We stay on Tortola once a year for 10 days. It only takes a day to get used to driving on the left side. We go to Smugglers in the rental. The rental companies are fine with this. They will only charge you extra if there is a lot of sand left in the vehicle. We have been up Sage mountain with no issues. We have covered the entire island over the years. Just make sure you get a 4WD vehicle. We will take a cab sometimes if we are planning on a late night out with some adult beverages. I don't find that the cabs are that expensive for one night. And everyone can enjoy a nice dinner with no worries about driving back to the villa.