Sail & Learn 4
- Sardinia
- Sicily
20.06.
– 27.06.2026
Transitalia Route
Transitalia Route
Due to high demand, we’ve launched a new kind of trip last year: the Sail & Learns.
These journeys are perfect for those who love to sail or want to learn the ropes.
There’s only one thing set in stone: the starting and ending port. How we get there? That’s up to the wind and weather. Unlike our regular trips, Transfers focus more on the sailing itself and less on a fixed itinerary or lazy bay-hopping. From night passages to quiet anchor stops, anything can happen.
It’s the real vagabond life at sea, just like those who live aboard their sailboats year-round. And since we cover more miles on these trips, they’re also ideal for collecting the mandatory miles for your sailing license. Sounds interesting?
Where learning to sail feels like an adventure.
Is this sailing Trip right for me?
Sail & Learn is for people who want more than a holiday. It is for beginners with zero sailing experience and for those who have been on the water before and want to build real confidence, collect sea miles and spend more time actually sailing.
You do not need any prior experience. What you need is curiosity, a sense of adventure and the willingness to be part of a crew.
What will I learn on a Sail & Learn trip?
You will build real, hands-on sailing experience as part of the journey itself. There is no classroom, no fixed curriculum. What you learn depends on the conditions and the route, and that is what makes it real.
Skills you may pick up along the way:
- Steering and basic manoeuvres
- Sail handling and trimming
- Knots and rope work
- Reading wind and weather
- Watch systems and night sailing
- Teamwork and communication on board
- The rhythm and responsibilities of daily boat life
You learn one mile at a time, naturally, as the trip unfolds.
How is Sail & Learn different from other Sailing Trips?
Most sailing vacations put you on a boat as a passenger. Sail & Learn puts you on a boat as crew.
There is no floating hotel, no fixed sightseeing schedule and no itinerary that has to be followed no matter what. Wind and weather shape the route. The crew works together. You are not just watching the journey happen. You are part of what makes it happen.
That is what makes Sail & Learn more raw, more real and often far more rewarding than an ordinary Sailing Trip.
What is life on board actually like?
It’s close, simple and genuine. You share a space with your crew, cooking and eating together, taking turns on watch and enjoying the sunset from the same deck.
Some moments are active and demanding. Others are slow and quiet. Morning coffee in the cockpit, long passages under sail, night watches under open sky, shared meals below deck. It is this mix of intensity and stillness that makes life at sea something you do not forget.
What should I expect from a Sailing Trip like this?
Flexibility is part of the deal. Routes shift with the wind. Plans change. Comfort on board is real but simple, not luxurious. Days can be long, salty and physically tiring.
If you are looking for a polished resort experience, this is not your trip. If you are looking for a genuine sailing vacation where you actually learn, contribute and feel the sea, you are exactly where you need to be.
What do I take home from a Sail & Learn Trip?
More than photos. You leave with new sailing skills, real sea miles under your belt, and a confidence on the water that only comes from having actually done it.
Most people also take home something harder to name: the feeling of having been fully present. Close to nature, shaped by wind and water, part of something that moved. You step out of your usual routine, focus on what actually matters and grow alongside people who were strangers at the start.
That tends to stay with you.
Original price was: 1.280€.1.120€Current price is: 1.120€.
Highlights
Set sail with a small crew
For anyone who wants to sail or learn how, with no more than 8 people on board.Night sails guaranteed
Learn the art of sailing, day and night.Log your miles — Get your sea miles confirmation
Thinking about getting your sailing license? Awesome! Earn your required miles with us.
Open Sea Crossings
Learn to Sail
Star Gazing
Route details
Sea State
Every Trip has some swell, but it is always bearable. The scale indicates whether the trip is rather calm or you have to expect a bit more swell.
Nature
The nature on our trips is always stunning, but some trips offer more focus on nature than others.
Adventure
Incredible experiences never come amiss with us. Some trips are more relaxed, while others provide a lot of action, e.g. in nature.
Sailing Time
The scale shows whether these Trips include more or less time for just sailing at sea.
What you need to know
Start
- Olbia, Sardinia, Italy *
- Check-in: 17:00
- Airports: Olbia Costa Smeralda Airport (OLB), Cagliari Elmas Airport (CAG), Alghero–Fertilia Airport (AHO)
Finish
- Tonnarella, Sicily, Italy
- Check-out: 09:00
- Airports: Palermo Falcone Borsellino Airport (PMO), Catania–Fontanarossa Airport (CTA)
* The exact meeting point and location of the boats will be communicated on Saturday.
Included
- All boat costs covered (deposit, fuel, captain, ports, etc.)
- All meals on board (Plant-based)
- All listed highlights and activities
- Bedding and towel
- Ocean-friendly shampoo, toothpaste, soap and sunscreen
- Guaranteed female cabin pairing
- Complete period supplies
- Our team does the weekly grocery shopping
- Pizza night with the whole crew
Excluded
- Your journey to the starting port
- Restaurant visits & alcoholic drinks
- Tips for the crew
Original price was: 1.280€.1.120€Current price is: 1.120€.
Not taxable according to § 3b para. 1
Out of stock
Your cabin
Sailing Boat
Your cozy home on the water
- Cozy and homely design
- Plenty of space on board
- Fully equipped kitchen with dishwasher on board
- Comfortable furnishing
- Premium equipment
- Internationals welcome! Boardlanguage: English
- High-Speed Wi-Fi
- Unlimited drinking and shower water, provided by the solar desalination system
- Enhanced safety
- Efficient sailing performance
- Air-conditioned and heated by solar energy
- Non-smoking boat, fresh sea air only
Philosophy
This is what Pirates stands for
Individual travel
Those who know us know that we focus on quality instead of quantity. For us, it's the person behind every booking that counts! With us, small group sizes instead of mass tourism are the order of the day.
Group feeling
As a small organizer, this is our hobbyhorse. Pizza nights, road trips, night hikes, funny stories. Be prepared for teamwork on board and shared experiences that you won't soon forget!
Safer space
It is important to us that every guest feels comfortable on board, regardless of their origin or sexual orientation. Therefore, for us it is quite clear: There is no place for racism, sexism, homophobia or discrimination of any kind! Solo female travelers can also count on a guaranteed female cabin pairing, so you always feel at ease on board.
Sustainability
We care about nature! We design our trips to be as environmentally friendly as possible. Our focus is on protecting the sea - we let ourselves drift with the wind, rely on environmentally friendly soaps and avoid unnecessary waste. Our merch is fair trade - even our web host is green!
Plant-based
Vegan lifestyle and a memorable vacation? With us, nothing stands in the way. We cook vegan food on our yachts. During our joint restaurant visits ashore, you’ll have the chance to enjoy local dishes. So if you eat milk products, eggs or meat, you won’t miss out on land either.
Creativity and freedom
We are hungry for adventure and want to experience something. Freedom and creativity have been driving Pirates of Paradise since day 1. With us you can live your life to the fullest!
