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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.

Captain Paul Sullivan
Gulf of Maine, Boston, Suffolk County, MA, USAJun 21, 2025

Distance

11.2nm

Avg. speed

4.8kts

Duration

2h 20m

Night Sailing Recap: Marblehead to Gallops Island – June 20–21, 2025

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.

Captain Paul Sullivan
Marblehead, Essex County, MA, USAJun 21, 2025

Distance

22nm

Avg. speed

5kts

Duration

4h 23m

Scituate to Marblehead – June 20, 2025

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.

Captain Paul Sullivan
Scituate Harbor, Scituate, Plymouth County, MA, USAJun 20, 2025

Distance

23nm

Avg. speed

5.5kts

Duration

4h 9m

Boston —> Scituate <> AS 106 Course

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.

Captain Paul Sullivan
Boston, Suffolk County, MA, USAJun 18, 2025

Distance

0.4nm

Avg. speed

1.9kts

Duration

11m

90-45-20 TECHNIQUE FOR DOCKING FOR MONOHULL SAILBOATS ⛵️

DOCKING DAY IN BOSTON! 🛥️ 
Today was all about docking practice with students at Charlestown Marina in Boston, MA 🇺🇸🌊 We focused on the 90-45-20 technique for monohull sailboats — learning how to use momentum, prop walk, and line handling like pros 🚤💨🪢 Here’s how to: 🧭 90-45-20 DOCKING FOR MONOHULL SAILBOATS 🔹 STEP 1: 90° – PERPENDICULAR SETUP * Line up with the dock at a 90° angle ➕ * Bow should aim roughly where your stern will end up 🎯 * Approach slowly in idle forward 🐢 * Be ready to shift into neutral to control speed ⚙️ ✅ PRO TIP: Shift to neutral when you can confidently say,
“I have enough momentum to get the rest of the way there.”
Slow ➡️ Controlled ➡️ Steerable. 🌬️ Compensate for wind or current drift as needed. 🔹 STEP 2: 45° – MID-APPROACH & REVERSE SETUP * Turn toward the dock to approach at a 45° angle 📐 * Aim for the midpoint or forward section of your slip 🎯 * Shift into idle reverse to slow forward motion 🔄 * If your boat has prop walk, it will begin swinging your stern in this phase 🚶‍♂️ * Stay on this 45° angle until you're about half a boat length or closer from the dock 📏 🔹 STEP 3: 20° – FINAL GLIDE & ALIGNMENT * Turn the helm to bring the bow in to about a 20° angle 🔄🧭 * Bow should now aim toward the start of your slip or the stern of the boat ahead 🚢 * Gradually increase reverse like a crescendo to stop the boat 🎵🛑 * This helps slow your forward motion while enhancing stern control via prop walk 🌀 ✅ CREW TIP: Crew should step onto the dock — not jump! 🧍➡️🛳️ 
Brief them ahead of time on which cleats to lead lines to 🧵🪢 🚤 Most cruising monohulls: 
Stern line first ➡️ then bow ➡️ then spring line ✅ CAPTAIN TIP: Stop the boat with your engine, not your dock lines ❌🪢 🚫 Beware of well-meaning “dockside helpers” —
If they grab or tie a line without knowing your plan, it can ruin a perfect landing 🎭👎
Especially dangerous: Tying the bow line forward of center while you're still moving ⚠️

Forrest Hardy
Boston Harbor, Boston, Suffolk County, MA, USAJun 12, 2025

Distance

7.1nm

Avg. speed

5.9kts

Duration

1h 13m

Wednesday Night Racing #1

The first Wednesday race night of the season! We had a full crew of 7 + @CaptainPaul and Captain @forrest. A great mix of folks including boat owners, former students, new faces and a couple people who have never even sailed before! It was a beautiful night with 75 degree weather and West winds at 15 knots gusting to 20 at times. A great day to shake the winter racing rust off!

Captain Paul Sullivan
Boston, Suffolk County, MA, USAJun 8, 2025

Distance

9.1nm

Avg. speed

4.2kts

Duration

2h 10m

Day 3 of AS 101 Basic Keelboat
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