How do you plan your trips?

USCoastieWife

This is the first year H and I both have almost 20 days of vacation.  The past few years we have both been on different schedules (military) and haven't been able to travel much.  I was just wondering how you plan your yearly trips.  We have a few places that we really want to go such as The Royal Playa del Carmen hotel for a week, San Francisco/Sonoma, and London.  

We are pretty flexible about when we would travel to these places.  How do you find out when the best rates to go would be?  I usually use Kayak for flights just to get an idea of what prices would be for which months, but do you have any other tips?  I'd appreciate any advice you have on planning trips.  TIA! 

PAGAS

DH has 5 weeks and I am a SAHM, so we map out things about 6 months in advance for the bigger trips.  We try to do one vacation without our daughter and the rest include her.  We usually look to spend/earn Continental or American miles and use/earn Hilton hotel points or Four Seasons preferred partner hotels.  I find the best place for flight prices is the airline sites, most allow you to browse flexible dates and that is how we start. 

For example, we booked a week in Paris on miles for the week of Memorial day.  For whatever reason, the hotel was 300+ euro unless you booked Sunday to Saturday, where it became 139 euro a night.  We found reward flights that worked with the Sunday to Saturday stay, even though it meant flying through Dulles, because the hotel savings were so good.  The best tip I have is to be flexible, you can find some great deals out there if you don't have to go on a specific day.

bringjoy2theworld

I wish I could say that we "plan."  We'd save a lot of money if we did.  What usually happens is about three months before we go, we go through a list over dinner or even on the way out the door to work which is what happened this year and we just pick somewhere and then look at our work schedules to see what we can make work.  Last year we did Australia on a whim as DH said he'd like to go there one morning as he left for work.  The trip was booked within a week after that.  We haven't had this year's discussion yet although I've mentioned a few places.  Considering your list, I'd probably check the calendars for the cities you have posted to see if there is anything going on that you are really interested in.  For instance, you have to consider the Olympics this summer in London.  San Francisco does a great July 4th celebration, but is pretty packed that week.  So, I'd get a general feel of some major events happening in the places you mentioned and see if you want to include any of those or avoid them.  

cheekywife

we've done a mix of planning 10+ months out, a few months ahead of time, and a month or less. some things are based on weddings/vacation time, etc... i was un/quasi-employed for most of 2010 and 2011 so trips were on hold for awhile.

the main trip we planned really far in advance was our 2.5 week trip to italy and prague (which was also our belated honeymoon). i've booked trips to prague and london like 3-4 weeks before going. our last trip was booked just over two months out. that was one where we based our decision on a few places we wanted to go and then searched kayak for deals for a few different places. we were initially looking at 5 days in montreal and but 7 days in barcelona were similarly priced so we opted for barcelona.

i usually keep an eye on kayak, expedia, travelzoo, and hotwire. when we went to london in 2009, i found the deal on kayak's weekly deal e-newsletter then booked on british airways. also, flying has become such an expense and hassle that we prefer to go places that are further. if we can take a train instead, we usually do.

desmerelda317

First we choose when we can go (DH is military too, so we didn't do much traveling when he was on his sea tour and he was often deployed; but right now he is on a shore tour - for Navy that means he's home-side and doesn't deploy - though he still travels a lot - so his schedule is more predictable for this particular tour and he's more likely to get his leave requests approved).  DH requests the leave.  If it gets approved THEN we start planning  

At that point, we'll choose a destination.  It helps to figure out the high season of your options.  I like traveling during low or shoulder season in order to save money.  For example, in a week and a half we're going to Venice - definitely low season in Venice right now.  But if we were going in February, the prices would be crazy high because that's Carnivale and Venice is swamped with tourists.  A good way to find the low/shoulder season of a particular destination is to head to your local library.  Every guide book has a "when to go" section (usually in their traveler's tips towards the back of the book) and tells you when the "best" times to go are - you can translate "best" as "popular" or "high season."  Choose a month or two on either side of that and you have shoulder season.  Choose the opposite side of the year and you've got low season.  Once destination is chosen I'll actually purchase a guide book of my own.  I'm a big fan of Rick Steve's books and also of the DK Eyewitness Travel books.  I love the Eyewitness Top 10 books because they all come with a handy pull-out/fold-up map that is the right size to make it easy to get around without being cumbersome.  Rick Steve's books give fabulous recommendations for walks that are usually really nice and some of them are off the beaten path too so you get a taste for the local culture.

As for accommodation, I love using www.vrbo.com  We're a family of four that travels with our kids (one toddler, one infant) and vrbo allows us to rent an actual apartment so we have a couple rooms and bathrooms as well as a kitchen.  Cuts down on eating costs because we can make our own meals and everybody sleeps better because the kids can sleep in their own rooms (we all sleep miserably when we're cramped together in the same hotel room).  Also, you can find really great prices on vrbo.com and pay a lot less than you would for a suite in a hotel and you often get to meet a local (the landlord or property manager of the apartment) and that's fun to get an insider's look into the place you're visiting. 

JoNi2010

We first decide how much vacation time we have.  This year, I have 4 weeks.  Then we decide how we want to split those (ie 2 2-week or 4 1-week).  Then we decide where to go - that depends on what we want (ie an adventure trip or a relaxing beach trip or just a backpacking trip).  We usually like to go during off-season time due to prices. 

For research we use tripadvisor.com, kayak.com, and the Lonely Planet online forums and books.

ReenaP

For each location you want to visit, find the TripAdvisor forum for that location (through Google).  Read old posts and various discussions in that forum.  You'll get some great advice.

Sibil

When we can go (h is also military) usually dictates where we go.  We always kind of have a bucket list, so it's a matter of choosing what location is the right one for the time of year, the length of leave, and where we're living at the time.  For instance, a European trip while we live in Hawaii is probably not happening.

I don't book anything until about a month out just b/c we're never guaranteed of his leave.  Yes, that makes it more expensive, but I'd rather than than scrambling to change plans.  In his job, it's not usually a deployment cancelling a trip so much as someone in charge deciding no leave gets approved for a given time period, so that's not really something covered by travel insurance. 

As far as the actually planning once we've decided our destination, I do a combination of tripadvisor and books usually.  If I'm lucky, I can find books in the library.  Kayak is probably my most used booking tool, but I've also used other sites like agoda. 

mxolisi

Last minute. For sure. We both do last minute international travel for work, so we can't plan much unless it's 12+ months out (and even then we end up canceling) or within a few weeks.

For example we're thinking about taking a 5 day trip over President's Day. We probably won't book something until Feb 1 or later.

Presently we have our eyes on Lisbon, Costa Rica, Madrid and a Scandinavian destination TBD. When we know for sure we're free we will choose a destination we're interested in visiting where we can find the most ridiculous airfare deal. Two years ago we took a trip to Rome for 5 days in Feb. for less than $2000 thanks to this strategy. And we didn't skimp on the eating!

Most of our travel is tacked onto business trips. Hence how I've seen most of the Caribbean and my husband much of Africa.