The questions people are too embarrassed to ask

There's no official rule anymore. MYBA, the association behind most Mediterranean charter contracts, removed its old 5–15% suggestion in its 2026 crew guidelines and now says the tip is entirely at your discretion — and must never be asked for. In practice, brokers advise 5–20% of the base charter fee: toward the lower end in the Mediterranean, higher in the US and Caribbean, where the written custom (CYBA's contract) is 15–20%. Work it out on the base fee only — not the APA, taxes or extras.

Sources:Vital Charters — How to tip yacht crew (2026): the custom, and what MYBA saysBoat International — Superyacht charter tipping guide

The custom is the end of the charter, usually the last evening, handed to the captain. Some brokers will also take a tip in advance and pass it on. Ethan tips upfront — see his story below — which is unusual, not the norm.

Sources:Boat International — Superyacht charter tipping guideVital Charters — How to tip yacht crew (2026): the custom, and what MYBA saysEthan Bixby, founder — first-hand account

Give it to the captain, who divides it among the crew. Most yachts split tips equally regardless of role, because the crew you rarely see may have worked just as hard as the ones you do. You can also ask for the tip to come out of any unspent APA.

Sources:YachtCharterFleet — Captain & crew gratuitiesBoat International — Superyacht charter tipping guide

Sometimes — but only with written approval, and many boats say no. The Moorings, for example, doesn't permit pets (service animals only, for a fee); some operators such as Marquis Charters are pet-friendly but require approval in the contract. Expect a security deposit, and know the crew won't dog-sit while you're ashore. Every country you stop in has its own entry rules. For Greece and the rest of the EU from the US, you need an ISO microchip implanted before the rabies shot, a 21-day wait after a first vaccination, and a USDA-endorsed EU health certificate, endorsed within 10 days of arrival. Start months ahead.

Sources:The Moorings — FAQ (pets)Marquis Charters — FAQ (pets)CharterWorld — Dog-friendly luxury yacht chartersUSDA APHIS — Pet travel from the US to GreeceEuropean Commission — Bringing a pet into the EU from a non-EU country

15–20% of the pre-tax bill is the standard etiquette guidance, and wine is part of the bill. Some diners who order a very expensive bottle tip the full rate on food and closer to 10% on the wine; that's a judgment call, not a rule.

Sources:Emily Post Institute — General tipping guideWine Spectator — Tipping a sommelier

Usually not. In most restaurants the sommelier shares in the tip pool. If they were particularly helpful, a separate tip handed to them privately is a gracious thank-you, on top of the normal tip.

Sources:Wine Spectator — Tipping a sommelier

Yes, even though you paid a tasting fee — and even if you bought wine. Visit Napa Valley's guidance: $10–$15 per couple at a stand-up bar, $15–$20 per couple for a seated tasting, $20+ at boutique wineries.

Sources:Visit Napa Valley — Wine tasting tips, costs & etiquette

Not if the winery allows it — and many do, but ask first. Robert Mondavi says yes if you tell them in advance. Chateau Montelena doesn't allow sharing in its reserved experiences but welcomes it at its walk-in bar. Seated, reserved tastings generally mean one seat, one fee.

Sources:Robert Mondavi Winery — FAQChateau Montelena — FAQ

Wine-country casual: nice jeans are fine year-round, darker denim for a more upscale winery. Bring a layer — caves and cellars are chilly, and Sonoma mornings can be foggy before a hot afternoon. Skip perfume and cologne; scent masks the wine for you and everyone near you. Dark colors hide spills.

Sources:Visit Napa Valley — Wine tasting tips, costs & etiquetteWine Spectator — 10 tips for attending a wine tastingSonoma County Tourism — FAQ (weather & what to wear)

Yes. That's what the buckets are for, and professionals do it all day. Pouring out what you don't want to finish isn't an insult — it's how you stay sharp enough to enjoy the last pour.

Sources:Wine Spectator — 10 tips for attending a wine tasting

On top of the caddie fee. Pebble Beach suggests $100+ per bag for a single-bag caddie, $75+ per bag for a double bag and $50+ per bag for a forecaddie (caddie fees there: $175 single, $250 double). At Bandon Dunes the caddie fee is $125 per bag, plus gratuity, paid directly to the caddie.

Sources:Pebble Beach — Caddie servicesBandon Dunes — Caddies

Yes — instructors rely on tips, and SKI Magazine calls it one of the tips that still matter. A PSIA-AASI national team coach's baseline, via SKI Magazine: $10 per hour for group lessons, $50 for a half-day private and $100 for a full-day private; 15–25% of the lesson price is another common rule. Cash is best; if you can't tip on the spot, follow up.

Sources:SKI Magazine — How much should I tip my ski instructor

Not for answering questions. $5–$10 for booking a restaurant or tickets, and $15 for hard-to-get tables or tickets (or 10–20% of the ticket price). Housekeeping: $2–$5 a day, left daily with a note.

Sources:Emily Post Institute — General tipping guide

It's appreciated but not expected, and some operators don't allow crew to accept tips — ask your broker or operator first. Many US passengers don't tip pilots; $50–$100 is fairly common when they do. Nobody publishes a standard for cabin attendants: unknown.

Sources:Forbes — Private jet tipping etiquetteACC Aviation — Private jet etiquette: are you expected to tip?