The Nicest & Most Considerate Below Deck Charter Guests

Captain Lee Rosbach, Kate Chastain
(Photo by: Charles Sykes/Bravo/NBCU Photo Bank)

Below Deck is a yachting-based series filled with affluent charter guests. Most of these high-paying clients arrive with very specific demands. When these demands are not met, the guests are known to throw fits.

That said, there have been a handful of guests over the years that have shown high levels of patience, even when their lives or onboard circumstances were met with challenges.

In honor of these individuals and the marks they’ve left on the series (and the world), here is a recap of the nicest and most considerate Below Deck charter guests thus far.

Below Deck Mediterranean’s Ashley Brinton

Ashley Brinton/YouTube

Below Deck Mediterranean‘s Season 4 charter guests, Dan and Sheree Funsch, listed on their preference sheets a very specific request. While onboard, they desired for their daughter, Ashley Brinton, to film a music video with the help of the crew.

Right off the bat, the Sirocco super yacht crew feared that this would be a stressful charter with an entitled family.

The crew, however, was wrong.

This group walked onboard displaying a tightly knit, supportive family unit. In addition, each member within showed thankfulness for everything that the crew did during their charter.

At the age of 18, Ashley was the opposite of entitled. Her manners were impeccable and her gratitude towards the crew was overflowing.

In return, the entire crew happily helped Ashley with the shooting, lighting and the water toys that were needed for her music video. In fact, Ashley still keeps in touch with Hannah Ferrier, Aesha Scott, and Anastasia Surmava. “All of the crew was amazing,” Ashley recalled.

Sadly, two years post charter, Ashley announced that she had been diagnosed with CML Leukemia. As seen on Below Deck Mediterranean, Ashley’s consideration for others once again emerged.

To aid with comfort during treatments, Ashley started a merchandise line called Chemobabes.

Our thoughts are with Ashley as she continues to fight.

Below Deck Sailing Yacht’s Kerry McReynolds

Chris Harrington/Instagram

Below Deck Sailing Yacht‘s Season 1 primary guest, Kerry McReynolds, chartered the yacht with her closest friends “to honor and celebrate her life and legacy” while battling stage 4 cancer, Captain Glenn Shephard read during the initial preference sheet meeting.

Chief Stew Jenna MacGillivray immediately felt a bond with Kerry, as her father battled cancer before his passing. “Considering Kerry’s health condition, her attitude is so positive. That takes so much strength,” Jenna said, adding “I’ve had personal experience with my dad dying of cancer, and I will bust my ass to make sure this is the best trip of her life.”

Throughout Kerry’s episode, her kindness never wavered. She displayed gratitude for each and every effort put forth from the crew. On-air, Kerry could even be seen uplifting several crew members as they worked, when she wasn’t on a water toy or flipping off of the side of the vessel.

When Kerry departed the sailing yacht, everyone from the crew to the producers shed tears, thankful for the reminders on living life fully.

On Feb 9, 2022, Kerry’s battle ended.

However, Kerry’s kindness, consideration for others, and zeal for life will live on indefinitely.

Below Deck Sailing Yacht’s Lane Merrifield

Lane Merrifield/Instagram

Below Deck Sailing Yacht’s Season 4 introduced viewers to Lane Merrifield, a multi-millionaire entrepreneur. Lane charted the Parsifal III for his closest friends with the sole purpose of celebrating his engagement to his girlfriend, Amanda Bourke.

In his preference sheet, Lane asked for a molecular gastronomy meal and a sail. However, due to extremely windy conditions, Captain Glenn had to deny Lane’s sailing request.

This type of news has sent many Below Deck guests of seasons past into hysterics. Lane, however remained positive.

Choosing fun, Lane included the crew in activities like a “sailors versus pirates” relay race and a “hurricane” drinking game. Lane also supplied the costumes and a winner’s trophy. The Below Deck Sailing Yacht crew appeared to enjoy every second of Lane’s charter.

While saying his goodbyes, Lane then turned towards Chef Marcos Spaziani, who had been grieving the loss of his best friends mother the entire charter. Here, Lane spoke words of life, expressing that he expects to see a Michelin star by Marcos’s name in the very near future.

On his departure, Lane presented the crew with $23,000, their largest tip of the season.

Below Deck’s David and Jackie Siegel

Jackie Siegel/Instagram

Below Deck has seen many gracious guests throughout its (currently) 10 seasons run. That said, one couple in particular showered the franchise’s beloved Captain Lee Rosbach with compassion, as the three “belong to a club that nobody else wants to belong to.”

During their Season 8 charter, David Siegel and his wife Jackie Siegel entered Captain Lee’s wheelhouse. As they conversed, Captain Lee shared that he had just lost his son, Joshua Lee Rosbach, to an opioid addiction. This was the first time that Captain Lee spoke on-air of his son’s death, and as his voice cracked, the Siegel’s leaned in with love.

Speaking in a tone of understanding, the Siegels then shared that their daughter, Victoria Siegel, also lost her life to an opioid addiction just a few years prior to Joshua’s death.

Understanding the crushing weight that he was under, the Siegel’s asked Captain Lee to join them for dinner. As the stewardesses served, the conversations at the table were soft, kind, and filled with support. When Captain Lee stated that every day is an emotional battle, David expressed, “we’re going to help you through it.”

In a rare sighting, an emotional Captain Lee told the cameras “it helps to talk to somebody that’s been there, and knows what I feel.”

Captain Lee’s friendship and support within this tragic club still holds firm, as the three remain in contact post charter.

As the Below Deck series continues to expand, hopefully, more stories like these will emerge. Until then, cheers to kindness, as we all sail through the waves of this life together.