Sailing Holidays and Sailing Adventures – UK and Abroad
A sailing holiday combines adventure, exploration and time at sea. Discover beautiful coastlines, visit remarkable harbours and experience life on board a yacht while sailing with a professional skipper or instructor. Unlike a traditional yacht charter, these are hands-on sailing holidays where people can take part in sailing the boat, learn new skills and enjoy the freedom of travelling under sail.
Norway Sailing Adventures
Join a Challenger 72 Norway sailing adventure. Offshore passage plus fjord exploration. Two voyages: UK to Norway or return.
Learn MoreNorway Sailing AdventuresSailing Holidays to the Isles of Scilly
Sailing Holiday to the Isles of Scilly. Sail from Falmouth and cruise this archepelagic jewel
Learn MoreSailing Holidays to the Isles of ScillySailing to France and the Channel Islands
Sail to France and the Channel Islands, build miles and explore
Learn MoreSailing to France and the Channel IslandsExplore the Dorset Jurassic Coast
Sail along the beautiful Dorset Jurassic Coast
Learn MoreExplore the Dorset Jurassic CoastDevon and Cornwall Sailing
Explore the Devonshire and Cornish coasts on a sailing holiday
Learn MoreDevon and Cornwall SailingChannel Triangle Mile Building Sail
Build miles and confidence with on a mile builder sail in the English Channel
Learn MoreChannel Triangle Mile Building SailMediterranean Preparation Weekend
Thinking about chartering a yacht in Greece, Croatia or Italy next summer? If you're chartering a boat for the first time or want to berth like a pro to impress family and friends look no further.
Learn MoreMediterranean Preparation WeekendCaribbean Sailing Holidays
Peak Caribbean season sailing trips in the Caribbean, variable durations, great locations, the perfect winter holiday for sailors & those looking for something a little different.
Learn MoreCaribbean Sailing HolidaysSail across the Bay of Biscay from Portsmouth to the Canaries
Sail across the Bay of Biscay from Portsmouth to the Canaries on an ocean going Challenger 72 yacht. October/November 2026.
Learn MoreSail across the Bay of Biscay from Portsmouth to the CanariesThe Atlantic Ocean: Sail from Antigua to Portsmouth
Sail across the Atlantic Ocean from Antigua to the UK. January/February 2027.
Learn MoreThe Atlantic Ocean: Sail from Antigua to PortsmouthWhat makes a sailing holiday unique?
A sailing holiday offers a complete change from everyday life ashore. After only a day or two at sea it becomes easy to switch off from normal routines and settle into the rhythm of life on the water.
Many people find that a couple of days sailing feels like a week away from normal life. Fresh sea air, changing scenery and the shared experience of travelling by yacht create a very different kind of break.
People join these trips in several ways. Some book individually and quickly find they have things in common with the rest of the crew. Others travel as couples or families who want to experience a holiday that is both active and rewarding.
Because every trip is run with a professional skipper or instructor, people can take part in sailing the yacht as much as they wish. Some enjoy learning new skills and getting fully involved with navigation, sail handling and watch systems. Others prefer to relax on deck and enjoy the journey.
As a professional sailing school, First Class Sailing combines adventure sailing with real learning and guidance from experienced instructors. The result is a holiday that is both memorable and genuinely rewarding.
An excellent learning holiday
Excellent, well organised course. A really fun week, where we learnt heaps but also had a fun holiday. would highly recommend.
M Hunter
Verified Customer






Different Types of Sailing Holidays
Sailing holidays vary widely depending on the destination and the style of trip.
Some voyages combine relaxed cruising with time exploring ashore. Trips to the West Country, France and the Channel Islands are good examples. These journeys focus on enjoying the sailing while also visiting beautiful harbours and coastal towns. Days might include sailing along dramatic coastlines, tasting local food, or walking through historic villages.
Other trips are more adventurous and involve longer offshore passages. Voyages to Norway, the Canaries or across the Atlantic require everyone on board to play a part in sailing the yacht. Watch systems are used so that the boat continues sailing day and night. Even on these longer passages there is still time to relax, read, watch the stars or enjoy conversations with fellow crew.
Some sailing holidays also involve racing. Events such as the ARC Rally across the Atlantic, the Round the Island Race and the Rolex Fastnet Race bring together amateur and experienced sailors from around the world. These trips provide an exciting and rewarding sailing experience while still being welcoming to enthusiastic crew.
For shorter adventures, explore our weekend sailing UK experiences, which offer a taste of offshore sailing in just a few days.
If you're exploring different types of sailing adventures, you can also browse our UK sailing holidays, which focus on shorter coastal trips around the South Coast, the Channel Islands and the West Country. For longer expeditions further afield, take a look at our sailing holidays abroad, which include offshore passages to Norway, the Canary Islands and the Caribbean. These pages provide more detail on the destinations, sailing style and experiences available.
Frequently Asked Questions About Sailing Holidays
What is a sailing holiday?
A sailing holiday is a trip where the journey takes place aboard a sailing yacht rather than staying in one location. The yacht travels between different harbours, islands or coastal destinations while the crew enjoy life at sea and explore new places along the way.
On many trips it becomes a hands-on sailing holiday, where participants can take part in sailing the boat. This may include helping with sail handling, navigation, watch systems and passage planning under the guidance of a professional skipper or instructor.
Some people enjoy getting fully involved with sailing the yacht, while others prefer to relax on deck and enjoy the scenery. Either way, a sailing holiday combines adventure, travel and time on the water in a way that few other holidays can match.
Do I need sailing experience to join a sailing holiday?
No. Many sailing holidays welcome beginners as well as those with some experience. A professional skipper or instructor is on board to guide the crew, explain the sailing and help everyone take part at a comfortable level.
Are sailing holidays hands-on?
Yes. These trips are active sailing experiences rather than passive yacht charters. Participants can help with sail handling, navigation and watch systems depending on the type of voyage and their level of experience.
Can I join a sailing holiday on my own?
Yes. Many people join individually and become part of the crew for the voyage. Sailing holidays are sociable and often bring together people who share an interest in travel, adventure and the sea.
Where do your sailing holidays take place?
Trips range from coastal cruising around the UK to longer offshore adventures. Destinations include Norway, the Channel Islands, the Canary Islands, the Caribbean and Atlantic crossings between Europe and the Caribbean.
Different Types of Sailing Holidays
