A dinghy sailor rounding a red racing mark
Photo: Unsplash
Portland · RYA training centre

Everyone remembers their first gust.

Learn to sail on sheltered Dorset water - kids from 8, adults at any age, and racers who want their roll tacks sharper. Small groups, warm wetsuits, patient coaches.

Book a £35 taster See the courses
Today's windSW 12kn
Water17°C
Fleet14 dinghies
This weekend2 spaces
Courses

Pick your ticket. We'll sort the rest.

Boats, buoyancy aids and wetsuits all included. Every course maps to an RYA stage, so what you learn here counts everywhere.

First time · any age

Taster session

Two hours on the water with an instructor at the helm until you want it. Most people are steering within the hour.

2 hrs1:2 coachingYear round
£35per person
RYA Level 1–2 · adults

Start Sailing weekend

Two days from "which end is the front" to sailing a triangle on your own. Our most-booked course, and the best value.

2 daysMax 6Apr–Oct
£195incl. kit & cert
RYA Youth Stages 1–4 · ages 8–16

Young sailors

Saturday mornings through the season - stages, badges, capsize practice and a lot of laughing. Waiting list moves fast.

SaturdaysTerm blocksAges 8+
£120per 6-week block
Improvers · racing

Race coaching evenings

Starts, mark roundings, boat-on-boat tactics - Tuesday evenings with video debrief in the clubhouse after.

TuesdaysOwn boat okMay–Sep
£18per evening

Not sure which? Book the taster — it counts off your next course if you carry on.

Why Chesil

Sheltered water, small groups, proper coaching.

  • The water does the teaching - flat, sheltered and shallow, so confidence comes fast and capsizes are a giggle, not a drama
  • Max six per group - you're sailing, not queueing on a beach
  • RYA instructors, first-aid current - safety boat on the water for every session
  • Kit included - boats, wetsuits, buoyancy aids, spray tops; just bring trainers you don't mind wet
Ask about a course
The training fleet sailing together near the shore
Two beginner dinghies on flat turquoise water
Photos: Unsplash
Two dinghies racing on open water
“Booked a taster for my daughter. Ended up doing Level 2 myself.
Hannah R. · taster → Start Sailing weekend, 2025
Photo: Unsplash
The season

A year that fills up fast.

Apr → Oct · four blocks
Spring20 Apr – 24 MayStart Sailing weekends · youth block 1
Early summer1 Jun – 19 JulAll courses · race evenings begin
Holidays28 Jul – 30 AugKids' holiday weeks · family tasters
Autumn7 Sep – 18 OctYouth block 2 · improver weekends
A Laser dinghy sailing with the fleet behind Photo: Unsplash
Race coaching · Tuesdays
A brightly-sailed catamaran on calm water Photo: Unsplash
Cat conversions · by arrangement
Get on the water

Start with a taster. Everyone does.

Call the clubhouse: 01305 000 002 Email: hello@chesilsailing.co.uk Find us: The Slipway, Portland · open every sailing day
RYA recognised training centre · safety boat every session · instructors DBS-checked · first aid current