Set Sail on 10 of the Top Sailing Tours Around the World

The Cabo coast of Mexico delights with some of the world's bluest waters. There are few things better than sailing along it, before taking a break to eat lunch and snorkeling among the tropical fish and coral reefs just below the surface. By the end of this adventure, which is perfect for beginners, you might just catch the sailing bug for good.

While some might come to Hawaii to surf, it’s a great spot for sailing, too. Head out on a sunset cruise, with the possibility of spotting dolphins, turtles, and whales. This luxury catamaran carries 49 passengers, and includes a full-service kitchen and bar, so you can enjoy the sunset in style.

The Blue Cave in Dubrovnik is crowded, so it’s best to book a private tour. On this half-day boat tour, you’ll make stops along the way for snorkeling and swimming before arriving at the famous Blue Cave itself. And if you don’t want to dedicate the entire day to the outing, as many tours do, this one will only use half, so you can spend the rest of your time enjoying the city center.

Set sail from the edge of Europe on this sunset cruise departing from Lisbon. It will return you to the lively port city when you’re done enjoying the Portuguese coastline at sunset, and sipping on Portuguese wine with cheese. You’ll have a one-of-a-kind view of Belem Tower, along with the picturesque sights of clear water and the bustling city in the distance.

This nearly 3-hour boat tour is the perfect way to dip your toes into sailing and snorkeling. Aboard this catamaran, you can sunbathe, relax, and enjoy the clear waters of Aruba. The crew will also provide snorkeling equipment if you’re interested, so you can see what’s going on just below the surface.

There’s more to Stockholm than the city alone—its archipelago is ripe for exploring, and a cruise is the best way to see it all. The tour, ideal in the warmer months, includes stops at several historic landmarks and provides a unique perspective on the Swedish capital, one you might otherwise miss ashore.

Costa Rica is known for its coastline, and the best way to see it is at sea, of course. Setting sail from Guanacaste, this catamaran is stocked with paddleboards and kayaks for you to glide along the open water on your own. Feel free to hop off and snorkel to discover the fish of the region, or stay aboard and just enjoy the views, which may include dolphins and whales.

The sunsets in Key West are beautiful, but if you want to escape the crowds, then this tour is for you. You’ll sail aboard a 70-foot (21-meter) catamaran, complete with delicious food, a full bar, and live music to make the entire experience one you’ll never forget. This tour is perfect for couples, groups, and anyone who appreciates the sunset and a friendly staff.

True to Chicago’s nickname, there’s enough wind to power you across Lake Michigan with ease. This skyline tour also comes complete with stories about the city’s unique architecture, told as you pass by, which allows you to experience it in a completely different light. It only lasts about 75 minutes, too, so it’s a great pick if you’re not all that seaworthy.

Gilligan, is that you? On this tour you’ll set sail from Fajardo (about 1 hour from San Juan) to the deserted island of Cayo Icacos, passing by the Puerto Rican coastline while sipping rum cocktails. You can then spend the day snorkeling and swimming in the clear blue waters—and who knows? You just might want them to leave you there.