Captain or Bareboat?
There are many reasons you might hire a captain for a sailing charter. The most common one is that your sailing resume doesn’t include the credentials needed to bareboat, but even sailors who are qualified to take a boat on their own will sometimes elect to have a captain aboard. After a recent one-week charter in the British Virgin Islands (BVI) with a captain for our Sunsail 454L catamaran, I came up with eight reasons why we were glad to have Capt. Paul onboard.

1. Route planning. A skilled captain will help you determine a route based on your goals and interests, the weather, water conditions, and the amount of time you have. Our captain asked us where we most wanted to go and what types of activities we most wanted to do. Our group of six had varying interests, and our captain made sure that everyone got to experience what most interested them. These activities included hiking, jogging, snorkeling, swimming, nightlife, dining on local fare, and experiencing the islands’ famous rock formations (The Baths and the Caves), as well as visiting some of the well-known waterfront bars (picture back flips off the deck at Willy T’s).
Beyond route selection, a captain can help keep you on schedule. On Anegada, we met a couple who had previously bareboated in the BVI, but on this trip they had hired a captain and first mate/chef. This couple had with them their adult children and their spouses. The couple told us, “We enjoy bareboating, but for this trip our priority was to relax with the kids and show them our favorite spots is the priority. We didn’t want to be concerned with driving the boat, watching the weather, cooking, etc. Halfway through the trip, we can say it was a good decision. Without the captain, we’d probably still be two islands back; he’s keeping us on track to visit all the places we want to share with our family.”
2. Insider knowledge and tips. Where are the most secluded anchorages? Which bays have the best views of the sunset? Will there be a current where we snorkel and which way will it push us? Are any areas experiencing seaweed? How about jellyfish? Which bays have flat water for paddleboarding? Which beach bars are daytime hot spots, and which ones are better for nightlife? Where can I go for a hike or take a jog? Where are the best places to cast a line for fishing? Where are the best spots to reprovision? Your captain will have the answers to all these questions and more.

3. Lightening the load. Charter boats have a reputation for being ridden hard and put away wet. Regardless of whether that stereotype is deserved, boats are boats, and stuff sometimes breaks: bilges leak, head back up, electronics unexpectedly go kaput, and AC units conch out at the most inopportune times.
If you experience such issues, a captain will step up and relieve you of troubleshooting and handling repairs. First, he or she will probably be capable of monitoring or fixing small issues. On this trip our boat had a couple of minor issues. Our captain was on top of them, so much so that we were not even aware of them until the end of the charter when we asked about any issues he had handled behind the scenes. Second, captains can phone a friend. We noticed that our captain occasionally fielded calls from fellow captains seeking his advice for simple repairs; using their phones for pictures or video they walked through how to fix minor issues.
If a more serious problem requires the charter base to send a mechanic, the captain can wait for the base to send help, while you go on with your snorkeling, paddling, bar-hopping, or other planned activity.

4. A designated driver. With a captain, you’ve always got a designated driver. That means all the guests can enjoy a cold adult beverage, read a book, or take a nap while underway. Perhaps more even more important, you’ve got a dinghy driver at your disposal—perfect when you’ve imbibed onshore and need to return to your boat, especially after dark.
Equally helpful, your group can divide up without choosing which group gets to take the dinghy. For example, our captain dropped off part of our party at Willy T’s and took the remainder of our group to shore to go hiking. When finished, the hikers texted our captain for a pickup. He delivered them to Willy T’s and returned later to bring the whole crew back to the charter boat.
We also appreciated delivery via dinghy to the snorkeling areas. If we wished, our captain would ferry us to the dinghy line, drop us off, keep an eye on us, and deliver us back to the boat when we’d had enough—a big help for our not-so-strong swimmers.

5. Help with the water toys. Okay, I don’t want to sound spoiled, but it is awfully nice to have someone ask, “Which water toys will you be using today,” untie the paddleboards, floats, and kayaks from the bow, put them in the water for you, and put them away when you’re done. At the end of the day, we helped bring the gear back onboard, and in doing so picked up our captain’s efficient techniques for corralling and lifting the toys onto the boat deck.
6. Shoreside excursions and reservations. Our captain took care of all the reservations we needed. He made suggestions for shoreside excursions, as well as restaurant suggestions, for which he booked our tables. At Anegada, he reserved a rental car for us. He also handled all mooring ball reservations. We benefited from his years of experience in that he had a good sense of when reservations would be needed and when they’d not be necessary, getting us to the ‘first come first served’ balls whenever possible. And when it was time to head to the ferry, he arranged our taxi.
7. Driving and parking the boat. Sailors like to sail. That’s a fact, but if you are chartering, you are likely on vacation and not in your home waters. Is your goal to improve your sailing skills or to relax, take in the views, and explore new places? If it’s the latter, a captain will allow you to take it easy without worrying about tides and currents, sand bars and coral reefs, or channel markers and boat traffic.
Anchoring and docking can be some of the biggest stress points of sailing in unfamiliar territory. A local captain will know if the bottom is sandy, rocky, or muddy. They will be familiar with the local winds and currents. They’ll know the dockhands at the marinas. And perhaps most helpful, they’ve got experience leaving and returning to your charter base, which on turnover days can be chaotic with so many vessels departing or arriving in the same time window.
And, of course, none of this is to say that you can’t sail the boat when you want to. We did!

8. The adult in charge. Many people are leery of about having a stranger aboard, and we were too. Will they be “weird?” Will it change the group chemistry? For us, hiring a captain enhanced our trip. Were we lucky? Maybe. Our captain was very professional, and, frankly, saved us from bickering among ourselves about how to do things and when and where to go.
Good communication helped. He asked a lot of questions to get to know us. In fact, he said that for him, the most challenging groups are the ones that are hesitant to tell him their likes and dislikes; those groups make it challenging to tailor the agenda to meet the group’s expectations.
Our captain did an excellent job of being friendly and available without inserting himself into our fun, disappearing at the right moments and reappearing at just the right time. I’d say the experience was in some ways analogous to hiring professional movers. Yes, you give up a bit of control and privacy, but, wow, are you thankful for the assistance.
With our captain as the “adult in charge,” we could rest, enjoy our family time, and soak up all the beauty and outdoor fun that they BVI have offer.
by Beth Crabtree




