1/6
Sept 11-16
US$4,250
4 spaces available
This round-trip passage from Newport around Long Island includes two overnight sails, coastal harbor stops, and full East River navigation through NYC. It’s perfect for sailors seeking bluewater experience, strong current management, and the satisfaction of completing a full circumnavigation (of Long Island) under sail.
Get a real taste of blue water cruising with this great round trip passage from Newport RI.
We believe real seamanship can’t be learned at a marina. Libra was built for the open ocean — and so was this program. Whether you're looking to gain confidence offshore, log serious sea miles, or chase the horizon just for the hell of it, you're in the right place. For over a decade, we’ve helped sailors step beyond the dock and into a full-spectrum passage-making experience. It’s hands-on and sometimes it’s rough & loud — but it’s real. Every passage is a team effort. There’s no standing back and watching here — you’ll be on the helm, trimming sails, navigating, standing watch, and learning what it really takes to move a boat. We meet you at your level, then build you up from there.
Real offshore and blue water cruising with a great owner skipper.
Your specific vessel is assigned based on your selected dates. All vessels meet our high standards for comfort and safety.
Bill Tripp - Custom Ketch
LOA: 60ft (18.2m)
Beginner
No sailing experience required. Perfect for newcomers.
Intermediate
Some sailing experience helpful. Comfortable on the water.
Advanced
Significant sailing experience required. Challenging conditions.
Active Crew Member
Full participation in all sailing activities.
Optional Involvement
Participate as much or as little as you like.
Passenger
Sit back and enjoy the ride.
No
All meals and cleaning are taken care of
18
A Newport-to-Newport Adventure THIS PASSAGE HAS 2 OVERNIGHT SAILS Experience the best of Long Island by sea as we set sail from Newport, Rhode Island, and circumnavigate the iconic Long Island on a passage that blends offshore challenge with inshore exploration. Over the course of this round-trip journey, we’ll complete two overnight sails, anchor at Block Island and New York City, and navigate the ever-shifting currents of Long Island Sound. This looped route is ideal for sailors eager to grow their confidence, gain bluewater experience, and see one of the East Coast’s most iconic cruising grounds from every angle — all in one trip. Newport to Block Island — Settling In and First Night Sail We’ll begin our adventure in Newport, with time to prepare the boat and get to know your fellow crew. After a safety briefing and sail check, we’ll set off into Rhode Island Sound and head for Block Island on Saturday. This leg introduces you to offshore conditions and includes: Watch rotation practice (3 hours on, 6 off) Helm time and sail trim Anchoring in Block Island’s Great Salt Pond Offshore to NYC — Into the Atlantic and the Hudson From Block Island, we head south and west into the Atlantic for an exhilarating overnight sail toward New York City. This is a true offshore leg, with the open Atlantic on one side and the glowing NYC skyline on the other. Expect full night watch rotations and hands-on offshore experience. We’ll likely anchor near the Statue of Liberty or moor at a nearby marina, giving you a front-row seat to the city from the water. The East River and Long Island Sound — Riding the Currents Leaving New York Harbor, we’ll ride the East River through Hell Gate, navigating tight tidal windows and strong currents. The energy of the city gives way to the more protected waters of Long Island Sound, where we’ll enjoy a different kind of challenge — sail trim finesse, local traffic management, and navigation around headlands, islands and Lighthouses. Return to Newport — Final Night Sail and Coastal Finish Our final leg takes us into the Sound for one last overnight sail, passing Montauk and re-entering Rhode Island Sound for a return to Newport. we arive back Tuesday evening hopefully in time for a Crew ashore and you depart from Libra on Wednesday. Expect an engaging combination of: Traffic Management Night helm time and route adjustments Watchstanding in offshore and coastal conditions We’ll arrive back in Newport with a complete loop of Long Island under our keel on entered into your logbook. Why This Passage is Special A Full Circumnavigation by Sea – Complete the loop around Long Island with two night sails and multiple anchorages Iconic Sights from the Water – Explore Block Island, Sail beneath NYC’s bridges (8 out of 9), and anchor by Lady Liberty. Diverse Sailing Conditions – Offshore challenge, inshore navigation, strong currents, and quiet anchorages Hands-On Experience – Ideal for building confidence in both offshore and coastal cruising environments Life on Board Libra You’ll sail as an active part of the crew under our standard 3-on, 6-off watch system during overnight legs. Days are balanced between focused sailing and anchorage time. You'll rotate through all aspects of sailing — helming, navigating, sail trim, lookout, anchoring, and galley duty. Meals aboard are wholesome and satisfying: pastas, fresh salads, grain bowls, and more — always with vegetarian options. Whether it’s coffee at dawn or a warm meal after a night shift, the crew keeps everyone fueled and connected.
No optional extras
18-25°C
Peak Florida sailing. Pleasant temps, steady winds.
22-28°C
Excellent conditions. Warm but not hot yet.
28-33°C
Hot and humid. Afternoon thunderstorms possible.
25-30°C
Variable conditions. Monitor forecasts closely.
18-25°C
Peak Florida sailing. Pleasant temps, steady winds.
22-28°C
Excellent conditions. Warm but not hot yet.
28-33°C
Hot and humid. Afternoon thunderstorms possible.
25-30°C
Variable conditions. Monitor forecasts closely.
Tried and tested sailing experiences, from our pick of the world's best operators
All our trips are led by qualified skippers and sailing instructors
We only work with the most reputable sailing operators and yacht providers
Perfect for solo sailors looking to join a crew or groups wanting to charter
Our team is on-hand 24/7 to help you before, during and after your adventure
From US$4,250 per person