berths4 cabins15 m2026
from
€2,950
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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.