For many people, a dream vacation is just that, a dream. But what if I told you that the amazing place you’ve always dreamed of is attainable? Sure, it takes some planning, budgeting, and discipline. But I assure that you can get there. Probably more quickly and easily than you think.

How We Started Traveling
Not wanting to deal with the headaches of a traditional wedding, my husband and I decided to get married in Hawaii. I don’t recall that there was anything that drew us there other than how easy it is to get married. It turns out that we absolutely loved Hawaii. Not only that, we discovered that we adored traveling together.
After that, we started traveling more. The following two trips were pretty safe, but it didn’t take long before we began taking the road less traveled. Each time we traveled, our trips got longer. We discovered that we’d rather take one three-week vacation instead of a few shorter ones. We really enjoy being able to dive into a place, get to know the culture, and not feel rushed.
Although our trips got longer, our budget hasn’t increased. The last couple of trips we took to Hawaii were three times longer than our first trip, but our expenses decreased. In this post, you’ll discover how we do this. Then your job is to take this information and use it to make your dreams come true.
Money Matters
First things first, let’s address some money matters. My husband, Jer, and I have identified some common responses to our travels that I want to tackle head-on. I can’t tell you how many times we’ve heard, “I’d never be able to afford to go there.” Or “it’s going to take you a long time to pay that off.”
Let’s talk about what it means to afford something. For many of us living in the Western world, it’s not really a question of whether not we can afford something. In many cases, it’s that we’re choosing not to spend money on something. If you say you can’t afford a vacation but have a giant mortgage, car payments, an overloaded activities schedule, and order takeout most nights, understand that these are choices you’re making. The first step is to recognize that everything is a choice and that we have the power to choose what we most value.
We all have different spiritual and emotional connections to the idea of money. The way that we feel about money determines our success with money. It’s impossible to prosper if the feelings you have about money are negative. So you want to be extra careful about saying things like “I can’t afford ______.” Your beliefs eventually become your reality.
Now let’s address the other issue, paying it off. If you’ve been following my story, you’re probably familiar with our financial practices. If you’re new, I invite you to learn more here. The bottom line is that my husband and I choose to not borrow money. That means no mortgages, no car payments, and no vacations on credit cards.
Some of you may vehemently disagree with what I’m about to say. That’s okay. Please don’t let that deter you from the lessons I share about traveling.
When it comes to vacations, I believe they are luxury items. Nobody needs them. I use credit cards, but firmly believe that you should never charge something that you don’t have the cash to pay for. I have never paid interest on a credit card. Therefore, under no circumstances would I accrue vacation debt on a credit card.
So how do we pay for these vacations?
We save up for them. The first step is to set up a budget and learn where your money is going. Once your living expenses are covered, you can decide how much you’re going to save. We have automatic transfers every other week to an account we don’t have easy access to. From there I allocate our savings into different categories: investments, emergency fund, car fund, home repairs, and a vacation fund. We continually fill these buckets so that we can address anything that pops up in life. I encourage you to do the same.
Enough money talk. Let’s talk about your dream vacation!
Here Are 20+ Ways to Afford Your Dream Vacation
Book Early
We’re usually pretty good about this so I never truly understood how important it is. Our most recent trip was planned rather last-minute and during the high season. Our rental car was $300 more than our last trip that was longer. Our average nightly expense for lodging was about the same, but the places were not nearly as nice. The earlier you book, the better deals you’ll get.
Travel During Low Season
A lot of locations, like Hawaii, are just as wonderful during low season. If you enjoy lower prices and fewer crowds, plan your trip outside of peak season.
Think Beyond the Resort
Again, this post is about our personal preferences. Take the opportunity to apply what I share to your preferences. Or maybe be open to trying something new. You might discover you enjoy something you didn’t expect.
When it comes to resorts, I’m not a fan. With the exception of one resort we visit in the winter, we prefer to find other lodging.
I live in the city, am a nature lover, and an introvert. When I go on vacation I want to find a private corner of the world where I can experience peace and quiet. The idea of a mega resort with thousands of vacationers and a tram that takes me to my room kind of stresses me out.
We prefer to cook as many of our own meals as we can while traveling. It’s a great option for both health and budget reasons. We also enjoy winding down after a day of adventure in a private space where we can chat, cook, and enjoy the view. For these reasons, we like to book places with full kitchens.
This can be anything from a small condo-hotel, to an Airbnb, or a vacation home on VRBO (Vacation Rental By Owner). In Hawaii specifically, rooms range from $40 a night in an Airbnb or a hostel to $15,000 a night in an oceanfront mansion. It’s important to consider how you will be spending your time and what amenities are most important to you.
If you’re the type of person who goes on adventures every day and just use your room to sleep you don’t need to spend much. We like to spend at least part of our trip in an oceanfront condo or cottage so we can relax and breathe in the beauty and privacy. That’s one benefit of longer vacations. It’s easy to justify cheaper lodging in one location so you can spend a little more somewhere else.
If you’re renting an Airbnb, VRBO, or resort room for that matter, always check the total price. There are plenty of property owners who list one price but when you include all of the taxes and fees, the total price is double.
One of the cottages we rented on our most recent trip was $200 more on Airbnb than through their website. Which brings up another good point. Never neglect the power of a thirty-second Google search.
And don’t be afraid to ask for a discount. If I’m staying somewhere for a week or during the low season and they don’t offer a discount upfront, I always ask. I’ve also been offered deals by savvy property owners without asking. So don’t be afraid to reach out and connect.
Getting There
Airfare can be one of the biggest expenses for your dream vacation. This is another reason it makes sense to stay for a while. That said, there are always deals to be found.
The first tip is to be flexible. I have a wish list on Trip Advisor where I track airfare to a number of destinations. Whenever there are price drops, I receive an email. Sticking with the Hawaii theme, I often see flights for less than $600.
Have you ever booked a series of one-way flights?
I hadn’t until our last trip to Hawaii. We ended up scoring some pretty great deals. We flew to and from Minneapolis and visited three islands for about $750 per person. We’re finicky about flight times and the number of layovers, so these were not bottom of the barrel deals. I found the flights to and from Minneapolis as a hacker fare on Kayak and booked the other flights directly through Hawaiian and Island Air.
Finally, stop checking bags. Baggage and overweight fees can add up fast. Besides, unless you’re headed to one resort and staying there, luggage can be a pain in the you know what. Plus you get the added bonus of not having room to bring home a bunch of trinkets from the gift shop, saving even more.
Getting Around
There are a lot of places where it makes sense to use public transportation. Big cities like Honolulu, Athens, and New York are not car friendly. I’ve found that public transportation is also efficient and effective throughout Latin America and Europe. It’s common for us to use a combination of both public transportation and rental cars.
When it comes to renting a car, do it as far in advance as possible. The prices for our most recent trip doubled two weeks before our arrival date. Most rental car companies have excellent cancellation policies. This makes it easy to grab lower rates as they become available. Check out Auto Slash where you can enter your rental details and they’ll email you when they find lower rates.
If you have a Costco membership map out their locations and get gas there when you can. In places like Hawaii, you could save more than $100 with this tip alone. Don’t forget to check car rental rates using your Costco membership. We’ve had great luck getting the best rates and upgrades with this free service to members.
Do Stuff
Activities can blow your budget. The price of some tours and theme parks blow my mind. While some things are definitely worth it, some of the best experiences are absolutely free. In fact, most of the things we like to do are free or very low-cost.
Check out the local hiking trails. Pack a picnic lunch and head to the beach. When it comes to activities like snorkeling, consider renting equipment on your own instead of booking a tour*. Getting creative will help you leave a little something in your vacation fund for your next trip.
*Use your best judgment here. The ocean is a dangerous place. If you don’t know what you’re doing, it’s worth spending money on professionals.
Food for Thought
Did you read the part in the lodging section where I talked about booking places with kitchens so you can prepare your own meals? Consider taking the money you save by eating in and putting it toward a nicer vacation rental. Imagine what it would be like to enjoy inexpensive oceanfront dinners and cocktails every night. Sounds like heaven to me.
When buying food to eat in, think Costco and farmers markets. Wal-Mart and Target are also good bets in expensive places like Hawaii.
While you’re at Costco, pick up some beer and wine for your room to avoid outrageous resort prices.
One time after arriving at a hotel booked with reward points, we discovered that they had an all-inclusive package we could upgrade to. We declined since that wasn’t our cup of tea. One evening we went down to the pool bar to grab a beer and were shocked to hear that they were $7 each. We were in Mexico and were used to paying a dollar or two. After that, we went to the supermarket across the street and picked up beer and tequila and brought our own to the beach. 😀
Which leads to my next tip, do as the locals do. Not many Mexicans would have paid $14 for two beers.
This also applies to dining out. Seek out the local food. When you stay at a resort, you’ll be surrounded by restaurants that cater to tourists. You know what else those restaurants have? Tourist prices. Some of the best food we’ve ever had was the local food we discovered while traveling. Food so good that we’ve learned to prepare it at home.
When you do eat out, consider skipping the drinks and tropical cocktails. Fancy cocktails often go for more than $10 a piece. Not to mention, they’re jam-packed with calories. A margarita can have over 700!
You could also consider only eating one meal in a restaurant per day. The fact of the matter is that a typical restaurant meal has about as many calories as you need for an entire day. You could take that meal and divide it in half, and take the rest with you for your next meal. Or you could supplement your meals with healthy snacks from the grocery store.
When we travel, we usually go out for a few meals and drinks. I love to look for happy hours and other specials. It makes for a nice break during a day of adventure. What could be better than a break that doesn’t break the bank?
Dream Vacation Bonus Tips
Skip the souvenirs. – What you’ll really value are the memories and experiences.
Use reward travel. – If you travel for work, don’t miss the opportunity to rack up points with hotels and airlines. We’ve saved thousands using points over the last fourteen years.
Travel like you live. – A vacation is not an excuse to blow your budget out of the water. It might seem like a once in a lifetime experience now. But if you follow these tips, you’ll enjoy trips like this for a lifetime.
Decide what’s important to you. – I’ll spend $25 to get into a national park. But I won’t spend $25 on a plate of shrimp at Bubba Gumps. (No offense Tom Hanks.) You get to decide what’s important for you to spend money on.
Enjoy the little things. – Enjoy the sunrise, the sunset, and the people you’re with. Because in the end, that’s all that really matters.
Practice the Golden Rule. – Treat others better than you want to be treated.
Each time we travel, we are shocked by how horribly visitors treat the environment, locals, and the people who serve them. Don’t be like those people. Instead, treat everyone with extra kindness, graciousness, and generosity. Not only will your trip be more enjoyable, but you might get a few extra perks. On our most recent trip, we got free extra days on our snorkel equipment and a free upgrade to a premium rental car.
Now it’s up to you to take these tips and make them your own. Travel has been one of the most amazing growth opportunities we’ve had. Stop letting it be a dream and start taking steps to make it happen.