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Join adventure sailing yacht Cherokee for a relaxed island-hopping voyage through the central Azores archipelago.
This 10-day adventure sailing around the Azores, explores the sailing area from Faial to Terceira and visits the neighbouring islands of Pico, São Jorge and Graciosa. Sailing distances are moderate, and there are no night passages, making this a more gentle and extended voyage with time to explore on land each day.
This sailing holiday is perfect for families who want to experience the sea at a gentle pace. Curious adventurers wanting to balance time onshore exploring new islands with active sailing will find this voyage appealing. No prior experience is required, and guests are welcome to help with sail handling as much as they want, but there is no obligation; simply being aboard, watching the islands unfold, is just as welcome.
- Island Hopping
- Potential dolphin and whale sightings
- Suitable for adventure seekers
- Great for solo travellers and couples
- Independent onshore excursions
- Full board
Need some help?
Talk to the team
Telephone: +44 (0)1872 487288
Email: [email protected]
WhatsApp: +44 7804 472592
Your Sailing Area
Faial to Terceira, The Azores
The voyage begins in Horta, on Faial. A harbour well known to ocean sailors. The quayside is lined with colourful murals painted by visiting crews, and the town has an easy, welcoming feel. It’s a good place to settle in, enjoy a meal together on board, and get used to life at sea before setting off the next morning.
The first leg is a short sail across to Lajes do Pico on the south coast of Pico. The crossing often brings dolphin sightings, and Pico’s volcanic peak rises clearly in view as the yacht approaches the island. Lajes is a friendly harbour with a small maritime museum where traditional wooden whaleboats are still preserved. The town sits between steep green slopes and the ocean, and there’s time here for a walk, a swim, or simply to wander the waterfront together.
From Pico, the voyage continues to Velas on São Jorge, sailing between the islands with views of Pico’s peak across the water. Velas makes an ideal base for exploring on land. A day here might include an easy coastal walk, a swim in the natural rock-pool swimming area on the eastern shore, and a visit to Café Nunes, where coffee is grown and roasted from Europe’s only coffee plantation. In the evening, Cory’s shearwaters return to their nests along the cliffs, and their calls can be heard across the harbour.
The final island is Terceira, where Cherokee arrives in the UNESCO-listed port of Angra do Heroísmo. The town’s streets, gardens and small squares are all easy to explore on foot. A day ashore might include a visit to Algar do Carvão, a volcanic cave you can walk inside, or a swim in the natural lava pools at Biscoitos. The voyage ends in Praia da Vitória, a calm harbour on Terceira’s east coast, where there is time to enjoy a relaxed final dinner and a slow breakfast together before disembarking.
Throughout the week, sailing days are short, with time to swim from the boat, visit small harbours, and enjoy the islands at a comfortable pace. The exact route may change with the weather, but every plan keeps the emphasis on time together, warm water, and exploring the Azores from the sea.
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: Horta, Faial
To: Praia da Vitoria, Terceira
Getting There
Horta, Faial, The Azores
Flights with stops/connections go to Horta Airport (HOR) from London Heathrow, London Luton, London Stansted, London Gatwick and Manchester with SATA and TAP Air Portugal.
Horta Airport (HOR) is an 18-minute bus ride into Horta operated by Farius that runs 4 times daily, Monday-Friday.
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
Island hopping to the Southern Azores
Tall Ship Sailing Across the Atlantic to the UK
Ocean Sailing training – navigation & island hopping
Atlantic Expedition Sailing Holiday to the Azores
More holidays on Cherokee
Sailing around the Central Azores
Island hopping to the Southern Azores
Mile Builder Sailing from the Azores to France
Cross-Channel Sailing to the Netherlands
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


























