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 22nd, 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

 

The Elizabeth Islands to Newport — Island-Hopping and Arrival

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

 

 

Why This Passage is Special

• Full Cruising Experience – Every day brings a new destination, harbor entry, and sailing opportunity.
• Protected Waters, Real Conditions – Navigate the complexity of the New England coast in safe but active sailing zones.
• Tide and Current Mastery – From the Cape Cod Canal to shifting coastal flow, you’ll sharpen your timing and route planning.
• Anchoring Confidence – Daily stops give you time to learn and refine anchoring, docking, and mooring skills.

 

 

Life on Board Libra

 

This passage offers a mix of structured sailing time and relaxed evenings at anchor. We’ll follow a rotating watch system during the day, with all hands involved in docking, anchoring, and coastal navigation. You’ll take turns helming, trimming, navigating, and managing lines — building comfort and confidence in all areas of the boat.

On this passage we will be eating at some of the areas best resturants some evenings, maybe even a beach camp fire.

Meals are fresh, hearty, and crew-style from pasta and grain bowls to hot breakfast and snacks underway. Once anchored, you’ll have time to relax, chat, enjoy the sunset, or go ashore (when local conditions allow). Libra’s vibe is always collaborative, never rushed.