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There is a running joke in my office. Every Friday, one of my co-workers will say to me “where are you running off to this weekend?” or “what exotic island are you visiting this week?” And I will answer “don’t I wish” with a devilish grin. Why the grin? Because little do they know, I am always less than 3 months away from my next beach adventure. How do I do this? How can I afford at least 6 vacations a year? And how can you do it too? Simple – PLAN THEM.

Now when I say 6 vacations a year, some of those are quick, long weekend get-a-ways; but at least one (or two) will be a week-long adventure. Here are a few rules I live by when planning my vacations for the upcoming year:

Rule #1 - FLIGHTS: I book flights at least 4-8 months in advance. I very rarely buy last minute flights, unless it's an absolutely can not pass up deal. I prefer to have as much of my vacation paid for prior to hitting the ground. By booking in advance the flight in advance, I have time to pay it off completely prior to traveling.

Booking my flight is a process. I typically have a price in mind for airfare to a particular destination because I have spent time tracking the airfare. I begin watching airfare at least a year in advance, checking the price during high and low season. This gives me an "average" cost and helps me determine how much I'm willing to pay for my airline ticket.

I typically spend time checking the obvious sites such as Orbitz, Travelocity, etc., however the ITA Software Matrix has become my best friend. On this site you can see airfare up to 30 days ahead of your requested departure date. This way, I can see what departure/return dates.

But I also check the actual carrier’s website for unadvertised deals and I’m able to play around with dates easily to find the best price. Most carriers have a calendar feature that will show prices for the entire month, so unless I’m traveling for a specific event, I will remain flexible with my dates (and location). I shop airfare for at least a week before booking and I prefer to book my airfare on a site that comes with a price guarantee so that I get a refund if someone books the same flight at a lower cost. I also know that Monday is the probably the worst day to book a flight and Tuesday and Wednesday are the cheapest days to travel. So, I keep this in mind when planning my escape. Also, I set up alerts on websites such as to keep an eye on flights I’m interested in. If a flight is rising above my threshold, I made a decision to buy; or reschedule that trip.

If booking my flight and hotel together is cheaper than booking separately, I do so. But I take the time to check and make sure it’s actually cheaper. I go to the hotel’s website directly and check the rates; again there could be an unadvertised special. I also call to see if the hotel can offer a better deal than what is being offered on the internet. You don’t know if you don’t ask.

Rule #2: A refrigerator, and maybe even a microwave, is a must in my hotel room. This way, I’m not blowing my budget eating out every meal of the day. For my long weekenders, I always keep quick breakfast items in my room. A bagel, breakfast bar, cereal, juice and some fruit will get me to lunch. I always take advantage of a continental breakfast that is included in the cost of the room.

When traveling for a longer period of time, or with my children, I prefer to use a timeshare unit with a full kitchen or rent a condo. This way, I can cook a few meals. I also keep snacks and items to make a sandwich for those days when we’re hanging around the pool to get us from lunch to dinner without buying another meal.

Another tip - a refrigerator to keep beer or other alcohol cold can save a bundle!

Rule #3: I try and bundle my trips. For instance, if I’m in Cancun, I will visit Cozumel and Isla Mujeres. When I went to St. Maarten, I took a ferry over to Anguilla. When I took my kids on a cruise to the Bahamas, we came back and spent a few nights in Orlando before flying home. Next year, I’m planning a trip to the U.S. Virgin Islands and will take a ferry over to the British Virgin Island of Tortola for a couple of days. Catch my drift? It’s much cheaper to extend your vacation a day or two and visit a neighboring city, island or country than to buy another ticket to return.

I also travel like the locals. I use public transportation versus cabs, or rent a car if I know I’m going to be doing a lot of moving around. I will also take advantage of any transportation the hotel offers, i.e. a shuttle bus into downtown or to a popular tourist spot.

So there you have it. I have other tips and tricks that I use, but these 3 will guide me to a year of what seems like, at least to my co-workers, constant vacation.

Happy Travels!

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