Montauk to Nantucket : A Holopuni Voyage in New England

Holopuni Ke Ala Maika’i

Model : Mark I

Built : 2000

Original home : California

Crew : Patrick Broemmel (Nantucket, MA), Jeremy Grosvenor (Montauk, NY) & Will Rich (Maui, HI)

Story by Patrick Broemmel

Our trip started with a text conversation between Jeremy Grosvenor and myself back in February 2021. Still in the throes of the Covid shutdown, we were talking about trips and he sent me a picture of a proposed route he had attempted back in 2013 but was unable to finish when his crew had to return home mid voyage.

We agreed that it was a great plan and that we would attempt it the following summer.

We needed a third person so I sent my good friend Will Rich a text with the details and in true fashion the only thing he asked was, “When are we leaving?”

Later on I would realize how critical it was to select the right people for a journey like this. A Holopuni voyage, especially one with open water crossings, is not a trip you just take anyone on. It requires a very specific skill set and attitude for when things get a bit more serious.

I knew Will was a good choice. In 2011 he and Mike Simpson paddled stand up paddle boards and camped from Key West Florida to Portland Maine, the first journey of its kind on SUPs. He mentioned in our initial talk that on their trip, they had taken the coastal route around the islands we were planning to visit on this trip and he’d always wanted to go back and see that section. And aside from years of channel crossing experience in Hawaii where he lived, Will had also been my partner in the Yukon 1000 canoe race back in 2018 where we paddled for 18 hours a day and slept 3 for seven and a half days straight. Difficult would be a gross understatement when describing the race and I knew from that experience that even under the most adverse conditions Will’s approach is to simply put his head down and go to work until the task is complete. No quitting. No complaining.

Neither Will nor myself had ever been on a trip with Jeremy but we knew of his reputation and that was enough. He would never admit it but he's a bit of a mythical figure around the North East ocean sports community. A dozen Kaiwi channel crossings on prone paddleboard, OC1 and OC6, half a dozen Catalina crossings, outrigger, 4 man surf canoe sessions solo in maxing winter surf, prone surfing, SUP surfing, body surfing, mat surfing, foil surfing, wing foiling, windsurfing, sailing, downwind foiling, diving, winter swimming off long Island (0 deg C water in speedos and a swim cap) surf mat, swim camping, the list goes on.

He's like an ocean sports version of Yoda, living in relative obscurity, surfing and paddling away from the crowds at out of the way places out at the end of Long Island, a place no one would expect to find someone with such a skill set.

When the truck breaks down, you can cancel trip or go. WE GO! Boston to Montauk via Uhaul.

Will flew in the afternoon of July 22 where I picked him up in the U-Haul moving van I had rented when my truck began to show signs of not being capable of making the trip. My truck is a 1969 ford that I had spent the better part of a year re-building and it had started making a very suspicious sound from within the motor the morning I was supposed to leave. Should the engine fail, not only would a year's work and resources be lost but our trip would be as well.

There was no way that was happening so the search began for alternative transportation. Being the peak summer season here on Cape Cod every rental car within 100 miles was sold out and U haul was the last resort. I got the weekly special, up to 7 days and 750 miles for $330 bucks. Just enough for the round trip to Long island and back.

Driving into a major international airport and doing laps around the terminals in a Uhaul moving van while your friend waits for his bags is quite an experience. After my third time through I thought it might be a good idea to find some place to park and wait before I was surrounded by federal agents and taken into custody for questioning. After a bit of searching, I followed some buses and found a somewhat empty street where bus drivers would go and sit between shifts but the suspicious looks kept coming as I sat there waiting.

An hour passed and Will informed me that the bags had appeared and after a stop for food we headed south towards our departure point of Montauk, New York. We would stay at Jeremys and leave the following afternoon hoping to ride the outgoing tide east towards our first stop of Block Island.

We had hoped to catch the ferry across Long Island Sound but missed it and wound up driving all the way around, through Queens, arriving late.

Excited and amped on adrenaline we stayed up late into the night discussing logistics and going over gear lists and maps until finally shutting it down around 1 am.

The next morning, we were up at 5 and on the road early headed for the boat ramp in Lake Montauk where we would get set up.

The traffic was already starting to fill in as we pulled over to get coffee and stock up on beans for the trip. A crew of cyclists in their spandex outfits had assembled in front of the coffee shop and shot us suspicious glances as we moved the traffic cones out of the way to park our 50 foot rig in the no parking zone out front.

We arrived at the town ramp just after 8 am and ended up assembling the majority of the boat on the trailer because there was no beach to set up on and the water off the end of the ramp was too deep to work in. It worked out in our favor though as we adjusted the lashing points to ideal working height by tilting the boat within the cradle on the trailer eliminating working off the ground.

Holopuni is floating, gear loaded, we are ready to leave Montauk

By 11 we got her launched and set up on a small patch of sand next to the ramp allowing Jeremy to take the truck and head home where he would park and get a ride back with his wife. Unfortunately, he was headed right into peak summer traffic that would probably make his trip a few hours at best. “You guys want pizza? I'll bring back some pizzas!” he said as he drove off. We went back to work, discussing the ever-increasing need for a public bathroom.

As we packed, I managed to slip on the deck and bring my arm down on the carbon gooseneck where it peeled a nice chunk of skin off of my forearm and I started to bleed all over the boat. We weren't even off the beach and we were already into the first aid kit and off to a good start!

Eventually it became evident that wondering about a restroom was no longer an option and finding one was now the top order of business so I tucked my freshly bandaged arm back into the sleeve of my shirt, slid on my sandals and headed up the road in search of a restroom.

Thankfully there was a marina a short distance down the street that had public facilities where I was able to take care of business and procure a roll of toilet paper for the trip which we had forgotten to bring.

I returned to the ramp and informed Will of my discovery, his only response being “Where?” and before I even had a chance to respond he was halfway up the road moving at a pretty good clip.

By the time Jeremy got back it was after two o’clock, way past our proposed departure time and tide window. We were still looking at a 20 mile crossing in a boat none of us had really paddled before but we were excited to go and Jeremy had made good on his promise of Pizza.

I was given the first shift at the helm and paddling out of Montauk harbor we looked like a drunken snake weaving our way between large power boats and a few commercial fishermen who gave us the look as if to say, “Here we go again. Summer dinks. Might as well call the Coast Guard now.”

We are sailing! First leg to Block Island

Somehow we managed to make it out to open water and we were finally on our way.

The first hour was spent figuring out how the boat handled and we were dealing with almost no wind so Will and Jeremy paddled while I attempted to keep us on a straight line.

As we neared the eastern end of the peninsula, Block Island came into view on the horizon and the SW sea breeze we had hoped for began to fill in.

The boat suddenly came to life. As the sail filled, we dropped the centerboard and the boat that just a few minutes ago was zig zagging across the water locked in and was sailing a straight line at about 10 knots under a light breeze.

Will jumped out on the tramp and Jeremy produced a cheese pizza from somewhere in seat one and we passed it around, celebrating our good fortune. Our line was such that we could choose our landing just about anywhere on the west side of Block but we had been joking all day about going out to dinner at the restaurant in the harbor so when we were close enough to see landmarks, we set course towards a few boats we could see were heading towards the harbor opening.

We sailed through the jetties at the entrance to the harbor under a steady breeze and headed into the inner harbor, weaving our way through the mooring field in search of dinner.

We found the restaurant, and about 400 people waiting around outside on the lawn. Jeremy said something along the lines of “I personally didn't come on this trip to be around crowds, but I'm game for whatever.”

We all agreed, turned the boat around and headed back in the direction we had come.

We made camp for the night on an isolated beach on the west side of the harbor entrance where we had freeze dried chili and smoked mackerel before going to bed.

After a very late start - 2pm - no wind for first hour and an 18 -20 mile crossing, in a boat we had never been on let alone sailed, we were stoked to reach Block island.

DAY 2

We left Block Island early with a group of sailboats doing our best to make way towards Point Judith but the wind had shifted to a more northerly direction making our path almost directly into the wind. Will did a great job tacking back and forth as we made our way up, attempting to pass the northern corner of Block where we would take a slight right and head towards the mainland.

As we rounded the corner we paddled into the famous (but unbeknownst to us) North Rip and a rising tide which made it seem as if the entire ocean was desperately trying to return to long island sound but in the opposite direction that we were going. With little to no wind the only way through was to paddle.

To the east we could see clean water and thought if we could reach there we'd have a much easier time paddling so we really started to put power to the paddles, punching through chop and dropping into troughs that were getting more and more precarious the closer we got to the edge of the shoal. We were maybe doing a half a knot at full power slowly creeping towards the calm side of the rip and within a few meters of reaching it when the standing waves went next level. We would teeter between peaks of standing waves then drop into a trough where the water began to come completely over the gunwales flooding the entire deck. Without the sprayskirts on we would have been in a very bad spot. Even with them in place we took a substantial amount of water into the boat so I stopped paddling and grabbed the pump to try and stay ahead of the situation. We agreed that we needed to get the hell out of there fast so Will got us turned around and we paddled with the current until we were clear of the rip.

We moved on against the tide slowly making our way east for about 2 hours when we decided to stop and let Jeremy take the helm.

Just off Narragansett we heard thunder and noticed a big dark patch of clouds with rain visible to the ground coming from the west beyond Newport. We could see it was heading our way and with it came the wind.

A sailboat which we had noticed was acting a bit strange seemed to be following us and it appeared that when they realized they would not catch us under sail, they went to engine power and came up on us quickly.

A man stood on the rail and shouted over “Are you OK? We saw the ____” then made paddling motions with his hands. We looked over, a bit confused, “Yeah! We're fine! Thanks for checking!”

All the while laughing and wondering why someone would think that a boat going ten knots clearly on an intended path, with guys laughing, would be in distress. There aren't many (well, none actually) sailing canoes in these waters so I guess he did the right thing by checking on us.

We began a more easterly direction to pass south of Aquidneck Island in hopes of reaching Newport’s Third Beach before the storm caught us but as the storm got closer the wind got stronger until we had a solid 15 knots blowing from almost directly astern.

The boat again came to life. As the swell built Will led the charge from seat one where he masterfully synced our strokes with the running bumps and Jeremy steered us with the precision of a surgeon. We were surfing. Like real honest to God, put the 30 foot boat on the face of the wave surfing. It was incredible to experience. Three guys, the boat, the sail, the wind and the swell all in sync.

We covered about 4 miles in 30 minutes and before we knew it we were closer to Little Compton than Newport. Flying past Sakonnet point, the first point of the mainland east of Aquidneck Island we could see our destination a few miles ahead. Sailing through huge balls of Pogie with birds dive bombing them, we reached Chase point and turned left up into the cove where we ran right up on the beach at South Shore Beach Park ,trying to stay as east of the public area as we could in hopes of avoiding a visit from the police in the middle of the night. Will had called ahead to our friend Mimi Whitmarsh and she met us an hour later bringing food and water and a vehicle which we used to drive to the local market to fill our bags with food for the rest of the journey. The day ended with more chili and Mackerel - which we ate like starving dogs - and a double rainbow appeared right over the mast of the boat as the sun began to set behind the fading storm clouds.

Camp for the night on the beach at South Shore Beach Park, Rhode Island

Our double rainbow blessing, South Shore Beach Park, Rhode Island

DAY 3

Reflecting on our experience with the shoals, it was determined that we should probably pay a bit more attention to the tides so we were up at 4 a.m. making coffee and breaking down camp for a 5 o’clock departure.

Our path would take us east about four miles skirting south of Gooseberry Island, crossing into Massachusetts, then a more southerly track across the mouth of Buzzards bay to the Island of Cuttyhunk.

We timed it so that we would be crossing just as the tide had ebbed completely and began its flood east back into the bay.

Dawn departure from Little Compton RI. Jeremy in middle seat , Will in seat one.

As soon as we passed Gooseberry an unexpected east wind came over our port ama and the sail filled once again allowing us to relax and enjoy the sunrise as the miles flew by.

We made the entrance to Cuttyhunk harbor in just under two hours from stepping off the sand in Rhode Island, a distance of just over 12 nautical miles. As we sailed through the jetties and into the harbor every head turned and stared. This continued until we reached a small backwater within the harbor where we tied up and came ashore. We learned of hot coffee and pastries on the town dock, so we headed over via the small dirt street where people came and went on foot and via small gas-powered carts. It appeared as though there were only a few full-sized vehicles on the entire island, the rest were golf carts and slightly larger side by side utility vehicles.

Cuttyhunk is like some place out of a movie. Twelve, Yes 12, year round residents, about 100 homes and a total land mass of about 580 acres the island population swells to a few hundred in the summer months, most if not all,coming by boat. On the dock was an ice vendor, a small take-out cafe and a tackle shop - which was closed - and up the street we were told there was a small store and a t- shirt shop and that was it as far as businesses went. Small groups gathered around a few tables for coffee and conversation, everyone seeming to be as happy as we were to be there. We sat on the dock eating warm egg sandwiches and when finished went back for seconds. Someone pointed out a salty old fisherman and told us that the previous winter he had frozen his beard to a winch on the deck of his boat and simply pulled out a knife and sawed through it to free himself.

The crew and Holopuni at Cuttyhunk harbor

Back at the canoe we hung out our wet clothes on every available surface and toyed with the idea of renaming the boat “Yard Sale” even typing the words into Google translate to see what that would be in the Hawaiian language. “Type in ,To display one's possessions for the purpose of selling them.” I yelled to Will laughing and assuming there was no such thing as a yard sale in ancient Hawaii.

It wasn't long before people began to stop and ask questions.

“We saw you come in this morning! What is that thing?” seemed to be the same words out of every person's mouth, wondering what exactly we had sailed in on.

An hour or so passed as we answered questions about our journey and sought information about the tides, trying to plan the rest of our day and the crossing of the Vineyard Sound where we would reach the Island of Martha’s Vineyard and our stop for the night.

Everyone one seemed to have a different opinion of the tide. Apps were referenced, the Eldridge Tide and Pilot Book - which Jeremy had brought- was sighted many times but with no consistent answer. The book continued to confuse us with a complex system of offset times based on one's location in relation to a regional home spot where tide times were referenced from. Eventually the decision was made that we were better off heading into the unknown than just spending the day answering the same questions on the street so we packed up and paddled our way out of the jetties and into Buzzards Bay.

We decided to take an easterly route along the northern side of the Elizabeth Islands, staying out of Vineyard Sound and the exposure it would subject us to had we misread the tides. Which we did. The Harbormaster had been correct in his reference to the tides running West and again in the opposite direction of our travel. Thankfully the current was light enough that we could still make good progress to the east but the boat traffic dramatically increased the closer we got to Cape Cod and large boats would buzz by us at what seemed like sixty second intervals.

The trip along Nashawena island and across the channel of Quicks Hole took about an hour and while crossing the channel the already complex tidal flows of this area confirmed their reputation when we discovered a northerly flow running between the islands.

Pasque Island went by quickly and as we approached Robinsons Hole, the channel between Pasque and the larger island of Naushon to the east, we could see that the current here was substantially stronger than the previous channel due to a narrower opening and a pinch where the land on both islands seemed to reach out like fingers pointing towards one another.

Under full power again we were barely making headway trying to overcome the rip that separated the waters of Vineyard Sound from those of Buzzards Bay.

Will Skillfully steered us into an eddy on the west side where we made way through a shallow patch of water and could see our progress as the stones on bottom seemed to pass by.

We were finally left with the only option of punching through the last bit of rip and within minutes we were free and into the waters of Vineyard Sound.

Once again the south west sea breeze began to fill in so I jumped out on the tramp to relax and enjoy the crossing as we headed due east towards the northern shore of Martha's Vineyard.

Will steering in Vineyard Sound between Naushon island and Martha’s Vineyard

Progress was slower than expected as the wind came and went and we traveled against the current. Eventually we approached the north west corner of the island known as West Chop and to our left we could see the infamous Middle Ground shoal and rip. We stayed in close, maybe 100 yards off the beach, in an effort to navigate the rocks and currents that were rapidly flowing around the point. We watched dozens of sailboats with spinnakers out make their way out and around the shoals in what we found out was the annual Around the Island Race, and looked on in amazement as large power boats filled with intoxicated thrill seekers flew past us at full throttle some coming within a dozen yards of us.

Making it around the corner and into the channel between West and East Chops, it seemed as if we had entered a major US interstate highway. Only instead of cars we were surrounded by amateur boaters with no sense of courtesy or common sense and sea conditions unlike any we had seen in the days prior. Pure chaos and the most unpleasant time of the trip.

At this point we had been on the water for close to ten hours and were discussing where we should come ashore for the evening. The original idea was to drop south and stop at the far eastern corner of State Beach to camp but that course would take us straight into the wind and would require another two to three hours of beating our way upwind.

Our current line had us directly on course for Cape Pogue, the northern corner of Chappaquiddick Island, and our jump off spot for our final and most challenging passage to the Island of Nantucket the next morning so we decided to stay on course and make that our home for the night.

With the end of a long day within reach Will and Jeremy leaned into the paddles as I steered and we made short work of the 4 mile crossing, hitting the sand forty minutes after making the decision to go there.

The boat was rolled up the beach, “we made it!” texts were sent and again it was freeze dried chili and smoked mackerel for dinner under a setting sun and good conversation.

Sunrise off Cape Pogue, Martha’s Vineyard

DAY 4

Up early again we had coffee and some breakfast before going over the boat one final time, making sure everything was tight and lashed down properly.

This would be our most technical crossing of the trip.

These waters and this channel in particular are littered with transient shoals, shallow sand bars that move and change depth with each passing season, and wicked currents. Many unsuspecting and inexperienced boaters have lost their boats and lives here.

One minute a person could be sitting in calm seas happily fishing away, then the tide turns or they drift a bit without knowing it and the next minute there are standing waves coming over the side rolling the boat.

We consulted the chart, determined our line - there was no land visible from where we stood, just an empty horizon- and pushed off the beach heading at about 100 degrees towards Nantucket harbor.

It wasn't long before we found ourselves navigating the shoals. At times the water was so shallow we could clearly see the sand bottom, crossing from smooth flowing patches of water over the bars, back into steep chop along the edges.

About an hour in we saw our first sign of land. It appeared to be the lone building on the tiny Island of Mukegetwhich lies about 8 miles southeast of Cape Pogue and 9-10 miles west of Nantucket harbor. We were farther north than we had hoped but still on what appeared to be a good course. Not long after spotting Muskeget the island of Tuckernuck came into view which is at the west corner of the main island of Nantucket, and then the water towers on Nantucket itself were spotted.

Now the wind was really picking up. At this point we were about 8 miles northwest of Nantucket and directly over the Tuckernuck shoal which, in combination with the strengthening breeze and ebbing tide was creating some very technical sailing conditions.

Will spotted the Great Point lighthouse which sits at the northern tip of the island and marked a kind of do-or-die heading for us. We needed to stay south of that point in order to make landfall, if not we were looking at two thousand miles of open water to the Azores.

It was clear that we weren't going to make it given the wind direction in relation to where we needed to go so Jeremy suggested we tack and try to make up some ground by heading back towards Muskeget. Turning around we sailed back over the shoal and beat our way across the wind trying to get ourselves a better shot at the harbor. The suggestion was made to reef the sail so we turned into the wind, only to find we were losing all the gains we’d made getting dragged backwards with the current and wind so we got back on course and Jeremy pinched as much as he could out of the wind and tide. It looked like our plan was working. We were now on a direct line to the outer beaches of Coatue on the northern shore of Nantucket, about five miles south of the Great Point light but five miles past the harbor entrance. That was fine by us.

As we made our way in we came upon a massive yacht that had clearly forgotten to make a reservation at the docks and was waiting out the storm on the north side.

We sailed by and could see the people on board sipping their mimosas on the upper deck, thirty feet up, and looking at us like we’d just landed from Mars. We laughed at them and agreed unanimously that even given our current condition, none of us would trade places with any of them.

We sailed straight into the beach rolling the boat up high and out of harm's way celebrating our amazing day with a round of high fives.

It looked as if the rain was about to return so we pulled a tarp up over the leeward ama and made a shelter to hide out in.

Hiding out under tramp after we over shot the harbor on Nantucket in a storm

Jeremy, having stripped down to his shorts, said “I'm going to go for a run and check this place out!” then turned and took off running down the beach toward the light that we guessed was about 6 miles away.

I set up the stove and boiled some water for coffee and Will and I hunkered down out of the rain.

About an hour had gone by and the rain was now coming down in sheets. We laughed at the thought of Jeremy out there in only his shorts. Thirty more minutes had passed when we began to wonder where he was. We agreed he'd probably tried to make it all the way to the light and before long we spotted a tiny spec on the outer beach heading our way.

15 minutes later Jeremy jogged into camp carrying a football and a small orange device.

“Where'd you go man? Did you make it to the light?” Will asked, laughing.

“Almost! I wanted to but I was almost there and I ran into these gnarly seagulls! They were acting really strange, unlike any seagulls I've seen before so I bailed. I thought they were going to attack my head! But hey! I found a shark tracker!”

Sure enough, the orange thing he held, upon closer inspection, was indeed a shark tracker.

A tiny label encased in resin read, Shark tracker, Please contact the New England Aquarium if found.

The waters north of here host one of the largest seasonal communities of Great White sharks on Earth and it was exciting to hold something that had possibly been carried around for years by a Great White while it was being tracked by scientists.

(Later we discovered it had been on a sand shark, another species the lab was monitoring. Bummer.)

Shark tracker from the New England Aquarium

The rain lifted and we took the opportunity to explore the beach, discovering multiple decomposing seal carcasses and dozens of nesting seabirds.

A quick hike across the barrier island revealed that we were not alone. Not three hundred yards from where we had set up our shelter, there were people blowing up kites on the beach, having boated out from town. Even more people were in the water kiteboarding in the clam waters the small spit of land had created out of the wind. Amazing.

We had just come off the water in a near survival situation, set up camp where we entertained the idea of spending yet another night out and were on a deserted beach that could have been in Namibia or Baja California, covered with rotting corpses and wild birds yet we were on one of the most expensive, exclusive islands on the entire planet.

We thought about it. We had just spent the last four days traversing one of the most densely populated areas of the United States during peak summer season and we had been basically alone and camped on wild beaches every night of the trip.

Proving that adventure doesn't require international travel and a bus full of gear. Most times it can be found by simply stepping out your front door and looking at the world with a different perspective.

About four o’clock we weighed our options and decided that hot food and beds sounded better than another night in the sand so we pushed the boat back into the water and paddled just off the beach, against the current (again), but in the lee of the wind towards town and covered the four miles in a little over an hour. There's a break in the east jetty for boat passage and thankfully it was wide enough for our fifteen feet of beam to pass through, saving us the 2 mile trip around the jetties.

A short blast across the harbor had us stepping off onto solid ground for the last time of the trip.

Tracy was there to greet us, and we drove home where I grabbed my car and headed back to pick up the guys for much needed warm showers, hot dinner and comfortable beds.

Rough course we took. Overall just over 130 NM covered in 4 days