Learn traditional ocean navigation on this Azores ocean sailing adventure with expedition yacht Cherokee
This 11-day voyage combines island-hopping in the Azores archipelago with guidance on the fundamentals of traditional ocean navigation. Embarking from the port of Ponta Delgada on the island of São Miguel, the sailing itinerary includes coastal sailing, one offshore passage and time to explore ashore, before disembarking in Faial on Horta island. All while gaining an understanding of the art of using the sun and time to determine position while at sea.
This voyage is well-suited to sailors who want to build confidence in watchkeeping, route planning, and interpreting weather at sea with a professional skipper. No prior knowledge of navigation is required. Participation in sailing tasks is always optional, and there will be opportunities to swim, walk ashore, and enjoy the marine life along the way.
- Island Hopping
- Navigational Training
- Suitable for adventure seekers
- Great for solo travellers and couples
- Independent onshore excursions
- Full board
- Night Sailing
Need some help?
Talk to the team
Telephone: +44 (0)1872 487288
Email: [email protected]
WhatsApp: +44 7804 472592
Your Sailing Area
São Miguel to Faial, The Azores
The voyage begins in Ponta Delgada on São Miguel, with the first day spent alongside to allow time to settle aboard Cherokee and prepare for the voyage ahead. During this time, guests will meet the crew and receive an introduction to solar navigation, chart work and the day-to-day structure of watchkeeping at sea.
A short coastal sail the following day provides a practical foundation: steering, trimming sails and observing how weather and sea state influence course-making. In the afternoon, the group will work through basic meteorology and plan the upcoming offshore passage together, using weather charts to set a route to the central islands. Depending on conditions, there may also be time to visit the Furnas geothermal valley and its famous hot springs before departing.
The offshore passage of approximately 130 nautical miles begins by rounding the volcanic Ilhéu de Vila Franca do Campo. During this passage, a running watch system will allow guests to use their ocean navigation skills by reading the sun’s altitude and time to track their position. Cherokee’s skipper and crew create a supportive environment: those keen to practice can do so, while those who prefer to observe are equally welcome. Dolphins are commonly sighted in this stretch of the Atlantic, and nights are often clear enough to see the Milky Way from horizon to horizon.
Landfall is made at Angra do Heroísmo on Terceira, a natural harbour that served as a key waypoint during early Atlantic crossing routes. Mooring here provides time to explore the historic town and understand its maritime significance.
From the island of Terceira, Cherokee continues to São Jorge, where steep green ridges fall directly to the sea. With time ashore, guests may walk coastal trails or swim in a natural rock pool formed by volcanic flows. A visit to Café Nunes, serving coffee grown on the island’s small plantation, offers a quiet end to the day.
The final leg to Faial offers more time to practice navigation, interpret weather patterns and refine watchkeeping routines. The voyage concludes in Horta, a historic meeting point for ocean sailors. The harbour’s breakwater is painted with murals left by passing crews, and a visit to Café Sport is a long-standing tradition at the end of a passage.
Throughout the voyage, sailing will take place during the day or through the night, depending on the stage of the route. The skipper will adjust the schedule according to wind and weather, ensuring a safe and instructive crossing with meaningful time ashore.
Please note that the above schedule is subject to weather, wind, and tide.
Things to note
Sailing vs Shore time
Night-watches
Travel insurance notes
As this is an active adventure holiday, we advise that everyone has the appropriate personal accident travel insurance whilst onboard in addition to standard travel insurance which would cover you in the time between making your booking and departing for your adventure. These policies can sometimes be combined so please check with your travel insurance provider.
Please read more information on our Insurance guidelines page.
This voyage will be more than 12 miles offshore.
Life on board Cherokee
A custom-fit charter vessel, Cherokee, has been designed to ensure her guests enjoy comfortable offshore sailing adventures.
GETTING INVOLVED
Sailing with Cherokee certainly ticks the adventure travel boxes with a continuous A to B sailing schedule throughout the season. Skipper Jouke (pronounced Yow-ka) believes this is the best way to experience as many destinations off the beaten track as possible and loves to share his sense of adventure with guests.
Guests are actively encouraged to get involved with all aspects of sailing under Jouke’s relaxed guidance. Take the helm, help with the winching of the sails, anchoring and basic chart navigation. Skipper Jouke was born at sea, the son of a Baltic Sea Captain and a naval architect. You could not be in safer hands when he’s back on land!
SLEEPING & RELAXATION
With four private guest cabins, comfortable bunks, and two bathrooms at either end of the boat, Cherokee can easily accommodate solo travellers, adventurous couples, or groups of friends or family. Clever storage offers plenty of locker space for guests in each cabin. The boiler runs off the cooling water of the generator, so there is plenty of hot water for washing and showering!
Below decks, she offers a comfy & spacious saloon perfect for eating, playing cards or reading a book. You’ll find beautiful panelled mahogany interiors, giving the ship that classic feel. A well-equipped galley opposite the saloon provides a perfect social space, ready to bring you delicious food after an exhilarating day of sailing. Eat under the stars if the weather allows in the spacious cockpit, offering comfortable couches and a good-sized table. If the weather takes a turn, the crew will put up the cockpit tent, offering you shelter and warmth in the fresh air.
AUTHENTIC OFFSHORE SAILING
The boat is owned and sailed by experienced skipper Jouke, and there is a ‘bosun’ who also cooks. The bosun will prepare dinner as you arrive and after breakfast on your first morning aboard Cherokee, you can be guaranteed a relaxed start to your sailing holiday.
Jouke and his crew try to use the engine as little as possible, sailing into port as much as possible. Cherokee only clocks up about 180 motoring hours yearly, which is pretty impressive. Due to this, as with most of our vessels, the days of your holiday are subject to the weather, using the tide as your clock. Guests aren’t presented with a tight schedule or itinerary for this reason, making the trip much more adventurous and flexible.
What’s included
- Full board (breakfast, lunch, dinner, snacks, hot drinks)
- All bedding (pillow, sheets & duvet) and wash towel
- Full crew plus tuition
- Fuel fees
- All tender trips to and fro the boat
- Lifejacket
- Use of onboard stand-up paddle-boards
What’s not included
- Swim towel or wetsuits
- Alcohol
- Any flights
- Transit hotels
- Travel to and from the boat on the day of joining/leaving
- Travel Insurance
- Sailing Insurance (Please read our Sailing Insurance page for more information)
- Crew tips
- Personal expenses
Kit list
Cherokee has limited space for possessions, so please be considerate and travel as light as possible. There is no storage for rigid cases – please bring your items in a soft bag.
We recommend a travelling light principal with lots of lightweight, easy-drying layers. Below is a list of recommended items, these are not mandatory and those that have sailed before may have their own preferences!
- Walking boots/shoes for onshore & light shoes/trainers (with good grip)
- Wash towel – micro fibre is lightweight and quick drying!
- Swimsuit and swim towel
- Lightweight, quick-dry clothes (base layers, fleece and synthetic tops are lightweight and quick-drying!)
It can be quite a few degrees colder out at sea, so please bring many layers even if the forecast seems like a warm week!
- Warm, windproof and waterproof coat and trousers
- Waterproof boots
- Sun cream (please use reef-safe, eco products where possible)
- Sunglasses and a warm hat/cap
- Small personal first aid kit and any medication you may need
- Camera/binoculars
- Refillable water bottle
- Personal wash kit (please use reef-safe, eco products where possible)
- Charging cables for personal devices
- EU 2pin adaptor
- A good book to read!
- We advise sleep masks and/or earplugs!
- Consider a small backpack/bag for onshore exploring.
From: Ponta Delgada, São Miguel
To: Horta, Faial
Getting There
Ponte Delgada, São Miguel, The Azores
Direct flights are available to Ponta Delgada Airport (PDL) from major London Airports Heathrow and Standstead.
Cherokee
Guest berths: 8 Rig: Cutter
Jouke sails with Cherokee all over the northern hemisphere, leaving her 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 for the adventure of a lifetime – think exhilarating sailing, bucket list destinations and top-notch hospitality.
Sailing with Cherokee is perfect for those looking to expand their sailing knowledge. From beginners to accomplished sailors, Cherokee’s sailing schedule accommodates all ages and abilities. From sailing training voyages across Oceans to family-friendly voyages in the Azores, there is something to suit everyone.
She has a relatively simple rig and winch system, so she is a great boat to learn the ropes. Get involved with all aspects of sailing from winching, taking the helm, route planning, chart reading and celestial navigation.
Skipper Jouke Lemmer purchased Cherokee in 2008 after spending years sailing with his father’s ship, amongst others. Cherokee was built in 2000 by award-winning boat builders J & J Design. 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 blue water sailing!
Deck plan

Berths on board
Single berth in shared Twin Cabin: Two single bunk berths.
Single berth in Double Cabin (double occupancy): Double cabin for two guests.
Private Cabin (solo occupancy): Private cabin for one guest.
More about CherokeeAre all meals included?
Yes, all meals on board are included in the price. (Breakfast, lunch, dinner and hot drinks) The last evening meal of the voyage is taken ashore.
Can you cater for dietary needs?
Yes, please let us know when making your booking. Gluten free guests may need to bring some items with them.
Are there any added extras?
There's an honesty bar for soft drinks and alcohol. Sailing suit and welly hire are additional costs if required. And onshore excursions and travel are not included.
What are the sleeping arrangements?
Cherokee has two twin berth cabins and two double berth cabins for guests.
Is there a porthole in my cabin?
Yes, all cabins have either a hatch or porthole.
How many toilet/showers does she have?
Cherokee has two toilet/shower rooms.
Are bedding and towels provided?
All bedding and a towel is included but please bring your own swim towels (if needed). Micro-fibres are a great lightweight, quick-drying alternative.
Is there a hairdryer on board?
No, please do not bring one. The sea breeze makes a great natural alternative!
Will I be able to wash my clothes?
No, Cherokee does not have laundry on board.
Is there heating onboard?
Yes, there is heating on board.
Do I need to tip the crew?
Tips are not mandatory but are welcomed by the crew!
What language is spoken on board?
English and Dutch.
Is there WIFI?
No! It's time to disconnect from the modern tech and reconnect with nature! When within shore range, you should be able to reach 4/5G. Please make sure you have international roaming set up on your data plan.
Can I charge my phone/Camera?
Yes charging facilities are available when the generator is running.
What is the currency on board?
Whatever the local currency is in the sailing destination.
Do I need sailing experience?
Not at all.
How do I get on and off the boat?
Cherokee is often at anchor so you'll need to be comfortable climbing in and out of the tender dinghy. She has a dropped transom with steps so getting on/off the boat is fairly easy.
Are there life jackets provided?
Yes.
Are Waterproofs provided?
You can hire Sailing suits for £50 for the week. Welly boots are available at £15 for the week.
Does the boat have any water toys?
No. However swimming from the boat is very easy using the stern flap and swimming ladder to access the water.
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.
Is there an age limit?
Over 12's on most voyages, unless stated as family-friendly!
More holidays in Azores
Azores Sailing Holiday Adventure
Sailing the Azores Islands
Azores Sailing Holiday Adventure
Mile Builder Sailing from the Azores to France
More holidays on Cherokee
Crossing the English Channel to London and Back
Cross-Channel Sailing to the Netherlands
Ocean Sailing training – navigation & island hopping
Mile Builder Sailing from the Azores to France
Inspiration for your voyage
Be inspired to discover the world under sail! Read our latest journals below. Be inspired to discover the world under sail! Read our latest journals below.
JOURNAL




























