Small ship sailing cruises

Sailing holidays are for voyagers who want to understand what’s going on behind the scenes of a cruise. Experience required ranges from absolutely zilch to Day Skipper qualifications that allow you to steer a yacht solo. Many small group sailing holidays can handle all types of abilities. Perpetually patient skippers will show complete novices the ropes, while letting sailors with some experience focus on perfecting their port manoeuvres. Each sailing will always begin with a safety and mission briefing, so you’ll get a handle on what’s required each day.
Sailing cruises that let you earn qualifications like the Competent Crew or Day Skipper along the way are more rigid in their approach. It’s hands-on stuff, with minimum textbook theory involved. If you don’t want a qualification, you’ll just get the pleasure of ending up with a sea miles log form that you can hang above the mantelpiece. A small ship cruise specialist will be able to find the right sailing holiday for you based on your capability, preferences and crew members (children are usually welcome).
One thing’s for sure: go small ship sailing, and you’ll be among fellow explorers and an international crew that really knows how to spin a yarn. After working, eating and living together for a week or two, you’ll have (ship)mates for life.

Types of sailing cruises

Bareboat sailing

Bareboat sailing is for the experienced sailor. You’ll get to charter your own boat for a week all for yourself, so if you don’t want a skipper on board then you’ll need a Day Skipper qualification. Most holidays head for the Mediterranean (Croatia and Greece) or the Caribbean (Antigua and Barbuda, for example). In fact, some would say that bareboat sailing is one of the best ways to see these heavily visited spots. You’ll experience them by blink-and-you’ll-miss-‘em beaches and population: 3 islands.
Itineraries are often tailor made, so you can take them with a generous pinch of seasalt. Boats come stocked with books with tips on the most beautiful bays to moor in or snorkelling spots where there are more turtles than people. Berths don’t tend to be pre-booked, so you’ll need to take special note of the tour operator’s advice about high season in your wish-list ports.

Flotilla sailing

Flotilla sailing is exactly what it says on the tin. You’ll sail as part of a fleet of boats, so your yacht is just for you and your friends or family. You can opt to have a skipper or not, depending on your level of experience. Whatever you choose, there’ll be an experienced guide leading the way. All you have to do is make it to that day’s meeting point by nightfall – be that the Amalfi Coast or the wide, flat bays of the British Virgin Islands.

Tall ship sailing

Make like Hornblower and sail the seven seas in a tall ship. You’ll get to muck in with a good-sized experienced crew, so it’s a great environment for learning how to sail. Have a go at climbing the rigging and unfurling the sails – even scrub the deck (but try to avoid walking the plank). You’ll be among likeminded people after a Napoleonic adventure – and there’s often room for a ship’s dog.

Our top Small ship cruising Holiday

Sailing in Croatia

Sailing in Croatia

A multi-activity adventure sailing cruise

From €580 to €790 4 days ex flights
Small group travel:
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Travel Team
If you'd like to chat about Small ship cruising or need help finding a holiday to suit you we're very happy to help.

Sailing holiday tips

Sailing is usually in small boats, so there’s limited space. Pack minimal luggage in soft bags that are easy to haul up and down ladders. If you’re travelling solo, you’ll usually share a cabin with someone of the same sex. If you want a private cabin, a single supplement will likely apply. You don’t have to be super fit to go on a sailing holiday, although activity levels all depend on the type of trip. You might have to set a sail or be awake for a night watch, so ask your tour operator if you’re unsure. Anyway, there’s always a team of willing shipmates to lend a hand.
Photo credits: [Page banner: Bobby Burch] [Top box: Josh Sorenson] [Bareboat (St Vincent & the Grenadines): _dChris] [Tall ship (Atlantic): Tobias Fischer]
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