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 73 of 82

night elli20% · Last minute

night elli

Bareboat

8 berths3 cabins12 m2023
from
€1,490
View →
Paris25% · Last minute

Paris

Bareboat

6 berths3 cabins12 m2024
from
€2,580
View →
Midnight Kiss

Midnight Kiss

Bareboat

8 berths3 cabins12 m2023
from
€2,570
View →
Nastazia

Nastazia

Bareboat

8 berths3 cabins12 m2023
from
€2,300
View →
Elektra

Elektra

Bareboat

8 berths3 cabins12 m2022
from
€2,400
View →
Thalassa

Thalassa

Bareboat

8 berths3 cabins12 m2024
from
€2,500
View →
Orla

Orla

Bareboat

6 berths3 cabins12 m2023
from
€3,400
View →
Henry Every

Henry Every

Bareboat

6 berths3 cabins12 m2024
from
€1,900
View →
SuElli20% · Last minute

SuElli

Bareboat

8 berths3 cabins12 m2024
from
€1,630
View →
Bona Res

Bona Res

Bareboat

8 berths3 cabins12 m2024
from
€1,563
View →
Lumina

Lumina

Bareboat

8 berths3 cabins12 m2024
from
€1,800
View →
Sea Pearl20% · Last minute

Sea Pearl

Bareboat

8 berths3 cabins12 m2024
from
€1,650
View →
Oskar

Oskar

Bareboat

8 berths3 cabins12 m2024
from
€1,850
View →
Little Tony

Little Tony

Bareboat

8 berths3 cabins12 m2021
from
€2,200
View →
Irene

Irene

Bareboat

8 berths3 cabins12 m2020
from
€2,200
View →
Bella Ciao

Bella Ciao

Bareboat

8 berths3 cabins12 m2024
from
€2,570
View →
Naias

Naias

Bareboat

6 berths3 cabins12 m2024
from
€1,900
View →
Bobo

Bobo

Bareboat

8 berths3 cabins12 m2024
from
€2,570
View →
Brasilia

Brasilia

Bareboat

8 berths3 cabins12 m2024
from
€2,400
View →
S. Raphael

S. Raphael

Bareboat

8 berths3 cabins12 m2023
from
€2,200
View →
Mare

Mare

Bareboat

8 berths3 cabins12 m2025
from
€1,800
View →
Maral

Maral

Bareboat

8 berths3 cabins12 m2025
from
€1,850
View →
Night Flower

Night Flower

Bareboat

8 berths3 cabins12 m2022
from
€2,100
View →
Colibri

Colibri

Bareboat

8 berths3 cabins12 m2025
from
€2,800
View →
Zheng Yi Sao (郑一嫂)

Zheng Yi Sao (郑一嫂)

Bareboat

6 berths3 cabins12 m2025
from
€1,900
View →
Oliver

Oliver

Bareboat

8 berths3 cabins12 m2025
from
€1,850
View →
Titzi

Titzi

Bareboat

8 berths3 cabins12 m2025
from
€2,700
View →
Tola Sunrise

Tola Sunrise

Bareboat

6 berths3 cabins12 m2020
from
€688
View →
Easy Skanking

Easy Skanking

Bareboat

6 berths3 cabins12 m2024
from
€757
View →
Evelina

Evelina

Bareboat

8 berths3 cabins12 m2019
from
€2,950
View →
Baghera

Baghera

Bareboat

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

Chimera

Bareboat

8 berths3 cabins12 m2021
from
€2,950
View →
Sunset Kiss

Sunset Kiss

Bareboat

8 berths3 cabins12 m2025
from
€2,570
View →
Anda

Anda

Bareboat

6 berths3 cabins12 m2023
from
€1,900
View →
Emotion

Emotion

Bareboat

8 berths3 cabins12 m2019
from
€2,950
View →
Lowe

Lowe

Bareboat

6 berths3 cabins12 m2025
from
€2,570
View →
Intrepida

Intrepida

Bareboat

6 berths3 cabins12 m2021
from
€2,400
View →
Naoussa

Naoussa

Bareboat

8 berths3 cabins12 m2022
from
€2,700
View →
Alaska

Alaska

Bareboat

8 berths3 cabins12 m2022
from
€2,300
View →
Psi Octantis

Psi Octantis

Bareboat

6 berths3 cabins12 m2022
from
€790
View →
Teti

Teti

Bareboat

8 berths3 cabins12 m2021
from
€2,550
View →
Ohana

Ohana

Bareboat

8 berths3 cabins12 m2020
from
€2,600
View →
Iliada

Iliada

Bareboat

8 berths3 cabins12 m2023
from
€2,320
View →
Iliada

Iliada

Bareboat

3 cabins12 m2023
from
€2,950
View →
Kairos

Kairos

Bareboat

8 berths3 cabins12 m2026
from
€2,650
View →
Myriana

Myriana

Bareboat

8 berths3 cabins12 m2026
from
€2,450
View →
Akita

Akita

Bareboat

8 berths3 cabins12 m2026
from
€3,200
View →
Thalassa Nova

Thalassa Nova

Bareboat

8 berths3 cabins12 m2026
from
€2,630
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.