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 66 of 82

Lucky Trader

Lucky Trader

Bareboat

11 berths5 cabins17 m2015
from
€2,300
View →
Dreamer

Dreamer

Bareboat

12 berths5 cabins17 m2016
from
€3,200
View →
Reminescence

Reminescence

Bareboat

10 berths4 cabins19 m2024
from
€8,500
View →
Ultreya

Ultreya

Bareboat

10 berths3 cabins19 m2017
from
€5,000
View →
Infinity15% · Last minute

Infinity

Bareboat

9 berths3 cabins19 m2024
from
€7,469
View →
Scorpio III

Scorpio III

Bareboat

9 berths3 cabins19 m2025
from
€6,190
View →
Eol I

Eol I

Bareboat

11 berths4 cabins19 m2015
from
€5,500
View →
Despina

Despina

Bareboat

6 berths2 cabins10 m2004
from
€1,000
View →
No regrets

No regrets

Bareboat

4 berths2 cabins10 m2007
from
€215
View →
Ariadne

Ariadne

Bareboat

6 berths3 cabins11 m2008
from
€1,250
View →
Naysika

Naysika

Bareboat

6 berths3 cabins11 m2008
from
€1,250
View →
Panorama

Panorama

Bareboat

6 berths3 cabins11 m2010
from
€1,100
View →
Milica

Milica

Bareboat

8 berths3 cabins12 m2006
from
€1,550
View →
Armenistis

Armenistis

Bareboat

6 berths3 cabins12 m2002
from
€1,150
View →
Crete

Crete

Bareboat

8 berths3 cabins12 m2002
price on enquiry
View →
Nemesis

Nemesis

Bareboat

10 berths4 cabins13 m2000
from
€1,500
View →
Hypo

Hypo

Bareboat

10 berths4 cabins13 m2003
from
€1,000
View →
Erika

Erika

Bareboat

10 berths4 cabins13 m2000
from
€2,000
View →
Derin

Derin

Bareboat

6 berths3 cabins13 m2007
from
€2,100
View →
Rose Runner

Rose Runner

Bareboat

10 berths4 cabins14 m2000
from
€1,300
View →
Seagull

Seagull

Bareboat

10 berths4 cabins14 m1997
from
€1,540
View →
Vori

Vori

Bareboat

9 berths4 cabins14 m2002
from
€2,200
View →
Chrysa M

Chrysa M

Bareboat

10 berths4 cabins14 m2005
from
€1,650
View →
Pigasos

Pigasos

Bareboat

10 berths4 cabins14 m2003
from
€1,650
View →
White Bird

White Bird

Bareboat

7 berths3 cabins17 m2022
from
€7,150
View →
Onyx

Onyx

Bareboat

9 berths3 cabins19 m2022
from
€8,000
View →
Olga V

Olga V

Bareboat

7 berths3 cabins19 m2017
from
€9,900
View →
Thora Helen

Thora Helen

Bareboat

10 berths4 cabins19 m2018
from
€4,220
View →
Parte II

Parte II

Bareboat

7 berths3 cabins16 m2007
from
€1,800
View →
Stavroula

Stavroula

Bareboat

10 berths5 cabins16 m2002
from
€2,450
View →
Delfios

Delfios

Bareboat

11 berths5 cabins17 m2008
from
€3,800
View →
Alexandria

Alexandria

Bareboat

12 berths5 cabins18 m2007
from
€1,950
View →
Alexandros

Alexandros

Bareboat

12 berths5 cabins18 m2007
from
€1,950
View →
Katerina

Katerina

Bareboat

11 berths6 cabins18 m2007
from
€2,000
View →
Christianna VIII

Christianna VIII

Bareboat

12 berths6 cabins18 m2005
from
€3,630
View →
Christianna VIII

Christianna VIII

Bareboat

12 berths6 cabins18 m2005
from
€6,050
View →
Black Bird

Black Bird

Bareboat

4 berths1 cabins9 m1982
from
€1,300
View →
Raceberry

Raceberry

Bareboat

8 berths3 cabins13 m2020
from
€3,350
View →
Windrausch

Windrausch

Bareboat

7 berths3 cabins11 m2023
from
€3,500
View →
Sail la Vie

Sail la Vie

Bareboat

7 berths3 cabins11 m2025
from
€3,000
View →
Ithaka

Ithaka

Bareboat

8 berths3 cabins14 m2025
from
€6,000
View →
Xavier

Xavier

Bareboat

6 berths2 cabins11 m2017
from
€1,800
View →
Heol Braz

Heol Braz

Bareboat

8 berths3 cabins12 m2024
from
€2,100
View →
Horizon

Horizon

Bareboat

6 berths3 cabins12 m2014
from
€3,350
View →
Neree

Neree

Bareboat

8 berths4 cabins13 m2019
from
€2,300
View →
St. Kitts

St. Kitts

Bareboat

5 berths2 cabins11 m2025
from
€2,648
View →
Piccola Strega

Piccola Strega

Bareboat

4 berths2 cabins10 m2013
from
€1,298
View →
Punta D'Oro

Punta D'Oro

Bareboat

6 berths3 cabins12 m2012
from
€1,548
View →

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.
Talk to a real charter expert

Real people

Talk to a human

A real person reads every message and replies within 24 hours — no bots, no auto-replies.

  • Honest advice from sailors, not salespeople
  • We reply within 24 hours
  • No spam, ever

Quick inquiry

Get three sailboat options from the team.

Tell us roughly when, where, and how many. we'll send three sailboat options the same day — three boats, three prices, the trade-offs.

Final boarding call

Why not you?

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.

60 seconds. No payment until you choose a boat.
Yacht under sail at sunset

Free quote

Get three real options.

Tell us roughly when and where. we'll send three real boats, three prices, the trade-offs — usually within the hour.