How We’re Planning our Hawaiian Honeymoon on a Budget

It’s been almost a year since Brad and I tied the knot and we’re just now gearing up for our honeymoon in the fall. I shared quite a bit about how we pulled off our dream wedding on a budget, and the reality is, there was simply no time or money leftover then for a honeymoon right away. 

In retrospect, I’m so glad we took our time and waited to plan our honeymoon, since planning a wedding is enough of a logistical challenge for year, and we only had an 8-month engagement! Plus, earlier this year, all our plans changed when Southwest Airlines announced they were finally opening routes to Hawaii. Originally we were planning a hiking trip through Yellowstone, but we couldn’t pass up the chance to head to Hawaii now that Southwest’s affordable flight options made that possible. 

We managed to squirrel away a total of $5,000 for our 10-day trip – which is already a longer and more expensive vacation than any I have ever taken in my life! We’re not taking off until this October, but I’ve already learned so much about how to stretch our dollar further, that I thought I’d share some of our best honeymoon planning lessons learned thus far. I’ll be sure to report back and update this post with more photos and key learnings after we return, too! 

1. Talk with a Local 

Hawaii is quite the travel destination, with a total of 8 major Islands, each with their own different vibe. In an attempt to better understand the lay of the land and avoid tourist traps, I’ve been reading lots of blog posts like this one, and had a good friend of mine in Denver over for dinner and drinks since she’s originally from Hawaii herself. Her parents still live on The Big Island, and since she’s in the midst of planning her wedding for this fall, we swapped all kinds of advice.  

If you have the chance to speak with a local, I highly encourage you to do so. She helped me understand that Honolulu is a bit of a tourist trap, that Maui is the best island for white sand beaches and unwinding at the spa, and that The Big Island is the rocky, volcanic adventure zone prime for hiking and roughin’ it a bit. She encouraged me to add must-see destinations to our itinerary like the Hilo Farmer’s Market and Mauna Kea Beach, and helped me avoid paying for overpriced experiences that don’t live up to the hype.

2. Southwest Points FTW 

I’ve written before about what a Southwest loyalist I am – and this post is no exception. With Southwest now offering flights to 3 of Hawaii’s islands (and more coming soon!), it’s never been more affordable.

Since I fly so often as a speaker, for Bossed Up Bootcamps, and on the Bossed Up Book tour, I’m always racking up Southwest Rapid Rewards points and have hit A-list status and snagged my Companion Pass (which means Brad flies for free wherever I fly!) for 3 years running now. 

I also should disclose that I use the Southwest Chase Credit Card for most of Bossed Up’s expenses and shop online using the Rapid Rewards Shopping Button Chrome browser plugin, which means I’m always racking up Southwest points on my everyday purchases, too. I’ve become quite the points fiend, I must admit.

But guess what that means?! After booking flights from Denver to Maui (by way of Oakland), then Maui to the Big Island, then the Big Island to Honolulu, where we’re spending 1 final night before flying back home to Denver, I was able to book everything using Rapid Rewards points for my own flights, and then just added Brad to my bookings using the Companion Pass. Each flight we booked did require a $5.60 processing fee, but that put our grand total for all our flights at $56.00. WIN!  

Total Rapid Rewards points used: 57,956

Cash spent: $56.00

Budget remaining: $4,944

3. The Marriott Bonvoy Credit Card from Chase

Once you tackle travel, the next biggest expense for any honeymoon is typically lodging. While I have no problem saving a few bucks booking with AirBnB (more on that later), I want to feel pampered on my honeymoon – at least for the first week! So I knew I had to be smart about how I could find our way to a posh but not-too-pricey hotel experience. Enter the Marriott Bonvoy program

I’ve long resisted aligning myself with a single hotel chain, instead preferring last-minute booking options like HotelTonight (which I’ve written about before here). But this year I knew that I needed to commit to a single brand in order to reap big rewards for our honeymoon.

After doing some research comparing programs, I decided to opt into the new Bonvoy program, which is the result of a merger between SPG and Marriott’s prior rewards program. You can still combine your points here if you’d like to merge your accounts like I did, too. 

Once I registered for Bonvoy rewards and downloaded the Bonvoy app, I received an email about a new introductory offer they were running for their Bonvoy Chase credit card, which is operated extremely similarly to the Southwest card I already use all the time. The offer was as simple as it was spectacular: earn 100,000 Bonvoy points (the equivalent of 2 nights in a really nice hotel in Maui) if you spend more than $3,000 on your credit card within 3 months of signing up. (The public offer has since changed – but I’ve got a great special offer for here you to get you 3 free night awards when you spend $3,000 within your first 3 months.)

It just so happened that we were doing some major electrical work on our real estate property that was going to run us about $4,000 within the next month, so I signed up right away, figuring we had to pay for it somehow, might as well earn some free hotel nights for it while we do. I used part of my final installment of my book advance (which I was paid the day my book published) to wipe that debt clear within the month. So while there was no interest payment to worry about for carrying a balance, the only downside was the $95 annual fee it took to open the card.

As a quick disclaimer here: I don’t recommend going into thousands of dollars of credit card debt – or opening a superfluous amount of accounts just for points. If I hadn’t been sure about where the money to pay it off was coming from (my book advance) and so confident in our ability to wipe out that debt right away, I wouldn’t have opted for this method. You can learn more about establishing a healthy financial foundation and building wealth from my live interview with Maggie Germano, Gloria Blackwell, and Cris Caruso here. I’ve worked very hard and benefited from a lot of privilege that’s allowed me to arrive at this point of relative financial freedom, which I’m always happy to share more about if so desired.

In addition to using the credit card to rack up Bonvoy points, I also started booking all work-related travel directly through the Bonvoy platform, including hotel stays for my 11-city book tour. While this did mean spending a little more up front on my business expenses for travel than I would normally using HotelTonight or AirBnB, I was able to earn points a lot faster.

In fact, I’m currently waiting for points to hit my account from three more work trips this month, including my stay in Chicago for this month’s Bossed Up Bootcamp. At that point, I should have racked up the 150,000 points I need to earn our 4-night stay at my dream hotel – The Westin Maui Resort & Spa, Ka’anapali.

And get this: when booking directly through the Bonvoy platform, I noticed that they’re currently running a special offer at that hotel: book four consecutive nights and you get the fifth one free – mega WIN!

While we’ll still have to pay a $467 resort fees and $35/day for valet parking, that puts our total hotel expenses for the first half of our honeymoon at $642 – or an average of $128 a night. While it’s certainly not free-free, and it’s basically the cost of a normal, affordable hotel, but it’s the freakin’ Westin in Maui, right on the beach!  

Total Bonvoy points used: 150,000

Cash spent: $642

Budget remaining: $4,302 

One more side note about the Bonvoy program: another thing I love about booking through the Bonvoy site directly is that if for any reason we aren’t able to rack up the total of 150,000 points I’m hoping for before we book, you can book your trip with a combination of paying for certain nights with points and other nights with cash. I love that flexibility. 

If you’d like to apply for your own Marriott Bonvoy rewards card from Chase, do so through my link here and you’ll earn 3 free night awards when you spend $3,000 in your first 3 months. Plus, you’ll be gifting me a bonus when you sign up, too!

3. Book Through AirBnB

Through talking things out with Brad and my friend from Hawaii, we decided we wanted to start our honeymoon with a relaxing, luxurious 5 days in Maui before heading to The Big Island for the remainder of our stay. If we could fly back to Denver from the Big Island we would, but we have to catch that departure from Honolulu, so we’re spending our final night there and spending the 4 previous nights in Hilo, a cute little town on the east side of The Big Island, in close proximity to volcanoes and waterfalls and all kinds of amazing flora and fauna. 

Since we’ll be coming off our fancy hotel stay in Maui – and frankly since I’m tapped dry on Bonvoy points – we opted for an AirBnB for our stay on the Big Island. 

I found us an adorable little private guest house on Reeds Island, 1 mile from downtown Hilo, situated on a little island within the island. It’s nothing fancy, but the reviews were all positive (always read the reviews – photos can be deceiving!) and it comes with an outdoor shower, which I love for a tropical, vacation vibe. Plus, even though groceries in Hawaii aren’t cheap, we’ll be able to save a little bit on food by cooking in the kitchenette and shopping at the Hilo Farmer’s Market for fresh produce. At $85/night it’s affordable for being just a 20-minute walk from downtown, and I already exchanged a few messages with the host, who was full of recommendations and advice.

Total cost: $360

Budget remaining: $3,942

4. Get Organized 

I’ve already spent 6 months researching and planning our honeymoon and we have another 3.5 months to go before we take off. A big part of how we’ve been able to save money and take advantage of all these special offers is because we got a jump on planning and stayed very organized. 

While I certainly don’t work on this every week, I do devote a few hours to planning our honeymoon every month. As the travel fiend and points guru in our household, I’m more than happy to take this mental load on for the both of us.

To keep me organized, I set up a simple Google Spreadsheet with separate tabs for travel information, the budget, and activities on our must-do and might-do lists. While it was absolutely essential to book our travel, car rental, and lodging early to save, I don’t believe in scripting out each day of our trip in terms of activities and culinary destinations we want to hit. Rather, I just did some cursory price-shopping to preserve room in the budget for the more expensive activities we want to do (a spa day, swimming with dolphins, attending a traditional luau, i.e.) and from there estimated a daily spend cap for us to try and keep our eating and drinking costs under control. 

It’s helpful that Brad and I happen to think some of the best things in life are free (we love hiking, biking, lounging on a beach, and bopping around exploring new places on foot). And to be honest, I still have more price-shopping and research ahead of me to ensure we’re not overpaying for any tourist traps. But with a healthy amount of budget remaining, I’m optimistic that we’ll be able to keep costs under control. 

The only other costs we need to factor in that I haven’t already addressed is the nearly $600 we’re spending on a rental car for the duration of our 10-day stay and the nearly $400 we’re spending on the dog-sitter while we’re away. 

Got any additional Hawaii travel tips to share?

I’d love to hear from you! Weigh in via the comments below or hit me up on social media at @emiliearies and @bosseduporg

I am a big believer in the whole #treatyoself mentality when it comes to planning your honeymoon, but there’s no better form of self-care than being prudent with your money. I know how un-romantic that sounds, but it’s true! Planning an indulgent, 10-day trip and knowing that I’m not going to come out of it with debt, riddled with guilt or feeling the shame spiral that comes with overspending is the best feeling ever. Plus, I like to think of it as a game, a game that you can win by staying organized, planning ahead, saving like a boss, and making the time and effort to find the best deals possible. 


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