Our Team
Additional Captain Options available
Greg Holloway ~ Owner
Greg’s life has taken many unexpected turns--long story short, he grew up in a small-town farming community and moved to Seattle after college. He worked at the corporate headquarters for a major cruise line--taking several cruises to the Caribbean, Mexican Riviera, and Alaska’s Inside Passage. Afterward, he was employed as a CPA in a firm where he was able to travel to Southeast Alaska on occasion.
A new job and transfer took him to London where he made the choice to say “Yes” to everything; in which he gained many interesting and lovely friendships. He further developed his passion for photography taking portraits and covering events with the support of his new companions. This eventually led to holding his own exhibition in both London and Seattle called “Electric Burlesque”—featured in TimeOut London. He was also given an opportunity to be a photographer at a private festival attended by A-list celebrities and English royalty. While pursuing photography he was asked to model for two Getty Images photoshoots—that at one time appeared on the cover of msn.com.
Greg began managing musicians that he met along the way at their request—which of course he agreed to in accordance with his decision to say “yes” to everything. This jumpstarted a career in the media and music industry and brought about a chance to open a business with Stevie Wonder’s manager. Although it received global press coverage with featured articles in Billboard Magazine, Music Week, and the LA Times, in addition to interviews on BBC Radio, it didn’t end up taking off—so Greg decided to move back to Seattle and found contract work for several tech companies.
In 1992, Greg bought his first boat--a 22’ runabout, and in 2017 he purchased his second boat--a 34’ cabin cruiser, both of which he still owns. With a new goal of moving away from his desk job (and also becoming a bit of a boat hoarder), he purchased the Oasis yacht in the spring of 2021. Oasis begins his journey into the luxury yacht charter business. One of the driving motivations for his increasing fleet is the stories he listened to about cruising the Canadian coast and Alaska’s inside passage.
Captain Dick
Captain Dick spent his first 20 years in Eugene, Oregon, where he developed his love for the water while sailing with his family. It’s also where his love for music began--playing in a local country band. If you’re lucky to spend an extended boat trip with him, he might whip out his guitar or harmonica! The water has always been a draw to him, whether sailing, pleasure boating, or fishing for elusive trout in many of the rivers in Oregon and Washington. He later moved to the beautiful Puget Sound area, eventually living aboard a 34’ sailboat on Bainbridge Island.
Dick has worked in many industries including singing telegrams, limousine driver, art investment sales, bartender, yacht maintenance, tug boat deck crew, and a flight attendant. All these jobs have honed his ultimate flexibility, creative mindset, and people skills, which he utilizes during his charters. Seeing a need in the marine industry, Dick worked diligently and developed his one-of-a-kind sail/canvas cleaning business in 1985. He has built this into a brisk business which he manages to this day. Additionally, he manages and maintains numerous properties in Kitsap County.
Captain Dick attained his 100-ton USCG Masters license in 1983 and is well equipped to drive the Oasis along with other power or sailboats. He has been boating for 55 years on lakes, the inland waterway from Olympia to Alaska, and the ICW in the Gulf—but his favorite boating destination is the Broughton Islands, in BC Canada.
Many people can captain a boat, but Dick has many skills beyond just driving that make a trip with him a memory to last a lifetime. He’s familiar with many destinations and can recommend great spots for beautiful anchorages or dockside towns. Many charter clients are repeat clients and have become lasting friends.
He is a jack-of-all-trades--able to offer a multitude of services while captaining a charter. Including, but not limited to mechanic, meteorologist, managing staff, fishing guide, entertainer, marriage counselor, baby sitter, bartender, wedding minister, concierge, janitor, cook, and life coach…he’s also an attentive audience with an appreciation for a good joke!
For a fun and memorable trip, ask for Captain Dick!
Captain Jim
Captain Jim is originally from Colorado. He graduated from US Merchant Marine Academy in 1977 and retired after decades of navigating offshore around the globe on many vessels. Throughout the years he also worked piloting yachts, fishing boats, charters, and deliveries—maintaining his principle “safety first is paramount”.
Now as a retired deep-sea Captain and a former owner of the Oasis, he still enjoys driving charters—after all yachts are more fun than cargo ships, even for the Skipper. When not driving the Oasis, he loves waterskiing from his home near Lake Tapps and skiing down the snowy slopes of Washington’s own Crystal Mountain as well as the Rockies.
Chaunda VanTassel ~
Charter Concierge
Born and raised in the Pacific Northwest, Chaunda grew up with all manner of outdoor activities including hiking, backpacking, and road-tripping. She discovered her love of being on the water during her teenage years while sailing and yachting with family and friends. So, it’s no surprise that her first job at the age of 16 was as a lifeguard for the local YMCA day camp.
Over the years she found work in a variety of fields—retail sales, personal trainer, dental assistant, and esthetician before returning to finish her Bachelor’s degree in media authoring studies. However, after several years in B2B sales and as a corporate development trainer it was time to make a serious change. A long friendship with Greg Holloway presented the perfect opportunity, more than she could have imagined when he purchased Oasis—he needed assistance and she desired a non-corporate job. Chaunda is building her own brand and currently works under the title of Charter Concierge, which encompasses the responsibilities of charter hostess, cleaning crew, caterer, deckhand, media manager, and personal assistant.
“I love the constant shift and change of working on the boat; always a new group of people, new needs and challenges, and new views out the ‘office’ window. I love being on my feet, tending lines, and making sure Oasis gets in and out of port without a scratch. I can see myself doing this for many, many years to come.”
When not working a charter, Chaunda enjoys traveling down to Portland, OR near her childhood home, to spend quality time with her sister and little niece and nephews.