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This week-long coastal passage from Portland to Newport includes daily stops at iconic New England harbors and hidden anchorages. You’ll practice real-world sailing skills in changing conditions, transit the Cape Cod Canal, and finish in the legendary port of Newport. A perfect passage for sailors looking to build confidence, rhythm, and coastal cruising skills. Please note the stops listed on this trip are possibilities not plans. Libra's routes are determined by weather.
A fantastic introduction into sailing these beautiful waters, learning the ropes as you go.
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.
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
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Discover New England: Portland to Newport Join us for a scenic and skill-focused week of sailing from Portland, Maine to Newport, Rhode Island, stopping each night to explore some of New England’s most charming coastal towns and hidden harbors. This is a sailor’s cruise — perfect for those looking to build experience through a mix of short offshore hops, inshore navigation, and hands-on boat handling in a wide range of real-world conditions. Over the course of 8 days, we’ll sail down the coast with possible layovers in places like Cape Porpoise, Isle of Shoals, Rockport, Boston, the Cape Cod Canal, Onset, and Cuttyhunk in the Elizabeth Islands. Each anchorage offers its own unique character, giving you a full taste of cruising culture in the Northeast. Coastal Maine to Cape Ann — Harbors, Headlands & Hands-On Sailing We’ll depart Portland on August 29th, setting sail for the scenic and rocky shores of southern Maine and Massachusetts' North Shore. With stops in places like Cape Porpoise, Isle of Shoals or Rockport, this portion of the trip will focus on: Line-of-sight navigation and buoy recognition Sail trim and reefing practice in variable coastal winds Anchoring and mooring in small harbors Harbor entry and exit procedures in tight quarters Expect light offshore hops by day and calm, scenic evenings at anchor or moored close to town. Boston and the Cape Cod Canal — Tides, Traffic, and Seamanship Continuing south, we’ll sail through Boston Harbor, with a chance to explore ashore before setting a course for the Cape Cod Canal. Transiting this narrow, tidal-controlled channel is a highlight of the trip — and a challenge in timing and helm control. Skills in focus during this stretch: Tidal planning and current optimization Harbor traffic awareness and AIS tracking Docking and line handling Route flexibility based on weather and harbor availability Our final leg includes potential stops at Cuttyhunk on the south end of Buzzards Bay and reaching Newport, Rhode Island. This leg will include: Close-quarters sailing and route adjustments Wind strategy through Buzzards Bay and Rhode Island Sound Mooring and anchoring practice
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