Chartered a 39' monohull sailboat from Sunsail in Roadtown, Tortola BVI for a week. Traveling with my wife, our 2 children (19 and 21 yrs old) and two 'stowaways' (friends of the kids), we arrived late on a Friday night after having flight issues. The staff was ready and waiting for us to check in. A little disorganized and no one available to help with luggage, but we were just happy to have a place to lay our heads for the night. Next morning, I went back to the main desk and had all my questions quickly and politely answered. There was an organized 'briefing' for all boat Captains and First Mates that was quick but informative.
We contacted Bobby's Market in Roadtown (via Web) to provision our boat. All groceries arrived promptly at 8AM Saturday morning as requested. They did a fine job of filling our requirements and we (mostly) did a good job estimating how much food we would need. Recommendation: get more bottled water than you think you will need! We supplemented our groceries along the way and had to get ice every day.
We rented a blender from Renport (on the dock at Sunsail). It was a 12v model that just did not have the high speed and strength necessary to make frozen drink concoctions properly. It just ground up the ice into small pieces. Pretty much a waste of $$.
Also paid for a fishing license and rented spinning equipment from 'Last Stop Sports' (also on the dock at Sunsail). Another waste of $$ since it was difficult to fish while sailing and not much around (for fish) at mooring sites. This is only worth it if you are serious about fishing.
The boat was approx 5 years old and in great condition. A few minor problems, but nothing that impacted the trip. The return process was easy and painless. Sunsail arranged for transport back to the airport and allowed us to use the spa facilities to shower before our flight home.
My son was the only experienced sailor in our group, and we were a little nervous about piloting a large sailboat with our limited skills, so we hired a Captain (from Sunsail) for a few hours to show us the ropes (no pun intended!). Derek was patient, instructive and confidence building as he helped us navigate out of the marina and showed us the correct procedures to pick up a mooring, anchor the boat and navigate from island to island. We were able to drop him off at Peter Island where he could catch a ferry back to Roadtown. Cost was very reasonable ($175 for the day plus ferry fare and gratuity).
Navigation is 'line of sight' and weather was beautiful, so our biggest problem was just deciding which beautiful spot to visit next! We (like most people) did a counter-clockwise circle around Tortola, visiting Peter Island, Cooper Island, Virgin Gorda, Beef Island (full moon party was fun!), Jost Van Dyke, Norman Island and back to Peter Island for the night before our charter ended. We had no problem finding mooring balls and had quiet comfortable nights for all except one. A large catamaran moored nearby at Norman Island decided to party until 3AM, blasting loud music for every boat in the bay to enjoy (not).
The only surprise on the trip was the high cost of everything you purchase in BVI. Groceries, Ice, Water, restaurant meals, drinks, souvenirs, etc are all double (or more) what you would pay for them in the US.
The best part of the trip was after we settled in and got our sea legs... spending time with our children disconnected from the world was worth every penny! Go and enjoy!
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