Sailing Trip W09-26: Ocean Passage from Madeira to the Azores (approx. 700 NM)

A unique mini-ocean crossing for adventurous sailors

At the end of the winter season, we set sail on a special voyage: from the subtropical island of Madeira to the lush green Azores. This is a unique offshore sailing experience covering around 700 nautical miles — perfect for anyone looking to gain ocean sailing experience or log qualifying miles for certifications such as CWO or RYA.

We begin our journey along the sheltered southern coast of Madeira, heading west. This first sailing day allows everyone to get familiar with the boat, the rhythm of life at sea, and the Atlantic swell. In the afternoon, we prepare for the open-water passage to the Azores.

4 to 5 days of non-stop sailing
The direct distance between Madeira and the Azores is about 500 nautical miles, but depending on wind direction and strength, we expect to be at sea for 4 to 5 days. We sail using a three-watch system (3 hours on, 6 hours off), which ensures enough rest and helps everyone stay sharp during their shifts — even during the colder night watches.

Along the way, we enjoy the deep blue Atlantic swell, breathtaking sunsets, a sky full of stars, and — with a bit of luck — dolphins or even whales.

Island-hopping in the Azores
If the wind is in our favor, we’ll have time to visit one or two Azorean islands after the crossing. Think of Santa Maria, the southernmost island, or the stunning São Miguel, with its crater lakes, volcanic hot springs, and green rolling hills.

Our journey ends in Praia da Vitória on the island of Terceira. To get there, we make one final overnight sail of about 100 nautical miles from São Miguel. On the last evening, we’ll enjoy a celebratory dinner at a cozy local restaurant to mark the end of an unforgettable trip.

A short ocean crossing – perfect for those who want to truly sail.

The daily sailing distances are between 42 and 550 miles. The above schedule is subject to weather, wind and tide.

Read more about our sailing holidays around the Azores

Information about this sailing holiday

Participants of this sailing holiday

Sailing holiday Prices 

The price is the rental cost for the ship with crew, including food and drinks on board, hence full board. The price mentioned is per person.

Included in the price:

– Food and drinks on board.
– Fuel, water, shore power, harbour fees and tourist tax.
– 1 towel set and bedding incl. duvet and, of course, a life jacket.
– For after sailing there is also wine and beer on board, based on average use. Should we run out, then you can purchase more yourself.

Not included:

– Your transfer, meaning your journey to and from the ship
– Sailing clothes and boots, you can rent these from us if you would like.
– Possible shore excursions such as renting a van, or visiting a museum etc.
– Food and drinks ashore, the last evening we will go out for dinner and this will be at your own expense. ( Should you wish to treat the crew as a thank you for a lovely sailing holiday, it would of course be greatly appreciated!)

On some of our sailing holidays, it is possible to book an extra overnight stay on board based on Bed & Breakfast (B&B, so without dinner) for €75 per person. This automatically applies when booking multiple trips in a row.

Duration & Time on Board

The listed trip duration refers to full calendar days. Since you embark on the first evening and disembark on the final morning, your actual time on board is on average about 1.5 days shorter. We use this format to keep our trips comparable with other providers – but we like to be transparent about the real time you’ll spend on board.

Sailing holidays discount

Customer Discount:
If you book a second sailing holiday with us within a year, you’ll get 2.5% off the ‘board price’.

Group discount:
If you book a sailing holiday as a group (more than 3 passengers), you will receive 2.5% discount per person on the ‘board price’.

Youth Discount:
If you are under 29 years old, you will get 5% discount on the ‘board price’.

Discounts can not be combined with each other.

Bonus Discount:
€25 extra discount when you choose a vegetarian menu on board.

Sailing holiday with your own private cabin

If you are a solo traveller and wish to enjoy the comfort of a private cabin (small room), then you can reserve it for 1.6 times the price (for crossings, category A, the rate is 1.9x).

Sailing holiday categories

Category A:
Offshore crossings, includes also sailing throughout the nights. Passengers will also be grouped in the watch system.

Category B:
Offshore sailing holidays, there will be no sailing throughout the nights, but occasionally a late arrival at the harbour (or an early departure), depending on the weather.

Category C:
Relaxed sailing holidays with shorter sailing distances, including more time for sightseeing and sometimes a nice land excursion.

Category D:
Sailing holiday specials, from ‘Sailing holidays with Yoga’ up to expedition sailing. Not every season available.

Category E:
Sailing holiday’s with extra sailtraining.

Category F:
Sailing holidays with also small children on board.