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 70 of 82

Pluto

Pluto

Bareboat

6 berths3 cabins11 m2013
from
€1,548
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Fearless

Fearless

Bareboat

6 berths3 cabins11 m2014
from
€1,150
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Oyster Shell

Oyster Shell

Bareboat

7 berths3 cabins11 m2014
from
€1,308
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Soprano

Soprano

Bareboat

8 berths3 cabins11 m2013
from
€1,150
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Topaze

Topaze

Bareboat

8 berths3 cabins11 m2012
from
€1,560
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b'elli 20% · Last minute

b'elli

Bareboat

6 berths2 cabins11 m2012
from
€990
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Simply The Best

Simply The Best

Bareboat

4 berths2 cabins11 m2023
from
€2,300
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Soca Sleigh

Soca Sleigh

Bareboat

4 berths2 cabins11 m2024
from
€629
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Nala

Nala

Bareboat

8 berths3 cabins11 m2022
from
€1,348
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Bright Elli20% · Last minute

Bright Elli

Bareboat

7 berths3 cabins11 m2022
from
€1,350
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Just Happy

Just Happy

Bareboat

7 berths3 cabins11 m2022
from
€2,300
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Ethra

Ethra

Bareboat

8 berths3 cabins11 m2022
from
€2,000
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Amelie

Amelie

Bareboat

8 berths3 cabins11 m2024
from
€1,383
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4 elli20% · Last minute

4 elli

Bareboat

8 berths3 cabins11 m2023
from
€1,820
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Filippos II

Filippos II

Bareboat

8 berths3 cabins11 m2023
from
€2,000
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Bura Kiss

Bura Kiss

Bareboat

8 berths3 cabins11 m2023
from
€2,150
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Princess Anja

Princess Anja

Bareboat

8 berths3 cabins11 m2024
from
€900
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Princess Marija

Princess Marija

Bareboat

8 berths3 cabins11 m2024
from
€900
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Princess Lara

Princess Lara

Bareboat

8 berths3 cabins11 m2024
from
€1,490
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Princess Tia

Princess Tia

Bareboat

8 berths3 cabins11 m2024
from
€1,490
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Aurora

Aurora

Bareboat

8 berths3 cabins11 m2024
from
€1,383
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Evita

Evita

Bareboat

8 berths3 cabins11 m2024
from
€1,383
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Ocean Breeze

Ocean Breeze

Bareboat

6 berths3 cabins11 m2022
from
€1,475
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Princess Anja

Princess Anja

Bareboat

8 berths3 cabins11 m2024
from
€900
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Princess Marija

Princess Marija

Bareboat

8 berths3 cabins11 m2024
from
€900
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Sea Kiss

Sea Kiss

Bareboat

8 berths3 cabins11 m2024
from
€2,150
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Red Kiss

Red Kiss

Bareboat

8 berths3 cabins11 m2025
from
€2,150
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Diana

Diana

Bareboat

8 berths3 cabins11 m2022
from
€2,000
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Philippa

Philippa

Bareboat

8 berths3 cabins11 m2023
from
€2,100
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Lidija

Lidija

Bareboat

8 berths3 cabins11 m2023
from
€1,500
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Leo

Leo

Bareboat

8 berths3 cabins11 m2025
from
€1,550
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Pelmare

Pelmare

Bareboat

8 berths3 cabins11 m2025
from
€2,300
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Pelor

Pelor

Bareboat

8 berths3 cabins11 m2025
from
€2,300
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Calypso Express

Calypso Express

Bareboat

6 berths3 cabins11 m2024
from
€655
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Derminica

Derminica

Bareboat

8 berths3 cabins11 m2025
from
€2,000
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Sunny5% · Last minute

Sunny

Bareboat

6 berths3 cabins11 m2022
from
€2,100
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Moon Kiss

Moon Kiss

Bareboat

8 berths3 cabins11 m2025
from
€2,150
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Kavinton

Kavinton

Bareboat

7 berths3 cabins11 m2025
from
€1,500
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Ancsika

Ancsika

Bareboat

7 berths3 cabins11 m2025
from
€1,500
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Euforica

Euforica

Bareboat

6 berths3 cabins11 m2023
from
€2,200
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Vida

Vida

Bareboat

8 berths3 cabins11 m2024
from
€1,500
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Verona

Verona

Bareboat

8 berths3 cabins12 m2016
from
€2,050
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Geneva

Geneva

Bareboat

8 berths3 cabins12 m2016
from
€2,050
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Agios Georgios

Agios Georgios

Bareboat

6 berths3 cabins12 m2016
from
€1,185
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Tina

Tina

Bareboat

8 berths3 cabins12 m2018
from
€1,400
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Amadeus

Amadeus

Bareboat

8 berths3 cabins12 m2018
from
€1,350
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Sissi

Sissi

Bareboat

8 berths3 cabins12 m2019
from
€1,500
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BarElli20% · Last minute

BarElli

Bareboat

8 berths3 cabins12 m2019
from
€1,490
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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.