Eye of the Wind Plymouth to Madeira EYE25/36

Embark	Disembark	Vessel	Duration	Voyage No
Wed 29-10-2025, 19:00Plymouth, UK	Wed 12-11-2025, 10:00Funchal, Madeira	Eye of the Wind	14 Nights	EYE25/36

Voyage Description

FULL VOYAGE DESCRIPTION

Setting Sail from Plymouth

Plymouth is a wonderfully historic port with lots to explore, so do spend some time in the city if you can! Take a walk up to the Hoe for fantastic views of Plymouth Sound, visit the Mayflower steps and the historic Barbican or take a look at the Devonport Naval Heritage Centre.

Stepping aboard Eye of the Wind, you’ll get to know your fellow crew over dinner and receive a full safety briefing, plus an up to date itinerary based on the latest weather forecast.

Along the Way

Your voyage to Madeira starts in beautiful Plymouth Sound, where you can begin getting your bearings and literally learning the ropes! Once clear of England’s South Coast, your route along the Atlantic’s Eastern edge will be dictated by the latest weather forecasts. Two weeks on board might seem a long time, but Eye of the Wind has over 1200 nautical miles to cover! You will soon fall into the rhythm of life on board, and enjoy the head-space the ocean provides.

En route the crew will get you as involved as you like with the sailing of the ship, and will teach you to steer, keep lookout, haul lines and set and trim sails.

Photo by Matthew Stuttard of Eye crew in the rigging

Arriving in Madeira

On arrival in the Madeira archipelago, a celebratory swim might be called for in the calm waters of Porto Santo, with its stunning 9km sandy beach. If the ship has made good time, you may have a few days in hand to explore these gorgeous islands, before setting sail finally for Funchal, a city perched on an ancient volcanic slope. Funchal is a mecca for hikers, cyclists and nature lovers, with its backdrop of impressive mountains and a UNESCO world heritage site natural park. If you can, spend a few days here before making your onward travel arrangements.

WINDS, WAVES & WEATHER

Part of the fun of an extended ocean voyage is the chance to experience sailing in a variety of conditions. You will doubtless have some glorious sunny days and some smooth seas, particularly as you get further South, but you should also expect big Atlantic swells, chilly night time temperatures and sometimes foul weather. It’s all part of the adventure!

A NOTE ON VOYAGE DESCRIPTIONS

On a sailing voyage we never use the word itinerary, as skippers will always be aiming for the best and safest sailing routes for the forecast. They are as keen as you to include some of the highlights described above, but when it comes to sailing, you have to go with Mother Nature, not fight her. The description provided is based on what we think might be possible, based on past trips, or prior experience, but nothing is guaranteed on a sailing voyage. As such, the scheduled joining ports, routes, activities and/or destinations may be altered. Due to the complexities of weather systems, this may be at very short notice.

HANDS ON HOLIDAYS

Whether you are an experienced sailor or a complete beginner, the professional crew will train you to be guest crew from the moment you arrive, with the intention that everybody works together to sail the ship. The common thread to all Classic Sailing holidays is ‘Hands on’ participation on ships that use ropes, blocks and tackles and ‘people power’ to set sail.

SAILING STYLE & LIFE ON BOARD

We cater for a wide range of ages and physical abilities and how much you are expected to do varies a bit between vessels. See the vessel tab above which explains all about the ‘sailing style’ and what to expect in terms of hands on participation. There is a lot of information about day to day life, the ships facilities and accommodation on the vessel pages.

Start & End Port

Plymouth, UK

Plymouth is dubbed ‘Britain’s Ocean City’ and for good reason. It has huge significance for the UK’s maritime heritage, and the Royal Navy are still primarily based here.

Funchal, Madeira

If Funchal is your leaving port then arriving into Funchal by sea, offers stunning views of the city perched on an ancient volcanic slope. Shadowing the city are impressive mountains covered in laurel bushes and banana trees, a natural park which was nominated a UNESCO Word Heritage site in 1999, Laurissilva of Madeira.

If you are flying in to join your ship then you may get a birds eye view of this volcanic jewel in the Atlantic Ocean, unless the trade wind mists are swirling on the summits.

Kit List

What to pack for a sailing holiday on the Eye of the Wind

Working Language on Board is German and English

Practical Advice for Eye of the Wind

Practical Advice for Covid 19 and Eye of the Wind

What is Included

Sailing Instruction
All meals to include refreshments throughout the day
Duvet, pillow and sheets
Hand towels

What is not Included

Waterproof jackets and trousers
Alcoholic drinks but there is a bar on board
Any entry visas required

What to Bring

Suitcases take up a lot of room in a cabin, so it is better to uses soft bags in a ship. A small rucksack for going ashore is useful.

Eye of the Wind does not supply waterproof jackets and salopette type trousers. Please bring your own waterproof clothing.
A mix of warm and wind proof clothing.
Lots of thin layers is better than one thick layer in cold destinations.
In tropical countries - long sleeves and long trousers to protect you from the sun
Footwear on board needs a good grip and soft soles- the decks are wood or steel.
Ashore stout, waterproof walking boots are best if you are in remote places.
Eye of the Wind has electric sockets in all the cabins 240 V
Cameras, spare batteries, chargers if you need them
Binoculars are handy for bird watching etc.
Suntan lotion, hats, sunglasses
Dont forget any regular medication, persciption glasses and spare
Euros for bar bill
Passport, travel insurance, tickets etc
To get ashore is usually by dinghy so be prepared to get wet feet. Rubber boots or quick drying sandals - depending on the location.
The ship provides hand towels but please bring a beach towel
snorkel and mask for caribbean if you like snorkelling (travel tip: swimming goggles pack up smaller than a facemask)
Bring insect repellant for Caribbean as can get mosquitos ashore in evening (rare at anchor)
ear plugs can be handy

Electricity

All the power to your plug sockets comes from the ship's generator which runs on deisel. The less the generators have to run to top up power, the nicer it is for the guests on board and also greener for the planet. Please don't bring loads of hairdriers, electric devices to charge.

There is no internet on board whilst at sea.

Review

Hello all at Classic

The trip went very well and was a great experience.

Everything was very well done, great captain, crew and guests.

Sea shanty singing lead by Matthew from the King's Pond Shantymen!
Best wishes, Bob. Eye of the Wind, Cadiz to the Canary Islands November 2024

A fabulous adventure! Words cannot convey the experience.
John, Tortola to Bermuda

Tortola to the Azores! What a great time. Thanks to Captain Pit and the crew. An awesome adventure with awesome people!"
F Coutreau

What a wonderful, lovely, great, awesome trip we've had from Malaga to Lanzarote! I loved and enjoyed every minute.

Thanks again for this wonderful experience. I miss you guys!
Andrea

Now that was a voyage! The EYE crew - all 10 - five women and five men - embody two words:

COMPETENT and KIND

And such a beautiful ship. Thank you beyond measure
Susan

Vessel Gallery

With red sails against a blue sky, Eye of the Wind is a photogenic ship. If you have any new images we would love to see them since Eye of the Wind has only recently returned to our website.