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 4 of 82

Black Pearl

Black Pearl

Bareboat

8 berths3 cabins11 m2024
from
€2,400
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Levante

Levante

Bareboat

6 berths3 cabins11 m2023
from
€2,580
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Freewise

Freewise

Bareboat

8 berths3 cabins11 m2025
from
€1,600
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Galini

Galini

Bareboat

7 berths3 cabins11 m2025
from
€1,950
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Velika Luka

Velika Luka

Bareboat

8 berths3 cabins11 m2025
from
€1,900
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Moya

Moya

Bareboat

8 berths3 cabins11 m2024
from
€1,850
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Williams

Williams

Bareboat

8 berths3 cabins11 m2025
from
€1,550
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Wilma

Wilma

Bareboat

8 berths3 cabins11 m2025
from
€1,550
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Asterix

Asterix

Bareboat

6 berths3 cabins11 m2024
from
€2,100
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Simea

Simea

Bareboat

8 berths3 cabins11 m2025
from
€2,400
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Babe

Babe

Bareboat

8 berths3 cabins11 m2024
from
€1,900
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Freya

Freya

Bareboat

7 berths3 cabins11 m2024
from
€2,120
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Ohana

Ohana

Bareboat

8 berths3 cabins11 m2024
from
€1,550
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Olivia

Olivia

Bareboat

6 berths3 cabins11 m2026
from
€3,100
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Xenia

Xenia

Bareboat

7 berths3 cabins11 m2024
from
€1,750
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Xiphias V

Xiphias V

Bareboat

8 berths3 cabins11 m2026
from
€2,400
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Alaia

Alaia

Bareboat

6 berths3 cabins11 m2022
from
€2,200
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Tena

Tena

Bareboat

7 berths3 cabins11 m2025
from
€1,891
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Maupiti

Maupiti

Bareboat

7 berths3 cabins12 m2020
from
€1,500
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Nomad

Nomad

Bareboat

6 berths3 cabins12 m2021
from
€2,190
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Horizon

Horizon

Bareboat

6 berths3 cabins12 m2021
from
€2,000
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Seawave

Seawave

Bareboat

6 berths3 cabins12 m2021
from
€2,000
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Fiesta

Fiesta

Bareboat

6 berths3 cabins12 m2021
from
€2,890
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Josef

Josef

Bareboat

8 berths3 cabins12 m2021
from
€1,600
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Past

Past

Bareboat

6 berths3 cabins12 m2021
from
€2,800
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Karpouzi

Karpouzi

Bareboat

8 berths3 cabins12 m2021
from
€1,700
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Sofia

Sofia

Bareboat

7 berths3 cabins12 m2022
from
€1,945
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Bella

Bella

Bareboat

8 berths3 cabins12 m2022
from
€1,400
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Srna

Srna

Bareboat

7 berths3 cabins12 m2022
from
€1,600
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SeaTime

SeaTime

Bareboat

7 berths3 cabins12 m2023
from
€1,800
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Calefijusa

Calefijusa

Bareboat

6 berths3 cabins12 m2023
from
€2,100
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Maraschino

Maraschino

Bareboat

8 berths3 cabins12 m2023
from
€1,650
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Playa Blanca20% · Last minute

Playa Blanca

Bareboat

8 berths3 cabins12 m2023
from
€1,409
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Mauvic

Mauvic

Bareboat

8 berths3 cabins12 m2023
from
€2,749
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Dna

Dna

Bareboat

8 berths3 cabins12 m2023
from
€2,618
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Bella

Bella

Bareboat

7 berths3 cabins12 m2023
from
€2,500
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Quick Point

Quick Point

Bareboat

7 berths3 cabins12 m2022
from
€2,000
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Relax

Relax

Bareboat

7 berths3 cabins12 m2023
from
€1,800
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Hope I

Hope I

Bareboat

8 berths3 cabins12 m2023
from
€2,300
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Leopard

Leopard

Bareboat

8 berths3 cabins12 m2023
from
€2,800
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Leopard

Leopard

Bareboat

8 berths3 cabins12 m2023
from
€1,819
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Arian

Arian

Bareboat

8 berths3 cabins12 m2022
from
€1,700
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Valesia

Valesia

Bareboat

8 berths3 cabins12 m2021
from
€1,660
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Kalispera

Kalispera

Bareboat

8 berths3 cabins12 m2022
from
€1,800
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Ermis

Ermis

Bareboat

8 berths3 cabins12 m2023
from
€2,240
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Aeolus

Aeolus

Bareboat

7 berths3 cabins12 m2022
from
€2,050
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Val

Val

Bareboat

7 berths3 cabins12 m2023
from
€2,000
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Supereva

Supereva

Bareboat

7 berths3 cabins12 m2023
from
€2,900
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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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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.