There are few places in the world where tips are not expected. In some, handing out the cash is actually required. Whatever the situation, it’s always a bit confusing and/or embarrassing.

For example, a friend recently booked an all-inclusive, one-week cruise for the amazing online price of $39.95. He packed bags, flew in and dashed up the gangplank. A steward looked at the ticket and escorted him to his assigned quarters. As they went down, down and down many decks, my friend assumed he’d get a cheap cabin because of the bargain price. But he wasn’t prepared when he was pushed through a hatch and chained to an oar. For seven days and nights he had to pull the oar while a big guy lashed his back.

A week later, as my exhausted friend debarked, he asked the steward, “How much do you tip the whipper?” Of course, I'm joking, but you get the idea that every server, no matter how good or bad, expects a tip.

The basic first step for tipping, before you start out on your journey, is to call or email in advance and ask about the tipping practices at hotels, cruise ships, restaurants, sports clubs and other service-oriented destinations for your trip.

Some will respond that there is no tipping required, because as advertised, it was included in the purchase price. However, they’ll add, if the service is good, etc., etc. I remember a restaurant experience where the service was lousy, and I left without tipping.

The waiter chased me outside, demanding a tip. In some cases I ignored that kind of intimidation, and in others I relented with a 10 percent tip. However, I did make sure that waiter knew how poor his/her service had been.

Today, for decent restaurant service, from ten to 15 percent is adequate. If you were more than delighted, 20 percent may be your choice. If you’ve dined in a buffet, where a waiter typically only serves you drinks, a tip of five to 10 percent a person is sufficient. 

Tipping on cruise ships can be intimidating, because in no other travel or restaurant situations do you see so many hands out. Let me count the ways. First, there’s the cabin attendant, who makes it up every day and puts a Hershey kiss on your pillow.

Your tip should be $3 to $5 per day, paid out on the last day. Then, there’s the even more friendly waiter. In the old days of cruising, passengers ate all meals in the dining room at the same table.

Today, there are all kinds of options, and you may see individual waiters only once or twice. The suggestion is to tip for each meal as you would in a restaurant of from $5 to $10 per individually-served meal. On some cruises, there are posh restaurants where passengers pay extra for more upscale meals. You may decide to up the tip to from $10 to $15 per meal there. 

Then there’s the back-up waiter, the one who trails the senior waiter, and puts out water, soft drinks, bread and other bus boy/girl duties. That person should get from $2 to $5 per day.

The rest of the dining crew, the bosses, should be paid amounts of your discretion or nothing at all. They march around looking important, maybe stopping by your table once or twice to ask how you’re enjoying your meal. You may give the headwaiter, wine steward and dining room maitre de $1 for each day of the cruise.

You’re also expected to tip others, such as room service waiters, bartenders and liquor servers at social events, each time you’re served, as you would in a hotel. Something like $2 to $5 per service performed, but be aware that some cruise lines add automatic 15% tip for individual wine and liquor bills.    

Some cruise lines require all tips to be automatically deducted from your cruise account. If you don’t want to have that added to your bill, state it at the ship’s service desk when you board. It’s actually a convenient way without having to tip for each service you get during the cruise, and/or seek out and pay each ship’s employee at the end of the voyage.

For instance, Carnival, Holland America and several other cruise companies may add $10 a day per passenger to each cabin’s account. This is supposed to cover the entire list of employees.

This makes it easier, but many frequent cruisers believe this takes away daily incentive for the crew to provide top service. If you want a simple way to pay all inclusive tips, sign up for the automatic deduction. If you believe choosing to decide at the end of the cruise who deserves what, do your own tipping as you see fit.  

When you cruise or vacation at a resort, understand that in most cases the service providers are paid minimum wages, and depend on tips for decent take-home pay. You need to decide on a balance between sympathy, quality of service and your personal rights.