Biggest Tips From Below Deck Charter Guests

Captain Lee Rosbach, Kate Chastain, Courtney Skippon, Simone Mashile, Kevin Dobson
(Photo by: Karolina Wojtasik/Bravo/NBCU Photo Bank via Getty Images)

For over a decade, the Below Deck crews have grinded away on their respective yachts. While some of these crew members do so because they are passionate about their jobs, others on the series have been a bit more candid. These crew members are working hard for one thing only—a hefty tip envelope at the end of each charter.

In Season 1, the tips started off quite low. During episode 8, the Below Deck yachties even received the franchise’s lowest tip to date. Following an incredibly high maintenance group’s departure, this tip envelope only contained $5,000 to disperse amongst the entire crew.

Ew, David.

Thankfully, (most of) the tips have greatly improved since this series’ 2013 Season 1 debut. Some of these amounts have even rendered the crews onboard speechless. Time to dust off those resumes and search casting notices, while reading up on mixed drinks, maritime law, and bowlines.

Starting at the top, these are the largest tips received from Below Deck charter guests to date. If you see us now trying to sneak onboard in our fake whites from Amazon, no you did not.

$40K – Jake Clopton


The largest tip across the entire franchise was seen in Below Deck Season 10. Over the course of Episodes 15 and 16, primary charter guest Jake Clopton and his frat-like friends partied hard, working the interior and exterior departments to their (likely desired) deaths.

Charter guest Angel even drove everyone so mad that Captain Lee Rosbach unsecured his floating bed (raft) from the yacht. Though the sleeping Angel only drifted away for a short time, the boat was so calm sans his presence.

Luckily, the crew’s efforts paid off. On Jake’s departure, he handed over the heftiest tip envelope to date, consisting of $40,000.

$35K – Timothy Sykes


Timothy Sykes caused Captain Lee to exclaim “what a d**khead” during his first appearance in Season 2. Here, he handed over a large tip envelope while asking for $5K back, as his then 19-year-old girlfriend was not impressed with Chef Ben Robinson‘s skills (she preferred nuggets, yes, nuggets). When Timothy returned in Season 5, he more than made up for his faux pas.

On his return charter, Timothy was equal parts demanding and fussy, as the Wi-Fi was spotty (bruh, you’re in the middle of AN OCEAN). After surprising his guests with a champagne fight involving whipped cream pies, Timothy left a mess for the crew to clean-up.

Timothy also left $35,000, which is the franchise’s second highest tip seen this far. Thank you, Season 2’s backlash.

$31K – Gigi Fernandez

Gigi Fernandez/Instagram

We’ve already discussed how Below Deck Season 10 gave us the best tip ever, via Jake Clopton. However, it also gave us an appearance from former tennis pro, Gigi Fernandez. Gigi walked off of motor yacht St. David with a tan and a smile, as her all-girl’s trip proved to be a success.

Gigi’s charter was a birthday present for a friend. This friend deserved this gift, as she was the egg donor for Gigi’s twins. Unfortunately, said friend was unable to make the trip due to COVID-19 restrictions. Instead, Gigi brought along six of her tennis friends.

Gigi also brought an envelope containing $31,000, which is currently the third largest tip in the Below Deck franchise. She also provided the crew with a calm charter, which is a gift in itself.

$30K – Bryan Guarnieri

Bryan Guarnieri/Instagram

Just like Timothy Sykes above, Bryan Guarnieri’s first round on Below Deck Season 8 brought troubles. Chef Rachel Hargrove almost quit over his particular preference sheet requests, but admitted to loving Bryan once he was onboard. However, when Bryan appeared again on Season 4 of Below Deck Sailing Yacht, his cruise received zero backlash from the eager-to-please cast.

The entire Below Deck Sailing Yacht crew fully celebrated Bryan’s LGBTQ+-themed charter. Gary King and Chase Lemacks danced in speedos while carrying rainbow-colored fans, as Chef Ileisha Dell whipped up multi-course meals using the colors of the rainbow. This crew’s hard work didn’t go unnoticed, or, uncompensated.

Bryan walked off of the Parsifal III stating that it was “the best charter ever,” while providing the crew with an envelope containing $30,000 for their tip. This amount is the fourth highest Below Deck franchise tip. It also earns a spot as the highest tip seen for this particular spin-off series.