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Boston MA
Captain Paul Sullivan Master Instructor • Serial Boat Whisperer • Owner of Too Many Clipboards Paul is a Master Instructor with the American Sailing Association and a six-time ASA Outstanding Instructor of the Year—basically the Tom Brady of sailing teachers (but with more SPF and fewer concussions). He’s the proud owner of SailTime Boston and the co-founder of First Reef Sailing School, one of Boston’s only ASA-accredited training centers and arguably the most fun place to hoist a mainsail without accidentally swearing in front of children. When he’s not teaching people how to safely crash less into docks, Paul can be found migrating boats up and down the coast, explaining for the hundredth time that “reefing” doesn’t involve coral, or telling stories that start with “So there I was, in 30 knots, making coffee...” If you see him on the dock, say hi—but be warned: he will probably try to talk you into a debate about the best single malt Scotch.
This weekend I had the honor of teaching two incredible sailors who are Deaf—and I walked away learning just as much as I taught. Their connection to the boat, the water, and each other was inspiring. Without relying on sound, they tuned into subtle cues: the feel of the wind, the pressure on the helm, and the shape of the sails. Every tack, gybe, and feathered-upwind course was a masterclass in awareness. We circumnavigated Spectacle Island, shared a lot of laughs, and found an easy rhythm as a crew. Communication was clear, focused, and full of trust—a reminder that great sailing doesn’t depend on words, just teamwork and presence. This is your sign to come sailing. The wind doesn’t care what language you speak. Let’s go.
Had the privilege of teaching AS 101 to two incredible Deaf sailors this weekend. Their connection to the water was instinctive — feeling the boat, reading the sails, and staying completely in tune with the rhythm of the wind. We practiced tacking, gybing, and feathering upwind as we circumnavigated Spectacle Island — even had a surprise encounter with the Navy on patrol 👀⚓️. No need for constant chatter — just sharp awareness, smooth teamwork, and pure sailing.
A perfect evening sail aboard our Fountaine Pajot Isla 40 catamaran as the sun set over Boston Harbor — warm breeze, calm seas, and a view that blended beauty with history. We cruised past some of the harbor’s most iconic lighthouses: 🗼 Boston Light — America’s first lighthouse, still guiding mariners since 1716 💡 Graves Light — guarding the outer approach with its rugged granite tower 🌊 Bug Light — short, stout, and full of charm at the entrance to the inner harbor And just as the sky turned gold, we passed Nixes Mate, a tiny black-and-white daybeacon on a shrinking spit of land with a haunting past. Legend has it that a pirate’s mate was executed there — proclaiming his innocence with his last words: “The island will sink into the sea to prove me true.” Over time, erosion has nearly swallowed the island, leaving only the beacon behind… a chilling nod to maritime lore ⚓️💀 History, mystery, and a glowing horizon — Boston Harbor never disappoints.
July 4th, 1776: Boston Harbor wasn’t filled with fireworks—it was filled with purpose. Just months earlier, the British had evacuated the city after the Siege of Boston, ending nearly a year of occupation. The harbor, once crowded with redcoat warships, now belonged to the people. Continental Navy schooners and New England privateers patrolled these waters, ready to intercept British supply lines and defend the fragile spark of liberty. Today, almost 250 years later, I had the honor of sailing that same harbor with a new crew of ASA 101 students. We tacked past Fort Independence, once known as Castle William, where British troops once stood guard. We trimmed sails by the telltales, just as colonial sailors might have done aboard sloops and schooners chasing freedom. On this Independence Day, we didn’t just teach sailing—we felt history in the wind. Red, white, and bluewater still runs strong in Boston Harbor. 🇺🇸⛵️
Last night’s sail from Marblehead to Gallops Island was a textbook summer night run—steady breeze, glowing skyline, and just enough complexity to keep us on our toes. We departed Marblehead after sunset and rode a close reach down the coast, eventually slipping into Boston’s main channel and sneaking through The Narrows before anchoring off Gallops Island. 🌬️ Breeze On All Night The wind held steady at 15–20 knots out of the west, giving us a beautiful and efficient sail. On a close reach, we had the boat powered up and slicing through the dark, holding good speed with just the right amount of heel. Once the sails were trimmed and balanced, we engaged wind-hold mode on the autopilot to maintain optimal trim—a must at night when it’s harder to visually monitor the sails. Heading-hold may keep you straight, but it lets trim fall apart if the wind shifts. 🌃 City Lights vs. Nav Lights As we approached the city, the light pollution made it tough to distinguish aids to navigation from streetlamps and shoreline clutter. Red and green markers all but disappeared into the visual noise of Boston’s skyline. We stayed sharp with binoculars, the chartplotter, and hand-bearing compass to pick out the real nav aids and confirm our position with bearings. 🛟 MO(A) Buoys: Hidden in Plain Sight Entering the harbor, we actively searched for all three MO(A) buoys, which flash white and mark the entrance to Boston’s main traffic lanes. These buoys are notoriously easy to overlook at night, especially with city lights behind them, but they’re critical for orientation. We called them out, logged bearings, and stayed just outside the channel to avoid commercial traffic. 🧭 Key Takeaways from the Night Run •🌬️ Wind-hold mode keeps you fast and trimmed when visibility is low •👀 Light pollution can obscure critical nav aids—don’t rely on sight alone •🧭 Confirm with multiple sources—bearing compass, charts, and plotter •💡 MO(A) buoys matter—they’re your guideposts for safe entry •⛵ Trim early, adjust as needed, then trust the instruments We takes up The Narrows, went head to wind just inside Gallops, and dropped anchor under a starlit sky with the city aglow just beyond the island. A perfect night to build skills, trust your tools, and enjoy the quiet beauty of Boston Harbor after dark.
Trip Summary: Yesterday’s sail from Scituate to Marblehead delivered classic early summer conditions—west winds blowing 20 to 30 knots, crisp visibility, and just enough challenge to make it exciting. With good planning and smart sail handling, it was a fast, smooth run up the coast. ⛵ Smart Reefing Before Departure We made the call to put the second reef in the main right on the mooring in Scituate before heading out. With breeze already in the mid-20s and building, we prioritized control and comfort. That decision gave us a well-balanced boat all day and kept us moving quickly without ever being overpowered. 🌊 Manageable Seas Thanks to the Wind Direction Despite the strong wind, the westerly direction meant minimal fetch along our coastal track. The seas stayed surprisingly manageable and organized, allowing us to sail flat and fast. The boat handled beautifully with minor tweaks to sail trim, and we made consistent speed in the 7–8 knot range. 🗺️ Lighthouses Spotted Along the Way We kept a sharp eye on navigation and had a little fun with some traditional piloting. Using a hand-bearing compass, we took bearings and plotted fixes on the paper chart throughout the day as we passed these iconic New England lights: • 🕯 Scituate Light – A final check astern as we departed the harbor • 💡 Minot’s Ledge Light – Stark and isolated offshore, guarding the rocks • 🗼 Boston Light – America’s first lighthouse, standing tall on Little Brewster Island • 🪨 The Graves Light – Marking the outer edge of Boston Harbor • ⚓ Marblehead Light – The familiar skeletal tower welcoming us into the harbor ⚓ Quick Lessons from a Big Breeze Day • ✅ Reef early—it’s easier to shake one out than put one in when it’s already blowing • 🧭 Use your tools—hand-bearing compasses and paper charts still have a place • 🌬 West wind = less fetch—know your geography, and you’ll know your sea state • ⛵ Trim smart, not strong—balance beats brute force every time • 📚 Every sail is a classroom—especially when you’re moving fast and thinking ahead Great wind, good teamwork, and a touch of old-school navigation made this one for the books.
We had an epic sail today from Boston to Scituate, making the most of a classic summer sea breeze and using it as a chance to practice some solid sail trim skills along the way. ⸻ 🌬️ Weather & Wind The day started with a steady southwesterly around 10–12 knots leaving Boston, which gradually built to 14–17 knots as we made our way toward Scituate. Seas were light early on but built slightly offshore, giving us a nice ride without being uncomfortable. ⸻ ⛵ Sailing & Trim We began on a beam reach, making great time down the coast past Minots Ledge Light. As the breeze freshened, we trimmed in and eventually put a single reef in the main to stay balanced and in control- no weather helm! The boat felt great—stiff, steady, and responsive with the reduced sail. The rest of the passage was mostly close-hauled. We focused on clean tacks and sail trim, using vang tension, out haul, and mainsheet/ traveler adjustments to flatten the sail, twist the sail, and reduce heel when needed. The breeze kept us moving consistently and made for some fun upwind work. ⸻ 📐 Laylines & Approach As we neared Scituate, we discussed laylines and planned our final tacks carefully to avoid overstanding. We managed to nail the final approach—just one tack into the harbor, right on time. ⸻ ⚓ Harbor Entry We kept sails up as we entered the harbor, easing sheets to slow the boat and maintain control. It was a great chance to talk through how to sail into tight quarters with confidence- best to take boats sterns and avoid getting your jeep near mooring chains. Once in the mooring field, we furled the jib on a deep broad reach, turned head to wind, luffed the main, and picked up the mooring cleanly under sail. ⸻ We’re moored now for the night—tired in the best way. Great wind, good learning, and a rewarding sail down the coast.