Join adventure yacht Cherokee for a passage sailing holiday from Rotterdam to London.
Sail from Rotterdam to London aboard Cherokee and experience a true offshore passage combined with river sailing and time ashore in the heart of the city. The route includes a Channel crossing, night sailing under a watch system, navigation through busy shipping lanes, and the memorable approach up the Thames to St Katharine Docks beside Tower Bridge.
This voyage is perfect for anyone looking to build sea miles, gain confidence with offshore and overnight sailing, or simply experience the movement and rhythm of a longer passage. No prior passage-making experience is required, and there is plenty of support from the skipper and mate throughout.
- Passage crossing
- Suitable for adventure seekers
- Great for solo travellers and couples
- Independent onshore excursions
- Full board
- Night sailing on a watch system
Need some help?
Talk to the team
Telephone: +44 (0)1872 487288
Email: [email protected]
WhatsApp: +44 7804 472592
Your Sailing Area
Rotterdam, The Netherlands to London
The voyage begins in the centre of Rotterdam, sailing past the city skyline and under the Erasmus Bridge. The route follows the Nieuwe Waterweg, a busy working waterway where large commercial ships move in and out of the harbour. The first afternoon is gentle, allowing time to get to know the boat, settle in on deck, and make a sailing plan for the crossing.
On the second day, the yacht sets out across the English Channel, a passage of around 140 nautical miles. Sailing here means navigating traffic separation zones, wind farms and commercial shipping lanes. The watch system runs in rotation, usually three hours on and six hours off, giving everyone time to rest. Nights at sea can be a highlight, with clear stars, radar screens glowing softly, and the quiet rhythm of the boat moving through the water.
Landfall is on the River Medway on the Kent coast. Once a centre of naval history, this quiet anchorage offers a calm pause after the crossing. From here, the voyage continues into the Thames, where the river gradually narrows and the London skyline rises ahead.
Don’t forget to look up as Cherokee sails beneath the iconic landmark of Tower Bridge.
Sailing through along the Thames in the heart of the city offers up an enviable view of the architecture and attractions along the banks, from the London Eye to Westminster and the neighbouring Elizabeth Tower housing the famous Big Ben bell.
Cherokee will moor in St Katharine Docks right in the centre of the city. After a good night’s sleep, spend a whole day in London. The docks sit within walking distance of the Tower of London, the South Bank, Borough Market and the riverside footpaths, offering easy access to explore the city on either side of the river. Wander through the historic Borough Market to the soundtrack of talented street musicians and let yourself be tempted by many culinary treats on offer from the food stalls filling the space.
Before beginning the return passage, there is often a pause for the tide in Ramsgate. This well-sheltered harbour offers good facilities, easy access to fuel and supplies, and a short walk into the town. The waterfront is lined with Georgian terraces and traditional pubs, while the marina itself has a relaxed, local atmosphere. It’s a pleasant place to stretch your legs after time at sea, with a few small shops, cafés and fish-and-chip stalls scattered along the promenade. Walk out along the breakwater for views over the harbour entrance and across to the white cliffs of Kent before setting sail once more across the Channel.
The final crossing back to the Netherlands covers around 160 nautical miles, once again with watches through the night and the experience of navigating shipping lanes and coastal approaches.
Approaching Rotterdam feels different from any other part of the passage. After days at sea, the horizon shifts from low sky and open water to cranes, harbour walls and the outline of the city rising ahead. The Nieuwe Waterweg is busy, purposeful water, shared with cargo ships, pilot boats and inland barges, so the navigation feels focused and absorbing. Negotiating the shipping lines at night on the approach to Rotterdam’s industrial outer harbours is an unforgettable experience, guided by the constant chatter on the radio from vessel traffic control.
As Cherokee continues upriver, views of the Euromast, the high glass towers along the Maas, and finally the sweep of the Erasmus Bridge welcome this adventure yacht back to her home port. Passing beneath the Erasmus Bridge by water is a moment many sailors remember with the expanse of the city opening around you on both banks.
Sailing under the final bridge marks the change from the industrial-centric outer approach into the historic Oude Haven, where classic Dutch sailing ships line the quays and cafés spill out onto the waterside. Stepping ashore in the heart of Rotterdam, with the atmosphere of the old port all around, is a perfect place to disembark from this exciting passage crossing sailing holiday.
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: Rotterdam, The Netherlands
To: Rotterdam, The Netherlands
Getting There
Rotterdam, The Netherlands
By Train
The Eurostar trains run directly between London St Pancras International and Rotterdam Centraal station. It takes just over 3 hours.
By Air
Direct flights from London City Airport and London Stansted to Rotterdam The Hague Airport in just under an hour.
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 Netherlands
Offshore Sailing Expedition from Svalbard to the Netherlands
Offshore Sailing Adventure from the Netherlands to Scotland
Tall Ship Crossing: France to the Netherlands
Offshore Sailing from Amsterdam to Inverness
More holidays on Cherokee
Island Hopping in the Western Azores
Mile Builder Sailing from the Azores to France
Ocean Sailing training – navigation & island hopping
Sailing around the Central Azores
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






































