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 42 of 82

Long Island

Long Island

Bareboat

12 berths5 cabins15 m2023
from
€1,200
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Epoch

Epoch

Bareboat

11 berths4 cabins15 m2015
from
€3,000
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Virginia

Virginia

Bareboat

12 berths5 cabins15 m2016
from
€2,600
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Lena

Lena

Bareboat

12 berths5 cabins15 m2017
from
€2,750
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Sasha

Sasha

Bareboat

12 berths5 cabins15 m2018
from
€2,400
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Escape II

Escape II

Bareboat

12 berths5 cabins15 m2018
from
€2,400
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Elysium I

Elysium I

Bareboat

13 berths5 cabins15 m2018
from
€1,200
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Bingo

Bingo

Bareboat

12 berths5 cabins15 m2017
from
€1,500
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Moonlight

Moonlight

Bareboat

12 berths5 cabins15 m2015
from
€1,851
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Lazy Days

Lazy Days

Bareboat

13 berths5 cabins15 m2018
from
€2,900
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Šuferina

Šuferina

Bareboat

3 berths1 cabins8 m2022
from
€1,250
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Šuferina

Šuferina

Bareboat

3 berths1 cabins8 m2022
from
€1,250
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Barboat

Barboat

Bareboat

4 berths2 cabins10 m2011
from
€1,250
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Rhea

Rhea

Bareboat

6 berths2 cabins11 m2011
from
€900
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Thetis

Thetis

Bareboat

6 berths2 cabins11 m2011
from
€900
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Nike

Nike

Bareboat

6 berths2 cabins11 m2011
from
€900
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Ultra First

Ultra First

Bareboat

6 berths3 cabins11 m2022
from
€1,000
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Mana

Mana

Bareboat

8 berths3 cabins11 m2024
from
€3,150
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Katina

Katina

Bareboat

8 berths3 cabins11 m2024
from
€3,150
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January

January

Bareboat

8 berths3 cabins11 m2025
from
€3,150
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February

February

Bareboat

8 berths3 cabins11 m2025
from
€3,150
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March

March

Bareboat

8 berths3 cabins11 m2025
from
€3,150
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April

April

Bareboat

8 berths3 cabins11 m2025
from
€3,150
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May

May

Bareboat

8 berths3 cabins11 m2025
from
€3,150
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June

June

Bareboat

8 berths3 cabins11 m2025
from
€3,150
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July

July

Bareboat

8 berths3 cabins11 m2025
from
€3,150
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August

August

Bareboat

8 berths3 cabins11 m2025
from
€3,150
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Ultra First

Ultra First

Bareboat

6 berths3 cabins11 m2022
from
€1,000
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September

September

Bareboat

8 berths3 cabins11 m2026
from
€3,150
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October

October

Bareboat

8 berths3 cabins11 m2027
from
€3,150
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November

November

Bareboat

8 berths3 cabins11 m2027
from
€3,150
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Kodo

Kodo

Bareboat

7 berths3 cabins12 m2005
from
€1,500
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Milena

Milena

Bareboat

8 berths3 cabins12 m2004
from
€2,300
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Checkmate

Checkmate

Bareboat

7 berths3 cabins14 m2023
from
€1,600
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Checkmate

Checkmate

Bareboat

7 berths3 cabins14 m2023
from
€1,600
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Titi

Titi

Bareboat

7 berths3 cabins14 m2024
from
€4,750
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Kuroneko

Kuroneko

Bareboat

6 berths3 cabins14 m2023
from
€4,750
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Homer

Homer

Bareboat

9 berths4 cabins14 m2027
from
€4,350
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Bart

Bart

Bareboat

9 berths4 cabins14 m2027
from
€4,350
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Marge

Marge

Bareboat

9 berths4 cabins14 m2027
from
€4,350
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Lisa

Lisa

Bareboat

9 berths4 cabins14 m2027
from
€4,350
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Maggie

Maggie

Bareboat

9 berths4 cabins14 m2027
from
€4,350
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Mr. Burns

Mr. Burns

Bareboat

9 berths4 cabins14 m2027
from
€4,350
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Edisa

Edisa

Crewed

8 berths4 cabins14 m1991
from
€14,525
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Extra mile

Extra mile

Bareboat

9 berths3 cabins17 m2023
from
€5,200
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Oktana

Oktana

Bareboat

9 berths3 cabins17 m2023
from
€5,200
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On y va

On y va

Bareboat

8 berths3 cabins17 m2023
from
€11,760
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Silhuette

Silhuette

Bareboat

7 berths3 cabins17 m2022
from
€5,400
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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.