If you've managed to save a lot or even a little, you're probably in a position to take a vacation. I'm currently constrained to the kind of vacations that one can take with a one year old, so my needs are much different than a single male or a couple vacationing without children in tow.
I only recommend vacations once you're out of debt.
Reminder: debt is defined by high interest luxury expenditures: car loans, credit cards, HELOCs, and any money you owe Vito. Mortgages and student loans are still technically debt, but they'll be with you for a long time and can be safely considered monthly expenditures.
The kind of vacation is up to you. And your budget. If you've got a ton of cash to burn, exotic locations and beach resorts are probably OK. But if once you buy your airfare and hotel, you're looking like you won't be able to eat or even rent a snorkel, it's time to think like a Minimalist.
1. Eat in. Always eat in, even if you're a billionaire. When Tammy and I took our babymoon in Kauai, our condo had a kitchen. We even got the discount card for the local grocery chain.
2. Off season is cheaper and more fun. Sure, it's hurricane season in Mexico, but the airfare was cheap, as were the hotels. Sure, an actual hurricane hit, but now I can say I weathered a hurricane. The most memorable experiences never happen in tourist towns during peak season.
3. Find appropriate lodging. Make sure it has a kitchen. On Tammy and mine's recent roadtrip down to Socal and back, we lodged only at the houses of our family. They have nice kitchens, of course, and you can repay your kind hosts with meals and chores. Or you can reciprocate when they come to the area. Good friends are also nice for accommodations, but I find that they have to be really, really good friends or I feel bad about imposing.
4. Don't buy trinkets. As a kid I remember loving to buy a cheap souvenir at all the places we visited. But it was totally unnecessary. They just wound up as bookends and are probably in the land fill right now. Souvenirs can be as simple as a jar of sand or pretty rock or a shell (I like the beach, can you tell?), or a picture, or a memory. Practical clothing is OK, and I still remember my trip to Buenos Aires whenever I wear my El Cid shirt.
5. Think short and simple. This is especially important for travelling with children. While the rappelling adventure through la selva Costa Rica sounds neat, getting your toddler to Costa Rica, much less the grueling, long, and very scary bus ride to the summit isn't worth it. Wait til they're older, then drop them with Grandma and go without them.
6. Avoid packaged tours. They'll only take you to the tourist destinations and the tourist restaurants and the well-beaten path. Stay in hostels and make new friends (even possible for folks travelling with kids). Get to the museum at opening time on free admission day and not only will you beat the crowds, you'll have money left over to splurge at the grocery store.
7. When travelling with young children, think local. Just like our produce comes from farms within 100 miles, so too can our weekend getaways. For instance, we're going to rent a cabin in the woods near a beach town. We can get there in under an hour and still feel like we're in a whole new country.
Plan your vacation in advance, even if it's just a sort-a kind-a gonna start in Costa Rica and finish in México two months later. For the young and unattached, a brief outline will do, and a good travel book (Lonely Planet is the publisher we use). For the attached and/or travelling with wee ones, specific destinations with naps timed to flights and car travel are a must. And most important, plan for the unplanned. Be prepared mentally and budgetarially to spent an extra night in any destination to a) recover from a stomach bug (Arles, France), b) not expose your newborn niece to your daughter's stomach bug (San Luis Obispo, CA), c) rest up from sheer exhaustion from an aborted trekking expidition through the Pyrenees (Girona, Spain), or d) escape a hurricane (Mérida, Mexico).
Travelling through Central America for two months with a backpack seemed hard, until I tried a one-week roadtrip with a one-year-old child. The latter was so much harder. We could always just stop in a town for a few nights to recharge, but with Viola we have to always be "on" and the entertainment options have to be geared towards duck ponds and swings and slides. My point is, know what you can handle--that means budget, distance, comfort, and amenities. If you need A/C in Léon Nicaragua because you can't take nights where it doesn't go below 90°F, then well, so be it, make sure you've got that in the budget somewhere ($40 vs $10 cada noche en 2002, FYI). If you need a toddler bed, that's going to cost more (which is why we have more family-oriented vacations right now).
Next time, I'm going to talk serious again, specifically about online banking. Why should you use it, and how to (again) make sure the banks don't screw you.