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 77 of 82

Navillera

Navillera

Bareboat

10 berths4 cabins13 m2023
from
€2,100
View →
Blue Aura

Blue Aura

Bareboat

10 berths4 cabins13 m2024
from
€2,800
View →
Jenny

Jenny

Bareboat

10 berths4 cabins13 m2024
from
€2,660
View →
Taurus

Taurus

Bareboat

10 berths4 cabins13 m2024
from
€2,250
View →
JoElli20% · Last minute

JoElli

Bareboat

9 berths4 cabins13 m2024
from
€2,220
View →
tam elli20% · Last minute

tam elli

Bareboat

9 berths4 cabins13 m2024
from
€2,220
View →
Virginia

Virginia

Bareboat

10 berths4 cabins13 m2022
from
€2,400
View →
Koala II20% · Last minute

Koala II

Bareboat

10 berths4 cabins13 m2024
from
€2,690
View →
Apollonas

Apollonas

Bareboat

10 berths4 cabins13 m2020
from
€2,020
View →
Cicerenella

Cicerenella

Bareboat

10 berths4 cabins13 m2019
from
€2,800
View →
Maryann

Maryann

Bareboat

10 berths4 cabins13 m2023
from
€2,800
View →
Aitna

Aitna

Bareboat

10 berths4 cabins13 m2020
from
€2,600
View →
Iddu

Iddu

Bareboat

10 berths4 cabins13 m2020
from
€2,600
View →
Nennella

Nennella

Bareboat

10 berths4 cabins13 m2019
from
€2,600
View →
Art  Vandelay

Art Vandelay

Bareboat

10 berths4 cabins13 m2024
from
€2,050
View →
tam elli

tam elli

Bareboat

9 berths4 cabins13 m2024
from
€3,900
View →
JoElli

JoElli

Bareboat

9 berths4 cabins13 m2024
from
€3,900
View →
Anima

Anima

Bareboat

10 berths4 cabins13 m2020
from
€2,600
View →
Sea Star

Sea Star

Bareboat

10 berths4 cabins13 m2020
from
€2,000
View →
Sun Kiss

Sun Kiss

Bareboat

10 berths4 cabins13 m2025
from
€2,660
View →
Milky Way

Milky Way

Bareboat

10 berths4 cabins13 m2019
from
€1,400
View →
Holiday Kiss

Holiday Kiss

Bareboat

8 berths4 cabins13 m2020
from
€2,000
View →
Frenetica

Frenetica

Bareboat

8 berths4 cabins13 m2020
from
€2,850
View →
Kiwi

Kiwi

Bareboat

10 berths4 cabins13 m2026
from
€2,000
View →
Tikal III

Tikal III

Bareboat

18 berths4 cabins13 m2019
from
€3,100
View →
Gojiberry

Gojiberry

Bareboat

10 berths4 cabins13 m2018
from
€3,385
View →
Negroni

Negroni

Bareboat

4 cabins13 m2019
from
€3,100
View →
Enrica

Enrica

Bareboat

10 berths4 cabins13 m2019
from
€2,940
View →
Erminia

Erminia

Bareboat

10 berths4 cabins13 m2019
from
€2,940
View →
Negroni

Negroni

Bareboat

10 berths4 cabins13 m2019
from
€2,470
View →
Karla

Karla

Bareboat

10 berths4 cabins13 m2023
from
€2,190
View →
Habibi

Habibi

Bareboat

10 berths4 cabins13 m2020
from
€2,230
View →
Trinity

Trinity

Bareboat

8 berths4 cabins13 m2023
from
€2,300
View →
Silvana D

Silvana D

Bareboat

10 berths4 cabins13 m2019
from
€2,800
View →
Bonbon

Bonbon

Bareboat

10 berths4 cabins13 m2022
from
€2,800
View →
Leona

Leona

Bareboat

8 berths4 cabins13 m2024
from
€2,050
View →
Ares

Ares

Bareboat

8 berths4 cabins13 m2024
from
€2,000
View →
Greta

Greta

Bareboat

8 berths4 cabins13 m2024
from
€2,050
View →
Airbender

Airbender

Bareboat

10 berths4 cabins13 m2016
from
€2,000
View →
Pižulot

Pižulot

Bareboat

10 berths4 cabins13 m2016
from
€1,600
View →
Beaujolais20% · Last minute

Beaujolais

Bareboat

10 berths4 cabins13 m2017
from
€1,450
View →
Kronos25% · Last minute

Kronos

Bareboat

9 berths4 cabins13 m2018
from
€2,730
View →
Gaia25% · Last minute

Gaia

Bareboat

9 berths4 cabins13 m2018
from
€2,730
View →
Alpha

Alpha

Bareboat

8 berths4 cabins13 m2017
from
€1,776
View →
Bravo

Bravo

Bareboat

8 berths4 cabins13 m2017
from
€1,776
View →
Charlie

Charlie

Bareboat

8 berths4 cabins13 m2017
from
€1,776
View →
Tortuga

Tortuga

Bareboat

10 berths4 cabins13 m2018
from
€1,600
View →
Port Royal

Port Royal

Bareboat

10 berths4 cabins13 m2018
from
€1,600
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.