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Sailing from Madeira to Lisbon

  • Vessel: Cherokee
  • Where: Portugal
  • Duration: 11 days
  • Embark: Funchal, Madeira - 14 April 2022, 18:30
  • Disembark: Lisbon - 24 April 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

Swap the island of Madeira for mainland Portugal as you tuck some sea miles under your belt.

Join modern yacht Cherokee for a Portuguese sailing holiday from Madeira to Lisbon.  The voyage is the perfect sailing adventure for those who want to experience a longer passage at sea and build up some sea miles.


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.

Portuguese Sailing

Begin on the Portuguese island of Madeira. With volcanic landscapes, green rugged cliffs and pebbly beaches, Madeira is the perfect backdrop to start your sailing adventure. Known as the land of eternal Spring, Madeira is well worth arriving to for some exploration before you join Cherokee.

After getting familiar with the boat, set the sails for mainland Portugal. After 455 miles of open water sailing that could take two days, spot the mainland of Portugal looming in the horizon. Depending on the weather forecast, you may stop at another harbour along the Portuguese coast before reaching your final destination of Lisbon.


VoyageSet SailDaysCost p/p
Sailing from Madeira to Lisbon14 April 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: Funchal, Madeira

To: Lisbon

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