Rent a Sailboat for a Tropical Adventure in the British Virgin Islands – Part 2

Part 2

I’m Kristi Rhodes and excited to continue my interview with Tom Thompson, Captain of Lucky Dog Sailing.  He answered my many questions about what it takes to enjoy a sailing vacation in the British Virgin Islands (BVI).

Part 1 of my interview with Tom follows this post. Backwards. Sorry.

This trip is on my bucket list, and I also really love just hearing about their adventures, where they go and how they manage it. Renting a sailboat to cruise around the (BVI) seemed like an unattainable vacation until they told me their story.  The only caveat is that Tom is a captain with many years experience sailing, both in Chicago and the Caribbean.  For less experienced or novice sailors, hiring a captain with the boat is a great way to enjoy the same adventure.

First, a little background, Tom is a U.S. Coast Guard certified captain, sailing out of Belmont Harbor, Chicago, IL.  He has fifteen years sailing experience on Lake Michigan and has made 5 charter sailing trips to the BVI and St. Martin/St. Barts. His wife, Kristi is the helms(wo)man and a wonderful photographer.


Pardon me for the tropical interruption.  This seemed like a good place for a video of Bob Marley.  Be sure to stop by iTunes, Amazon MP3 or Google Play to purchase this song, Satisfy your Soul by Bob Marley and The Wailers


Snorkel adventure at Monkey Point. Photos provided by Kristi Moen. Click on photo to enlarge.

Do you snorkel a lot? What is favorite activity on trip? 

Yes, we snorkel almost every day, and it seems that each spot is better than the last.  We’ve seen great coral formations, sea fans, sea turtles, stingrays, octopus, dolphins, squid, crabs and an abundance of fish.  There is one spot named Monkey Point, just off Great Guana, that is a “must see”.  In addition to the normal sea life, there are giant schools of 4” long silver fish that completely surround you, but stay about a foot away from you, as you swim through the school you can’t see anything else.  It’s amazing.

What’s the funniest thing that’s happened to you?

The list is long, but generally it has something to do getting the crew of 8 into and out of the Zodiac style Dinghy.  Add in a couple cocktails and a moving boat and somebody is going swimming…


Oh, and a particular taxi ride comes to mind….  Our first year, our flights arrived late, so we made reservations to stay at a hotel that said it was near the airport.  8 of us were on the same flight, so all loaded into one mini-van type cab – a guy in our group negotiated a rate of $40 for all of us – what a deal!  As you can imagine, with all of our luggage, we needed to sit on laps and were packed in like sardines.  It took a while, but we finally got the doors closed and left the airport.  About a block away, the cab took a right, went about 100 feet, and stopped.  We thought he might be getting directions, or that we were too overloaded to go any further.  Nope.  We were at the hotel.  It took us longer to unpack the van than to get there, and we certainly could have walked.  Lesson learned?  Google your hotel location before you travel!  The cabbie probably laughed as much as we did later that night (and I’m sure we weren’t the first or last to do this).

  What’s the scariest thing that’s happened to you?

I’d have to say, the scariest moment(s) are usually weather related.  There are frequent late afternoon squalls – luckily you can see them coming, but you have to reef the sails quickly to prepare.   One trip to St Martin, we had to bring the boat in a day early due to a tropical storm approaching.  It was still sunny, but the wind and waves were building quickly.  The channel into the harbor is very narrow and winding with a lot of reef, and we had to navigate it in 10-12 foot seas.  A harbor boat came out to lead each boat in, but trying to navigate a Cat through that was a workout for sure, and the lead boat kept disappearing beyond the large waves.  It was a welcome moment when we tied up to the dock that afternoon!

Rough Seas-not the rough seas they encountered, just generic rough seas:) –added for dramatic effect.

What percentage of trip is done doing what?  Like, sailing from spot to spot 50%, hanging out on deserted island 40%, cleaning and preparing meals 10%.

It’s rare the winds are going to be in the direction and strength you need each leg of the trip, so, we sail some and motor some each day.  But in general – Traveling from place to place – 30%, Stops for lunch and snorkeling – 40%, Time on boat and on shore at overnight accommodations – 30%.  Other “chores” really happen concurrently, but we share the load.

Do you dock and sleep?  Or does someone sail overnight or at night?

The charter companies prohibit night sailing, so we’re usually on the mooring ball by 4pm, just in time for Happy Hour!

How about fishing?  Do you eat mostly fish?

You can fish off the boat as long as you buy and license and you’re not in a Marine Park.  The onshore restaurants have the best fish you’ve ever tasted.  It’s all caught locally, never frozen, and when it’s gone, it’s gone, so plan to eat dinner early – and, in high season – radio ahead for a group reservation.

What’s your favorite place to dock and visit?

Baths on Virgin Gorda. Photographs provided by Kristi Moen. Click on photo to enlarge.

In the BVI we actually have two favorites…The Baths on Virgin Gorda and the island of Jost Van Dyke.  The Baths is a spot right on the beach with very large granite boulders that look like they were stacked by a Giant from outer space.  There are marked paths through the boulders that lead you to ponds and little secluded beaches.  Some call the Bathes the 8th Wonder of the World.  Note – get there EARLY in the morning, as it gets incredibly busy and hard to get through by late morning.  Jost Van Dyke is a small island on the north side of Tortola with several famous bars (Foxy’s & Soggy Dollar), and Sidney’s Peace & Love restaurant.  Don’t want to miss Jost!

Tintamarre Island Beach looking back at St. Martin. Mike soaking:) Photo provided by Kristi Moen. Click on photo to enlarge.

In the St. Martin area (Il Forche), we spent a night on a deserted island where we were the only sailboat in a harbor, and woke to do a morning hike to the top of the highest point on the island at sunrise.  Looking out over a deserted island surrounded by ocean as far as you can see really makes you feel small and also how much “work” really matters.  It was a morning I’ll never forget.

Have you met any really great locals? Tell me about them.

Kristi, Foxy (from Foxys Bar on Jost Van Dyke) and Tom. Photograph courtesy of Kristi Moen©

We met Foxy (from Foxy’s on Jost Van Dyke) – he was casually playing his guitar in the morning at his beach bar.  He would ask folks where they were from, and then make up a song with that city in it.  He also told really colorful jokes that will make even sailors blush!

We also had the opportunity to meet Sidney (from Sidney’s Peace & Love on Jost) and a lot of his extended family.  He served us lobsters that were as tall as we were (when you held antennae, which he had you do for a great photo moment before he cooked them).  It was a quiet day, and he introduced us to his family and visited with our group for most of the afternoon.  Also gave the Captain a free lobster meal!  Sadly, Sidney passed away 2 years ago, but we will always remember this day with him and his family.

From left to right Sidney (from Sidney’s Peace & Love on Jost), lobster, Tom, lobster, Kristi & Mike. Photo couresty of Kristi Moen©. Click on photo to enlarge.

How hard is it to walk off the boat after a week in the tropics and leave on the plane for home?

It’s a hectic morning – coming into the dock, packing, disembarking, grabbing a cab, getting to airport, transfers in Miami, etc…

One funny thing to mention is that on the boat, you’re always barefoot and deck is generally wet, so your feet get a little water-logged.  It feels sooo good to put on a pair of dry socks after the trip.  You wouldn’t think it’s such a big deal, but it really is.

Is this type of trip horribly expensive? 

Well, let’s just say it’s worth every penny!  But, yes, it’s more than your average vacation.  There are some ways around this – going in off/shoulder season, looking for special discount weeks with the charter companies, going on a monohull, etc.  The catamarans are almost double the price of the monohulls, so if you’re going alone or only have 2-3 couples, a monohull will save a lot of money, but you will spend a LOT more time sailing from spot to spot vs. enjoying the stops (cats are much faster).  With a group of 8 on a cat, we plan on about $200 per person per day, which includes the boat, meals/drinks on the boat, moorings, etc. (Airfare, transfers, shore meals/drinks, etc. not included).

What if someone wants more information?

For charter questions, contact Sunsail or The Moorings either online or call them and request a brochure.  The brochures are full of options and pictures of the different islands that they have mooring base locations.  I really would recommend the BVI, especially for your first charter trip due to the favorable sailing conditions and abundance of mooring balls for overnight stays.

For trip advice, leave your name in the comments section and I’ll forward your request to Tom, you know, just to avoid spam and all.  He loves to hear where people are going and always glad to share his experiences.

Tom and Kristi–Thanks again! Photograph courtesy of Kristi Moen©

Thanks so much to Tom and Kristi!!!!!

We’d love to hear your favorite tropical adventures, let us know in the comment section.

Thank you for stopping by!


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2 thoughts on “Rent a Sailboat for a Tropical Adventure in the British Virgin Islands – Part 2

  1. Kristi,
    What a great interview with Tom and Kristi! An amazing adventure! I always look forward to reading your blog. I look forward to you next post!

    • Hi Erin:

      Thanks so much! I agree about Tom and Kristi, I love to hear about their adventures. They have already said they’re up for more interviews, so over the next few months they’ll be sprinkled around.

      Thanks again for stopping by.

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