Sailing voyage Z06-26 Island hopping around the central & northwestern Azores

Adventure, nature, and relaxation in one of Europe’s most beautiful sailing regions

Join us on an unforgettable sailing journey through the rugged and enchanting Azores. We begin on the island of Terceira and set course for Graciosa, a small and tranquil island with a charming Portuguese harbor. With around 50 nautical miles, it will be a lovely first day of sailing. We stay an extra day here to descend into the impressive Caldeira, an ancient volcanic crater where the earth still gently bubbles. After a scenic hike, we’ll enjoy lunch with panoramic ocean views and unwind in the warm thermal waters of the spa — perhaps alternating with a refreshing dip in the sea.

After that, depending on the wind forecast, we’ll sail on to Flores, the northwesternmost island of the Azores and one of the most untouched and spectacular in the archipelago. At around 160 nautical miles, this means an overnight passage with a watch system. With a bit of luck, we’ll spot dolphins or even whales along the way, and we’re guaranteed at least one beautiful sunset or sunrise. Weather permitting, we’ll arrive at Flores by late afternoon the following day. In summer, the Azores are typically calm thanks to the well-known Azores High – ideal for relaxed and comfortable sailing, although we may not sail quite as fast as usual. Because the harbour on Flores was destroyed by a winter storm, we need stable weather in case we need to anchor off the island instead of mooring. In short, this voyage depends a little on nature’s cooperation, which is why we’ve planned it with flexibility.

If conditions allow, we’ll spend a day on Flores – a chance to rest, but also to explore its stunning natural beauty, such as the dramatic waterfalls and forest trails of Poço Ribeira do Ferreiro.

From there, we’ll sail to São Jorge, another overnight passage of around 145 nautical miles. Again, we’ll stay an extra day to explore the island. One of its highlights is the natural swimming pool on the east side, surrounded by volcanic columns and filled with clear azure ocean water – a perfect cool-down after a hike through the lush hills. We’ll also stop for a coffee at Café Nunes, where they serve beans from the only coffee plantation in Europe. The harbour at Velas is distinctly Portuguese in charm, and in the evening you’ll hear the unique chorus of hundreds of Cory’s Shearwaters returning to nest – a magical experience.

Our final leg takes us to the atmospheric sailing town of Horta on the island of Faial. We wrap up this extraordinary voyage with a cozy dinner — and of course, a farewell drink at the famous Peter Café Sport, the legendary meeting place for ocean sailors from around the world.

Daily distances vary from 20 to 160 nautical miles depending on weather and tide. The itinerary described above is subject to change based on conditions – flexibility is key on a sailing voyage like this.

Land excursions are not included in the price and are of course not mandatory.

Read more about our sailing holidays around the Azores

Information about this sailing holiday

Participants of this sailing holiday

Sailing holidays 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!)
– Optional tips. These are, of course, entirely voluntary, but always appreciated. Any tips are shared between the skipper and crew, as some guests assume that a tip is primarily intended for the Bosun, while the skipper is just as much a part of the team that makes the voyage possible. Contrary to what many guests assume, the skipper on board the Cherokee does not receive the highest salary.

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’.

Sailing holidays 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’.

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

Sailing holidays discounts can not be combined with each other.

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

Private charter

You can also rent the ship and crew for a privat charter. Then multiply the price with 7. For a private charter, you can choose one of the offered sailing holidays, provided there are no other bookings for that sailing journey. If you would like more information on private charter, please contact us.

Sailing holidays with your own private cabin

If you are a solo traveler and would like the comfort of a private cabin (room), you can reserve it for 1.6 times the price (for crossings, it will be 1.9x).

Extend your sailing holidays with an extra day B&B

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 € 125 per person. This automatically applies when booking multiple trips in a row.

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.