Larry Ellison, the gazillionaire who runs Oracle software, was recently quoted as saying he thinks he went a little too big when he built his yacht, Rising Sun, at 452 feet long. Perhaps what helped him draw this conclusion was having no room to anchor in a Caribbean harbor, or having to fork over $100-per-foot for dockage fees in the Med. (Then again, when the boat itself is worth $200 million, what’s a mere $45,000 for a night’s stay at a marina?)

No matter what brought Mr. Ellison to the realization that 45 stories long is perhaps a wee bit too big for one person’s boat, he has finally joined the rest of us who believe that boating vacations are all about scaling back. There’s a reason that we choose trawlers instead of cruise ships, sailing cats instead of luxury liners. The intimacy of boating—of arriving in a tiny harbor and being able to go ashore without gobs and gobs of other people around—proves that good things do come in small packages. Often, the smaller the package, the better.

I was reminded of this recently not only by Mr. Ellison’s pronouncement, but also by a brand-new 100-foot motoryacht I saw at the Newport Charter Show. Now, I know that to bareboaters a 100-foot yacht is pretty big, but in the world of crewed charter, a 100-foot motoryacht is on the smaller side. And this 100-footer—a Hargrave called Cocktails—sure packed a lot of big-boat punch into her relatively small charter boat hull.

Cocktails, you see, is owned by one of Florida’s pre-eminent builders, a guy who’s done houses for everybody from Oprah to Sly Stallone, not to mention Donald Trump’s hotel and a few other towering pinnacles of consumerism on the Miami’s South Beach. The yacht’s owner took a lot of the high-end interior design ideas from those plush palaces and packed them into Cocktails, things like hand-woven, seamless wool carpeting that feels like it actually massages the soles of your feet when you walk on it. I squished my toes deep into the $63,000 pile as I made my way across the main saloon to the lighted onyx bar, a spot I think many charter guests will favor while enjoying a white wine cocktail after a day of snorkeling in the sun.

My point, of course, is that if you’re in the market for a crewed charter yacht and want to get as much big-boat luxury as you can, don’t necessarily limit yourself to the biggest fully crewed boats out there. Cocktails, part of The Sacks Group fleet, is proof that you can have a lot of the most indulgent décor afloat at a base rate of $35,000 per week for eight guests (about $5,500 per person for the week with 25-percent expenses included).

That just might be a deal Mr. Ellison’s accountant should have him consider.

International Yacht Collection announced this week that the 130-foot fully crewed motoryacht Sacajawea is seeking charter guests who love to golf. The yacht is moving north from Florida to New England, and along the way the captain has organized itineraries that include some of the most picturesque links in the Carolinas.

The announcement reminded me about what fun it can be to combine a yacht charter—bareboat or crewed—with a favorite hobby. The hobbies that spring to mind first are water sports like snorkeling and fishing, but if you think a bit about your itinerary and destination in advance, you can combine a private yacht charter vacation with pretty much any hobby you choose.

My family and I did just that last summer onboard the 60-foot motoryacht Irony, which has two crew and takes six guests for a base rate of $12,500 per week (about $2,600 per person with 25-percent expenses added). We chose to charter Irony in the Chesapeake Bay and set our waypoints up the Wye River offshoot for a place called Pintail Point, where there is an outstanding sporting clays course just a short golf cart ride from the dock. Our favorite family hobby, you see, is blasting orange clay “birds” out of the sky with shotguns, so we worked with Capt. Dan Cole to arrange an itinerary that gave us a few days’ worth of scenic cruising combined with a few days of shooting wobbler, poison bird, and other sporting clays games.

The beauty of private charter yacht vacations is that you can plan a highly personalized itinerary like this no matter what your hobby. I’ve heard of wine-tasting charters, scuba charters, even charters based solely on a search for the best conch fitter stands in the Bahamas. On a charter yacht, bareboat or crewed, you’re not at the mercy of pre-planned itineraries and quickie shore excursions. You can linger and lounge as long as you’d like, doing whatever you choose, wherever you want in the world.

If golf is your thing and you’re interested in a crewed yacht for ten guests, I recommend you talk to a reputable charter broker about that Sacajawea advertisement. The Carolinas have some of the East Coast’s most gorgeous greens, and you can enjoy them with a full crew at a base rate of $70,000 per week (or $8,750 per person with 25-percent expenses included).

I recently had the pleasure of chatting with Betsy McDonald, the chef onboard the 150-foot motoryacht Magic. I’ve known her and her husband, Capt. Mac McDonald, for a half-dozen years, ever since they ran the 114-foot motoryacht Camille. They’re one of those couples who have made a lifetime career out of serving on fully crewed yachts, working their way up to more and more expensive boats as their skills have improved. As Betsy describes her work today: “These people are paying $155,000 to $165,000 a week to charter my boat. I sincerely think that what I owe to them is to always keep going, to do one more thing, to be a little bit more impressive.”

That attitude comes second nature to Betsy, and it’s exactly the sort of enthusiasm that you should look for when booking a crewed yacht of any kind. Charter brokers spend countless hours getting to know yacht crew at every level—from the captains to the deckhands—just so they can pick out the Betsy McDonalds of the industry and recommend them to you for your next charter vacation.

This is Betsy’s 17th year working onboard boats and her third with Magic, which is part of the Koch Newton/Merrill-Stevens fleet and takes ten guests. What she loves about this yacht’s owner is that he helps her to build on her base of skills from the Culinary Institute of America, sending her to Michelin-starred restaurants to sample new cuisines in Europe and to Greystone, the Culinary Institute’s continuing education school in Napa Valley, California. Magic’s owner even lets Betsy organize wine tastings onboard the yacht for the crew, so they, along with Betsy, will know what vintage to recommend when you ask them for a suggestion during dinner.

The yacht owner’s investment in Betsy’s skills pays off for you, the charter guest, because she can handle pretty much any culinary request you throw at her–a skill that all top-notch charter chefs should have.

“We’re hopefully great cooks who don’t specialize,” as Betsy puts it. “We’ve got to be beautifully proficient in Japanese, Italian, French, spa cuisine–we’ve got to do it all.”

When you’re talking with your charter broker about a crewed yacht, be sure to ask not only about the chef’s specialties, but also about her attitude, her training, and her yacht owner’s investment in her continuing education. Betsy is one among many incredible chefs working on boats today, and at the end of the price spectrum where her yacht lies, you deserve to have only the finest crew.