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 25 of 82

Herbie

Herbie

Bareboat

6 berths3 cabins11 m2017
from
€1,548
View →
Nice to Have

Nice to Have

Bareboat

7 berths3 cabins11 m2017
from
€1,548
View →
Freedom

Freedom

Bareboat

7 berths3 cabins11 m2017
from
€1,548
View →
Cetus

Cetus

Bareboat

8 berths3 cabins11 m2017
from
€2,100
View →
Ithaque

Ithaque

Bareboat

8 berths3 cabins11 m2018
from
€1,760
View →
Kiss the Life

Kiss the Life

Bareboat

8 berths3 cabins11 m2017
from
€1,305
View →
Barka

Barka

Bareboat

8 berths3 cabins11 m2018
from
€1,800
View →
Wanderlust

Wanderlust

Bareboat

8 berths3 cabins11 m2015
from
€1,382
View →
Lia

Lia

Bareboat

5 berths2 cabins11 m2017
from
€1,398
View →
Elena

Elena

Bareboat

8 berths3 cabins12 m2022
from
€1,650
View →
La Luz

La Luz

Bareboat

6 berths3 cabins12 m2022
from
€2,590
View →
Paris

Paris

Bareboat

6 berths3 cabins12 m2023
from
€1,990
View →
Juleroga3

Juleroga3

Bareboat

8 berths3 cabins12 m2023
from
€1,900
View →
Ino

Ino

Bareboat

8 berths3 cabins12 m2020
from
€1,623
View →
Yaya

Yaya

Bareboat

6 berths3 cabins12 m2023
from
€1,140
View →
Pixie

Pixie

Bareboat

6 berths3 cabins12 m2019
from
€1,040
View →
Alma Libre IX

Alma Libre IX

Bareboat

8 berths3 cabins12 m2023
from
€1,630
View →
Stella Marie IV

Stella Marie IV

Bareboat

8 berths3 cabins12 m2023
from
€1,900
View →
Rubens

Rubens

Bareboat

6 berths3 cabins12 m2024
from
€1,270
View →
Gin Fizz

Gin Fizz

Bareboat

8 berths3 cabins12 m2020
from
€1,440
View →
Olmato

Olmato

Bareboat

6 berths3 cabins12 m2020
from
€1,150
View →
Easy Living

Easy Living

Bareboat

8 berths3 cabins12 m2020
from
€1,900
View →
Avajava

Avajava

Bareboat

6 berths3 cabins12 m2021
from
€2,000
View →
Arya

Arya

Bareboat

8 berths3 cabins12 m2022
from
€2,350
View →
Joy 5

Joy 5

Bareboat

6 berths3 cabins12 m2023
from
€2,420
View →
Martini

Martini

Bareboat

8 berths3 cabins12 m2019
from
€1,440
View →
M'Amour

M'Amour

Bareboat

8 berths3 cabins12 m2023
from
€2,950
View →
Barracuda

Barracuda

Bareboat

8 berths3 cabins12 m2019
from
€1,600
View →
Friend Planet

Friend Planet

Bareboat

8 berths3 cabins12 m2019
from
€1,880
View →
Sara

Sara

Bareboat

8 berths3 cabins12 m2019
from
€1,544
View →
Nika

Nika

Bareboat

8 berths3 cabins12 m2019
from
€1,544
View →
Nunet

Nunet

Bareboat

8 berths3 cabins12 m2020
from
€1,600
View →
Maša

Maša

Bareboat

8 berths3 cabins12 m2020
from
€1,544
View →
Mimi

Mimi

Bareboat

8 berths3 cabins12 m2020
from
€1,544
View →
Klara

Klara

Bareboat

8 berths3 cabins12 m2020
from
€1,544
View →
Alexia

Alexia

Bareboat

7 berths3 cabins12 m2020
from
€1,742
View →
Sympathy Planet

Sympathy Planet

Bareboat

7 berths3 cabins12 m2021
from
€1,880
View →
Mercury

Mercury

Bareboat

8 berths3 cabins12 m2021
from
€950
View →
Coast to Coast

Coast to Coast

Bareboat

7 berths3 cabins12 m2021
from
€1,741
View →
Barone

Barone

Bareboat

8 berths3 cabins12 m2022
from
€2,500
View →
Esko (ex Manca)

Esko (ex Manca)

Bareboat

8 berths3 cabins12 m2019
from
€800
View →
Agnes

Agnes

Bareboat

6 berths3 cabins12 m2022
from
€1,900
View →
Theodora

Theodora

Bareboat

8 berths3 cabins12 m2022
from
€1,900
View →
Maestro

Maestro

Bareboat

8 berths3 cabins12 m2021
from
€1,700
View →
Souel

Souel

Bareboat

8 berths3 cabins12 m2021
from
€1,850
View →
Jelo

Jelo

Bareboat

8 berths3 cabins12 m2021
price on enquiry
View →
Les Copains D'abord

Les Copains D'abord

Bareboat

8 berths3 cabins12 m2020
from
€1,700
View →
Nafrayou

Nafrayou

Bareboat

8 berths3 cabins12 m2022
from
€1,900
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.