Charter Vacations

We organize, plan, and skipper a private bareboat charter at one of many available destinations around the world. You can also turn any charter vacation into a private ASA sailing lesson!
Embark on the ultimate sailing adventure with our charter vacations aboard 45 - 50 foot sailboats in the destination of your choice. Picture yourself cruising through crystal-clear waters, exploring pristine beaches, and experiencing the beauty of some of the world's most exotic locations.
Moorings 4500 / Leapord 45

Discover Paradise

Our carefully selected destinations offer unparalleled beauty and unique experiences. Imagine sailing through the vibrant coral reefs of the Caribbean, anchoring in secluded coves in the Greek Islands, or exploring the lush landscapes of the Whitsunday Islands. Each destination provides a perfect blend of relaxation, adventure, and cultural immersion, ensuring that your journey is as enriching as it is enjoyable.
U.S. Virgin Islands

U.S. Virgin Islands – The Ultimate Charter Experience

Set sail on an unforgettable adventure in the U.S. Virgin Islands, where you can book a skippered charter vacation with one of our experienced instructors or captains. The Virgin Islands offer breathtaking natural beauty, crystal-clear turquoise waters, and ideal sailing conditions that cater to both novice and seasoned sailors. Whether you explore the stunning shores of St. Thomas, the serene bays of St. John, or the vibrant culture of St. Croix, you'll find perfect anchorages in every direction. With consistent trade winds, calm seas, and sheltered bays, the islands provide smooth sailing while offering endless opportunities for snorkeling and diving in the vibrant coral reefs that surround you.

Greek Islands – A Dream Charter Destination

Embark on a charter vacation through the enchanting Greek Islands, guided by one of our expert captains or instructors. With over 6,000 islands scattered across the Aegean and Ionian Seas, the Greek Islands are renowned for their diverse landscapes, crystal-clear waters, and rich cultural history. From the iconic Cyclades to the serene Ionian Islands, each destination offers unique charm, whether it’s secluded bays, stunning beaches, or picturesque villages. Ideal for sailors of all skill levels, the Mediterranean climate provides reliable winds and calm seas. As you sail, you’ll have the opportunity to swim in turquoise waters, explore ancient ruins, and immerse yourself in the breathtaking beauty that has made the Greek Islands a top sailing destination.
Greek Islands
Whitsunday Islands / Australia

Whitsunday Islands, Australia – A Sailing Paradise

Discover the breathtaking Whitsunday Islands off the coast of Queensland, Australia, with a charter vacation led by one of our experienced captains or instructors. This stunning archipelago, home to 74 islands, is a sailor's paradise with its crystal-clear turquoise waters, pristine white sand beaches, and vibrant coral reefs. Thanks to the protection of the Great Barrier Reef, the Whitsundays offer calm seas and consistent winds, perfect for sailors of any skill level. Sail to iconic destinations like Whitehaven Beach, famous for its powdery silica sand, and enjoy unforgettable snorkeling and marine life encounters in the Coral Sea. Every anchorage promises a unique and awe-inspiring adventure in this world-renowned sailing destination.

Personalized Experiences

We believe in crafting personalized experiences tailored to your preferences. We have partnered with Be Well Traveled, who coordinates, organizes, and plans all of our clients' charter vacations. Our experienced team will work with you to create a custom itinerary that caters to your interests, whether it's snorkeling in vibrant reefs, exploring historic coastal towns, or simply relaxing on a pristine beach. Every detail is taken care of, allowing you to fully immerse yourself in your vacation.

Reach Out to Us

Ready to set sail on the adventure of a lifetime? Contact us today to learn more about our charter vacations and start planning your dream getaway. Our team is here to answer all your questions and help you design a sailing experience that you will cherish forever. Don’t wait – your perfect escape awaits with Outbound Sailing.
Experience the world from the deck of a luxurious catamaran and create unforgettable memories with Outbound Sailing. Reach out now and let us turn your sailing dreams into reality.