Exploring the Virgin Islands by Catamaran

This is a trip I’ve been wanting to go on for over twenty years. Several of my friends and people I’ve met skiing have all raved about cruising around the virgin islands on a catamaran. There were some barriers to entry which delayed this epic trip for me. But like anything else, a barrier to entry is often needed to protect the sanctity of anything worthwhile.

Surfing used to be like that, until those clowns at Wave Storm started selling foam surfboards for $100. Now every douchebag with a Costco card thinks they are Laird Hamilton and the lineup is chock full of pool floaties. In years prior you actually needed some skills to get out there and more importantly the ability to pony up $500 for a proper fiberglass board.

The barrier to entry for exploring the virgin islands mostly centers around your crew. Putting together a crew for this trip is more difficult than it appears. You have to go through all your friends and family and ask yourself, “Do I really want to spend ten days on a boat with this person?”. Not everyone makes that cut! I also discovered that many friends are not real comfortable on boats, which shrinks your talent pool further. It’s also difficult finding people who are not parenting and can get a couple weeks off work. Not to mention it’s going to cost about $4000 per person.

Lastly it took me a few years of honing my captain skills to a point where I felt confident in driving a million dollar yacht into a new waters, ensuring everyone had a good time and was safe. I was never interested in the hired skipper option. What’s the fun in that? Then you are on the Pirates of Caribbean ride at Disney. Zero adventure, might as well be one of those lame all inclusive resorts being spoon fed coconut shrimp every hour.

What Are The Virgin Islands

The Virgin Islands are an archipelago in the Caribbean Sea consisting of over 90 islands, most of which are uninhabited. The islands are divided into two main territories: the United States Virgin Islands (USVI) and the British Virgin Islands (BVI).

The Virgin Islands were ground zero for piracy in the early 1700s as many European countries were exploring the area. The pirates were mostly ripping off the Spanish and British as they moved goods and established maritime trade routes. Many pirates operated in the region, including famous figures like Captain Kidd, Blackbeard, Calico Jack Rackham and Sir Francis Drake. Yep, Sir Francis Drake was a pirate, but he was British so he is called a privateer. Oh those wankers sure are clever rewriting history.

The scenery in the Virgin Islands showcases the entire color spectrum, including lush greenery, white sandy beaches, crystal-clear turquoise waters, and stunning underwater coral reefs. The islands are all fairly close together so you are never in a place where you cannot see a neighboring island. You really get a feel for how the pirates used to pick off ships with all the hidden coves. This is why the Virgin Islands are at the top of the list when it comes to sailing destinations.

Exploring Virgin Islands By Catamaran

We finally got our crew together and reserved a 43′ Power Catamaran out of Road Town, Tortola in the British Virgin Islands. We used a company called Moorings. Moorings has sail and power catamarans in many destinations around the world including the Caribbean and Mediterranean seas. Some day soon I hope to sail these waters, but for our virgin trip to the Virgin Islands, a power cat is perfect. Ours was aptly named Motley Crew. Here she is getting prepped for our departure!

How To Get To The Virgin Islands

Our journey began the second week of June, which is the beginning of the offseason in the Caribbean and not coincidentally, also the beginning of hurricane season. Most hurricanes come much later in September/October so we felt reasonably safe. That said, the first Cat-4 hurricane ever recorded whipped through the Caribbean one week after we returned!

Getting to British Virgin Islands is not easy coming from California, or cheap. We took a red eye flight to Miami, then a surprising 3 hour flight to St. Thomas (USVI). I thought our destination was much closer to Miami, but the Virgin Islands are actually much closer to Venezuela than Florida. Once arriving in St. Thomas (USVI) we decided to power through on our limited redeye sleep until we got to Tortola where we could stay the night and be fresh in the morning close to our boat. After departing the airport in Charlotte Amalie, we hopped on the fast ferry to Road Town and cracked a couple of Caribs, the local beer. I highly recommend the fast ferry as it doesn’t make any stops and gets you to the heart of Road Town in Tortola where you go through customs, because now you are in the UK mate!

Moorings does a pretty good job of preparing you for your Virgin Islands excursion before you arrive. We all had to watch videos, name a captain, name a first mate and sign our life away. One of the coolest things they do is handle your provisions (fancy boat word for grocery shopping). There is no reason to do this yourself, the grocery store is also owned by Moorings and there is no markup for the products or service fee. It sure is nice to board your vessel, open the refrigerator, crack a beer and see all your favorite food items.

What they could do better is getting you off the dock at a reasonable time. You will be lucky to get off the dock by 2pm, meanwhile you are charged a full day. You hear me Moorings?! We didn’t shove off until 430 because we had to circle back after hearing what we later termed our ‘port side rumble’. Every time we hit 10 knots, the boat started vibrating significantly so we decided it was best to come back and have their wonderful lead engineer Linden take a look. He was glad we circled back and also credited us a half day for future reservations. Not bad. Linden told us not to worry about the rumble. It also helped that we didn’t plan on going more than 8-10 knots during the entire trip. We were all on island time now and in now hurry … and it sure felt good.

Virgin Islands Itinerary

I had mapped out a course before we departed and now we are on our way. We will head south to Bight Bay at Norman Island where we will find a mooring and spend our first night. There is a floating bar/restaurant there which will be welcomed by the crew after 2 days of travel. We will then go counter clockwise around Tortola stopping at 5 of the surrounding islands for the night. The moorings cost $40/night and are typically owned by local businesses. A man comes out on a skiff each morning to collect the dues. We did schedule one night in a slip at Scrubb Island Resort so we could fill our water tanks, food provisions and enjoy the comforts of a swimming pool, long shower and normal toilets. They have an awesome grocery store/deli on site with just about anything you would need including booze.

The night before we departed from Road Town in The Motley Crew we met two really cool couples on the dock from Key West. They had chartered a course very similar to ours so we exchanged phone numbers. We would see them every other day at a different island and eventually started mooring next to them when possible. It was super fun to partner up with another boat and meet for drinks on land and on the 0ur boats. Shout out to Kevin and Janna and the crew from the Conch Republic!

Planning Your Trip To The Virgin Islands

While it seems overwhelming when you are planning your charter and learning all the islands, after a few days of reading you get most of it down. I took some notes so I could refer to them each time we went to a new island. There is a pretty well traveled route that most boats take to hit the popular spots and activities. Stressing about getting a mooring to spend the night was always on my mind as captain.

It sure helped that we went in offseason, as there were plenty of moorings available in every bay we pulled into. I would go around the same time again. It was such a load off to not worry about mooring reservations every morning at 7am. It allowed us to make decisions on the fly about where and what we wanted to do next. Having flexibility on a trip is necessary in my opinion. You have to make room for calling an audible!

We called our audible as we cruised through Spanish Town on Virgin Gorda island. We pulled into harbor and it looked really hot and kind of dumpy. We had a quick team meeting and the crew decided to skip it and keep cruising to Leverick Bay on Virgin Gorda. I wanted to spend two nights in Leverick Bay any way. Oddly it reminded me of Lake Tahoe. Funny though, when we went to Saba Rock restaurant in Leverick Bay and asked if there was any live music around, they said yes! Then told us we had to go to Spanish Town. I knew there was a reason I planned to stop there, but didn’t have it in my captain notes.

Summary

The journey is always the best part of a trip, not the destination. Since this trip is all journey with multiple destinations, I will spare you any further details and let you discover how to navigate the Caribbean on your own. Here are a few photos from our journey.