How to Plan the Perfect Island Vacation

Five Lessons from Maui


If you’re a planner like me you understand how much research and energy it can take to create the perfect itinerary.  I’m the girl that creates spreadsheets to make sure all our options are covered and that we always know what we’re doing next.  Well, maybe you’re not that extreme but it puts me at ease knowing that I have a plan in a foreign place.

Maui was different.  As I mentioned in my last post, I decided to go to Maui with a couple of girlfriends at the very last minute.  I was literally emailing friends days before our trip for their suggestions of things to do.  I was nowhere near prepared for this trip and had no time for spreadsheets.  But I’m so glad that I had nothing prepared.

I realized island vacations are not meant to be planned, they are meant for relaxing and being open to the adventure.  But it also helps when you’re staying at a lovely resort and know that you will be taken care of.

Lesson #1: Take advantage of the concierge desk at your resort to book excursions

The benefit of spending a little extra cash for a great resort are all the amenities that are included that make your life easier.  We had 8 days to explore the island but didn’t know where to start.  Luckily, we just went downstairs to the concierge desk and they helped us plan our entire trip (check out the fun activities we covered in my next post).  Not only did they offer suggestions based on what we were looking for but we were able to book and pay for everything on the spot.  I saved so many hours that I would’ve otherwise spent on google!!  Well, more time to spend at the beach!

Lesson #2: Pack light and book a place that has a washer and dryer

Let’s just say, I’m an over-packer.  I was up late packing for this trip because I pretty much took everything I owned; I made sure I was prepared for every occasion.  It also didn’t help that I was so unprepared for the trip overall that I overcompensated with clothes.  Needless to say, I ended up packing a huge bag.  I showed up at the airport and my friend had a little carry-on for the entire week! She has obviously done this before. After this trip, I realized you don’t really need that much clothes when you’re on an island because the attire is usually swimsuits, shorts, flip flops and sun dresses.  We also had a washer and dryer in our condo/resort, which no one told me about, and would have saved me from packing my entire life.  Lesson learned.

Lesson #3: Stop by Costco to save a little cash on food

You might have already guessed it but island living is expensive!!  I was on a budget and looking to save where I could.  A couple of friends suggested we make a stop at the Costco by the Kahului airport (OGG) to save on food costs and I’m so glad we did.  We picked up a case of water, beach towels, snacks, and easy meals which ended up saving us a good amount of money.  We mostly ate breakfast and lunch at our condo (we had a full kitchen) and ate out for dinner.

Lesson #4 : Travel with friends who are flexible and independent

I went with two college friends who know how to have a good time but didn’t always have the same preferences.  We had no problem relaxing on the beach together or exploring different parts of the island but each of us had certain activities we wanted to do and had no problem doing them on our own if the others weren’t interested.  For me, it was zip-lining; for Kendra it was hiking 7 miles; and for Tasha it was relaxing on the beach with a good book.  To me this was perfect.  I loved how we all got to do our own unique adventures but came together for meals and general fun.

Lesson #5: Rent a car

While renting a car is an added expense, it was well worth it. We had the freedom to explore the island and see remote areas.  The best part was when we did the Road to Hana; a journey from one side of the island to the other, with various sights and activities along the way.

Embrace the journey, make unforgettable memories, and get out there and explore!

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