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Island Hopping in central Azores

  • Vessel: Cherokee
  • Where: Azores, Portugal
  • Duration: 11 days
  • Embark: Praia da Vitória, Terceira - 10 July 2022, 18:30
  • Disembark: Horta, Faial - 20 July 2022, 10:30
Single berth in Twin Cabin £1,480 £370.00
Double Cabin (single occupancy)£2,220 £555.00
Double berth in Double Cabin £1,480 £370.00

Explore the central islands that make up the fascinating archipelago of the Azores under sail with modern yacht Cherokee.

Join Cherokee for an adventure sailing holiday in the Portuguese archipelago of the Azores on the island of Terceira.  A small archipelago in the Atlantic, the Azores is popular destination for sailors on Atlantic crossings to and fro the Caribbean but it is an untouched tourist destination far away from the usual holiday hustle and bustle. The islands are still mostly underdeveloped from resorts and retain their traditional Portuguese island charm. With so many islands and anchorages to choose from, exploring the Azores under sail is certainly the best way to see as much as possible with ease.


As with all of our sailing holidays, exactly where you stop and explore will be entirely dependant on the weather and tides. As you board Cherokee, owner and Skipper Jouke, will have a better idea of a route and what to expect from the week.

No experience is needed to climb aboard but a list for adventure is a must as there will be some longer passages on the water with a need for “all hands on deck”. Get involved with hoisting the sails, taking the helm, some basic navigation and night passages along the way.

Sailing the Azores

From the island of Terceira Cherokee will likely sail along the coast to Angra do Heroismo and then on to the small island of Graciosa. Dolphins and hopefully whales should join us along this 46 mile sail and we port here overnight with chance to spend the next day exploring the island ashore. Perhaps visit the impressive old volcano of Furna do Enxfre lined with beautiful forests and an impressive lava cave. The cave is accessible by a 183 step spiral staircase!

The wind forecast determines our planning, but the rest of the sailing trip we will be island hopping, amongst others, to Sao Jorge, where we will be staying in the harbour the following day to explore the island. A possibility is Miradouro do Ouvidor, with a beautiful walk in the mountains with a beautiful view over the ocean and other islands. From here you can walk down to the secluded ‘Fajã do Ouvidor’ and swim in crystal clear seawater among spectacular basalt rock formations. 

We will also sail to the island of Pico. Pico has a small shallow harbour with crystal clear waters and a fascinating museum about whaling with beautiful wooden boats. A day exploring here with a trail to explore the old crater Caldeira is a lovely onshore break from the water. Our last stop will be the harbour town of Horta on the island of Faial.


VoyageSet SailDaysCost p/p
Island Hopping in central Azores10 July 202211£1,480Enquire now


Guest berths: 8 Rig: Cutter

In 2008, Jouke Lemmer purchased Cherokee after spending years sailing with his father’s ship amongst others. Cherokee was built in 2000 by award-winning boat builders J & J Design and a year after buying her, Jouke refitted Cherokee radically, transforming her into a truly comfortable charter vessel, giving her a cutter rig and space for a generator so as to offer his passengers power and hot showers!

She is a fast, 16m vessel with a stunning teak deck and spacious cockpit, and she operates with two crew members (her skipper and the bosun/chef). Cherokee is exceptionally good at what she was built to do – pure sailing. Read more about what to expect with life onboard here.

Jouke sails his ship all over the northern hemisphere, leaving Cherokee’s home port of Rotterdam in May and sailing anywhere from the Hebrides and the Channel Islands, the Faroe Islands and Ireland or even down to the North coast of Spain before making the journey back to Holland in October. Join him and his wonderful ship for the adventure of a lifetime – think exhilarating sailing, bucket list destinations and top-notch hospitality.

Deck plan

Cherokee Deck Plan More about Cherokee


  • Are all meals included?

    Yes, all meals on board are included in the price. (Breakfast, Lunch, Dinner and soft/hot drinks) Alcohol is not included.

  • Can you cater for dietary needs?

    Yes, please let us know when making your booking.

  • What language is spoken on board?

    Dutch and English.

  • What are the sleeping arrangements?

    Cherokee has two twin berth cabins and two double berth cabins for guests.

  • How many toilet/showers does she have?

    Cherokee has two toilet/shower rooms.

  • Are bedding & towels provided?


  • Is there an age limit?


  • Do I need sailing experience?

    Not at all.

  • Is there WIFI?

    No, but you should easily be able to reach 3G/4G from the shore.

  • Can I charge my phone/Camera?

    Yes charging facilities are available when the generator is running.

  • Are there life jackets provided?


  • Are Waterproofs provided?

    You can hire Sailing suits for £35 for the week.

  • Will I be sea sick?

    Everyone reacts differently but we recommend if you are at all worried to take some medication 24 hours before departure.


From: Praia da Vitória, Terceira

To: Horta, Faial

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