About a thousand nautical miles up the Inside Passage and beyond, into Alaska’s waters, is a place that countless boaters dream of cruising. The region is teeming with whales, glaciers and scenery that towers high above the anchorages in majestic grandeur, but also presents the challenges of routine fog, 20-foot tidal swings, and distances between ports that are so long and remote, even the most experienced skippers can feel hesitant to leave the dock.

Those challenges are why so many boaters from around the United States and beyond are booking bareboats as part of captain-led flotillas, says Brian Pemberton, the former-owner-turned-spokesman for Washington-based NW Explorations. The majority of the company’s bareboat clients who book Grand Banks, Ocean Alexander, Kadey-Krogen and similar boats, he says, are already boat owners themselves. Some have spent lifetimes on the water, aboard everything from lake-cruising boats to offshore trawler yachts.

In booking a bareboat to a place like Alaska, he says, those boaters are trying to push their own cruising boundaries, whether geographically, with a larger or different style of boat, or with a longer liveaboard stay than they’ve done in the past. Having a lead boat in a flotilla with a locally savvy skipper at the helm, not to mention a tech-savvy crew and naturalist at the ready if needed, gives those bareboaters the confidence to cruise in places they simply don’t want to try and go alone.

“These are people who have a range of experience,” Pemberton says. “It’s really about taking the opportunity to be prudent while you have the adventure. You get the safety net to cruise in these absolutely spectacular waters.”

The trend of boaters booking bareboats to expand their skills, knowledge and horizons—aboard monohulls and catamarans, power and sail alike—is so strong right now that numerous companies are adding and expanding flotilla and instructor options to their bareboat programs.

Dream Yacht Charter recently formed a partnership with Nautilus Sailing that lets bareboaters have an instructor come aboard for new certifications. 

Dream Yacht Charter recently formed a partnership with Nautilus Sailing that lets bareboaters have an instructor come aboard for new certifications. 

MarineMax Vacations is planning to host flotilla charters for bareboaters for the first time in 2020, with a program similar to the one at NW Explorations, only in the British Virgin Islands. The Moorings, which has put together a flotilla charter with BoatUS every year since 2014, used its most recent flotilla in the Virgins to let boaters test out the BoatyBall mooring-reservation service, without fear of actually having to get stuck without a mooring. Sunsail is offering beginner, intermediate and advanced sailing classes aboard its bareboats, including on flotilla charters. Southwest Florida Yachts is offering combination courses for bareboaters, allowing them to earn multiple levels of certification at once. And Dream Yacht Charter, whose bareboats are available everywhere from the Caribbean and Mediterranean to the South Pacific and Indian Ocean, recently formed a partnership with Nautilus Sailing that lets bareboaters have an instructor come aboard for new certifications anywhere that Dream Yacht Charter operates.

Even longtime sailors are requesting liveaboard instructors as part of their bareboat vacations, says Tim Geisler, the lead sailing instructor at Nautilus, which is an American Sailing Association school. While many sailors already have earned ASA 104 certification for bareboating, they want to do other types of boating that expand their horizons, with higher levels of certification.

“If people want to charter catamarans, that’s a different certification,” Geisler says. “It’s called the 114. We’re hearing from a lot of people who have sailed monohulls for a long time, who now want a catamaran with more space and light and less rolling. They have their 104 and have done a bunch of charters, so now they want to do that 114 course. Some people really like offshore sailing and want to get some passages under their belt; for them, the ASA offers offshore certifications. You can’t just go out and do that in the BVI, but you can do it between two Dream Yacht Charter bases. Maybe you leave out of Martinique and you sail down to Grenada. That would be a good, serious offshore leg that you could do in a week with night passages, using the radar, advanced weather prediction and all of that. We also can offer celestial navigation with those classes.”

Nautilus Sailing provides instruction for beginners as well, Geisler says, but more and more often, it’s experienced boaters who are asking to incorporate new certifications into their bareboat vacations. “It’s really fun to work with people who have a lot of boating experience and want to take it to the next level,” he says. “There’s a lot to learn when you move up to a big cat.”

Raul Bermudez, vice president of the charter division at MarineMax Vacations, says his company decided to add captain-led flotillas of bareboats after receiving requests that came, in part, from longtime sailors switching over to book powerboats after years on the water. “We are getting a lot of first-timers, especially on our 36-footer, the two-cabin boat, and then we’re also seeing people who want to bring a captain for the first two or three days,” he says. “I think it’s because powerboat bareboating is kind of new.”

Routine fog and 20-foot tidal swings in Alaska are reasons why bareboat clients of Northwest Explorations are signing onto captain-led flotillas.

Routine fog and 20-foot tidal swings in Alaska are reasons why bareboat clients of Northwest Explorations are signing onto captain-led flotillas.

The plan at MarineMax Vacations is to host three flotilla charters in 2020, starting in late February, May and July. Each flotilla will be capped at 10 bareboats, with a lead boat that has a captain who is well versed in local knowledge. Even for a bareboater who has cruised in the British Virgin Islands before, Bermudez says, having that kind of support system can enhance the itinerary—say, if a skipper has long wanted to make the crossing to Anegada, but shied away because the island is about 15 miles north of Virgin Gorda or because the reefs on approach to Anegada have caused hundreds of shipwrecks throughout the years. “We can show them all the tricks of where to go, plus any seamanship skills they want to work on with the crew of three on the lead boat,” Bermudez says. “There will also be a technician for any problems.”

Geisler says that when Nautilus Sailing offers a bluewater sailing opportunity with an instructor for Dream Yacht clients, it sells out inside of a few days because so many people are looking to add a little adventure as part of their bareboating vacation. And it is, still, a vacation, he says; even though a new certification is being achieved, bareboaters are cruising in a beautiful destination, enjoying fun in the sun and stopping at shore attractions along the way.

“More and more often, people don’t have a lot of time for vacations, so we really try to make it a liveaboard experience,” Geisler says. “It’s not like you’re in class the whole time. You’re going to have a vacation while you’re learning.”  

This article originally appeared in the January 2020 issue.