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 65 of 82

Retsina

Retsina

Bareboat

12 berths5 cabins16 m2020
from
€3,200
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Bluescape II

Bluescape II

Bareboat

12 berths6 cabins16 m2020
from
€2,500
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Glafki

Glafki

Bareboat

13 berths5 cabins16 m2023
from
€2,600
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Aloha

Aloha

Bareboat

12 berths5 cabins16 m2021
from
€2,425
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Dalia

Dalia

Bareboat

13 berths5 cabins16 m2024
from
€2,700
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Captain George

Captain George

Bareboat

12 berths5 cabins16 m2020
from
€3,100
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Panthata

Panthata

Bareboat

13 berths5 cabins16 m2022
from
€3,500
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Olga

Olga

Bareboat

12 berths6 cabins16 m2023
from
€1,800
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Dima II

Dima II

Bareboat

12 berths5 cabins16 m2018
from
€2,700
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Selinde

Selinde

Bareboat

13 berths5 cabins16 m2024
from
€3,630
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Spyros

Spyros

Bareboat

13 berths5 cabins16 m2022
from
€2,700
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Eli

Eli

Bareboat

13 berths5 cabins16 m2024
from
€2,700
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First Friendship

First Friendship

Bareboat

11 berths5 cabins16 m2024
from
€2,470
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Seaduction

Seaduction

Bareboat

13 berths5 cabins16 m2024
from
€1,950
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First Heartbeat

First Heartbeat

Bareboat

11 berths5 cabins16 m2023
from
€2,380
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Lima

Lima

Bareboat

13 berths5 cabins16 m2019
from
€3,600
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Avocado

Avocado

Bareboat

13 berths5 cabins16 m2019
from
€3,600
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Malafemmena

Malafemmena

Bareboat

12 berths5 cabins16 m2019
from
€4,100
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San Blas

San Blas

Bareboat

12 berths5 cabins16 m2021
from
€3,900
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Saint Michel

Saint Michel

Bareboat

12 berths5 cabins16 m2018
from
€3,900
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Promitheas

Promitheas

Bareboat

11 berths5 cabins16 m2022
from
€2,825
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Elise

Elise

Bareboat

12 berths5 cabins16 m2020
from
€3,200
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True Wind

True Wind

Bareboat

12 berths5 cabins16 m2019
from
€3,200
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Velvet Dice

Velvet Dice

Bareboat

12 berths5 cabins16 m2019
from
€3,800
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Bolero

Bolero

Bareboat

11 berths5 cabins16 m2019
from
€3,800
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OceanChill

OceanChill

Bareboat

12 berths5 cabins16 m2025
from
€2,300
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Forkys

Forkys

Bareboat

12 berths5 cabins16 m2023
from
€3,100
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Barracuda

Barracuda

Bareboat

11 berths5 cabins16 m2019
from
€3,200
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Elise

Elise

Bareboat

12 berths5 cabins16 m2020
from
€4,900
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Aquaris

Aquaris

Bareboat

13 berths5 cabins16 m2026
from
€4,200
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Libery

Libery

Bareboat

12 berths5 cabins16 m2023
from
€4,120
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Salma 20% · Last minute

Salma

Bareboat

12 berths5 cabins16 m2018
from
€2,800
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Glafki

Glafki

Bareboat

12 berths5 cabins16 m2023
from
€2,600
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Dodo

Dodo

Bareboat

8 berths3 cabins16 m2022
from
€3,300
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Tinčika

Tinčika

Bareboat

7 berths3 cabins16 m2026
from
€4,290
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Tinčika

Tinčika

Bareboat

7 berths3 cabins16 m2026
from
€4,290
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Orange

Orange

Bareboat

12 berths5 cabins16 m2026
from
€2,800
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B-52

B-52

Bareboat

13 berths5 cabins16 m2026
from
€2,650
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B-52

B-52

Bareboat

13 berths5 cabins16 m2026
from
€2,650
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Kos 52.1

Kos 52.1

Bareboat

11 berths5 cabins16 m2026
from
€4,500
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Amorgos

Amorgos

Bareboat

11 berths5 cabins16 m2026
from
€6,500
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Sirena De Oro

Sirena De Oro

Bareboat

10 berths5 cabins17 m2009
from
€2,574
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Spring Song

Spring Song

Bareboat

9 berths3 cabins17 m2023
from
€5,200
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Eve One

Eve One

Bareboat

7 berths3 cabins17 m2024
from
€3,290
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Captain John

Captain John

Bareboat

9 berths4 cabins17 m2009
from
€2,450
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Alex

Alex

Bareboat

10 berths4 cabins17 m2009
from
€3,080
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Inspiration

Inspiration

Bareboat

11 berths4 cabins17 m2009
from
€2,800
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Esther

Esther

Bareboat

12 berths4 cabins17 m2017
from
€3,000
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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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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.