From lazy summer cruises to winter adrenaline adventures, sailing holidays vary widely, but share some common themes. Trips tend to run for a week or more, although short breaks of four nights sailing are possible in southern Europe and Scotland. Typically, you’ll sail for three to four hours daily, dropping anchor for a swim, snorkel, or dive, or to explore quiet harbour towns, hike to a hilltop or cycle a coastal path. Breakfast and lunch are often served on board, unless you’re heading way off the charts, in which case full board catering is the norm, with fresh fish caught off the boat a highlight. There’s often an itinerary, but it may not get stuck to. If dolphins are frolicking around the prow, lunch may get pushed back. If the wind is whipping up choppy seas, the skipper may choose a different route. But this is where the similarities between sailing holidays end. Each offers something unique, in terms of location, style and experience.

Leisurely sailing trips

The opportunity to relax on deck, cool off in crystal clear waters and relax on deck some more is the top offer of Greece, Italy, Turkey and Croatia sailing trips. Come in the summer and you can escape the crowds clustered on the resort beaches, sailing to quiet bays and escaping back to your vessel each night. Meals are prepared for you (typically breakfast and lunch) and the crew sail the ship, too, so you won’t be called upon to read the charts or hoist the sails (although you’re welcome to help sail if you like). There will always be the option to kayak or snorkel, explore island ports or potter round pretty churches, but you don’t have to!

Active sailing trips

Some sailing trips have a two-for-the-price-of-one style, offering a specific activity alongside super-duper sailing. Go to the Cyclades in Greece to sail and scuba dive, walk or cycle, while in the Dodecanese you can combine rock climbing and mountain hiking with sailing. The truly intrepid traveller might be lured to northern Norway in winter, to try randonnée skiing on the untouched pistes of the Lofoten mountains, with new slopes reached by yacht each day. On some sailing trips, the sailing itself is the activity, with guests invited to be involved in the whole adventure; navigating, steering, hoisting sails and preparing meals for their fellow ship mates and crew. You may also fish from the boat for supper or, in Scotland, gather in lobster pots, too.

Wildlife watching & conservation trips

There’s obviously no better place to observe marine life than from a boat, and some sailing adventures make wildlife watching their focus. In Scotland, wildlife sailing holidays bring you closer to the west coast’s seals, cetaceans and seabirds, and can even include the study necessary for a marine biology qualification, with an instructor and high-powered microscope on board. You can cruise around the Galapagos Islands in a tall ship, or go deep into Spitsbergen’s fjords to see polar bears, walruses and reindeer. In the Ligurian Sea in Italy you can participate in conservation research into whale and dolphin populations on a six-day cruise, or head to the Aegean in the company of a naturalist guide and conservation expert.

Trips with a twist

Some sailing holidays (in Croatia, for example) include land-based accommodation with daytime excursions to islands – perfect if you want a little space to spread out and sleep in, but love to explore by sea. It’s also possible to find fully participatory trips, requiring you to shop for provisions, sail, cook and clear up. These are great for building camaraderie and tend to be cheaper, too.
Trips that take children are available, too, although there’s usually a minimum age limit of around seven, or you may have to book out the entire yacht. Scotland is a great destination for family sailing holidays, with a chance to learn about sailing, spot wildlife, kayak and explore on land, and if you can only get away during school holidays, it’s cooler here than southern Europe.
If you'd like to chat about sailing or need help finding a holiday to suit you we're very happy to help.
Rosy & team

01273 823 700

The best of boats world

What does a sailing holiday entail?

Life on board

Around six to eight guests and a small crew of two or three are typically on board, although really exclusive, luxury holidays might feature a yacht with space only for a couple. Private charters are available, so a family or group of friends can book out the entire boat, giving you complete freedom to tailor make the trip, adding on days or tweaking the itinerary. On standard small group sailing holidays with fixed departures, sociability is key as space is limited. Make friends with your fellow passengers and, if travelling alone, be ready to share a cabin with another solo shipmate of the same sex.
Expect comfy accommodation on board, but not acres of space; this is sailing, not cruising on a floating hotel. Cabins are for sleeping in and that’s about it, often with twin beds and shared bathrooms. This shouldn’t be a problem, though, as you’ll be spending most of your holiday on deck, in the sea or exploring on land. In fact, it’s the intimate, personal nature of a sailing holiday that sets it apart from a small ship cruise with 40 or so passengers. You’ll get to know everyone on board and also the crew, who can really bring the whole experience to life. Learn about sailing from the skipper and local food from the ship’s host, be directed to the best family run restaurants, find out more about marine wildlife and listen to local yarns and myths as the sun sets over the wide horizon.

“It’s the sense of freedom! When you hoist the sails and let the wind do the work, the only noise you’ll hear is the sails blowing in the wind and the waves splashing against the side of the boat. Relaxation comes in a close second as for many trips there will be a couple of hours without WiFi, or in Myanmar it will be a week without Wifi and the internet. You are ‘forced’ to relax; you get to watch the world go by, talk to your fellow travellers, read a book, listen to music or catch up on some sleep.” – Dianne Muldoon, from our supplier Intrepid Travel
Photo credits: [Trips with a twist: John Shave] [Entail intro: Nevit Dilmen] [Helpdesk: Ian Burt]
Written by Joanna Simmons
Sailing in Croatia

Sailing in Croatia

A multi-activity adventure sailing cruise in Croatia

From €580 4 Days ex flights
Luxury gulet cruise in the Aegean 2023

Luxury gulet cruise in the Aegean 2023

5 star services while cruising the Greek Islands in luxury

From £1250 8 Days ex flights
Greek Islands sailing holiday, Santorini to Mykonos

Greek Islands sailing holiday, Santorini to Mykonos

Sapphire waters, whitewashed villages & history laden ruins

From £1176 8 Days ex flights
Dubrovnik to Hvar sailing holiday

Dubrovnik to Hvar sailing holiday

Active sailing adventure around Croatian Islands

From €920 5 Days ex flights
Sailing holiday in Greece, Mykonos to Santorini

Sailing holiday in Greece, Mykonos to Santorini

The boat, the beach and inviting Greek villages

From £1251 8 Days ex flights
Yoga and sailing retreat in Greece

Yoga and sailing retreat in Greece

-A week of relaxation and yoga while sailing the Ionian sea!

From £850 7 Days ex flights
Liveaboard diving and sailing holiday in Greece

Liveaboard diving and sailing holiday in Greece

Combine a sailing and diving adventure in the Greek islands

From £719 7 Days ex flights
Photo credits: [Page banner: Markos Mant]