Why choose an overseas sailing trip? It’s partly for the sense of adventure; that feeling that anything is possible and that you can just follow the wind over the horizon. Well, there’s more to a sailing trip than that -- but what so many sailors love is the amazing sense of escape and freedom experienced away from land and everyday routines.

On yachts there’s always a new skill to acquire; you can learn to navigate, handle the ropes, put up sails, reef them in, helm -- and anyone can do it. Sailing teaches you to work as part of a team, respond to others quickly, and respect the part your whole crew plays in getting a job done. And sailing teaches people to react to the natural environment, listen to the wind, and be aware of water currents and the weather.

Whether you want company as part of a flotilla or to spend some "me" time alone on the water, you’ll enjoy a thorough mental and physical workout while experiencing new sights and making new friends every day on your sailing trip.


The legendary Whitsunday Islands off the coast of Queensland provide some of the best sailing in Australia, located right on the Barrier Reef and renowned for their spectacular sea life, including dolphins, harmless reef sharks, turtles, and rays. You’ll discover crystal-clear seas, sugar-white beaches, and tranquil anchorages.

Organize a sailing trip to sub-tropical Queensland between June and August, when temperatures are a pleasant 75–77°F and the seas are warm enough for swimming -- chances are you might get to see whales as they migrate to the Whitsundays to give birth in the sheltered seas around the islands.

The Caribbean

There are several island group options for sailing tours of the Caribbean, depending on your sailing skills, ranging from the Bahamas in the north to the Grenadines in the south. Destinations such as the British and US Virgin Islands offer calm, line-of-sight sailing suitable for all standards, plus the freedom to moor up on deserted beaches or in fully catered marinas.

The reefs around Antigua and neighboring Barbuda offer challenges for more experienced sailors. The best time to be sailing in the Caribbean is between January and April when temperatures sit around 77–82°F and there are regattas throughout the islands.


Some of the best sailing in the Mediterranean is found around the 6,000 islands off Greece, from the Cyclades to the Dodecanese. You’ll have the choice between peaceful anchorages on uninhabited islets, scenic harbors surrounded by seafood restaurants, and buzzing marinas on party islands.

The best time for Greek sailing trips is late spring, when the temperature sticks around 70–75°F, the seas are calm, the islands are covered in lush greenery, and the major influx of tourists has yet to arrive. At the height of summer, the strong Meltemi winds can blow in the afternoon, causing choppy seas.


The tropical waters of the Andaman Sea and the Gulf of Thailand offer a choice of easy line-of-sight sailing around spectacular limestone-backed islands and anchorages on soft sandy beaches. You’ll find a well-established infrastructure for sailors, from chandlers in well-equipped marinas to beachside cafés serving up spicy Thai dishes on a budget.

The country is a year-around sailing destination, with temperatures ranging between 73–90°F; the dry north-east monsoon runs from November through April, while the wetter and windier south-west monsoon means trickier sailing conditions in May to October.

What to Look for in a Sailing Tour

If you’re an expert sailor with the certificates to back your experience up, chose a bareboat charter for complete freedom. Alternatively, join a flotilla and sail on a boat crewed by experts. You’ll make new friends and benefit from the crew’s specialized knowledge while seeing the best local sights and enjoying the best sailing conditions.

When choosing your sailing trip, pick a credible charter company, look carefully at where they are based, and check the age of the fleet offered for hire. For example, a sailing boat that is more than five years old may not have the latest navigation aids on board.

Average Sailing Tour Cost & Length

The cost of a sailing trip will range from budget-friendly to expensive, depending on the type and size of craft you hire and how many amenities you want aboard. However, this price can be shared out among a group of you if you decide to sail together.

If there’s an expert sailor among your travel companions, chose a bareboat charter; the price of the trip will reduce as you are not hiring a crew for the boat. Otherwise, joining a flotilla is the best option, with prices starting from around US$550 per week, including flights, skipper, and a cook on board.

Likewise, there’s no average length of sailing trip, but most last from a weekend up to two weeks. A short vacation will give you a taste of life on board a boat, and a week’s voyage gives you the time to learn the basics of helming and handling the sails. By the time two weeks are up, you’ll be hooked for life.

Packing Tips & Gear Rental

Obviously the biggest expense involved in a sailing trip is the hire of your boat, but once you’ve sorted that, you’ll need to pack one or two essentials alongside your passport and travel documents.

Take casual clothes, including shorts, T-shirts, swimwear, sandals or deck shoes, and a sweater for cool nights. You’ll need towels, sunglasses, and a sun hat for spending time on deck, plus a mask and flippers for snorkeling around the boat. Girls, leave high heels at home as they’ll mark the deck. Flip-flops are also not a good choice, as you may trip while navigating your way around the deck.

In your wash bag, include seasickness pills, lip salve, insect repellent, and anti-histamine lotion in case of bites.

Bring playing cards, books, and board games. Water-sports gear and fishing rods can be rented at most marinas, where hire cars can also be organized.

Other Tips

Leave your valuables at home. Take waterproof cases for cameras, phones, and iPods (great for music on board while sailing), as well as waterproof covers for your travel documents, money, and credit cards.

Visa information will vary from destination to destination. If you’re bare-boating, remember to take duplicates of your qualifying certificates, as they will be required when you pick up your boat. Novice sailors should also take their sailing log to be filled in by the captain at the end of the sailing trip.

Qualifications & Training

If you’re hiring a crewed boat, you won’t need any qualifications to enjoy a vacation on the ocean wave. However, most charter companies require some form of formal sailing qualification before allowing a bareboat charter, so at least one of your group will need American Sailing Association (ASA), Royal Yachting Association (RYA) or International Certificate of Competency (ICC) proof of sailing competency.

If you’re a novice sailor, all your training can be done on board while you’re enjoying your sailing trip.

Activity Risks

Statistically, sailing is more dangerous than downhill skiing but less so than driving. Accidents involve collisions with other boats and people falling overboard and it’s vital to have a well-trained skipper who knows exactly what they’re doing, especially because weather and water conditions can change quickly.

Safety Tips

It’s common sense, really. Always check the weather and never head out to sea if storms or strong winds are forecast. Wear your life vest at all times when the boat is on the move. Be a competent swimmer and practice your man-overboard routine. And rule number one: never, ever drink alcohol while sailing.

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