New York City to Portland, ME
Coastal
About This Trip
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.
Itinerary & Operations
Arrival: After 3pm Friday, June 19 and before 2pm Saturday, June 20 Saturday: Review boat, safety and weather. Provision for trip Sunday: Depart by 10am. Sail through the night to Newport, Rhode Island Monday: Arrive in Newport. Dock, anchor or grab a mooring ball for the night. Enjoy Newport Tuesday: Depart by 10am. Sail to a Buzzard Bay anchorage for the night Wednesday: Depart by 10am. Sail to Provincetown, Cape Cod for the night. Enjoy Provincetown Thursday: Free Day. Enjoy Provincetown Friday: Depart by 10am. Sail through the night to Portland, Maine Saturday: Arrive in Portland. Departure: Sunday
Additional Notes
Approximately 300 Nautical Miles | Estimated 7 Travel Days Storyteller (Monohull) - Three private double occupancy cabin berths (beds/sleeps 2) are available each trip. Meals and safety gear are included while aboard 1 guest/$3800 or 2 guest/$4800