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Island Hopping in Southern Azores

  • Vessel: Cherokee
  • Where: Azores, Portugal
  • Duration: 9 days
  • Embark: Horta, Faial - 21 July 2022, 18:30
  • Disembark: Ponta Delgada, Sao Miguel - 29 July 2022, 10:30

Explore the Southern 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 Faial in the harbour of Horta.  A popular destination for sailors on Atlantic crossings to and fro the Caribbean, the archipelago of the Azores is an untouched tourist destination far away from the usual holiday hustle and bustle. 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. The islands are still mostly underdeveloped from resorts and retain their traditional Portuguese island charm.


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

Set the sails from the world famous sailors harbour of Horta. From here, we will island hop through Sao Jorge, Graciosa and Terceira before reaching our final destination of Ponta Delgada on the island of São Miguel.

The harbour of Angra do Heroismo on Terceira is steeped in maritime history once serving as a main stop-over on the shipping route between Europe and America. Its ancient history and heritage have made this historic town a World Heritage Site. Enjoy a forest walk in the ‘Reserva Florestal de Recreio da Lagoa das Patas’ and/or visit the volcano caves of ‘Gruta do Natal’. 

From Terceira its a 92 mile overnight sail to reach the island of Sao Miguel, one of the most southern islands of the Azores. Hopefully dolphins and even whales will join us along the way to mark the sunset or sunrise. Arriving onto Sao Miguel should leave us some time for some onshore exploration, with the volcanic mountain lake of the Miradouro do Pico da Barrosa.

The last sailing day is short, but the plan is to anchor at Ilhéu de Vila Franca do Camp. A kind of mini volcano with a perfect circular swimming place in the middle, a real mini paradise with a lovely cliff walk as well. We will end the sailing trip in Ponta Delgada on Sao Miguel. 

Similar voyages

VoyageSet SailDaysCost p/p

All voyages for Cherokee

VoyageSet SailDaysCost p/p
Sailing from the Azores to Spain30 July 202213£1,750.00Enquire now
Sailing the Spanish Fjords & Iles Cies12 August 202210£1,320.00Enquire now
Sailing the Spanish Fjords22 August 20229£1,180.00Enquire now
Sailing the Bay of Biscay31 August 20229£1,180.00Enquire now
Sailing the French Coast11 September 202212£1,500.00Enquire now
Sailing the French Coast & Channel Islands23 September 202210£1,220.00Enquire 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


  • What COVID policies are in place for sailing with Cherokee?

    There are currently no Test & Sail policies in place for the 2022 season. Guests will just need to ensure they are following any international guidelines to travel to the boat.

  • 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.

  • Do I need to tip the crew?

    Tips are not mandatory but are welcomed by the crew!

  • 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: Horta, Faial

To: Ponta Delgada, Sao Miguel

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