5 Sailing Trips to Book Now for Summer


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Summer will be here before you know it, so what better way to enjoy the warm breeze and blazing sunshine than from the bobbing deck of your very own sailboat? Whether you’re an old pro or just starting out, sailing is a relaxing pastime that can take you around the world. From the Caribbean to the Mediterranean, here are five desirable destinations for your next sailing trip.

The Greek Islands

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The Greek Islands are an obvious choice, but for good reason. From the bold blue color of the Mediterranean Sea to the sun-kissed fishing villages that dot the coastline, this is the quintessential place for a summer sailing trip. While the popular choice is to sail between the famous islands of Santorini and Mykonos, breaking free from the pack and exploring another set of islands promises to be just as rewarding. We recommend heading slightly further west to explore the Cyclades in the Aegean Sea.

Hop from one small patch of paradise to another as you explore Serifos, Sifnos, Kythnos, and Milos. Discover Greece and all its secluded glory by enjoying deserted beaches, tiny villages with authentic taverns and restaurants, and welcoming locals. The highlight is Moon Beach along the coast of Milos, which features strange-shaped, wind-whipped white rocks that form a lunar-like shoreline.

The Bahamas

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Situated just off the coast of Miami, the Bahamas beckon boaters off the mainland with clear waters, picturesque harbors, and plenty of opportunities for sailing trips. While it’s hard to pick a favorite spot, we suggest first-time boaters head to Great Abaco Island. Cruise Abaco offers a “Captained by Day, Bareboat by Night” option, which allows first-time sailors to enjoy the best of both worlds. A captain remains on board during the day to guide the boat around the different cays to stop at the best snorkeling spots. In the evening, the captain securely anchors the boat on a mooring and disembarks the boat — allowing passengers to enjoy tranquil reflection of the moon at sea.


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Mild temperatures, sun-filled days, sapphire seas, and calm winds make Croatia one of the best destinations in the world for newbie sailors. Over 1,000 islands closely cluster off the Dalmatian Coast and the short distances between them make island hopping an easy feat — even for less-experienced boaters. With only 48 of these isles inhabited, it’s completely feasible that you’d find yourselves alone on a private piece of utopia. When you’re ready to socialize, the islands of Hvar and Pag draw merry-makers with promises of the best beach parties in the country. And when it’s time to break free from the crowds, set sail for sleepy, nature-dense islands like Murter or Mljet to help the body and mind reset. Bareboat charters (no crew or captain on board) are extremely popular with most parties setting sail from either Dubrovnik or Split. YachtHoliday can set boaters up with a bareboat rental — or if you’re not as confident, a crewed and captained vessel.

Catalina Island, California, USA


Just 22 miles off the coast of Los Angeles, Catalina Island’s pristine nature makes it feel much more remote and secluded than it actually is. Easily accessible from mainland California, the comfortable sailing conditions tempt beginners offshore to explore what feels like a whole new world. Famed for its kelp forest scuba diving, deep-sea fishing, and abundant marine life, Catalina Island also boasts two harbors, plenty of moorings, and a lively boating scene. With this plethora of activities, you can bet you’ll make some new friends fast.

Catalina Sail offers captained day trips including everything from dolphin, seal, and whale watching to swimming, kayaking, and sunset tours. Those with some experience can bareboat it with Harbor Yacht Club in Long Beach and enjoy complete privacy and a spontaneous schedule. If you lack sailing experience (but Catalina has got you motivated to try), Blue Pacific Yachting runs a three-day course designed to boost skills and confidence levels for those just starting out.


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If you crave that deserted-island feel, look no further than the Seychelles. Located 1,000 miles off the coast of Kenya, the Seychelles offer untamed beauty in the form of powder-white beaches, pristine corals, exotic wildlife, and miles of rugged coastline. Beginner sailors need not be too intimidated. The Seychelles' warm winds and relatively calm seas create a welcoming environment.

With 115 islets making up the entire archipelago, island-hopping from one paradisal bay to another is a breeze. Mahé, the largest of the Inner Island Group, boasts over 65 beaches in addition in a multitude of hidden caves and grottos. Days could be spend strolling around Mahé, however a visit to Praslin and La Digue (or any of the other 42 closely gathered islands) will enhance your journey. Chartering a boat from Mahé is easy since the island has over 30 boat rental outfitters. Bareboat, skippered, and crewed charters are all available from reputable companies like Dream Yacht Charter, and The Moorings Seychelles.

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