Back in 2012, someone approached me with one simple question: “How can you guys take so many vacations?” I answered her as honestly as possible – it’s a combination of planning, leveraging opportunities, and making travel a financial priority.
While I’m no longer working with people who say things like, “you’re gone so often” (which wasn’t true) or “must be nice to be rich” (we weren’t) there are still those who think we spend a fortune on travel. I’m not going to lie to you. Some trips have been very expensive (Alaskan expedition cruise) and are outside the means of many typical Americans. It truly was the trip of a lifetime and I am so thankful that we were able to make it work.
I don’t apologize for the expensive trips we take, but at the same time I don’t think anyone should feel bad (about themselves, or us) for not being able to do them.
For every two week trip to Alaska or Tofino that we take, there are many more trips to Hawaii done on the cheap. I don’t think anyone out there would say that going to Hawaii isn’t an equal comparison. They are quite different trips, but Hawaii is no slouch in the awe department.
So, following the conversation referenced above I sat down and wrote a pretty long post on the old blog about some of the ways we’re able to bring our vacations to fruition. Not all of the information I shared then holds up today – we’re very different people than we were even three years ago – but a lot of it is still pertinent.
So here, my friends, is how we travel so darn frequently and how you can too (updated for 2015).
1. Don’t Stay in Five Star Hotels
When looking to travel it’s nice to salivate over the ocean-front resort or the posh place in the middle of the city, but the reality is those places can be expensive. Ask yourself if the money you’re going to spend on a room is worth not spending the money elsewhere. This is sometimes hard to do because the websites and pictures of these places are designed to draw you in, to make you feel like staying anywhere else would surely be a sacrifice. Most times, it’s not a sacrifice at all.
Over the years we’ve stayed in five star properties that were somewhat lacking. For example, the last time I traveled to Portland for work I stayed downtown instead of in the suburbs. My company’s travel partner only had one hotel downtown that I could book and so I did. It was one of the highest ranking hotels in the city and it was expensive, but still somehow within the allocated budget so I booked it. Almost everything that could go wrong with a hotel stay did. Our room wasn’t ready until well past check-in. The room they put us in was right over the kitchen and was incredibly loud. They switched my room but that one was dirty and needed an update. The valet took 40 minutes to bring me my car and I missed an early morning meeting. I had wanted to stay at that hotel because it was supposed to be a luxury experience. It wasn’t. You know what was? The hotel up the street that we stayed at on our previous trip and paid nearly $100/night less for.
To that point, I’d say that more times than not, my experience is that a hip, well-regarded boutique hotel will always be a better experience than the big five star property. Of course there are exceptions to the rule, but I would wholeheartedly recommend you check out those properties first.
If you do have your heart set on a five star property, I recommend looking at Priceline or Hotwire for your booking, although I say this with a huge caveat. As you know, you won’t know which hotel you’re booking in advance, but in general these sites work with the major brands. A handful of times we’ve gotten a boutique property that I’d put squarely in the three star range, but that was an anomaly more than the norm. What I will say in warning is that sometimes Hotwire especially will classify a property as five star when it is decidedly not. An example of this was the Sheraton Wall Centre in Vancouver. It was a large property and on paper had all of the amenities you’d expect of a luxury property, but in reality the hotel had seen better days and was in desperate need of a refurbishment. It had become a tourist-class hotel and the staff there did not treat its guest as you would expect in a five star property. Since then it has been downgraded to a four star, I believe, but I’d say that’s even a stretch. So … buyer beware.
2. Consider Renting a Condo, Apartment, or House
The majority of our trips to Hawaii are condo style vacations. We enjoy the flexibility this provides us, including the ability to cook our own meals and have separate space when our sleep schedules don’t sync up (that’d be me). I can’t tell you the amount of money we save grilling fresh fish, sometimes straight off the boat, at these condos compared to what we would spend eating out every night. When we were in Maui for our 10th anniversary we ate at our resort’s restaurants nearly every meal and it was pricey.
What’s more, we’re finding that frequently these condos are coming equipped with beach furniture that means we don’t have to buy our own which saves you a lot of cash. The condo we rented in Kona in 2011 from VRBO came equipped with a garage full of snorkel equipment, boogie boards, chairs, and coolers. The condo we exchanged for in Kauai in May 2012 and 2013 came with a cooler and beach chairs. The last two condos we’ve exchanged into in Kona didn’t come with this equipment, but we were able to rent it from the manager immediately upon checking in, saving us a trip to the store to hunt down everything we needed, and the full price of brand new items.
In terms of straight rentals (not timeshare exchanges) if it’s just two of you traveling it can sometimes be hard to find a nice, small unit. I fully admit this. I looked into booking a place up in Lake Tahoe for this year’s 4th of July holiday and the only nice places available were giant cabins that could easily sleep 8-10. Obviously they are priced accordingly so they were outside of our intended budget.
The other problem with sites where anyone can put their property up for rent is that there is no such thing as quality control. You have to review the pictures carefully, read the reviews, and ask the owner questions about anything that is of particular interest to you. For our trip to Maine next month, this is the first time in the history of our travels that we have rented a place that has zero reviews on the rental site. I feel okay with this because I know that the house has been in the same family for years and they have only now made it available to outside parties. The woman who manages the bookings asked for testimonials from friends of the family who have used it throughout the years, so I am confident that the place we’ll arrive to will be as described in the photos.
(Note: if you’ve been interested in buying into a timeshare but you think it’s too expensive, we have been looking to sell ours and are willing to talk. It really is a great option for families but as it’s just the two of us, more and more we’re finding that we’d like to travel using alternative methods of lodging.)
3. Find a good rewards program
Over the years we have belonged to a handful of rewards programs, some more lucrative for us as travelers than others.
The first program we signed up for was the Citibank Premier Pass and over the years we made it to Elite level status. The first trip we ever booked with those reward points was roundtrip airfare on British Airways from SFO to Rome. Our entire flight was paid for. Back then international flights weren’t the expenditure they are these days, but it still saved us nearly $2000 on the total cost of the trip. That was in 2006 and was without a doubt the best value we ever got from this card.
[A note about that trip to Italy: We spent less than $4000 for *everything* on that trip, including hotel, food, and train. Having our airfare paid for was a huge savings, but we were able to keep costs low by staying at a quaint, three star property in Rome that was steps from the Trevi Fountain that cost $139/night and a small b&b in Florence directly opposite the Duomo that cost $125/night and both were completely adequate for our needs. Even now with much more experience under my belt, I’d go back to the property in Florence in a heartbeat. In fact, if we ever return – which we plan to do – they will be my first stop in trying to book.]
Over the years we used that Citibank reward program to book flights to Vancouver when they were over $700/person, and several times we’ve gone to Hawaii by using our points.
Last year we stopped using this card because the fees had gone up while our perceived value had gone down. While it no longer worked for us, I wouldn’t hesitate to recommend it to someone that was looking for a card that had good reward offerings. (Note: I think they’ve phased out this program and have a similar option under another name.)
Even though we no longer planned to use the card, we still had a number of reward points left to use so to spend them we booked a week in London at the Hilton Hyde Park. If we had spent our own money, the hotel would have been anywhere from $299/night to $349/night, depending on when and where I checked rates so it effectively saved us anywhere from $2100 + tax to $2400 + tax. Since London was a place that we’d really wanted to go to for several years, while somewhat last minute in terms of how we travel, it wasn’t a trip that was necessarily booked on a whim. We only took advantage of it because we were able to combine several rewards to get to London and back.
As you can imagine, flights to London from SFO aren’t cheap. In fact, to my point above, we probably wouldn’t have taken the trip if we also didn’t have more Virgin Atlantic reward points than we knew what to do with. We’d only flown Virgin Atlantic one time prior, but after a more than 24-hour delay to Scotland, the company flooded us with reward points as a gesture of good will. For our trip to London we used them to get seats in Premium Economy (which I find fantastic on this airline!) for the price of economy (coach) seats. So yes, airfare was still expensive considering, but we had a really excellent flight by cashing in our rewards. We still have thousands upon thousands of reward points and I have no idea how we’re going to use them before they expire. Maybe once we’re in Ireland we’ll pop over to London all the damn time?
Alaska Airlines has another reward program that we’ve made use of throughout the years. A handful of times we’ve used our points on free flights to Hawaii, and once to upgrade to first class. I’m not flying up to Portland as frequently as I used to, and the few recent flights we’ve taken where Alaska has a route ended up being cheaper on Southwest so we’re not racking up rewards as quickly as we used to. I don’t think we’ll be able to make use of the points we do have before we move to Ireland, so it’s no longer the right rewards program for us, but if you live on the west coast and fly routes here frequently, it’s definitely worth looking into. Also, they have an excellent companion ticket program that we didn’t know about until last year, so if you sign up for an airline rewards program, definitely be sure to look into that.
And finally, here is the last point I want to make but I think it’s probably the most important one of all.
4. Be Flexible!
Flexibility is absolutely important if you’re looking to get the best possible deal on your vacation. If you absolutely have to be at a certain hotel in a certain part of town, Priceline and Hotwire are never going to be the option for you. If you need top-of-the-line resort style condos, timeshares aren’t your cup of tea either.
And using the timeshare? They have what they have and you need to roll with it. For our last trip to Kauai, there were no timeshares available that I was willing for us to stay in during the week that I wanted to travel (note the use of “I” versus “we” in this statement – I plan everything, and Alan says yay or nay and then comes along for the ride). The following week there were three options. True, it meant that we wouldn’t be on vacation during my birthday, but it also meant that we could be in one of my favorite places in the world the very next week.
When all is said and done, does three days really make a difference? In this particular case, no. For some it might. I know that I was adamant about being in Maui *on* our 10th wedding anniversary, so in that case, flexibility was not an option. That was a very special occasion, and I would never advise you to compromise during some of life’s most important moments. But for the everyday ones? Yeah, flexibility never hurt anyone (except me, physically … I can’t even do the most basic yoga poses). This year was our 13th wedding anniversary. Quite the reason to celebrate, but still … nothing available with our timeshare during the week of our anniversary. What did we do? We waited a week and airfare dropped to $400/person roundtrip direct (this price has been particularly hard to find the last couple of years) and we booked a condo at a place we really liked. When we checked in there were some problems, but we ended up with an ocean view. Our celebration of our love was no less because it happened four days late.
5. Don’t Travel During High Season
The absolute #1 part of my “be flexible” rule above is to TRAVEL DURING OFF SEASON. I know that’s not always possible for everyone, especially if you have kids and the only time you can take a family vacation is the middle of summer, but if there isn’t anything preventing you from traveling during shoulder and low seasons, you should definitely give it a try. We managed to spend 12 days in Ireland in November staying in amazing hotels, manor houses, and castles for a fraction of what one week would have cost in July or August. The trade-off, of course, is that you may encounter less than ideal weather but for us that’s not really a consideration since I can’t deal with high summer temps anyhow. Also, keep in mind that if you travel in the winter your daylight hours are limited so you really have to pack everything into a shorter window. That’s fine since our vacations tend to be go, go, go and we’re not at all the types to simply hang out in the room when we could be off exploring. If you value a more leisurely pace, that’s definitely something to consider when making your own plans.
By traveling during typically off times, we’ve had the Colosseum practically to ourselves, saw not another soul at Dunluce Castle, had a personal tour at Bushmill’s Distillery, and any number of other experiences that weren’t marred by hordes of other travelers milling about.
If you have any questions, would like anything clarified, or want some advice about your own trip, do not hesitate to ask in the comments section below.