Vagabond Sailor

Amphibious Trail Running

While Solo Sailing The Mediterranean Sea in Your 70’s

Adagio at anchor off east shore of Ithaca, Greece

The cove on Ithaca island in the Greek Ionian Sea looked idyllic and, equally as important, checked out as a protected and secure anchorage. I verified this both visually as I slowly motored into it on Adagio and with the sailboat’s navigation graphic display at the helm.

There was no sign of civilization apart from what looked to be an abandoned villa on the south arm of the cove, No other boats were in the anchorage. Which is to say not much has changed since the peripatetic Odysseus saw Ithaca upon finally reaching ‘home’ in Homer’s epic poem “The Odyssey” over 2000 years ago. The rolling hills were covered with dense pine and lenga forests that dropped down to the crystalline water’s edge which was fronted by a pebbly beach.

There was one thing I had yet to verify. Opening Google Earth on my IPad I located the cove and then searched for trails, or in this case, dirt roads, that led into the cove. Having confirmed one that seemed to track roughly along the water’s edge and went on well north and south of the anchorage, I dropped the anchor, secured it and settled in for the evening. As the water turned a cobalt blue, twilight and then darkness slowly accentuated my solitude in this isolated cove.

Awaking at 8:00am I brewed my daily cup of coffee and prepared for the day’s run.

Amphibious trail running for me starts with the notion that you’re going ashore to run either via Adagio’s inflatable dinghy of 70lbs (ugh!) or, what’s easier and delightfully more refreshing, by swimming. The water temps in the Ionian Sea this time of year were comfortably in the upper 70’s. So I filled my waterproof bag with the essentials — shoes, socks, shorts, t-shirt and a liter of fresh water and towel. The Mediterranean is notoriously salty.

Running a volcano, Aeolian Islands, Italy. Adagio anchored below.

Dropping Adagio’s transom allowed me to slip into the water and swim with short fins while towing the floating waterproof bag with a rope around my neck to the beach 75 yards away. Once ashore, I rinsed off, put on my running attire and arbitrarily decided to jog south on the dirt road. I came across olive groves, a herd of goats, an abandoned fishing boat and the ruins of a stone farm house during my 6 mile out and back jog over gently rolling hills. Putting shoes and running gear back into the bag and with fins on, I swam back to Adagio and her warm fresh water shower in the cockpit.

During breakfast, I heard the low rumble of a powerboat offshore getting noticeably louder. Looking at it through my binoculars it was a grey boat heading toward Adagio at a very high speed. The only grey powerboats that travel that fast in the Med are the coast guard — presumably they can afford the cost of fuel at that speed. Sure enough, it was the Greek Guardia Coasteria. As they roared into the anchorage, they did a sharp U turn some 75 feet around Adagio, gave me a quick ‘look over’ and then, without slowing down or as much as a wave or acknowledgement, high tailed it back out to sea. I guess they reassured themselves I had no illegal migrants aboard. Hah, I fooled them again! The boat’s violent wake and the raucous noise of his engines had rudely disturbed my tranquil morning. Paradise, or the illusion thereof, I reminded myself and not for the first time, is inevitably at best a temporal phenomena.

A goat herd in Greece. An integral part of the landscape.

I checked the weather forecast, especially for wind speed and direction, and sailed south seeking further anchorages but with no definitive plan in mind. A fixed itinerary is not only unrealistic given the weather but precludes being open to interesting places that show up. Vagabond sailing, I call it. But in some comfort.

The Beginning: Getting Ashore To Run Trails

I began amphibious trail running some twenty five years ago on California’s Channel Islands which lie 18 to 30 miles offshore my hometown of Ventura, California. They are entirely protected by both the NPS and Nature Conservancy. Which is to say no dwellings save for a few campsites run by NPS and the caretakers modest residences. Nor are there, from a sailors point of view, any moorings or docks to secure to. You anchor, sometimes precipitously, 50 to 150 feet offshore. That plus the often rambunctious seas and winds of the Santa Barbara Channel keep ‘fair weather’ sailors close to their mainland harbors. High surf often required that you swim ashore. Dinghy’s or even kayaks can frequently get upended.

What this means is that even in the summer you can find a cove and anchorage by yourself. Running the islands over 100 miles trails is a throwback to when California was its native self. And gone, as in removed, are the herds of cattle, sheep, elk and even the feral wild pigs introduced by civilization in the past 150 years.

Why Do It?

The freedom of sailing one’s own boat allows a trail runner to literally get off the beaten track along any coast that has suitable anchorages.

This for me, in addition to southern California’s offshore islands, has included a couple winters in Mexico’s amazing Sea of Cortez, the Hawaiian Islands (windy with few secure anchorages), and summers in the Pacific Northwest to include Alaska. Amphibious trail running in the year round frigid waters of the northwest necessitates using my dingy or kayak to get ashore. Hypothermia is not an option. Nor is encountering an aggressive brown bear. My deterrent of choice? A small air horn which I fortunately did not have to test.

This sport, dare I call it one, is seemingly a solitary pursuit or really a lifestyle. I believe it calls for a personal love of sailing and trail running combined with a curiosity and thirst for discovery and a passion for fitness. And if you are committed to make it a lifestyle you must be able to deal with the vagaries of weather, a constantly changing, and often challenging, coastline and frequently sparsely inhabited interiors not even acknowledged in Trip Advisor. Thank God!

For me it has been a chosen lifestyle that has involved living on Adagio for a total of 15 months over four consecutive years during May/June and early July and then back for September/October. July and especially August are too crowded and hot mid summer.

My ride. Adagio berthed at Bonifacio, Corsica. A 41 foot, 2013 Hanse 415

The rewards in the Mediterranean? The ‘discovery’ of unnamed, perhaps historically insignificant, but nevertheless fascinating ruins. For example, in Greece and Italy running to the top of any good sized mountain or hill will almost guarantee that you find a small, abandoned stone church of indeterminable age. For me this beats the crowded cathedrals and citadels of the big cities. Been there and done that.

There are also the magnificent vistas that one can fantasize have only been seldom, if ever, appreciated by tourists. Also running past small villages and farmhouses brings you face to face with rural inhabitants that are invariably courteous, friendly and helpful. Alas, few speak English but they communicate volumes through their smiles and gestures. They’ll not just try to verbally give you directions but literally take you by the arm and walk you several hundred yards to a cafe or other point of interest.

Oh, did I mention getting lost? As a reconnaissance platoon leader in the army during the Vietnam war I had plenty of opportunities to get lost. And then subsequently find myself and my unit one way or another. Sooner, hopefully, than later. Of course today it’s virtually impossibly to get lost with GPS on your wrist. Yet as some pundit said, ‘you only discover things when you are lost’. To include, of course, things about yourself. Being ‘lost’ I find brings forth in me an awareness that fully activates my senses. You’re outside your comfort zone. Yet I’m not above leaving small piles of stones, or self made cairns, at forks in a trail or road to make returning to the anchorage less uncertain.

Lost and Alone: An Opportunity

The joy of solitude. I’m a true believer of the stoic philosophy that one’s circumstances in life have little to do with one’s happiness or sense of well being. Solitude in an alien environment, I believe, provokes an introspection and self learning that can seldom be achieved in one’s familial setting. For me this brings out a deep appreciation of the long, tumultuous and many layered history of the Mediterranean and one’s own relative insignificance. I am both awed and humbled by the experience.

Me with Clint at the recently reconstructed circular “Sad Hill Cemetery” — in background — in Spain. The site of the final gunfight in the 1966 classic “The Good, Bad and the Ugly”. A 5 mile out and back run from Santiago de Los Silos.

Lest one think that I am a total misanthrope or sailing hermit, for me one the most profound advantages of solo sailing and running versus sailing and running with friends is that I find myself much more inclined to engage with strangers. This can include other boaters in a marina or anchorage who have been to places you have not been to and vice versa. Or folks sitting next to you in a restaurant let alone locals you meet casually in the market. I recall having a lengthy conversation with an Austrian in a restaurant in Trieste, Italy. Saying goodbye he said, “so you travel around and meet people like myself and we become friends and then you never see them again?”. “Yes”, I replied, “something like that”. He looked at me querulously and then shook his head in a manner that suggested total incomprehension.

A ‘stranger’ encountered on a run up and down the rock of Gibraltar. The famous rock apes of Gibraltar.

My mantra: be curious and adapt. In the most desolate of places there is always something to experience if you leave yourself open to possibility. And yes I’ll even concede that Trip Advisor or Fodor’s travel guides can help.

Possibility Amidst Uncertainty

Entering Croatia I was forewarned could be a bureaucratic nightmare. As I walked into the immigration office at the harbor of Cavtat I was greeted by a pleasant middle aged woman who would handle my paperwork. In making small talk with her she said she had an unusual sport. You guessed it, trail running. This not only significantly facilitated the entry process but led to an enjoyable trail run along a Big Sur like coast with an informed guide.

You’re constantly dealing with an uncertain environment. Did I mention the vicissitudes of weather? The placid Mediterranean is a myth. Then there are separate country entry procedures for you and the boat, marina ‘med mooring’ solo (an art I’m still trying to master), or boat issues — yes, of course something is always breaking. It can be frustrating and time consuming. Like taking a whole day to find a laundromat, learn it’s nuances, and then do your laundry. Or even trying to find a decent meal in a strange village. But, as I often have to remind myself, this all part of the adventure.

There is also the uncertainty of a trail run on unmarked trails that may lead to the town dump, a pack of barking dogs or even a cemetery. But cemeteries in the med can be fascinating and, yes, even useful.

On one very early am run in hot and humid Turkey on my return I had emptied my water bottle with a mile or two to go. There was a very modest, small cemetery along the trail. At the head of one of the graves was a gallon plastic jug with about a quart of, hopefully, potable water still in it. The flowers the jug had served to water were clearly dead, as of course was the deceased. After a moments hesitation, I determined that I could use the water more than either of them could. It was a but very brief moral dilemma for me.

RIP Ramadan and ‘Tesekkur ederim’ or thank you, in Turkish to your thoughtful descendants. The propitious water jug in Turkey.

Uncertainty keeps you present in the moment. This can, of course, be both liberating and unnerving. Unnerving in the moment and liberating once you’ve experienced it. Much like having sailed through a gale at sea.

In Albania having rented a car for a week I chose to explore the interior. The coastline being flat and alluvial offered few attractive anchorages or running routes. One of my destinations was the so-called ‘Albanian Alps’. A bit of a stretch compared to the ‘real’ Alps but nonetheless scenic and their foothills were runnable. I parked the car next to a trail head whose only attraction was that it led toward some snow capped peaks in the far distance. A compelling vista for a run.

Albanian trail run. I know that he’s down there waiting for me!

After a couple miles I had seen no habitations or people and the trail was increasingly bordered by dense, reedlike vegitation. Then I spotted a man. He was an older fellow wielding a long machete with which he was ‘harvesting’ the reeds for God knows what purpose. Near him was a rusty motorcycle with a basket on it half full of this prolific yet somehow valuable weed. He looked at me grimly with a stern almost hostile countenance. I waved but his steely expression didn’t change.

Over the next mile the weather quickly deteriorated to a light drizzle as the skies darkened ominously.

I turned to run back hoping to beat the storm. I was then overcome by a pernicious dread. What if this fellow was waiting to ambush me on the way back? No one would ever know or hear my cries for help. I quickened my pace as I neared his location and picked up a baseball sized rock. Running past him he barely looked up as I strove to avoid eye contact with my would be assailant. Whew, I dodged that bullet, or rather, machete.

Running the ruins, Corinth, Greece

Creative Adaptation — With a Purpose

In the world of solo sailing and trail running I find the need to create my own rituals, however simplistic. As in, I will run every other day. On alternate days I will spend one hour on my portable rowing machine. Or lifting weights or attending yoga or Pilates classes, as below, in a gym or hotel. Daily meditation. A daily journal entry. Some time each day reading the stoic philosophers. Audio books and podcasts on a Bluetooth speaker in the cockpit are the perfect companion for a solo sailor on a long day. I try to pick those that relate to the history of the geography I’m in. Homer’s “Odyssey”‘, of course in Greece. And Dumas’, “The Count of Montecristo” in France and Corsica. Yes, there really is an very small Italian island called Montecristo but you’re not allowed to go ashore?? Which, of course, tempts me to go ashore.

On a sailboat it’s easy to drift mentally and physically into lethargy. I need some direction and purpose, yet with flexibility, that is adapted to my circumstances. You need to create your own ‘balance’, if there is such a thing, as you go.

Marinas, with their towns and cities and fellow sailors dockside can offer a welcome respite from the solitude of anchoring. And along some coast lines in the med given the weather, you have no alternative. There are no protected anchorages. There’s usually some interesting history if only the ever present harbor citadel, good restaurants, and plug in electricity dockside with fresh water in these towns. They’re also an opportunity to do some cross training. I’ll Google local gyms and check out their website and ‘likes’. Some are comparable to US gyms but some, I’ve experienced, are reminiscent of US gyms of the 50’s or 60’s kind of like “Rocky’s gym” complete with the memorable odor of stale sweat. In which case I’ll call the swankiest hotel in town and inquire about their day rate. Usually for 10-15 euros you’ll have the run of their facility to include gym, luxury spa, sauna, and should I chose, the indulgence of a massage.

Perhaps the biggest trade off is loneliness. Despite my coping mechanisms noted above there are times where you may go days without being to have a conversation with someone in English. I tell myself this builds self reliance and fortitude but it’s always good to see a boat with a north European flag on it — they will speak English. Note: I have only encountered one other solo sailor in 15 months during four seasons in the Med. He was a 70 year old weather beaten Australian I met in a Tunisian marina in 2016 with 40 foot sailboat that had a busted transmission and tattered mainsail. Like most Aussies, John was typically phlegmatic about his predicament as he drank his beer. “Yeah, I don’t know how long I’ll be here but it’s all OK. No worries, eh, mate?”, he said to me. I admired his stoic indifference.

Being Crazy May Be A Consequence or a Prerequisite

Other sailors tell me they have run into one or two solo sailors. But they consistently describe the individual as in “yes, he was a crazy Brit”, or “crazy Swede”. Having met only a half dozen crewed American boats during my time in the Med, I have no doubt I’ve earned the moniker of “Yes, he was that utterly crazy American sailor— who also ran”.

Jim, beached albeit temporarily.

Jim Eisenhart is an avid trail runner, sailor and skier. He has completed over 35 marathons and ultras. His last marathon, the Catalina Island Marathon, he completed at age 70 in 2018. When not living the life of a vagabond sailer and trail runner he lives in Ventura, California.

Be yourself; Everyone else is already taken.

— Oscar Wilde.

This is the first post on my new blog. I’m just getting this new blog going, so stay tuned for more. Subscribe below to get notified when I post new updates.

2 thoughts on “Vagabond Sailor

  1. Jim
    Read your article with great interest. It is excellent. In addition to your many talents you are also a accomplished writer. Your sense of adventure is an inspiration to all those young guys that want to follow in your foot steps. Paul forwarded me the article.


    1. Per,

      Great to hear from you! Where are you and what the hell are you up to? Thanks for the comments. Hey, Trail Runner magazine wants to publish it — but I have to edit it down to 800 words, ugh.

      Best Regards,



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