Spanish Virgin Islands: Sailing to Culebrita

The lighthouse in Culebrita, Puerto Rico.
View from the lighthouse of Culebrita harbor.

Paradise Found: Sailing The Spanish Virgin Islands

By Jean Miller Spoljaric

Culebrita harbor, Puerto Rico. photos by Jean M. Spoljaric.
Culebrita harbor, Puerto Rico. photos by Jean M. Spoljaric.

My tan lines may have faded, but my memories of circumnavigating the Spanish Virgin Islands on a 38’ sailboat will last forever.

It’s pretty much the norm that most people plan land vacations, but until you’ve spent a week on a sailboat with complete strangers, you haven’t begun to live. Many people have never heard of the SVI. The SVI chain is most enchanting because of its remote charm, pristine beaches, and crystal clear blue waters.

I swam with the turtles on Culebrita’s Playa de las Tortugas and snorkeled the reefs amongst the most colorful fish on Cayo Icacos and Bahia Tomarindo.

Off the boat, I hiked up to an old, dilapidated lighthouse that offered 360-degree views of the crystal clear waters below. And, amid the old and the beautiful, Mother Nature tested our seafaring skills with a squall in the Canal de Cayo Norte on the way to Culebrita.

A Night on the Town

My adventure started in Old San Juan. I had arrived one day early to meet the boat, so I found myself with one night to explore the old city. I met my soon to be Captain and a few crew members and we all decided to grab some Monfongo (a fried plantain-based dish from Puerto Rico) and then spend the evening shooting pool and drinking Medalla, the finest local liquid gold beer.

I questioned the beer cans small stature as the 10 ounce can felt dwarfed in my oversized hand.

However, it soon became a more sought after staple than a can of spam. Much fun was had at the local dive bar called El Batey. The graffiti-covered cement walls and open air ceiling gave me a slight feeling of hanging in a bombed out war zone.

The jukebox screamed tunes that I haven’t heard in years and the braless bartender was, perhaps, a little too attentive. Many a Medalla were guzzled and the entire night nurtured the developing bonds of friendship amongst my new mates.

Rainbows and Hangovers

Waking up in paradise, I laid in bed listening to the rain falling outside my window. The skies had opened, but just as quickly as it started, it had ended. As I grabbed a coffee, I looked out and saw a big double rainbow. Enthused, I made my way down to Puerto Del Rey Marina in Fajardo to meet the other crew members and climb aboard one of the two boats we had leased for the week. My boat was the ‘Eugenie’ and all 38 feet of her presented a beautiful site in the harbor. Across the way was the 49 foot “Big Blue,” the sister boat in our convoy.

Family Boat
Family Boat

The Family Boat

After the crew of the Eugenie met, we seemed to bond quickly and comfortably. We soon renamed our boat the ‘Family Boat’ and assumed our new roles. Our Captain Max’s dad was along for the trip and he became the ‘Poppy’ on board.

It seemed only fitting that I, as the oldest female on board, was the Mamacita. Max’s sister Ana, his cousin Alexis, and ‘sister’ crew members Susan and Rachel, rounded out ‘our family’. All of the ‘20 and 30 somethings’ were across the way on Big Blue. What we all had in common was a love of sailing.

In Captains We Trust

The licensed captains organized the trip through their company, the Sailing Collective. They had contacted the leasing agent, Sail Caribe, and lined up everything from provisions for the week to scheduling taxies to and from the marina.

They knew Sail Caribe’s fleet of recent vintage Hunter monohulls and Lagoon catamarans were located at a convenient harbor. From the Puerto del Rey Marina, they knew island hopping would be easy. The nearest islands, tiny Isla Palominos, and Isla Palominitos, are both visible from the base.

Part of me wants to keep this special place a secret, but the other part wants to tell everyone about the joy of beginning a sailing week on the right foot. Once at sea, the steady trade winds, crystal clear waters, pristine beaches, local rum, and native fish all fed the senses. This is the reality of bareboat sailing in the SVI and how good planning created a paradise of circumnavigation of the small, pristine, sparsely inhabited islands off the eastern tip of Puerto Rico.

Seven Islands in Seven Days

One of my favorite islands amongst the chain was picturesque Culebra. Its quaint little island town was filled with small shops, restaurants, and bars all painted in bright blue, pink, and purple hues. For the freshest local seafood, great service, a rum punch that will knock your flip flops off, and a fun mix of locals and tourists alike, stop by Mamacita’s Restaurant.

If you’re looking for a more down and dirty local ‘hole in the wall’ spot, I recommend The Dinghy Dock. I loved this place! I visited the Dinghy Dock twice, once in the morning I had a killer breakfast burrito and later that night I had a Margarita with a guy who hadn’t shaved in 50 years. Good company made for lots of laughs and lasting memories.

Death of our Dinghy

At some point after leaving Culebra and before mooring in Culebrita, our dinghy incurred a broken fuel line. It’s not a good thing to be dinghy-less! A search of the nearby marine boat yards failed to find the part that we needed. Luckily, we were sailing with Big Blue and they were happy to share their dinghy with us for our trips back and forth to land.

As it turned out, most times, unless we were dressed for dinner, most of us swam to shore instead of relying on the little rubber boat. For Poppy, necessity became the mother of invention. You see, Poppy is a neurologist and he performed a surgical procedure on the ailing dinghy. Armed with a ballpoint pen and a pocket knife, Poppy made a stint for the fuel line and resuscitated the dinghy!

Free Moorings

Much of the uninhabited islands, as well as parts of Culebra and Vieques, are wildlife or nature preserves. Thus, except for the small towns, much of the beachfront in the SVI is undeveloped land reachable only by boat and/or four-wheel-drive vehicles. In the interest of protecting the sea floor, there is an abundance of free mooring balls installed in virtually every harbor.

BBQ on the boat in the Spanish Virgin Islands
BBQ on the boat in the Spanish Virgin Islands

Lighthouses, Paella, and a Full Moon Culebrita, better known as ‘baby Culebra’, is a very special island. As we moored our boat, several turtles swam by as if to greet us and welcome us to their home. It was a magically uninhabited area with white sand, blue water, and wildlife. Blessed with a full moon and a starry night, Captain Max prepared a terrific paella party.

It was perfect! Great food, funny stories, and big smiles all around made for a great night. The next morning, we decided to go on a land adventure. We swam ashore and hiked up to an old abandoned lighthouse on top of the island. As I climbed the rickety, rusted out spiral staircase with a few missing steps, I was wondering aloud, “When was the last time I got a tetanus shot?”

The old metal stairs led the way to the working solar panel that provides the building’s beacon of light for all boaters. Although the coast guard removed the rotted lighthouse’s roof in 1984, the marble floor entry still reflects the beauty that once was. It was a great adventure!

Back to Civilization

On day five we were back to relative civilization as we anchored (only the second time we didn’t get to moor) off the town of Esperanza on the south side of Vieques. After one unsuccessful attempt to anchor, we finally secured our boats and headed for lunch and rum punch on Esperanza’s colorful Malecon waterfront. The pretty promenade is bordered with funky bars, shops, and restaurants. Duffy’s Bar had great service, a large assortment of island cocktails, and a gorgeous view of the sunset. It was now time for dinner.

Climbing the lighthouse at Culebrita.
Climbing the lighthouse at Culebrita.

Operation “Calf Rescue” Poppy had a friend, David, who had moved to Vieques a few years back, and he assisted us with reservations for seventeen at the Trade Winds Restaurant. It was just up the street from Duffy’s, so I accompanied David on the short walk to make the reservation.

My sea legs were in full form as I wobbled my way up the uneven street. Along the way, we came upon an old beaten up Toyota pickup truck with two men and two calves. One calf was in the back of the truck and the other had made its way off the truck. The music from a nearby bar was drowning out their pleas for help.

The calf in the street was still tethered by a skinny frayed piece of rope and he didn’t want anything to do with getting back in the truck. David and I knew what needed to be done, so we set our rum punches down and picked up the calf. With a ‘heave and a ho’, we loaded the little guy back onto the truck. The driver gave us a double beep and a wave and off they went.

Bombing Zone No More Up until 2003, the U.S. Navy had been using the island of Vieques, the largest of the SVI’s, as a bombing range and munitions test site. And, until the last couple of years, those few cognoscenti who wanted to sail the SVI had to persuade a charter company in neighboring St. Thomas that it was safe to take one of their boats to Vieques.

Now, with a charter company based in Fajardo on the east end of Puerto Rico, these amazing cruising waters are slowly opening up to charter sailors. Puerto Ricans with their own boats has made Vieques their weekend playground for years.

Just Do It!

So, if you’re an accomplished sailor, or just starting out, and you’re looking to take a sailing adventure trip, I highly recommend the team at the Sailing Collective. If you’re single, it’s a great way to meet others. If you’re married and have a family, I suggest chartering the full boat. They have several trips planned in the near future.

If you love the adventure of camping on land, then a sailing vacation may be for you. Living on a boat means being lulled to sleep by the gentle waves, waking up to the sunrise, and exploring new areas, some isolated and some civilized. It’s living in paradise, every day!

Other Helpful Information:

About the Sailing Collective:

Fixing the dinghy in the Spanish Virgin Islands.
Fixing the dinghy in the Spanish Virgin Islands.

What had started out as a dream for a few sailing buddies has become a reality and has blossomed into what is now officially known as the Sailing Collective. The idea behind the Sailing Collective was to organize a team of young, ambitious sailors to form a high-quality unit and to offer affordable sailing vacation destinations in locations around the world.

Dayyan Armstrong thought about destination sailing vacations in early 2011 and, over the course of the year, formed a partnership with Ross Beane, Max Kufner, and Taylor Collins, to create the Sailing Collective.

Their collaborative efforts and business structure support a team of captains and diverse personalities that allow the customer to receive specialized services. By November of 2011, they presented their first sailing vacation. Since then, they have organized a number of group sailing vacations and personal sailing trips for customers. They have group sailing vacations organized in the Caribbean throughout the winter season and have expanded to trips to the Mediterranean beginning this summer.

A sailing trip in Dubrovnik, Croatia, and a second sailing vacation takes place in Naples, Italy, July 7th – 14th. The Sailing Collective can accommodate any size group as well as provide excellent service to those vacationers traveling solo. The team at the Sailing Collective really knows how to make all of your sailing dreams come true.

NOTE* Croatia is totally sold out, but there are openings for the Italy, Brazil, and Pacific Northwest trips. If you’re interested, book your sailing vacation now!

For more info or to book your sailing adventure, check out their web page at

Captain Dayyan Armstrong can be contacted at: or call him at: 603.969.3186
Captain Max Kufner can be contacted at or call him at: 845 706 2277.

Food and Drink

If you’re in Puerto Rico, saunter into the best old ‘dive bar’ in all of Old San Juan. They don’t have a website, but you can find them at this address. Be sure to bring a sharpie to leave your mark on the walls.

El Batey Bar in Old San Juan
101 Cll Del Cristo, San Juan, 00901, Puerto Rico
+1 787-725-1787

Sunset from the Eugenie
Sunset from the Eugenie

For some of the best Monfongo in San Juan, check out The Punto De Vista Restaurant. Again, no website, but they can be found at:

1 Cll Juan Antonio Coretejas
Plaza Covadonga
San Juan, PR 00901
(787) 725-4860

When on the Island of Culebrita, check out the following places:
Mamacitas for fresh local fish, friendly atmosphere and killer drinks.
Mamacita’s website

Or, if you feel like hanging with the locals, head on over to the Dinghy Dock. As it turns out, the Dinghy Dock doesn’t have a web address either but can be found at:
Cll Escudero
Culebra, PR 00775
(787) 742-0052

On Vieques, check out the following hot spots:
The Trade Winds Restaurant and Guest House. Make sure to have the rum punch here!

Duffy’s Bar

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