I have to admit that I’m woe­fully behind in plan­ning my travel for 2013. 2012 really kicked my butt and the end of the year left me with lit­tle time—and even less energy—to get down to busi­ness and make reser­va­tions for all the events on my dance card.

Now that’s it’s offi­cially 2013, I have to make some reser­va­tions! I men­tioned this to a friend I was chat­ting with at a New Year’s Eve party and she asked where I begin when plan­ning a trip. I thought I’d out­line my process here and share the online travel tools I can’t live without.

Where and When

I begin my trip plan­ning by fig­ur­ing out where we want to go in the first place. My hus­band and I have a long list of des­ti­na­tions we’d like to visit—as I’m sure you do too—so this part is usu­ally quite easy. Once we know where we want to go, I do a quick search to fig­ure out when is the best time to visit that loca­tion. WeatherUnderground.com is invalu­able in this regard. The site pro­vides detailed fore­casts as well as archived data so you can look up weather pat­terns in pre­vi­ous years in order to deter­mine how likely it may be that you’ll encounter hot or cold weather, snow, rain, sleet, etc. Maps and satel­lite images are pro­vided along with astro­nom­i­cal infor­ma­tion like moon phases. It’s a good first stop when plan­ning a getaway.

Flights

My next step is to secure our flights and ground trans­porta­tion. We have nearly three mil­lion fre­quent flyer miles so we gen­er­ally fly on award tick­ets. That takes a bit more plan­ning thanks imply buy­ing a ticket. I begin by search­ing Kayak.com. I want to see who flies to our tar­get des­ti­na­tion and what con­nec­tions make the most sense.

Book­ing Fre­quent Flyer Award Tickets

Once I know who flies our pre­ferred route, I deter­mine if I’ve got enough fre­quent flyer miles in my account to cover the tick­ets. Rather than log­ging in to each account sep­a­rately, I use Award Wal­let to keep track of my bal­ances at a glance. The only down­side of Award Wal­let is the fact that some air­lines like Amer­i­can and United won’t play ball and don’t allow the site’s app access to your indi­vid­ual mileage data. That means I always have to log in to a few airline-specific sites to check bal­ances before deter­min­ing what account has the miles I need to book the award tickets.

Join Award­Wal­let for free and the first ten Lux­ury Travel Mavens read­ers to use coupon code free-qamsth will get a free upgraded membership.

With my fre­quent flyer bal­ances in hand, I log on to Expert­Flyer, a site that shows award and upgrade avail­abil­ity for many air­lines in addi­tion to flight avail­abil­ity and seat­ing maps. This is a paid ser­vice so you’ll need to pick from a Basic mem­ber­ship ($4.99) or Pre­mium ($9.99). Expert­Flyer allows you to track award and upgrade avail­abil­ity and even has Seat and Flight Alert fea­tures that you can pro­gram so the site will con­tact you as soon as your pre­ferred flight opens up award tick­ets. This is per­haps the one site I use most when plan­ning my trips.

Lux­ury Travel Mavens is an Expert­Flyer affil­i­ate. If you feel you’d ben­e­fit from the ser­vice, we’d appre­ci­ate it if you’d sign up via our link below. Thank you!

Get the most from your Fre­quent Flyer Miles — Find Flight Avail­abil­ity, Flight Upgrades & Awards, Fre­quent Flyer Infor­ma­tion and more with ExpertFlyer.com

Help from the Masters

When I hit a snag and can’t get the air­line award seats I need, I call in a pro for help. I like both Points Pro (a knowl­edge­able team lead by rock star blog­ger Ben Schlap­pig of One Mile at a Time) and Book Your Award, which is run by the mas­ter of miles and points: Gary Leff of View from the Wing.

Ground Trans­porta­tion

With air­line con­fir­ma­tions in hand, I move on to book­ing any nec­es­sary ground trans­porta­tion. We gen­er­ally take a car ser­vice to the air­port and my favorite is GroundLink. This isn’t the cheap­est way to get to the air­port but it’s the fastest and most con­ve­nient. You can book online or via an app on your smart phone. The app alerts you when your car is approach­ing and it makes for con­nect­ing with your dri­ver at the air­port a breeze. It’s well worth the pre­mium price but there’s always a coupon code to be had. Just Google “Groundlink” and “coupon code” and you’ll find a bunch of options. I’m gen­er­ally able to shave 10–15% off the orig­i­nal rate using this method.

We don’t rent cars often but friends of mine rave about AutoSlash. This aggre­ga­tor will show you rack rental rates as well as dis­counts for any codes you pro­vide. The bonus is that if you book through AutoSlash, the site will re-price your rental sev­eral times a day. AutoSlash will rebook your reser­va­tion if it finds a price drop or a bet­ter dis­count code. That’s very useful.

Trip Insur­ance

We tend to plan some mam­moth vaca­tions in terms of dis­tance from home. We’ve spent time in Sin­ga­pore and Bor­neo, French Poly­ne­sia and South Africa. Some­times we self insure but for big trips we opt for travel insur­ance. We main­tain an annual Met­Je­tAs­sist mem­ber­ship so I don’t worry about mede­vac ser­vice since we’ve got that covered.

For tra­di­tional trip insur­ance, I use two sites to com­pare pack­ages and prices: Square­Mouth and Insure­MyTrip.

On-Route Assis­tance

Once we hit the road, I rely on an app called TripIt. It stores and presents all of our flight, hotel, ground trans­porta­tion, and rental car reser­va­tions in one easy-to-access app. You can load it onto your iPhone, iPad, Android, Black­berry, or Win­dows Phone 7. There is a free ver­sion as well as TripIt Pro for $49/year. Pro offers a lot of good fea­tures like instant alerts about flight delays and gate changes as well as help­ing you find alter­na­tive flights when there’s a mechan­i­cal or weather issue.

Cranky Concierge can help get you home when things go wrong at the airport.

If you’d pre­fer a live per­son help­ing with your on-route travel, con­sider work­ing with Cranky Concierge. This ser­vice is the brain­child of blog­ger Brett Sny­der. He and his team will per­son­ally mon­i­tor your flights, watch for prob­lems liked delayed air­craft and research alter­na­tive flights to get you on your way. Domes­tic flight mon­i­tor­ing is $15 each way and inter­na­tional itin­er­aries are $30 one way.

What Online Travel Tools Do You Use?

I’d love to hear about the online travel tools you use to keep your trips run­ning smoothly. Com­ment below and happy travels!

—Andrea M. Rotondo for Lux­ury Travel Mavens