Live Like a Local: Islandhop the Caribbean

Using your frequent-flier miles, you might be able to visit two cities on one ticket. For example, my wife and I always trade in our Delta miles when we visit our daughters in Dallas and San Francisco. Because we have to fly through Dallas to get to San Francisco on Delta, we can stop over in Dallas for as long as we want before continuing on to San Francisco—and we use only one frequent-flier ticket each.

When I travel for business, I usually tack on a few extra days to do something active like hike in a nearby national park. I find that by taking two small suitcases instead of a single large one, I stay better organized and less burdened. I keep my business clothes, papers, and laptop in one bag and hiking clothes and gear in another. I leave the suitcase I'm not using at the time in the rental car and easily carry the lightweight case with the equipment and clothes I need into my hotel.

I always pack a Petzl Tikka Plus headlamp. It's small, weighs next to nothing, and is perfect for reading in bed at night without disturbing my husband. They're sold online and at outdoor-gear stores for about $33.

If you're traveling with someone, discuss a central meeting place in case you get separated. My husband and I were in Paris waiting to board the Metro. He was able to board the train, but I was left behind on the platform. Having a plan saved both time and needless anxiety.

It can be difficult for parents to find a place to bathe their infant while on vacation. Showers obviously won't work, and the miniscule sinks generally found in hotel bathrooms aren't appropriate either. On our last cruise, we eliminated the whole problem by packing a small, inexpensive inflatable bathtub. (Ours cost only $7.99.) When we arrived, we blew it up and placed it in the bottom of the shower for an instant, safe baby bath.

If you wait to buy a discount-granting Entertainment Book until around six months before it expires (expiration is usually scheduled for November), you can often buy a $20 to $47 book for as little as $10, plus $5 shipping. Online access to the coupons is sold for $7 a month. These are great for vacations out of town.

Don't save the best for the last day. If you wait until the end of your trip for "must-do" activities, you won't be able to reschedule if something unforeseen happens. I planned a snorkeling excursion for my final day in San Diego, but the waters were too rough, and the trip had to be canceled.

I've created files--some general (Southeast Asia), some specific (Hawaii)--for articles and clippings about places I'd like to visit in the future. I don't want all the good tips, restaurant recommendations, and out-of-the-ordinary itineraries to go to waste just because I'm not planning an immediate trip. The files don't have to be super organized--just throw in the clippings, and you can weed through them later. You'll be glad you have the information when you do get a chance to go away.

Try to book the first flight out in the morning, because those planes often arrive at the airport the evening before. You won't have to rely on an incoming plane, which could be delayed or canceled due to bad weather elsewhere, resulting in your own flight being delayed or canceled.

Create your own postcards by writing on the back of photographs that you've taken and developed while still on your trip.

When traveling with my kids, I bring a Ziploc bag that includes four things: Benadryl, children's ibuprofen, one of those little medicine cups, and a thermometer. This all-purpose kit will help with minor ailments, or treat a more serious flu until you can get to a doctor. Best of all, it saves Dad from driving around at 2 a.m. looking for an all-night pharmacy.

Pack a couple of mountaineering carabiners. Clip one through the handle or strap of your bag and secure it to something solid wherever you may be (to a bench in the park or in a train station, to the railing of an overhead compartment on a bus, etc.).The carabiner adds a bit of security, especially if you're snoozing.

When buying bottled water, look at the bottle cap to see if the seal is still intact. While visiting the Acropolis on a very hot day this summer, I caught a young boy refilling empty water bottles from a tap and recapping them. He was then selling the bottles to thirsty tourists.

Some international airlines still give passengers a goody bag that includes a toothbrush, an eye mask, and socks for the flight. Keep those socks: They're handy when visiting temples in Thailand, Vietnam, and Cambodia, where you must remove your shoes before entering. I slipped on the socks and my feet stayed both clean and warm!

On my first trip to Cancun, I noticed that my hotel room had a damp, musty odor. The next time I went, I brought two plug-in air fresheners: one for the bedroom and one for the bathroom. This helped tremendously. It was a pleasure to walk in and have a fresh-smelling room. Just make sure you have an adapter, if you need one.

When you travel to a beach destination, bring your own snorkel gear. We bought snorkels, masks, and fins at home for half-off (at an end-of-summer sale) before a trip to Hawaii. They didn't take up much room in our luggage, and we would have spent as much or more renting the equipment.

If you start to feel a painful blister coming on, put some lip balm or Vaseline on the hot spot--it'll help stop the rubbing.

Recycle the long plastic bags in which you receive your home-delivered newspapers. Slip your shoes into the bags before packing them in your suitcase.

If you're divorced and plan to travel out of the country with your children, check the legal requirements in advance. When I tried to take my kids to Cancun, I learned too late that Mexico requires a notarized letter of consent signed by both parents for minors traveling alone or with one parent or guardian. If the parents are divorced, a copy of the parental custody agreement is allowed instead. The airlines enforce this rule before you get on the plane.

If you're looking for authentic street food--whether you're in New York or Bangkok--don't buy from the pitifully lonely vendor who has no customers. Head to the cart with the longest line of hungry people in front of it. Locals know which vendors serve the best (and safest) food. Even if you have to wait, your stomach will thank you.

When traveling with your kids, give each child his or her own small carry-on bag. Fill it with new, surprise treats to occupy the downtime--layovers, long flights, time in hotels--as well as a few familiar items from home. Include a notebook and encourage your child to keep a travel diary.

Travel soap dishes--the colorful plastic ones that have hinged lids--stop small, fragile items from getting damaged or lost in your bags. I can easily label and use them again and again and again.

Use the shoeshine mitt often found in hotel bath- rooms to store your sunglasses. They fit nicely inside the pouch, and when you take them out, you have a soft material to clean them with. For extra protection while traveling, I store my sunglasses inside the shoe-shine mitt, fold the end closed, and then place it in my glasses case.

Avoid spills in your Dopp kit. Cut up plastic grocery bags into little squares and place them under the tops of toiletries to prevent leaks. Discard the squares upon arrival, but bring extras for the trip back.

To ensure the studs of pierced and delicate earrings don't get damaged, I put them in a film canister. An added benefit is that they're less likely to be stolen when left in a suitcase or hotel room, because thieves presume there's nothing inside but film.

Though they're often the best deals around, don't assume that packaged vacations always offer the biggest bang for your buck. My wife and I were ready to book an air/hotel package to Maui when we noticed a sale on Aloha Airlines ($280 round trip from Oakland). I added up the total cost of the trip if purchased separately and saved $400 over comparable packages from various tour operators. We used the extra money to stay in a nicer hotel and to rent a convertible!

Don't assume you can save a spot at the pool with your towel. Cruise lines give you one pool towel at the start of the cruise. If you don't have it (or a cleaned trade-in) at the end, you'll get charged. If you let it out of your sight, you run the risk of losing it or having it stolen by a fellow cruiser.

Spring skiing often means a wild temperature shift from morning to afternoon. If you want the option of removing outer layers or switching to a lighter ski jacket midday, attach the lift ticket to your clothing with a split-ring key ring. You'll be able to move your ticket as the weather warms up.

A small compass is a great travel aid. Aside from the obvious benefits during country drives or hikes, it's extremely helpful in navigating winding city streets and orienting yourself once you exit a subway station.

If you're stranded overnight at an airport and receive a "distress rate" voucher, call the hotel of your choice before blindly following the airline's suggestion. You may find that for that discounted rate (or a few bucks more) you can stay in a hotel with a lot more amenities than the one the airline would put you in. After a long, mishap-filled trip, anyone can appreciate a really good mattress, a top-notch restaurant, and an indoor swimming pool.