My husband and I recently sailed the British Virgin Islands with another couple, who are experienced sailors and have been taking the same trip for the past 20 years.  It was a “one for the memory books” vacation, with stunning shades of ocean blue I had never seen before, plenty of activities to choose from, and an abundance of islands with few tourists.  You can choose to rent a boat and sail on your own or hire a crew to do the work for you.  Either way, it is an adventure that is perfect for just the adults or the whole family.

sailing the BVI

Vacationing with friends in the BVI. Photo credit Sherry Wernicke, Luxe Traveling Mom.

When our friends asked if we wanted to go sailing with them this year, we didn’t even hesitate. We have heard over the many years of our friendship what an amazing time they have sailing in the British Virgin Islands or BVI. Normally, they are with their twins, their twins’ friends, or other family members, but this time, it would just be the four of us.

This trip had added significance for me as it was truly the first vacation we have taken that I hadn’t planned. I actually got to see how my husband has traveled since we’ve been married and now that it’s over, let me tell you, I could really get used to it. All I had to do was show up; every step of the vacation had been planned. The biggest decision I had to make was how much rum to put into my Pain Killer!

The Moorings in Tortola, BVI

We flew into St. Thomas from JFK the day before our 7-night sail.  We then took a ferry to Tortola and a short taxi ride to Road Town, all of which was part of the package with our sailboat charter company, The Moorings.   There were other choices for charter companies, but our friends have been sailing with The Moorings for years and have always had a good experience, so why rock the boat?


The company sends you a complete list of information you will need well in advance, including a travel checklist, information about renting equipment, provisioning, and your itinerary.  And, based on past experience, our friends knew to bring certain snacks, zip lock bags, and plenty of coffee and then what to order in advance from The Moorings Provisions to be stocked on our boat before we set sail.

sailing the british virgin islands

Our 51.5 monohull sailboat. Photo credit Sherry Wernicke, Luxe Traveling Mom.

We stayed at The Mariner Inn the first night at the same harbor.  While not a four star resort, it certainly met our needs and had a really nice restaurant, Charlies, where we discussed our upcoming journey over our first rum drinks.  We had chartered a 51.5 foot boat with four berths, each with their own bathrooms; rented two SUP’s for fun; and had it stocked with our favorite food and beverages.

We ate breakfast and lunch on board most days and then had dinner on the islands where we were mooring.  To make sure we had some fresh food and extra munchies, we took a walk to the local grocery store that morning and got the rest of our supplies before going on board.  While we slept on board each night, many of the islands offer small hotels, where you could stay on land should you be in need of a long, hot shower!  So, you do have the option.

sailing the BVI

The inside of our sailboat. Photo credit Sherry Wernicke, Luxe Traveling Mom.

Before we were allowed to set sail, the staff of The Moorings checked everything out with us, went over where everything was, and quizzed our captain just to confirm he knew what he was doing. Then we got the galley and our rooms set up.  By noon we were motoring out of the harbor, hoisting our sails, and heading for our first overnight on Norman Island, with our dinghy happily bouncing behind us…

British Virgin Islands

Our friends planned the itinerary ahead of time, picking their absolute favorite harbors to moor in and for how long.  They wanted our first trip to be special and did they ever succeed.  We would sail during the day, but the longest sail was only a bit over four hours, so we were never at sea for too long.  They made sure we got into the next harbor in plenty of time for some fun and happy hour!

What amazed me most of all about the islands we visited was how deserted they were.  They are definitely NOT overpopulated or very touristy.  Most are only visited by people on sailboats and very few, like Scrub Island, had a hotel that you could get to if not sailing.  I loved it, because you got a Robinson Crusoe feel, but could do a little shopping, have someone cook you a great dinner, and throw a massage in if you were in need after hoisting all those sails!

sailing the bvi

White sand beach and stunning blue water. Photo credit Sherry Wernicke, Luxe Traveling Mom.

While we were two couples, we saw tons of kids on boats that passed us at sea and on shore and everyone seemed to be a having a lot of fun.  Plus, as I noted, our friends have been vacationing with their kids since they were six years old, adding teenage friends to come along as they got older.

Our itinerary for the sail included:

Night 1:  Norman Island The Blight

Night 2: Marina Cay (east end of Tortola)

Night 3:  Bitter End Virgin Gorda

Nights 4 & 5:  Anegada

Night 6:  Jost Van Dyke

Night 7:  Cooper Island


It’s not an inexpensive vacation and is certainly not all-inclusive.  The only inclusive was the transfers from St. Thomas to The Moorings.  Your costs will vary greatly depending on the size of the boat, monohull vs catamaran, crew vs no crew, time of year, eating on board vs on shore, your ad-ons, and air fare.  You can go relatively inexpensive to an all out splurge.  I have to say I didn’t find prices on the islands to be out of line at all, which actually surprised me.  Typical expenses will include:

  • Boat rental
  • Add-ons, such as wifi and water sports
  • Crew
  • All food and drink
  • On shore activities and purchases
  • Air fare

For our trip, the total cost was right around $8,000.  We chose to have a larger boat and no crew.  But for us, it really wasn’t any more expensive and actually less than spending a week at a luxury resort, such as one of our favorites, The Four Seasons Hualalai.  We brought about $800 in cash (everyplace took US $), but most places also took credit cards.

sailing the bvi

We were very fortunate to have this be the perfect vacation where truly nothing went wrong.  While it rained a bit our first day out, the rest of the trip gave us perfect weather; sunny skies, temps in the low 80’s, low humidity, and just enough wind to get great speed on the water.  We even got last moorings and last dinner reservations at places we wanted to go.  No Plan B’s were needed.  I know it can’t be replicated, but I certainly hope to get the chance to try!

In future posts, I will be detailing the islands we visited, discussing life on a sailboat, and giving you the ultimate, must have packing list from 30 years experience.  Stay tuned!