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 22 of 82

Papalina

Papalina

Bareboat

12 berths5 cabins16 m2007
from
€1,700
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Principessa

Principessa

Bareboat

12 berths5 cabins16 m2009
from
€1,900
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Fairy

Fairy

Bareboat

12 berths5 cabins16 m2008
from
€2,050
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Azzuro

Azzuro

Bareboat

12 berths5 cabins16 m2007
from
€2,500
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Lui

Lui

Bareboat

12 berths5 cabins16 m2008
from
€2,800
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Leonidas

Leonidas

Bareboat

12 berths5 cabins16 m2007
from
€2,000
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Rosso20% · Last minute

Rosso

Bareboat

11 berths5 cabins15 m2020
from
€2,000
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Bianco20% · Last minute

Bianco

Bareboat

11 berths5 cabins15 m2022
from
€2,350
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Dion

Dion

Bareboat

8 berths4 cabins15 m2025
from
€4,500
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Luna Blu

Luna Blu

Bareboat

9 berths4 cabins15 m2025
from
€5,000
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Aurora Blu

Aurora Blu

Bareboat

10 berths5 cabins17 m2022
from
€5,000
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Sofia Blu

Sofia Blu

Bareboat

10 berths5 cabins17 m2023
from
€5,000
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Elly Blu

Elly Blu

Bareboat

10 berths5 cabins17 m2023
from
€5,000
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Kaiba

Kaiba

Bareboat

10 berths5 cabins17 m2023
from
€5,600
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Six on the Sea

Six on the Sea

Bareboat

10 berths4 cabins17 m2025
from
€4,400
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Sauvignon Blanc

Sauvignon Blanc

Bareboat

12 berths5 cabins17 m2015
from
€2,500
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Burin Blu

Burin Blu

Bareboat

12 berths5 cabins17 m2017
price on enquiry
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Rioja

Rioja

Bareboat

12 berths5 cabins17 m2016
from
€1,950
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Elisa

Elisa

Bareboat

12 berths5 cabins17 m2019
from
€2,250
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Redshift

Redshift

Bareboat

8 berths3 cabins11 m2014
from
€820
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Stina24

Stina24

Bareboat

8 berths3 cabins11 m2019
from
€1,548
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Neree

Neree

Bareboat

6 berths3 cabins11 m2015
from
€2,345
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Aurélie

Aurélie

Bareboat

7 berths3 cabins12 m2023
from
€1,700
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Jenny

Jenny

Bareboat

7 berths3 cabins12 m2024
from
€1,725
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Bubba Gump

Bubba Gump

Bareboat

7 berths3 cabins12 m2024
from
€1,725
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Lieutenant Dan

Lieutenant Dan

Bareboat

8 berths3 cabins12 m2025
from
€1,725
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Mrs. Gump

Mrs. Gump

Bareboat

7 berths3 cabins12 m2025
from
€1,725
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Carla

Carla

Bareboat

7 berths3 cabins12 m2025
from
€1,725
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Forest Gump

Forest Gump

Bareboat

7 berths3 cabins12 m2026
from
€1,725
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Just B!

Just B!

Bareboat

7 berths3 cabins12 m2026
from
€1,725
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Ship Happens

Ship Happens

Bareboat

7 berths3 cabins12 m2026
from
€1,725
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Dolcevita

Dolcevita

Bareboat

6 berths3 cabins12 m2024
from
€2,050
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Hugo

Hugo

Bareboat

8 berths3 cabins15 m2023
from
€2,100
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Damis Jolie

Damis Jolie

Bareboat

4 berths2 cabins11 m2021
from
€3,619
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Ziriguidum

Ziriguidum

Bareboat

4 berths2 cabins11 m2023
from
€3,619
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Nossa Toca

Nossa Toca

Bareboat

6 berths3 cabins13 m2021
price on enquiry
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Nuestro

Nuestro

Bareboat

6 berths3 cabins13 m2022
from
€4,928
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Seu Vessel

Seu Vessel

Bareboat

6 berths3 cabins13 m2022
from
€4,928
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Infinity II

Infinity II

Bareboat

6 berths3 cabins13 m2025
from
€4,928
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Pura Vida

Pura Vida

Bareboat

6 berths3 cabins13 m2025
from
€4,928
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Akanni II

Akanni II

Bareboat

6 berths3 cabins13 m2025
from
€5,800
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Delta 465

Delta 465

Bareboat

8 berths4 cabins14 m2024
from
€7,000
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Delta 465 New

Delta 465 New

Bareboat

8 berths4 cabins14 m2026
from
€7,000
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Amica

Amica

Bareboat

7 berths2 cabins15 m2003
from
€2,300
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Apolonia

Apolonia

Bareboat

4 berths2 cabins10 m2014
from
€1,120
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Mio

Mio

Bareboat

6 berths2 cabins10 m2018
from
€1,050
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Dudu

Dudu

Bareboat

4 berths2 cabins10 m2017
from
€1,248
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Expensive Toy

Expensive Toy

Bareboat

4 berths2 cabins10 m2015
from
€1,550
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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.