Culebra & the Wild West of the Spanish Virgins

Sunday morning. ‘God’s day’ as I like to joke with Mia. Means I can’t do any work today! That recent Mr. Money Mustache blog I referenced on Facebook the other day has inspired me to do more of this kind of writing – pursuing creativity, as he put it, rather than thinking of it as work. I’m on my second cup of coffee and beginning that pursuit.

We’ve been anchored in Ensenada Honda now, the humongous bay that frames the eponymous town on Culebra. We sailed in, as we’re wont to do. It’s a huge harbor, but there is one small bit at the entrance where you have to sneak between the edges of two reefs. It’s marked with large bell-buoys so doesn’t require any tricky navigation. But the Trades have been south of east lately, so the entrance is dead downwind. We were careful not to accidentally jibe the big mainsail as we snuck through the channel markers and into the Bay.

I had a thought yesterday morning as I was sitting outside and drinking my coffee, about why more sailors don’t actually sail? I won’t repeat myself here, but check out this link to the FB post I wrote. It must have touched a nerve, because LOTS of people threw in their two cents in the comments.

Mia and I had a late lunch onboard that first day here so decided to head ashore to the Dinghy Dock for some fried plantains and a drink, rather than eat a proper meal. By the way, thanks to our friend Pedro for all the local recommendations – the ‘tostones’ at the Dinghy Dock are indeed tasty! I’m in the process of working on an essay podcast about the finances behind the Isbjorn Sailing business we’re creating and the lifestyle we’re living. On the surface it probably looks like we’re living large down here in the islands, enjoying a vacation-style existence that most people only dream about. On one hand that’s true – we get to experience all of these magical places as a simple part of daily life. But on the other hand, the reality of our lifestyle is probably far from what people expect.

We haven’t been in a marina since we left Nanny Cay at the end of the 1500, haven’t even been to a dock! That’s part preference and necessity – we love anchoring out and enjoying nature, so we never feel the need to go to a marina. But it requires that we lug our jerry cans full of water every time we ever go ashore in the dinghy.

We don’t eat out. When Lisa was here visiting, we had one evening of tapas in Old San Juan with her as a treat. Mia and I ate veggie burgers for lunch one day in the Miramar neighborhood of San Juan, and had our tostones at the Dinghy Dock the other night, and that’s it. Mostly it’s been homemade burritos, veggie stir fry’s and other meals we cook for ourselves about the boat.

We don’t drink out. I like to have a glass or two of wine in the evenings while I read my book, but I take it from the ship’s stores, and we rarely spend more than $10 per bottle.

All of this is our way to enjoy this lifestyle but still be able to afford it. Instead of going nuts for a week or two on a sailing holiday down here, we stretch that money to last us a whole season. We have to – this lifestyle is our careers too, so there’s no choice.

Anyhow. Thanks to our new friends Rob & Joyce whom we met at the Dinghy Dock the other night, we were able to stretch the funds even further. As I said, Mia and I had intended on getting some tostones and a few drinks at the bar in lieu of dinner, then going for a walkabout in town. I discovered that my new favorite island drink is a sugar-free mojito – clear rum, muddled mint, lime and seltzer. Quite refreshing, and without the sugar, pretty darn healthy, relative to other boozy drinks.

When we arrived to the restaurant – the place is literally called ‘The Dinghy Dock’, and you tie up along the row of tables where folks are eating and drinking at the water’s edge – a nice guy called Rob (we later learned this) took the painter and helped us ashore. Mia and I retreated to a high-top table by the bar. The place was crowded and it was the last table available. It’s not quite high-season yet for tourists, so the bar was lousy with locals, and boy were there some characters. Top-heavy, middle-aged women in tank-tops, so tan and wrinkled they appeared twice their age, with fraying, matted hair bleached in the sun and saltwater,  tattooed to the hilt. Men who didn’t look much different. It was like the pirate-version of that classic bar scene in Star Wars with all the different characters about and loud music pumping on the speakers. Most of these people were sailors, as we watched them leave in their dinghies. They’re truly living the life down here, fitting into that stereotype of the wandering cruiser who came here and never left.

Before we had a chance to order, Rob came over to our table, introduced himself, and invited us to come and sit with him and his wife, Joyce. ‘We’re sailors too,’ he offered. ‘Sailed from Maine all the way to New Zealand! Come join us.’ So we did.

Rob & Joyce had flown in to Culebra to celebrate her 50th birthday and had rented a small cottage on the top of a nearby hill. They’d never been to the island before either and we’re unsure of how they’d find their way back to their place in the dark. In the early 2000’s, Rob & Joyce quit their jobs and sailed a Hinckley Bermuda 40 yawl from Maine to New Zealand over the course of almost ten years.

‘We used to be motorboaters,’ they said. ‘I always dreamed of having a Bermuda 40, since I was a kid,’ added Rob. ‘My dad thought I was nuts. When we got the boat, he came out for a daysail with us and took the helm. We had the genoa out and we’re heeled over pretty good. He said ‘Gosh! Now I know why you goddam sailors always have the right-of-way…I can’t see shit!’ So we taught ourselves how to sail and off we went.’

They’d originally intended to circumnavigate, but family intervened when Rob’s parents got older, so they only made it as far as New Zealand.

‘There was a big patrol plane with ORION painted on the wings that kept flying over us as we approached Cape Rainga on the northern tip of the North Island. They called us on VHF and asked our intention. ‘You know, there are 400 boats in Opua, where you’re headed, and half of them are American,’ the ORION crew told us. It scared the crap out of us! Those kinds of crowds are what we were trying to escape!’

Instead, they stayed at sea for another seven days, sailing down the west coast of the North Island and finally making landfall in Nelson, in the Marlboro Sounds region of the South Island (the same area, in fact, where Mia and I met and where she had her first sailing experience aboard the tiny 28-foot Southern Endurance that we’d chartered with friends way back in 2007).

Rob & Joyce bought a car, like we had done, and toured all over the South Island, even taking the ferry out to Stewart Island, the last bit of land before Antarctica. After spending 8 months in New Zealand, they flew home and had the boat shipped back via Dockwise. They still have it.


After our drinks and tostones with Rob & Joyce – who were nice enough to pay our tab – Mia and I explored ‘town.’ There’s not much to Culebra, we soon discovered, but what was there was right up our alley. I had a hunch that these so-called ‘Spanish Virgin Islands’ would be like a combination of the laid-back culture of the Bahamas with the geography of the mountainous Virgin Islands. I wasn’t far off. The dusty back streets and dive bars had a distinctly Wild West feel. We popped into ‘The Spot,’ a tiny hole-in-the-wall bar that Pedro had recommended for another sugar-free mojito (the healthiness of which must steadily decline after you’ve had three or four!). A few 20-something backpacker-types walked in, but otherwise it was mostly locals talking Spanish. We walked down to the ferry dock and onto a rocky, deserted beach where the water was crystal clear and you could see deep into it thanks to the streetlights.

Yesterday morning we planned a mission to hike to Bahia Flemenco, ‘Flamingo Beach,’ reportedly one of the nicest in the world. We’d tried to sail into the bay last week but got scared off from the ground swell. Upon reaching the place on foot, I wished we’d had sailed – it was much bigger than I thought and would have been quite easy to get into and out of, and big enough to anchor in the middle and avoid the ground swell altogether. Next time.

I couldn’t find any information online regarding hiking on Culebra, and we don’t have a guidebook. Instead, I consulted Google Earth and did a low fly-by over the harbor and the hills backing it. If we followed the main road to the east of the airport, eventually it would run out and turn into what looked like a dirt path that snaked into the hills to the north and eventually down into the eastern-most end of Flamingo Beach.

We packed the backpack with water, trail mix and sunscreen and set off from the town pier where we tied up the dinghy. Several times along the main road that wraps around the harbor we were offered lifts from locals in their golf carts and Jeeps. We declined, excited to stretch our legs.

Past the roundabout by the airport, we continued north and east (going left at this fork in the road takes you to Flamingo Beach via the main road, the route we’d return on). We continued around the other side of the airport and on towards where I thought the road would run out. After a steady climb and past fewer and fewer houses, it did.

The way turned into a concrete road of sorts – no pavement in the middle but 18-inch strips of concrete so one could presumably drive a Jeep along the path. The place used to be overrun with military, so it was probably built for them. Up into the hills we went, the way very steep. We’d stop often in the shade of a mango tree and sip some water. It was the middle of the day and hot.

Eventually even the concrete path ran out near the top of the island and a dirt path jutted out from the left. We followed this into a small ravine and up another hill, coming to a locked gate that barred the way towards the top of another peak where a large solar-panel array was set up and appeared to still be under construction. We snuck around the locked gate, careful not to get caught in the barbed wire, and continued on our way. It was Saturday, and all the heavy machinery was quiet and nobody was around.

Eventually the concrete road started again, and over a few ridges we could catch a glimpse of Flamingo Beach far below to the west. At a fork in the road, we explored to the right. After a hundred meters or so, we came to a large concrete clearing at the very top of the island, presumably an old helicopter landing pad from the island’s military days. It had views down to another deserted beach to the east, one we tacked past a few days before. It looks incredible from the water, but even more so from above. Idyllic.

Eventually the concrete path wound past a few newly built houses overlooking Flamingo Beach and we made our way down to the sand. We had definitely treaded on private property, as the way to the beach was barred by more barbed wire, which we again carefully negotiated. I don’t believe, had anyone seen us, that we would have gotten in trouble simply out for a walk, but nonetheless I suppose it was risky hopping that first gate. Eh.

The beach is stunning. It was Saturday afternoon, and yet there were hardly any people there. No hotels back the sand, just palm trees and nature. The water is crystal clear, transitioning from that gorgeous turquoise blue over the shallow sand into the darker blue of the deeper water and eventually the greenish brown of the surrounding reef. The sand was clean and powdery.

Mia and I walked the length of the beach and went swimming at the far end, discovering a beautiful campground along the western edge of the beach where folks had setup tents and towels and were living at the water’s edge. There were even outdoor freshwater showers for the campers that we took advantage of after our swim. A large group of pelicans were fishing together at the far western end of the beach, dive-bombing the shallow reef in twos, three and fours, feasting on the population of small fishes. Two abandoned tanks from the island’s military days rusted in the sand as people climbed on them to take photos.

On the way back down the beach, we passed four 20-soemthing guys in short shorts, two of them with big hipster beards, all of them fit and tanned. Even from 100 yards away Mia and I both immediately identified them as Swedes – there’s just something in the way Swedish people carry themselves that makes them stand out instantly to other Swedes. Plus the short shorts are usually a dead giveaway. Our suspicion was confirmed as they neared when we noticed on of the guys wearing soccer shorts emblazoned with an ‘ICA’ logo, the largest grocery story chain in Sweden. We eventually went and said hi to them. They were out backpacking together for a few months, having already been to Miami, Key West, Puerto Rico and now Culebra, enjoying being young and free from real-life responsibilities. We left them playing soccer on the beach and walked back to town on the main road.