We love to travel and we've found these three principals have served us very well: Research, Patience, and Decisiveness...
Research: We typically end up going to Vegas and Disneyworld at least once a year. I find if I start scouring the travel forums (redflagdeals, fatwallet, flyertalk) I can usually find a good deal or two for the time period that we're looking at going. I am a research nut, so this part is actually fun for me!
Patience: We are fortunate to both have jobs that allow us some flexibility on when we take our vacations. Sometimes if we're willing to even wait a month or two we can literally save ourselves hundreds if not thousands (i.e. Disney Dining Plan for free in Sept)
Decisiveness: If we have done our research and we know what the avg flight prices have been looking like, and what the general hotel rate is, then when we see a good price on either we pounce. Patience is necessary, but we don't let it become procrastination!!
If you're looking for vacations in popular destinations (Mexico, Cuba, Jamaica, etc), and you are able to leave on short notice, then try watching for last minute deals on websites like selloffvacations.com, travellastminute.ca, sunquestvacations.ca, and other websites you can find through google searches.
If you'd rather have more time to plan your trip, try searching for flights on kayak.com Depending where you live, sometimes you can get the flights even cheaper by flying Westjet to a major city like Toronto or Vancouver first. So try using other cities where you would normally change planes as your starting point, and see if you can find a good seat sale.
Last year I got a flight from Vancouver to Bangkok for under $700 (incl taxes), and I just paid another $320 to fly Westjet to Vancouver. There's no rule that says you have to buy all your tickets in one place, just make sure you have enough connection time!
Here in Montreal, instead of flying from Montreal to Las Vegas or to Florida we used the discount air lines from Burlington airport and Plattsburgh airport. The destinations are pretty limited since those are small (read tiny) airports. You need to drive to those airports but the fares are so cheap that it is worth the drive (approx 2h from Montreal depending on the border wait time). Also the parking is free at Plattsburgh airport (don't remember for Burlington).
And to give you an idea, to go to Florida from Plattsburgh the price was at least 50% cheaper than from Montreal and we could have got a better deal if we would have bought the tickets last minute.
Book a hotel room as a backup that can be cancelled and then use priceline or hotwire to get a good deal. You can use sites like betterbidding and biddingfortravel which help you figure out strategies to get the hotel you want. I've used this technique VERY successfully to save THOUSANDS on travel. For example I stayed in a very nice Marriott hotel in Fort Lauderdale before a cruise once for $40 a night using priceline.
We like to camp which saves us a lot on accommodation. Breakfast is in camp, we carry coolers and stop in parks for lunches. This allows us plenty of discretionaru funds for meals in restaurants and going to see attractions. If the weather is too wet then we can book into a room. Often the meal out of the day is lunch which is always cheaper than dinner out.
I also regularly use PriceLine and HotWire to book hotels and rent cars. A good tip is to book hotels that are close to the airports of the city you plan to visit...these hotels normally have shuttle buses that ferry passengers back and forth from the airports to the hotels and vice versa...save you some money on the cabs as well as the time and distance traveled...you certainly do not want to miss your flight, especially with all the security measures the airports have put in place.
Another tip is try to combine multiple activities in 1 trip (My wife doesn't agree with this but we always find a compromise). I am a HUGE NFL fan who would love to attend at least a game in all 32 stadiums in the league. We did a cruise last year from Miami and i was able to go to a Miami Dolphins game after we disembarked...it's unlike we will come back to Miami again, been there and done that so it was nice to get what we wanted in 1 shot...we also plan to visit Vegas this fall and I will once again rent a car to visit the Grand Canyon and attend an Arizona Cardinals game. My philosophy is because we are already there, may as well kill 2 birds with 1 stone.
Sometimes getting off the tourist bandwaggon can save you a ton of cash.
Countries like Guatemala can offer you a great opportunity to see and do many amazing things at amazing prices. You pay for being catered to, so if you can get away from tourist packages, you can often put together a great (cheaper) trip yourself. Researching and a little language training goes a long way.
I usually pack food for long car rides and plane trips, although I got in real trouble once when I apparently tried to "smuggle" apples along for a plane trip to California.
Someone else has pointed out that having a kitchenette in your accommodation usually can save a lot of money by avoiding eating at restaurants.
I've signed up for the Fairmont Presidents' Club (free) and get periodic emails about pretty great deals in their hotels. Being a member also gets me other stuff like free Internet in my room. I'm sure other hotel chains have similar programs.
Once in a while I can find a conference in my professional field, in a place that I'd like to visit. Usually I can get some money from my employer, my union, and professional association to help cover some of the costs.
Oh yeah....I also try not to do my traveling during vacation season. It's cheaper to travel off-peak, plus the summertime is the only time we have any decent weather around here....I'd hate to miss it.
Another thing I have used is a City Pass http://www.citypass.com/
This is a bundle of tickets to major attractions in about 10 different cities. If you are planning to see the tourist sites of a place like, for example, New York, this can save you some cash.
Although not appealing to everyone www.couchsurfing.com is a great way to meet local people and have a place to stay. Probably the ultimate frugal accommodations.
Also, instead of staying in hotels, try looking up short term apartment rentals. Especially when travelling in groups. 4 people could easily stay in a furnished apartment or villa for $1000/week or $250/pp
I think deciding where to travel last minute helps save money and adds some excitement! If you can have no plans until last minute, shopping for a vacation this way can save you a lot of money (I know, comparing a NECESSARY long-term planned vacation, with an advertised price for the same location and hotel on a last minute basis!). As a bonus, you have a greater likelihood of having great weather, basing it on weekly trends instead of hoping what the weather will be like months in advance.
Don't travel, that is. There's nothing more pleasant than a two-week vacation spent in Veranda Beach: your back yard. No flight connections to make, no luggage to lose, no overpriced meals and a ton of savings. You could of course eat out a little more during such a home-based vacation, rationalizing that you're on holiday.
Here's my recent account of my own "Holiday from hell."
I've driven across Canada, Spent a month in Europe back packing, Spent time in several US cities, and now going to spend 2 weeks in Hawaii. Despite the cost and frustrations that arise I wouldn't trade that for anything. I think seeing new things is definitely worth the cost and I just make sure I have the funds to do it and it doesn't take me away from my retirement plan.
Even one of my dumbest trips is filled with great memories....drive 17 hours to Halifax...spend 22 hours there....drive 17 hours back and all for the McLobster at MacDonald's.
I've found cottage (cabin, for your westerners) rentals to be a really enjoyable and economical vacation plan. It's not your own cottage, so you actually get to relax, and it gives you a base in a new locale to explore from.
Before kids, we used to travel the world, and saved money by staying in hostels. Most had private, basic rooms for just a bit more than the shared accommodation, but still way cheaper than a full hotel room.
Now we tend to 'stay-cation', doing road trips within a 1000km radius, usually for 4-5 days at a time. That's enough to satisfy our traveller souls for now, and long enough to be on the road with young children!
Agree with MFD, though, not travelling is not really an option for us. My hard work keeping our finances sound is done so that we have money to do things like travel.
I have to disagree with you folks who think traveling is not recommended/a good idea. The world is a big playground and there are lots of places to see and things to do, even within Canada itself, i wonder how many folks here have gone from coast to coast...
Canadians are well-respected around the globe and we have a great reputation. I personally think traveling opens your eyes and minds and it will teach you a lot of lessons. Jon, as a matter of fact, the front page story of last Saturday's National Post talked about kids traveling and volunteering during their gap year, if memory serves me well.
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