Sailing has long been one of the top choices for intrepid travelers looking to experience new places and cultures. The smell of the ocean, a swift breeze, and numerous options for where to dock next are all a part of the appeal of bareboat sailing adventures. With the right qualifications you can charter your own boat and set sail anywhere you like. From the Grenadines and Belize to the islands of Greece, no matter what destination you choose to drift toward, there will always be fantastic vacation rentals to choose from when you’re ready to spend some time on land.
Belize sailing vacations
If crystal-clear waters, ancient Mayan ruins, and diverse landscapes sound like your shopping list for a great vacation, then you’ll love Belize. Set between the Caribbean Sea, Mexico, and Guatemala, the country is a tropical wonderland and Belize sailing vacations offer the perfect opportunity to explore the second largest Great Barrier Reef in the world. Snorkeling and diving are 2 of the region's biggest draws, and you’ll have no trouble getting up close and personal with interesting coral and fish species. After a long day exploring underwater playgrounds, bed down in a vacation rental with a glorious view of both the sea and the sunset. Or if you’re keen to be on the reef as long as possible, stay in Caye Caulker so that you’re never far from the action.
Sailing Greece and the Mediterranean
Greece is a sailor's dream. From the the Dodecanese islands off the Turkish coast to the stunning Cyclandas and charming Ionian locations like Corfu, sailing Greece offers a vast variety of areas to explore. And whether it’s charming villages on Kefalonia that catch your eye or the traditional white houses of Santorini, there are some amazing villa rentals that will provide the perfect base for your Mediterranean sailing trip. Featuring everything from private chefs to infinity pools and saunas, Greece vacation homes can be as luxurious as you want them to be. And when you're not in your incredible vacation rental, you’ll be able to enjoy the endless amounts of cultural history, hidden beaches, and amazingly fresh seafood that Greece has to offer.
Sailing the Grenadines
Blissfully warm days spent on white-sand beaches are a common occurrence for Caribbean sailing vacations, which is undoubtedly why bareboat sailing around the Caribbean islands has become a bucket-list trip for people all over the globe. The real question is, with so many diverse and beautiful parts of the Caribbean to choose from, where do you go? If you’re an experienced sailor then the answer is the Grenadines. Set between Saint Vincent and Grenada, this gorgeous chain of secluded islands has managed to retain the idyllic and enchanting vibe so often chased by lovers of remote vacations. And, while there are plenty of suger-white shores and jungle-covered slopes to discover, there's also a great selection of vacation rentals to relax in after a satisfying day of soaking in the sun.
Hawaii sailing vacations
Hawaii may not be the first place that comes to mind when you think of a bareboat sailing vacation, but that shouldn’t stop you from exploring the Hawaiian archipelago once you know the wonders you’ve been missing out on. Stunning mountain scenery and volcanic peaks, fantastic surfing, and a rich cultural history are just some of what the Aloha State has to offer. And for diving and snorkeling enthusiasts, Maui is particularly alluring with the partially submerged Molokini crater, located 3 miles off the coast and featuring a colorful array of fish species to admire. From the Big Island to Kauai and Oahu, a Hawaiian sailing adventure could be just what you’re looking for—just don’t forget to book 1 or 2 fabulous vacation homes to relax in along the way.
Sailing in Chesapeake Bay
For those wanting to stay a little closer to home, Chesapeake Bay is one of the best locations for a short and sweet bareboat sailing trip, offering plenty of interesting coves and islands to explore. Secure a vacation rental in St. Michaels for easy access to some of the best restaurants in the area and outstanding cultural sites like the Chesapeake Bay Maritime Museum. Make sure to book early if you’re hoping to go in the middle of summer, or if you’re not one for crowds, visit during the beginning and the end of the season in May and November.
Santa Barbara sailing trips
If one of the reasons you love sailing is the incredible marine life you can only spot from aboard a boat, then Santa Barbara is probably already on your list of destinations to visit. Known for its amazing sea lion, dolphin, and whale watching opportunities, a Santa Barbara sailing trip is sure to entertain the whole family. And when you’re not seeking out the creatures of the sea, you’ll also be able to witness some of the best sunsets you’ll ever see—ideally from the relaxing balcony or outdoor deck of your lovely vacation rental.