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Atlantic Island Hopping, from Madeira to the Canaries

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Embark Disembark Vessel DurationVoyage No
Fri 10-11-2023, 10:00Funchal, Madeira Wed 15-11-2023, 10:00Santa Cruz, Tenerife Santa Maria Manuela 5 NightsSM101123

Escape the humdrum with this varied adventure: the ideal mix of island hopping and open ocean passages. Explore the stunning islands of the Madeira and Desertas groups, before setting sail for the Canaries. This passage of over 250 nautical miles will give you a taste of big ocean sailing, as well as the chance to stand watch with the crew and experience the night sky like never before. You’ll stop over in the hidden gem of La Gomera, with time to get ashore and discover the lush forests and black sand beaches, before finishing up in Santa Cruz in Tenerife.

  • Voyage
  • Vessel


  • Sail through the remote and rugged Selvagen Islands & Ilhas Desertas, home to rare seals and undisturbed sea bird colonies
  • Enjoy a mini ocean passage
  • Explore the stunning variety of these Atlantic Island groups
  • Take the helm, trim the sails and help to navigate

Santa Maria Manuela

Vessel type / Rig Gaff Schooner
Guest Berths 50
Beam 33ft
Draft 18ft
Deck Length 173ft
Overall Length 225ft
Tonnage 992 tons
Year Built 1937
More about the Vessel

Voyage Description


Wildlife spotters, keen sailors, beginners and anyone wanting a varied and fascinating holiday with a taste of deep ocean sailing as well as the opportunity to explore some of the most beautiful islands in the world.

share the sunset with your shipmates
share the sunset with your shipmates


A 5 night voyage from Funchal, the capital city of Madeira, including an ocean passage of over 250 nautical miles. As trainee crew you will recieve training to sail this ocean going sailing ship.

Having set sail from Madeira’s green shores, it’s just a day’s sail to the south of Madeira’s Ilhas Desertas lie the Ilhas Selvagens marine park, which, in 2021 celebrated 50 years of protection by extending the zone to become Europe’s largest at 2.677 km2.  If the weather and sea state allow we may have the opportunity to use our zodiacs go ashore to spot for the mystical Shearwater, and maybe even the Mediterranean monk seal, the rarest in the world.

With 285 nautical miles of open ocean ahead there is an open invitation to get fully involved in all aspects of sailing, from standing watch with the crew, helming and trimming sails and from navigation to going aloft.  When you are not involved in the sailing there’s plenty of time to fish, read, play board games or share sailing stories by the bar.

On an ocean passage like this the crew is divided into four watches so you only have to be involved in sailing the ship when on watch. It could be an overnight watch for 4 hours with only the glow of the ships navigation lights to give any clue that a 225ft sailing ship is slipping through the waves. The dawn watch often brings sunrises, deck swabbing and the smell of baking bread and breakfast. Off watch in the daytime you might find a deck chair or a coil of rope in the sun to curl up and read a book, or you might chose to climb the rigging for a birds eye view.

After a couple of nights at sea, you arrive on the black sandy shores of La Gomera, where, if time allows, you’ll have leave to explore ashore in the dense, palm filled valleys.

Your final port of call is Santa Cruz in Tenerife, where you can easily extend your break with a shoreside holiday, or begin your onward journey with some fantastic memories of life on the open waves.

Santa Maria Manuela
Santa Maria Manuela by H Boehm

Ocean Passage

If you are new to tall ship sailing there are lots of seamanship tasks to learn, from coiling like a pro to making lines secure on belaying pins. Learning the sail names is fun, whatever language you prefer. Even if you are an experienced sailor, it takes a bit of getting used to 4 masts. They are called Mizzen, Main, Aft Foremast and Foremast. You could just watch the waves go by and marvel that this ship used to catch all of its cod from small dories it took with the ship all the way to Newfoundland and the rich, iceberg infested grounds of West Greenland. Hear how tough Portuguese fishermen launched a small fleet of dories from the mother ship and reeled in the cod with a rod and line.

hands on sailing on an ocean passage
hands on sailing on an ocean passage


As you leave Madeira you will be heading south and picking up the North East Trade winds. These are perfect sailing winds to push Santa Maria Manuela south.

It gets hotter and hotter the further south you go. You need good sun cream as the air here is so pure, so the UV light can be pretty strong.


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.


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.


Every customer sailing with us will need to fill in basic medical questions on their booking application. If you are not sure if your current level of fitness and agility are up to a voyage, then please ring the Classic Sailing Office on 01872 58 00 22 and we can chat through your concerns and possibly find options that might suit you better.


  • Skipper & professional crew
  • Personal Safety Equipment
  • Sailing Instruction
  • All meals, snacks and refreshments
  • Port and landing fees
  • Linen and duvets
  • Third Party liability insurance


  • Travel to Joining Port
  • Travel from end port
  • Alcoholic Drinks
  • Towels
  • Waterproofs

Start & End Port

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.

Santa Cruz, Tenerife

There are cheap flights to Tenerife from all over Europe as it is a major winter sun holiday destination. You can probably find a flight from regional airports too. There are too many discount airline options to mention.

The harbour in Santa Cruz de Tenerife is huge, with two marinas and miles of harbour wall and quaysides for cruise ships and bigger tall ships. Berths for tall ships are small fry for the port authorities as the bigger more profitable ships get priority, so the sailing ships captain will have to go where ever the port authority puts them, and they may not get to stay there for very long. Please book a flight that gets in at a sensible time for you to get to the ship on time, even if it means getting there the day before and booking into a hotel.

If your vessel is small enough to get into one of the marinas then we can usually be a bit more specific as to where to find the ship beforehand.

The ships exact location in port is often controlled by the port authorities and they will only allocate a docking position a few days before. You will be informed as soon as possible of their exact joining location.

Any changes will be communicated to you before your voyage start date. Make sure you make a note of the ship’s number found in your confirmation email in case of any problems on the day.

Take a Photo of your Ship

We recommend you take a photo of your ship with you to show taxi drivers so they can get to to the right ship!

You can usually see the ships masts on the other side of the harbour, but the taxi drivers will know the shortest route to get to that berth. If you are the independent type with a rucksack walking from the bus depot, chose your route with care, or ask a local, or you could end up walking miles without finding the cruise ship / public entry to the dock.

Kit List

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

Below is a recommended travel packing list for a sailing voyage. See bottom of page for Diving Holiday Kit List


  • Sailing Instruction
  • Safety Equipment (Life jackets and harnesses)
  • All meals to include cooked breakfast, lunch, dinner and refreshments throughout the day.
  • Bed linen, duvet, towels for cabin (but please bring your own beach towel)

What is Not Included

  • Waterproof jacket and trousers
  • Travel to and from the start and end port
  • Optional trips or tours taken ashore unless otherwise stated
  • Alcoholic Beverages , but you can purchase drinks from the bar (you can set up a tab and pay at the end).

What to Bring

For any destination north of Cape Verde warm and waterproof clothing is very important, as it can get cold during sailing, especially at night, even in the summer. A waterproof and windproof jacket is recommended to help keep warm and dry. Waterproof rubber soled boots or shoes are also recommended to keep your feet dry and warm. It is a good idea to bring two pairs of shoes in case one gets wet as salt water soaked shoes take a while to dry. Madeira, Portugal and the Azores in summer can get pretty hot and it is easy to get sunburn at sea as the air is clear. The Cape Verde are in a tropical climate so a good sun screen is essential. Please remember that space on board is limited and pack accordingly. Pack comfortable and practical clothing for all weather circumstances, the key is layers!! It is recommended to pack in a soft bag that can be easily stored away as there is no room on board for suitcases. Electricity on board is European 2 pin sockets, please be sure to bring any adaptors you may need.

Passports, Visas and Insurance

If you voyage is sailing in foreign waters, you will require a full passport that is valid for at least 6 months after the end of the voyage. You will be responsible for obtaining any necessary visas. We have Third Party Liability Insurance and recommend all those sailing with us to take out relevant travel insurance to cover their voyage.

Medical Conditions and Special Diets

Please inform us in advance of any medical conditions you have and medication which you might need to bring with you. If you have any special dietary requirements it is essential you inform us prior to your voyage. We will make every effort to cater for all diets with prior notice.

Personal Items

This is a list of the items we recommend you bring with you.
  • Warm hat and sun hat
  • gloves - either sailing gloves or gardening type gloves
  • Wet weather clothing – water proof and windproof jacket
  • Clothing – enough clothing for all weather circumstances (think layers!!)
  • Trainers or deck shoes
  • shorts and t shirts
  • nightwear (ear plugs ?)
  • Toiletries
  • Towels
  • swimwear (googles are useful)
  • Sun cream
  • Sunglasses
  • Sea sickness medication
  • Personal medication
  • Book
  • Small torch (head torches are good!)
  • Camera
  • Log book (if you have one)
  • Valid passport (voyages outside the UK)
  • Travel insurance
  • Musical instruments
  • games or cards
  • book/kindle
You can buy Santa Maria Manuela caps on board.

Diving Holidays on Santa Maria Manuela - Kit List

Please note the ship will only be carrying scuba diving equipment on the specialist diving voyages. On a diving voyage - Bottles and weights are included in the voyage price. If you need diving equipment other than bottles and weights it is €150 extra Nitrox costs €5 euros a dive Classic Sailing will expand on this kit list shortly.


We had the most amazing time. The crew were so friendly and helpful, the food was great throughout, and the cabins were really comfortable. We both climbed the rigging as the sun was setting over Porto Santo to round off a brilliant last day with the new friends we met. Thanks for the wonderful experience.

Ian & Dayna

I have sailed many times on tall ships, this is by far the best yet.

sailing for beginners


Terrific crew and ship and a lovely passage to the Azores. Crew and guests were very good and patient with someone who only spoke English. This is a terrifically well run vessel. Excellent accommodation, well serviced by a professional crew. All very friendly, helpful and willing to give information throughout. Many opportunities to get involved in most aspects of the ships operations. Very many thanks.


An amazing ship and amazing crew.


We had a terrific and adventurous time on board during Sachsen Sail in the Bay of Biscay. Thank you to all Santa Maria Manuela crew members!


Un voilier merveilleux avec un équipage très sympathique. Merci pour tout.

A splendid ship with a very kind crew. Thank you for everything.


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