Coastal Sailing Adventures

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Hilton Head Island Sail (round-trip) - Offshore passage training route: CoastalPassage

Hilton Head Island Sail (round-trip)

Coastal

4/26/2026 - 5/3/2026

Set sail on a seven-day round-trip cruise to Hilton Head Island, SC. This trip has been designed to assist you in gaining knowledge and confidence while coastal cruising, and covers a minimum distance of 320nm (nautical miles). Ocean sailing through the night, traveling the Intracoastal Waterway (and it's challenges), anchoring in remote locations, cooking and cleaning are part of the experience.

$2,200 / $3,2008 Days2 of 2 available
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Coastal Sailing Adventures
Passage

Myrtle Beach, SC to New York City

Offshore

6/5/2026 - 6/14/2026

Prepare for an exhilarating offshore challenge as you embark on the first leg of our 2026 sailing season: a direct, non-stop passage from Myrtle Beach, South Carolina, to the iconic New York City skyline! This approximately 530-nautical-mile voyage, expected to take 4 to 5 days, is designed to immerse you fully in the rhythms and demands of true ocean sailing. Your adventure begins with arrival at the boat after 3:00 PM on June 5th or before 2:00 PM on June 6th. We'll then set sail on June 7, setting a course north. You'll sail strategically around the formidable Frying Pan Shoals, Cape Lookout, and the legendary Cape Hatteras—a region famously known as "The Graveyard of the Atlantic." This is an unparalleled opportunity to navigate these historically significant and challenging waters, honing your skills in a truly dynamic environment. The journey culminates in a breathtaking arrival in New York Harbor, where you'll sail directly to the Statue of Liberty to anchor behind her for the night, a truly unforgettable experience. As a valued working crew member, you are not just a participant; you are an essential part of the vessel's operation every step of the way. You will actively engage in all facets of the journey, fostering deep learning and practical skill development. This includes adhering to a proper watch schedule, gaining hands-on experience in steering and helming, and mastering the art of trimming sails for optimal performance in open ocean conditions. You'll gain practical knowledge in navigation, meticulous weather monitoring, and the crucial task of recording logbook information. Daily life aboard will also involve contributing to cooking and cleaning, ensuring the smooth operation of the sailboat. Whether you are a beginner seeking a comprehensive introduction to offshore life or an advanced sailor aiming to refine your capabilities, this passage offers a robust learning environment tailored to your ambitions. For those pursuing formal certification, if you meet the qualifications, you have the option to add ASA 106 Advanced Coastal Cruising ($800 per person) to your passage, solidifying your expertise. This non-stop passage is more than just a trip; it's an intensive, adventurous, and incredibly rewarding educational experience that will push your limits and deepen your understanding of the sea. Prepare to challenge yourself and emerge with newfound confidence as you conquer the open Atlantic and arrive at one of the world's most iconic harbors. Please call Jason (843-241-6874) if you have any questions or would like to learn more. Are you following the ASA curriculum? If you qualify you may: add ASA104 Bareboat Cruising ($600 per person) or ASA106 Advanced Coastal Cruising ($800 per person) to your monohull passage

$3,200 / $4,20010 Days3 of 3 available
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Coastal Sailing Adventures
Passage

New York City to Portland, ME

Coastal

6/19/2026 - 6/28/2026

Get ready for a captivating coastal passage from the vibrant heart of New York City to the charming maritime city of Portland, Maine! This approximately 300-nautical-mile leg of your 2026 adventure, with an expected 7 days of travel, is a masterclass in diverse sailing, combining intricate navigation with picturesque cruising, promising an exciting and educational experience. Your journey begins with arrival at the boat after 3:00 PM on June 19th or before 2:00 PM on June 20th. We'll then set sail on June 21, 2026, with an unforgettable motor through the iconic Hells Gate route. Imagine the sheer epic-ness of navigating your vessel directly through New York City's bustling waterways, past towering skyscrapers, and into the expansive Long Island Sound. As evening falls, you'll set your sails and experience the unique thrill of an overnight passage, sailing under the stars as you make your way to Newport, Rhode Island. After a well-deserved night's rest in this historic sailing hub, you'll continue your voyage to a serene anchorage in Buzzards Bay, where you'll hone your anchoring techniques. The next day brings another highlight as you transit the impressive Cape Cod Canal, a vital shortcut that connects Buzzards Bay with Massachusetts Bay. From there, you'll sail to the unique and lively town of Provincetown, Cape Cod, where you'll enjoy two nights, giving you time to explore its vibrant streets and artistic community. The final stretch of this passage will take you north along the scenic coastline, culminating in your arrival in Portland, Maine. As working crew, you'll be immersed in every aspect of this active learning environment. You'll participate in a proper watch schedule, gaining hands-on experience in steering and helming through varied conditions. You'll master the art of trimming sails for optimal performance, refine your navigation skills in complex coastal waters, and diligently monitor weather patterns. Essential daily tasks like recording logbook information, cooking, cleaning, and practicing anchoring/docking will be part of your routine, solidifying your practical sailing knowledge. This passage offers an incredible opportunity for skill development, whether you're building foundational knowledge or refining advanced techniques. If you qualify, you can enhance your credentials by adding ASA 104 Bareboat Cruising ($600) or ASA 106 Advanced Coastal Cruising ($800 per person) to your experience, further certifying your expertise. Prepare for an enriching adventure that blends the excitement of navigating iconic waterways with the beauty of coastal New England, making you a more confident and capable sailor.

$3,800 / $4,80010 Days3 of 3 available
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Coastal Sailing Adventures
Passage

Maine Cruise

Coastal

7/10/2026 - 7/19/2026

Prepare to immerse yourself in the breathtaking beauty and quintessential charm of Mid-Coast Maine on this unforgettable coastal cruising adventure! This approximately 156-nautical-mile journey over an estimated 7 travel days is designed to provide you with a hands-on sailing experience while exploring some of Maine's most captivating islands, coves, and harbor towns. Your journey begins with arrival at the boat after 3:00 PM on Friday, July 10th, or before 2:00 PM on Saturday, July 11th. We'll then set sail, navigating through the pristine waters that define Maine's rugged coastline. You'll discover the tranquility of secluded anchorages like Tottman Cove and Burnt Island, where you'll experience serene nights under the stars, perfecting your anchoring skills in picturesque settings. Imagine the quiet beauty of these hidden gems, perfect for dinghy exploration or simply soaking in the peace of nature. Further along the coast, you'll drop anchor in the vicinity of Vinalhaven, Maine's largest offshore island. This working fishing community offers a glimpse into authentic island life and a chance to explore its unique character and unspoiled natural beauty. A highlight of this passage will be a visit to Rockland, famously known as the "Lobster Capital of the World." Here, you'll have ample time to step ashore and explore its vibrant downtown, discover the renowned Farnsworth Art Museum, or simply soak in the atmosphere of a bustling working harbor. From there, you'll sail to the sheltered Linekin Anchorage, providing another classic Maine coastal experience under the open sky. Your adventure continues with a visit to the charming town of Boothbay Harbor. This popular destination boasts a picturesque working waterfront, quaint shops, art galleries, and, of course, delicious seafood restaurants, offering a fantastic opportunity to explore and enjoy its coastal allure. As your cruise draws to a close, you'll enjoy a scenic return sail to Portland, where you'll dock for a final celebratory night. Portland offers a vibrant food scene, the historic Old Port district, and unique boutiques, providing a fantastic last evening before your departure on Sunday, July 19th. As working crew, you will be deeply immersed in every facet of this journey, contributing to an active learning environment. You'll adhere to a proper watch schedule, gain practical experience steering and helming, and master the art of trimming sails for optimal performance in coastal conditions. You'll refine your navigation skills in intricate waterways while monitor weather patterns. Daily life aboard will also involve contributing to cooking, cleaning, and mastering various anchoring and docking maneuvers. This cruise offers an incredible opportunity for skill development, whether you're building foundational knowledge or refining advanced techniques. If you qualify, you can enhance your credentials by adding ASA 104 Bareboat Cruising ($600) to your passage, further certifying your expertise in coastal cruising. Prepare for an enriching and authentic Maine experience, blending hands-on sailing with the charm of coastal towns and the tranquility of secluded anchorages, making you a more confident and capable sailor.

$3,200 / $4,20010 Days3 of 3 available
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Coastal Sailing Adventures
Passage

Portland, ME to New York City

Coastal

7/24/2026 - 8/2/2026

Prepare for a captivating southbound coastal passage, tracing the stunning New England coastline from Portland, Maine, to the iconic New York City skyline! This journey is designed to be an exhilarating blend of scenic beauty, challenging navigation, and hands-on learning, perfect for expanding your sailing repertoire. Your adventure begins in the vibrant city of Portland, Maine, a hub of maritime charm. From there, you'll set sail south, making your first significant stop in Provincetown, Cape Cod. Nestled at the very tip of the Cape, this lively and historic town offers a unique blend of artistic flair and scenic beauty. You'll have the chance to explore its charming streets and soak in its distinctive atmosphere. Continuing your journey, you'll sail to a serene anchorage in Apponagansett Bay, a peaceful setting perfect for practicing your anchoring techniques under the guidance of experienced instructors. The next destination is the historic town of Mystic, Connecticut, where you'll enjoy two nights. Immerse yourself in this charming seaport, renowned for its maritime museum, historic ships, and picturesque downtown. This stop offers a fantastic opportunity to step ashore and explore a quintessential New England nautical village. From Mystic, you'll make your way to Charles Island, where you'll experience the tranquility of an overnight anchorage, further refining your skills in selecting and securing a safe harbor. The grand finale of this passage is an exhilarating offshore leg culminating in a spectacular approach to the Statue of Liberty, where you'll anchor for the night beneath her majestic gaze. Imagine the thrill of seeing the New York City skyline emerge from the horizon, a truly unforgettable end to your journey. As a valued working crew member, you are an essential part of the vessel's operation every step of the way, fully immersed in an active learning environment. You'll participate in a proper watch schedule, gaining hands-on experience in steering and helming through varied coastal conditions. You'll master the art of trimming sails for optimal performance, refine your navigation skills in complex waterways, and diligently monitor weather patterns. Essential daily tasks like recording logbook information, cooking, cleaning, and practicing anchoring/docking will be part of your routine, solidifying your practical sailing knowledge. This passage also provides ample opportunity to hone your practical skills in locating and utilizing suitable anchorages or mooring balls for overnight stays. This passage offers an incredible opportunity for skill development, whether you're building foundational knowledge or refining advanced techniques. If you qualify, you can enhance your credentials by adding ASA 104 Bareboat Cruising ($600) or ASA 106 Advanced Coastal Cruising ($800 per person) to your experience, further certifying your expertise. Prepare for an enriching adventure that blends the excitement of navigating iconic waterways with the beauty of coastal New England, making you a more confident and capable sailor.

$3,800 / $4,80010 Days2 of 2 available
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Coastal Sailing Adventures
Passage

New York City to Myrtle Beach, SC

Offshore

8/7/2026 - 8/16/2026

Be apart of the return sail from this extraordinary 2026 Maine adventure with an exhilarating non-stop ocean passage from New York City back to Myrtle Beach, South Carolina! This approximately 530-nautical-mile voyage, expected to take 4 to 5 days, is a profound opportunity to synthesize all the skills you've acquired and experience the pure exhilaration of offshore sailing. Your journey begins as you depart from the magnificent backdrop of New York City, heading out into the open Atlantic. This passage will challenge you with continuous offshore conditions, allowing you to truly settle into the rhythm of the sea. As you progress, you'll be navigating the waters offshore of the notorious "Graveyard of the Atlantic," reflecting on the vast history beneath you as you complete your ocean transit. As a working crew member, you will be deeply immersed in every aspect of this active learning environment, applying all the skills you've honed throughout your Maine passages. This continuous offshore leg demands constant vigilance and teamwork. You will maintain a rigorous watch schedule, skillfully steering and helming through all conditions, both day and night. You'll master the nuanced art of trimming sails for optimal speed and efficiency on long hauls, while expertly executing navigation duties and diligently monitoring weather patterns to ensure a safe and efficient passage. The essential routines of recording logbook information, cooking, and cleaning will become second nature as you contribute to the smooth operation of your vessel. This concluding passage is designed to be a capstone experience, offering intensive, real-world application of your growing expertise. Whether you've joined for the learning vacation of a lifetime or to achieve specific certifications, this leg provides invaluable offshore mileage and confidence. If you qualify, you can enhance your credentials by adding ASA 106 Advanced Coastal Cruising ($800 per person) to your passage, solidifying your expertise in comprehensive offshore navigation and boat handling. This non-stop passage is your chance to truly feel the majesty of the ocean, consolidate your skills, and arrive back in Myrtle Beach a more accomplished and confident ocean sailor.

$3,200 / $4,20010 Days2 of 2 available
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Coastal Sailing Adventures
Passage

Charleston Sail (round-trip)

Coastal

10/19/2026 - 10/25/2026

Gain coastal cruising experience on a seven-day round-trip cruise to Charleston, SC. This trip has been designed to assist you in gaining knowledge and confidence and covers a minimum distance of 200nm (nautical miles). Ocean sailing through the night, traveling the Intracoastal Waterway (and it's challenges), anchoring in remote locations, cooking and cleaning are part of the experience.

$2,200 / $3,2007 Days3 of 3 available
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