Planning the First Ocean Passage - SailNet Community
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Planning the First Ocean Passage

The author and his boat have become a team ready to face the challenge of sailing in the open ocean.
Block Island lies 17 nautical miles off Montauk Point, Long Island, a distance my catboat Kirsten has covered in sheltered waters in less than four hours. The difference in sailing to Block Island is that those 17 nautical miles are open ocean. I'd be riding the heaving swells, out of sight of land, for the first time.

I'm a worrier by nature, and that small stretch of blue water has had me worrying since last winter when I conceived the scheme of making Block Island my summer cruising destination, the big trip of the season. Choosing this destination would stretch my skills—hopefully within the range of my abilities—and help build my confidence.

There are about two yards worth of books on my shelves about cruising and voyaging, but they don't do much to help me prepare for this short sail in local waters. The general principles and guidelines are all there, but on a grand, globe-girdling scale. Somehow I have to collapse them down to Lilliputian-size for the voyage I have in mind.

Cruise planning seems to involve just three factors, but they are complicated factors: logistics, safety, and seaworthiness.

Logistics involves charting out the trip, identifying places to anchor or dock, arranging for crew, and timing it all to fit within a vacation and coincide as favorably as possible with weather and tide conditions.

Safety involves provisioning with adequate food, water, fuel, first aid materials, charts, safety gear, communications gear, navigational gear, and the knowledge of how to use them and how to respond in emergencies.

Seaworthiness is the big one—can the boat and the skipper handle it?

Dealing with the first two factors is fairly simple and straightforward, and it involves the pleasures of poring over charts and guidebooks, making lists and shopping. Seaworthiness is a combination of philosophical and engineering challenges. How will a 20-foot catboat, with its shallow draft and wide beam, handle large seas? What is the best reefing system? What should I do if I'm midway to Block Island and get caught in a thick fog or a storm?

"On recent trips I've been replacing other people's adventures with my own."
Some of these questions simply can't be answered in advance. Research and more hours under sail in different conditions and locations can only go so far.

I've spent months and many dollars preparing for the Block Island cruise in one way or another. It will be a trip with three legs out and three legs back, each leg less than 20 nautical miles, easily done in about half a day with Kirsten's top speed of five knots. The first leg would be a familiar one, from the marina in Flanders out to Shelter Island, where I could dock for the night at Greenport or Sag Harbor, or drop the hook in an anchorage. The next legs would take me into strange waters, to Montauk, and from there on to New Harbor (aka Great Salt Pond) on Block Island.

If the prevailing southwest winds are in working order, I will have an easy run from Montauk to Block Island. The drawback is that, in a following wind, it could be insufferably hot. I hope instead to have the morning offshore breezes from the northwest to keep things cool on a broad reach, and to arrive before the mid-day dead calm that can last several hours before the southwesterly sets in. At least, this is the habit of the wind that I know from the bays, but it may have an entirely different set of habits on the ocean.

Coming back, the southwesterly may head me, forcing lengthy tacks or even a different route, a higher, slightly north-of-west route toward Greenport or Shelter Island. Either way, the return leg could well be over twice the distance of the outbound leg.

The main question is whether Kirsten and I can do it. I know that other catboats have sailed to Block Island by the longer and more challenging route from Connecticut, a route subject to strong currents, heavy commercial traffic, and even the occasional submarine. But knowing that it has been done doesn't guarantee that we can do it.

With less than a year at the helm of Kirsten, the largest boat I have ever sailed on my own, I haven't had much time to gain experience. I've been an armchair sailor longer than I've been a real skipper.

Passing the Montauk Light turns a coastal cruiser into an offshore voyager.
Having read about rough conditions, my imagination quickly takes flight when the wind is above 15 knots. At that wind speed, white caps abound and waves can look intimidating. Amplify those waves with boat wakes, contrary tides, and shoals, and I begin to think of Cape Horn.

On recent trips, however, I've begun replacing other people's adventures with my own. On one brisk day, Kirsten seemed to come to life and leap eagerly into the waves when the wind whistled through the rigging and the bow spray reached to the back of the cockpit. We even surfed down some large following waves. And on another trip, when a mega-motor yacht set up steep wakes that flung the crew about the cockpit and rolled Kirsten's lee rail and the end of the boom into the water, she rolled back, shook herself off, and continued plunging along. And in one long hot day that took me around Shelter Island and briefly into the swells of Gardiners Bay, I managed over 30 nautical miles single-handed. I've also slept on board and know how difficult it can be to get a good night's rest in a ship's berth.

It all adds up to sharper instincts and a better understanding of what's involved. I have learned to trust that Kirsten knows how to behave like a good boat, and consequently shed some landlubberly anxieties. Observing her strength and resiliency firsthand increased my confidence.

We are now a team, Kirsten and I, and we are almost ready to take on that open stretch of water.

Block Island is a regular destination for many cruisers, with up to 2,000 boats crowding into New Harbor during the summer holidays. It was a port of call on the annual summer cruise for Anthony Bailey, who wrote the following about Block Island's Crescent Beach in The Coast of Summer: " We've been coming to to this beach for thirty years to walk, swim, and doze. It is one of those places that marks the passing of time—here we are again, another summer—but also makes time pause."

However, even after 30 years of sailing to Block Island, the journey could still stir up some anxiety in Bailey as he prepared to set out from Newport. "I know on rising just what sort of day it's going to be. A strong sou'wester—a deep reef in the main—damp foul-weather gear—everything below needing to be stored properly … As I brush my teeth, I feel the same suspense in the stomach one has before standing up in a public meeting to make a complicated point."

There are other ways to get to Block Island aside from sailing. Ferries depart for Block Island from several points in Rhode Island, Connecticut, and New York. There's even a small airstrip. Over the decades, Bailey remarked with regret, Block Island had become crowded. Was it still possible to relax anywhere, doze on a beach, and make time pause?

The island has its own website ( and a webcam aimed out at Great Salt Pond. During the winter months, I checked this site from time to time, and found the harbor empty except for fog. It looked peaceful and inviting. Now that the season has arrived, so have the boats, and the webcam now shows full docks and anchorages.

The goal for the end of the voyage—here's to fair winds, calm seas, new friends, and Mudslides at The Oar.
Busy or serene, is not really the issue now. First, I have to get there.

I've read whatever I could find in narratives and guidebooks about how to sail there. I've walked the needle points of a compass across the chart several times along different routes, and checked the tide tables. During the winter and spring, I mulled over changes in the rigging, setting up reefing lines and tinkering until they worked right. I equipped Kirsten with handheld and base station VHF radios, a GPS, and a safety harness to attach myself to the boat. A self-steering rig of some sort is also on the list. These are items that will rarely see any use in the sheltered bays where I usually sail, but they seem essential for venturing offshore.

Reefing, GPS, and anchoring skills need to be practiced, particularly if I do the cruise single-handed. While I will be sailing during the week when transient slips are usually available, it's best to be prepared, just in case. And at $2 a foot and more for a slip, anchoring would be preferable, especially at Shelter Island and Montauk, where I don't plan on going ashore anyway. At Block Island, where I do plan to go ashore, I'll pay for a slip. If one isn't available and I have to anchor or take a mooring, water taxis can take me to and from shore, so it won't be necessary to tow a dinghy. I haven't towed a dinghy before, and this cruise already has a steep enough learning curve.

At times, all the preparations seem out of proportion for such a short cruise. But after I posted a message on an Internet bulletin board to solicit local knowledge for the trip, I realized I hadn't even scratched the surface of what I needed to know. In addition to getting helpful tips on where to anchor, dock, and shower in New Harbor, respondents also provided the names and nicknames of bartenders and waitresses, and the scoop on where to get the best Mudslides.

One cruiser, planning to visit Block Island during the same week, scheduled a time and date to call me on the radio.

With those responses, I began to realize all the preparation is not so much for getting me to Block Island, but for taking me from daysailing to the wider world of cruising. Here's to fair winds, calm seas, new friends, and Mudslides at The Oar.

Bruce Caldwell is offline  
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