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.

Australia

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.

Greece

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.

Thailand

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.

Sailing Trips Abroad

Displaying 1 - 15 of 25 programs
Explore Whitsundays Sailing Adventures
Whitsunday Islands Maxi Sailing Adventures
Australia
9.8 •5 reviews

Explore the Whitsundays, sailing and snorkeling, swimming and relaxing...

Smart Trip Europe
Croatia Weekend Trip
Croatia
10 •7 reviews

Spend a weekend around ancient walled towns, pristine sapphire waters...

Look At Egypt Tours
Treasures of Egypt Tour – Egypt Explorer 9 Days
Egypt
10 •1 review

Treasures of Egypt tour explore Egypt in-depth in this 09-day Egypt...

Sail in Greece
Harmony Cruise - Small Ship Cruise from Athens
Greece

Our Harmony Greek Island Cruises are a perfect option for those...

Smart Trip Europe
Amalfi Coast Weekend Trip
Italy
10 •4 reviews

Explore the pearl of Italy - Amalfi Coast! Start your adventure by...

Dominican Expert
Short Trip for Water-Lovers 5 Days / 4 Nights
Dominican Republic

This short trip has been designed for all the water lovers and...

Wild Women Expeditions
Greek Goddess Sailing Adventure
Greece

Dreaming of crystal-clear sapphire waters, whitewashed villages...

Burma Boating
Andaman Island Expedition, Thailand-India
Multiple Countries

Join an adventure trip to one of the most remote island groups in the...

Sail Ningaloo
3-Night Snorkel & Dive Getaway
Australia

On this 3 night Ningaloo Reef tour, we’ll take you to the best places...

Sail Ningaloo
5 Night Ningaloo Escape
Australia

During this 5 night Ningaloo Reef Tour spend 6 days aboard Shore Thing...

Andean Trails
Lonesome George Catamaran
Ecuador

Beautiful eco-catamaran Lonesome George combines active itineraries...

What People Are Saying

I did this trip while I was studying abroad and it was one of my favorite things I did! The staff were amazing and traveling with them was so easy! Smart Trip provided everything from transportation...

View from Anacapri

I had the best experience in Croatia, everyone was nice and I even went mountain climbing. Trip was organized and the staff was incredible, met so many cool people during the trip. The hostel that we...

Mountain climbing in croatia

My group of friends and I used Smart Trip for a weekend excursion to Split, Croatia. It was nothing short of amazing! I 10/10 recommend the Croatia trip and using Smart Trip in general to any students...

My friend and I enjoying ourselves in Croatia

Related Tours & Trips Articles