Oh hello, it’s me, your favorite travel blogger! Just kidding, of course. I’m your favorite blogger who resisted choosing a niche and ignored all blogging advice but somehow I’m still writing it and you’re still reading it. This post is in response to popular demand for my hotel front desk staff schmoozing skills, and also in an effort to be more transparent about how my husband and I afford to take so many fancy vacations as non-fancy people who shop at Costco (and, at least in my case, was raised on peanut butter sandwiches consumed in a Crown Victoria station wagon overflowing with children en route to the Holiday Inn). I wrote it on my flight home from vacation with a glass of wine in hand so please excuse my typos, bad jokes. and rambling tangents. I hope this changes your life?
Thanks to my work travel demands, we get to do a lot of travel for free,* like last year when we stayed at the Ritz Carlton in Hawaii entirely on points. We enjoyed a beautiful room, amazing views, and an incredible pool — and we could have easily racked up expenses on food, drink and things that didn’t add value to our trip, but we didn’t because we are very strategic spenders on vacation even when we’re not paying for the accommodations.
We just came back from a trip to Bermuda where we couldn’t use points because there are no Marriott properties on the island (WTF, Marriott?!) but we were able to plan an affordable four star experience staying at the Fairmont on our personal dime thanks to some thoughtful planning and creativity. As I shared highlights of our trip on Instagram, I got some questions about how we can afford to take luxury vacations and realized that I might be sending the wrong message by not sharing the facts behind how we plan and pay for our trips.
So the purpose of this post is to shed some light on our vacation budget management strategy for those who might find it helpful. I believe one of the reasons we have a growing gap in financial literacy — especially in women (who earn less, save less, spend more and struggle at much higher rates than men) is because we don’t talk enough about money management in general, or how we afford our lifestyle choices in detail. Although we tend to get uncomfortable talking about money, I think it’s not doing us any favors in a world where we’re constantly referencing highlights of people’s lives on social media. It has the power to make us believe things about wealth that are not true — specifically, that “being rich” is basically spending frivolously and thoughtlessly, funded by an endlessly replenishing bank account. Every successful person I’ve ever met would say the exact opposite is true, and that’s what we’re going to talk about in this post.
Although Wes and I are very privileged (in our backgrounds, our education, and our careers), we know that there’s no such thing as a guaranteed future, an endlessly refilling bank account, or a magical retirement plan that will materialize for us when we hit 65 — and we also know that our financial responsibilities and accountabilities will only grow larger with time.
We want to be as smart as possible with our money in order to live our best lives today, while also setting our future up for success long term — two polar opposite, but equally important, goals that can only coexist with strategic thinking and good habits around money. I love learning about philosophies for saving, investing and spending from smart people who I respect and who also have lifestyles I admire to add to our book of tricks on this topic. (I personally don’t have a lot of billionaire friends with unlimited trust funds who are able to spend thoughtlessly, and even if I did, I think I’d find their POV on money philosophy pretty boring.)
Below are some of the tips and guidelines we use in planning and during our vacations that have helped us to travel and have a four star experience on a two star** cost structure — I hope you find it valuable!
*I use the term “free” lightly — technically I paid for it in time I’ll never get back working for the man.
**I use the expression “two star” lightly — we still pay quite a bit, but these tips can be applied at any budget to make your money work harder when it comes to vacation.
Tip #1: Get really clear on what you really value in a vacation, and spend ONLY on that
One of the best pieces of advice related to money philosophy I’ve ever heard is to focus on what you value, spend liberally on that, and save everywhere else. We’re really intentional in our planning and in our habits while we travel so that we’re not mindlessly wasting money on things that don’t add to our experience or give us joy.
From a beach vacation perspective, Wes and I value the geography — going to a place with great weather, staying in as nice of a hotel as possible so we can be in a super walk-able location with great built-in amenities to use the whole trip (like pools and beaches), and attractions for a history buff and an art lover.
We also value efficiency in how we spend our time and value the ease of our experience so we’re focused on relaxing and enjoying each other’s company. We don’t value food, drinks, souvenirs or pricey excursions so that’s where we save.
Tip #2: Book all flights to be on “off” travel days — typically a Tuesday or a Wednesday — and limit variable expenses
This is pretty easy. Most business travelers fly on Mondays and Thursdays, most leisure travelers fly on Fridays, Saturdays and Sundays, so the other days that are left are typically the best departure and return dates for cheaper pricing. We typically find the best deals 6-8 weeks ahead of time. Also, we like to pack our own snacks, bring a water bottle and use the filling stations at the airport for health reasons and for humoring my CPA husband's aversion to $7.99 Smart Water. It’s just water, but Jennifer Aniston drinks it so we forget that some people make that amount for an hour of work. So.
Tip #3: Choose accommodations based on what you value
We value location, where we can leave the property to explore, dine locally, and have access to amenities that we’ll use every day — like an amazing pool and beach access. We’ve booked four star hotels in the most expensive cities for under $400 / night.
We can plan to spend $400 / night on a hotel room because we know that we won’t be spending hundreds on food / drink and will be saving on experiences because our cost includes built-in entertainment.
If we were spending $200 a night, $50 in transit, and another $150 on food / drink each day it would amount to the same but not a “four star experience” in our book because we’d be schlepping our own towels taking trains and taxis, losing time and over-spending dollars (and wasting calories) on meals we don’t care about.
Tip #4: Book the cheapest option at the best hotel you can afford, and charm your way into upgrades
First and most obvious, price shop well in advance and choose the absolute cheapest room option in the best hotel class you can afford.
Second, after booking, call the hotel directly, ask to speak to the front desk manager, ask for the name of the person and USE it. Follow this script, adjusting for your own facts / desired outcomes: “Hi there, [person’s name], my name is [your full name] and I just booked a room at the hotel arriving [date]. I’ve never been to [city] and am so excited for my stay — your hotel is top of my budget, but I was convinced that I had to stay with you when I read the wonderful service reviews — it’s obviously incredibly well-managed property, [name of person], and I’m sure it’s not easy for you to get those kinds of glowing ratings so if it means anything, please know that’s why I chose not to stay at [rival property].
I know you must be incredibly busy, and I’m not sure if you are the right person who can make this happen, but I wanted to know what it might take to get an ocean view for my stay. It would make this stay a once-in-a-lifetime experience for me!
If they don’t immediately say yes, they will most likely tell you that they’ll gauge demand and certainly arrange a view if it’s possible for that week. Ask if they’d mind you calling back when the trip got closer to check in, and they will say of course. Be effusively thankful to them for being so generous.
Call again a few days before arrival, inquire and USE the original front desk persons name. You can also submit a note to the hotel on the online contact form complimenting that person by name for their excellent service in considering this request for you. Guarantee they’ll get it since those forms are 99% complaints or solicitations.
On arrival, mention the name of the amazing front desk manager who was helping you and ask if they’re working that day. If not, mention they said they’d arrange an ocean view for you and it would absolutely make your stay if they were able to make it happen.
This has like a 75% success rate in our book — I don’t have empirical evidence of this, but I believe it also helps to be dressed well and in a great mood. The times it hasn’t worked, the hotel has typically given a credit to the restaurant or put a gift in the room.
I think the reason this works is because hotel front desk managers typically deal with all the angry patrons and bullsh*t, and rarely get genuine appreciation or respect for the level of power they yield in making or breaking your experience. They’re trained in customer experience, and having an *actual super fan* of a customer matters to a well-trainer service oriented leader. Taking a few minutes ahead of your stay to build a relationship with one front desk person can go a very, very long way.
Tip #5: Create an intentional strategy to limit food / drink expenses
Even though Wes and I don’t place a lot of value on food and drink, we still obviously need to eat and imbibe! Here are some of the ways we save in this area that I think even Michelin-star-chasing foodies might appreciate to add more dollars into their dinner budgets:
Plan out your days and the times where you know you’ll want to eat out or have a “special occasion” meal - we use the hotel concierge to make the reservations for us, whether it’s a special meal or just at a local pub
If you know anyone from the area, ask for great local, affordable recs! Otherwise do some Yelp research for the neighborhood where you’re staying and have a few good lunch / dinner spots
Forget breakfast and brunch unless that’s something you value — we like to get up and go, so make coffee in hotel room and enjoy it on the balcony; if they offer free breakfast or have a lounge, we use it!
Buy duty free alcohol and do DIY happy hours — we do this for most of our international trips, and saves a ton and also lets you get better drinks. We will pick up a couple of the hotel branded tumblers & full then ourselves, or use the coffee cups and bring to the pool instead of ordering the overpriced full service drinks. (Although every once in awhile, we’ll spring for a coco-frojito!)
Tip #6: Stock your itinerary with free attractions
We find it helpful to plan ahead a bit and have a short list of the free or nearly free things to do, and plan our stay around visiting those attractions — we like to anchor a day around a specific activity and explore the area, eat and walk around the area. We love art and history, and think outside the box on where to find and explore free arts districts and galleries, which are often in hip, up-and-coming neighborhoods. Street festivals, fairs and farmers markets for eating and exploring. If there are free walking tours, do them! Also great way to get local recs for great dining on a budget.
We also like to visit 4-star properties and use the pool. Some expect this, you can get a drink and stay all day. Others probably don’t but don’t worry about asking permission — just look the part and be the kind of guest they want. Or get kicked out, but no one knows you anyway so who cares.
Tip #7: Skip the hotel workout (and cab fares) by adopting the 20k steps per day rule
Make it a challenge to get 20k steps per day and you’ll save on taxis / Ubers and earn dessert :-) This should also impact your shoe choices — I always have a good pair of flats that I can walk for miles in. We’ll take advantage of local rental bikes or scooters if there’s an attraction that’s a bit further away, and plan stops along the way.
Tip #8: Pack smarter to avoid unnecessary “emergency” purchases
This could be a whole blog post. I think the reason people end up needing to buy stuff in vacation is because they’re not thoughtful packers. Being a little smarter up front will save that. First, check the weather and plan for worst case scenarios. That means that you’ll need at least a pair of pants and a sweater even if it’s supposed to be warm beach vacation. Second, plan outfits for each day you’re there, using items you love that are in the same color family so you can mix and match. Only pack shoes you’ve already broken in, and bring just-in-case things like Advil, Neosporin, and Band-aids so you’re not scrambling at the gift shop when you need them.
Tip #9: Place parameters on souvenirs
Packing light is another way to save money, because you literally don’t have room to bring stuff back. Although we’re not really into souvenirs we do like to buy local art when we find it, most of which can be rolled up and carried on in a mailing tube, or shipped directly. Any superfluous things just don’t make the cut. I like to take pictures of things I like and then buy them online later — for example, I fell in love with garnet earrings in Poland and later found them online at a fraction of the cost. They still make me think of Poland when I wear them, because that’s where I found the inspiration!
Tip #10: Be a homebody before and after your trip
Wes and I are introverted homebodies anyway so this isn’t something that’s hard for us to do, but it helps that we do a full week of cooking at home and limiting expenses the week before and the week after a vacation. We look at what we have on hand in the pantry and make a big soup for the week, bring lunches to work and limit other variable expenses like coffees out or Amazon purchases we don’t absolutely need. It’s small, but that stuff adds up and knowing we have a couple weeks of belt-tightening helps alleviate the big cost of a vacation. It also has the ancillary benefit of making us appreciate the vacation more, because we have more time at home together beforehand to talk about it which builds our excitement, and extends the relaxation when we get home because we don’t have big plans or added expenses to worry about.
The end, I’d love to know what you thought of this post in the comments, especially because I typed the entire thing in-flight on my iPhone while getting elbowed by the woman in the middle seat, which was hard, and I appreciate validation. So positive comments only, is what I’m saying.