Captain Justin Smith of S/Y KAI shared with us an adventurous charter option in the Spanish and U.S. Virgin Islands for anyone interested in seeing the not-so-explored parts of these idyllic islands.

Captain Justin Smith and his partner and 1st mate, Sarah Ford.

For the last few years, I have been exploring the less traveled areas of the Spanish and U.S. Virgin Islands. The secluded anchorages, gorgeous white sandy beaches with no footprints, and awesome culture are such a contrast to the more touristic islands, like St. Thomas and the British Virgin Islands.

I really like Culebra. I had the chance to meet with dive groups on the island and spend time some time exploring the island’s pristine reefs full of life and color.

Culebra’s Flamenco beach is considered by many as one of the best beaches in the Spanish Virgin Islands. The pristine sand is interspersed with palm trees and old tanks, used in military exercises by the U.S. Navy since the early 1900s. The town is small, full of color and very lush. A small canal travels from one side of the island to the other.  The canal is lined with fishing shacks, an old lifting bridge, and cute little bars tucked off in a lush mix of palm trees and mangroves.

There are great hikes all over the island and it is possible to walk nearly everywhere if you’re up for it.

S/Y KAI underway.


Culebrita is an amazing little island just next to Culebra. It offers more white sand beaches, and naturally made bubbly pools. There is also a nice hike up to an old brick lighthouse, which started to operate in 1886. The hike isn’t very hard and takes about 30 minutes. The view from the top is breathtaking.

One of the old tanks on Flamenco beach in Culebra.

Puerto Rico

Puerto Rico has endless adventures. I spent one month sailing the west, south, and east coast of Puerto Rico, 20 miles at a time. I am open to charters on the west, and south side of Puerto Rico, but I would prefer to focus on the east coast.

I find Fajardo a unique, and sweet little spot. Marina Puerto Del Ray is one of the largest marinas in the Caribbean. There are rental cars right on the property. It’s a 30 minute drive to San Juan airport, which for     guests is an extremely cheap exit to the main hub.

There are easy provisions for the yachts and marine stores for hardware supplies. 15 minutes down the road is El Hippie, a naturally formed swimming pool. Not far away there are petroglyphs carved by the original inhabitants of the island: the Taínos.

There are plenty of trails to explore, although a guide is recommended. Rock climbing, sky diving, amazing beaches, and just about anything you can think of doing is close by.

Anchored behind the reef in Culebra.

St. Croix

St. Croix, is one of my all-time favorite spots. Of the four years of sailing the Caribbean, I think St. Croix is my favorite island in the U.S. Virgin Islands. When you sail into St. Croix, you go from 16,000 feet of water directly into 20 feet of water, and then quickly turn behind a reef. The anchorage is normally crystal clear, with a sandy bottom. You can hear the surf breaking just a few hundred feet in front of the boat as you fall asleep. Usually, it is very calm behind the reef.

The town is sleepy, full of great restaurants, bars, and gift shops. A day can easily be spent touring the fort, visiting beer drinking pigs, snorkeling the reef, getting lost in the rain forest, or driving around checking out the views. There is the option of visiting the huge satellite that is part of the Very Long Baseline Array, a group of satellites that read radio frequencies throughout the U.S. This satellite is the eastern most satellite in this series.

The view from the lighthouse on Culebrita.

Who would enjoy a trip like this?

This is a trip that requires an adventurous group. Groups that like peace and quiet, more than 4 hours of sailing, and want to be active. The trips between the islands are longer than in the more frequented island of the U.S. and British Virgin Islands. It’s also exposed waters, meaning it can get rough if the wind is right. This is what we would call “real sailing” or “open water sailing.”  Don’t worry, Kai is a large vessel being 70 feet and a very able yacht for all the conditions. Guests must want real sailing to be part of their holiday experience.

Sailing on S/Y KAI.



For the best experience, I would advise that guests come onboard Kai upwind of Puerto Rico. St. Thomas is a good port to fly in to and begin the trip.

Day 1.)

Fly into St Thomas. Drive to Yacht Haven Grande Marina to Water Island and explore honeymoon beach.

Day 2.)

Water Island to Christiansted, St. Croix. This can be 4 hours or more of sailing and fishing. Anchor off the town in St Croix for the evening.

Day 3.)

Explore St. Croix.

Day 4.)

Sail from St. Croix to Culebra. This is more than 4 hours of sailing and fishing. Arrive late afternoon. Anchoring behind a beautiful reef just inside the bay.

Day 5.)

Explore Culebra.

Day 6.)

Explore Culebrita.

Day 7.)

Sailing to Fajardo, Puerto Rico.

Day 8.)

Explore the sites near Fajardo. I suggest a late flight, or stay for a night in San Juan, the capital of Puerto Rico.

Flamenco beach in Culebra.



For more information on S/Y KAI, contact Christopher Patrick at +1 321-777-1707 or email [email protected]

The eastern most satellite in the U.S.

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