How a Financial Planner Books a Vacation
By AJ Ayers, CFP®, EA, CEP
When we ask our clients what their financial goals are and generally what makes them happy, nine times out of ten the answer will be “travel more!” Travel has never been easier or cheaper and the only thing standing between you and a memorable vacation is probably the courage to ask your boss for time off. Oh, and not getting Coronavirus. Like many folks, I love to travel. And I really love luxurious travel.
If you are also this type of traveler you may find this guide very helpful. My business partner Shane would call me a bougie traveler, and that I cannot deny. I love to see new places, eat new things, meet new people, see incredible sights, and stare out of balconies. I’m not super adventurous when it comes to activities – you won’t find me whitewater rafting down the river, but you will definitely find me splashing around in the tide pools or visiting the botanical garden. Is there a lazy river at your 5-star resort? I’m there! Am I going on the midnight Bengal tiger safari with live cricket eating? Nope!
We can’t talk about travel without acknowledging the fact that we’re going to a place to experience another’s culture – their way of drinking, eating, getting around, dating, etc. When tourists come to New York, they expect incredible pizza and bagels and Broadway shows. When I go to Mexico City I expect tacos, fabulous art, and a Lucha Libre fight. Sometimes tourism is ugly and harmful to local economies so don’t be an ass and be respectful when you travel and try to actually support the local economy. There’s also the idea of sustainability when it comes to travel, and The United Nations World Tourism Organization (UNWTO) defines sustainable travel as: “tourism that takes full account of its current and future economic, social and environmental impacts, addressing the needs of visitors, the industry, the environment and host communities”. So yeah, do that.
I’d consider myself moderately well-traveled for someone in their thirties. I’ve been all over the US, to Europe a bunch, a few countries in Asia, the Middle East, and South America. There are pretty large glaring holes in my globe-trotting. Korea and Iceland are at the top of my bucket list.
So when it comes to booking a trip I’ve developed a sort of dragnet approach to booking the perfect experience. I realize my approach is a bit mad, but I’ve also been on some pretty incredible trips. So I hope you’ll find this comprehensive guide helpful.
The Rewards Programs and Credit Cards
In the quest for the perfect hotel in my opinion there are two websites you must use: Hotels.com and Tablet.com. Let’s start with Tablet Hotels because that’s often where all of my vacation planning begins. Tablet, now owned by the Michelin company, is a curated list of “boutique” hotels. I’ve found some of my favorite hotels in the world via Tablet – they really nail the sweet spot of great places in great neighborhoods that aren’t too expensive. Tablet is free to use but there’s also a perks program called Tablet Plus that costs about $100.
Now, is Tablet Plus worth it? Probably not? But again, it depends on what kind of traveler you are. Do I get a surge of happiness when I show up in my hotel room and there’s a cheap ½ bottle of wine with a handwritten note welcoming me? YES. Yes, I do. Is it worth it for everyone? Nope.
It all depends on what you value most when you travel. I am the type of traveler who likes to stay in a fabulous boutique hotel in a neighborhood that isn’t the sterile or touristy downtown.
So let’s say I’m going to Barcelona. I’ll do a search on Tablet to see their curated list of mostly affordable (I define affordable as $200/night) boutique hotels to see what the landscape is like. A great Tablet find in Barcelona was Casa Bonay. Then I’ll go to Hotels.com or even TripAdvisor.com to look at actual photos provided by real people – you know the ones that show the peeling paint and the gross bathrooms that the glossy filtered photos don’t show. That’s also a great way to comparison shop. Sometimes booking directly through Tablet is best, sometimes it’s Hotels.com, and sometimes I’ll get a free night if I can pay with credit card points.
Hotels.com generally has the best deals AND has an awesome rewards program where every tenth night is free. I’ve taken advantage of this 10th free night at least three times over the past few years. I usually find hotels via Tablet or one of the resources mentioned below and then book them on Hotels.com. Hotels.com has an awesome interface that makes it very easy to see what you’re getting: what’s the cancellation policy? Is breakfast included? SOMETIMES IT’S CHEAPER TO BOOK DIRECTLY THROUGH THE HOTEL WEBSITE SO CHECK THERE FIRST BEFORE YOU SMASH THE RESERVE BUTTON.
Credit Cards
I use credit card points like any self-respecting upwardly mobile millennial but I’m not a nut about it. If you want that, go to The Points Guy. I probably get the benefit of 2-3 nights in a medium fabulous hotel a year from my credit card points – about a $1,200 value. Considering what I pay in credit fees (more than $500 for the AMEX platinum card), it’s still a great deal considering the other perks like Delta lounge access, Uber credits, and a few other little things that add up. You don’t need a fancy credit card to travel like a pro – you just need a basic rewards card.
Personally, I have an Amex Platinum card and a Chase Sapphire Preferred card. So I pay $650 in credit card fees a year. The Amex travel portal I believe is better than the Chase one because I think there are more options. Again, I’m not a NUT about credit card points and I’m probably not optimizing my points EXACTLY in the best way but I think I do okay. I really like the Amex “Fine Hotels & Resorts” perk and it seems like you can get great deals on 5-star hotels. I mostly fly Delta so the free lounge access is a MAJOR perk for me with the Amex Platinum card. Card membership means access to Priority Pass which is a global network of lounges you’ll have access to. Generally, the US ones are TERRIBLE. The Priority Pass lounges in Asia and Europe are generally fabulous – get a full Italian breakfast (for “free”) and even shower in some lounges during a layover. One of my favorites is the Centurion Lounge in Mexico City. There are three Amex lounges at Benito Juarez airport so make sure you head to the one in Terminal 2 – that’s the one with the steakhouse and secret Zen Room. There’s also a full spa and nail salon. You may not be the type of traveler that needs an airport lounge…but if you are, the Amex Platinum is a must.
General Travel Tips
Plan Ahead - Duh
Plan at least two months ahead and choose your dates wisely. Six months ahead is even better because the good stuff (the AirBnbs, hotels, restaurants) get booked way out. Note that many famous museums and sites must be booked way ahead of time - like the Ghibli museum outside Tokyo, or the Ceaușescu Mansion in Bucharest.
If your dates are flexible, try not to stay in a major city or expensive resort on a Friday or Saturday night. Saturday nights in hotels are almost always more expensive. I’ve stayed in some pretty incredible hotels on a Monday night for less than half the cost of a Saturday night stay. I generally start with an aggregator like Google Flights, Skyscanner or Kayak just to get a sense of the prices and flight times. If you’re going to a remote place, you may only find that there are flights or ferry rides at certain times – this will impact your hotel plans and dining plans of course!
Mix Formulated Adventure with Spontaneous Adventure
When I’m going to a new place, I like to get the lay of the land. What I’m about to say may be controversial but hear me out. I LOVE hopping aboard one of those super touristy double-decker buses when I’m in a new city. In my opinion, it’s the best introduction to the city and I’m often scribbling down cool cafes and shops I want to come back to later as the bus careens across the major boulevards. Generally, the cost is between $20 and $40 USD and is so worth it. In Turin, Italy I saw parts of the city I would have NEVER found otherwise. Look, I love spontaneous adventure as much as the next person, but when you’re in a new place it can be stressful to try to navigate an adventure without a guide. In my old age, I’ve come to love guided tours through Viator.
Organize Your Hit List
So you’ve done all this research and friends have given you lists of spots to check out. It’s spread across emails and google docs and texts and is going to be a nightmare when you actually get to your destination. I am a BIG fan of starred places and lists in Google maps. Lookup a place, STAR it and Save it to a new city-specific list. I find this essential for walking around big cities. You can also add to your list while you’re there and then share with friends. Even better - revisit that list when you come back a few years later. My husband swears by Foursquare for restaurants but it’s hit or miss in different cities.
Do Your Research
Have your go-to websites and blogs to help you plan your trip. Sure you’ve got your hotels and flights booked but what about the food you’ll eat, the neighborhoods you’ll explore, the museums you’ll go to? For that, you’ll need to dig a little bit deeper.
The key sites I visit when planning a trip:
Atlas Obscura - An outre resource that I almost always consult. Their suggestions tend to be a bit “off the beaten path” like “this old abandoned mine is really cool.” One of my favorite museums in the world is the DDR Museum in Berlin which I found out about via Atlas Obscura.
Goop - Whatever your opinion is of Gwyneth Paltrow we can probably agree that she lives a very nice life so I generally trust her hotel and restaurant choices when I’m going to an unfamiliar city. If you love a great hotel, trust Gwyneth.
The Culture Trip – I’m not sure what this website is. I think it’s crowd-sourced? Anyways, I’ve found amazing restaurants and bars in towns that aren’t likely to be covered in the major travel magazines.
Travel and Leisure – Pretty traditional recommendations, but a good guide to get your bearings.
Eater – a MUST for any major city. Check the “essential list” for the city’s newest and most exciting restaurants.
Book the Right Flight
Save on airfare but splurge to arrive and depart at the right time
I’m all about finding a good deal and saving when I can but I also avoid red eyes and don’t like to arrive too early in the morning when I know I can’t check in to my hotel till around 3 pm. This can be a problem when you’re staying in an Airbnb – there’s nowhere to drop your bags while you go find coffee and explore the city after a long flight.
Start with Kayak or Google Flights to get a sense of the price. I often end up booking something directly through Kayak which is an aggregator.
Then go to Skyscanner or book through your preferred airline.
Scott’s Cheap Flights is also great for once-in-a-lifetime deals.
Have a great trip!