Solo in Maui: TFM’s Guide to Traveling Alone

“Why are you here alone?” I was asked at Honolua Bay, just after snorkeling with schools of shining fish and colorful coral. “Are you here for business?” I guess it is kind of strange, going to the most romantic island out there, Maui, by myself.

To be honest, I had a flight credit to Hawaii from a trip that I didn’t end up taking last year, and since I’m not dating anyone and none of my friends could take a last minute Hawaiian vacation, I decided that I would just go alone – and to be honest, it was one of the best trips of my life. Here are some tips for solo travel – to Hawaii, or anywhere else you may feel compelled to explore:

Put it on facebook

This is the second time that I’ve travelled alone, and both times it served me well to post on Facebook requesting my friends to connect me with anyone they knew who was living in my vaca destination. This time it yielded me two local friends of friends in Maui who helped me feel as though I wasn’t there truly alone if any sort of emergency were to occur (like when I was surfing and sliced my foot open on coral). They also led me to the best ice cream in town – which is equally important. Especially somewhere like Hawaii, people are always happy to help someone out who is travelling alone. Don’t be shy.

Don’t plan too much ahead of time

I honestly went to Maui with NOTHING booked but a rental car. I would suggest booking your first night or two of accommodations but giving yourself the freedom to explore and spend time in other towns that you may end up liking better (if there is that option). I stayed near Lahaina the entire stay, a busier town with lots to do, but I wanted the option to stay in Paia if I ended up liking it better.

I also resisted booking any activities and tours until I actually got to Maui and had a chance to ask locals what was worthwhile. I ended up skipping on the Luau ($115 and full of couples and old people), and was able to discover the island of Lanai (an incredible snorkel spot not everyone gets to see). I was able to stay free and open to the universe guiding my journey, and it did an incredible job.

Get used to saying YES

I was on the boat to Lanai for that snorkel excursion and was lucky enough to sit next to a very cute guy who was heading to the island to take a group scuba diving. I got even luckier when he said his group was cancelled, and I could skip the snorkel tour and go diving with him instead…if I wanted to. I could have pulled a “stranger danger”, I could have been scared of all that could go wrong diving with said stranger, but instead I said HELL YES. It was an unforgettable experience, and that stranger ended up taking me cliff diving (my tailbone is still bruised) and showing me the island from the back of his motorcycle.

You become very good at listening to your intuition when you’re traveling alone. My gut told me I was in safe hands, and since I was open to whatever came my way, I received an incredible adventure.

Treat yourself

You know that this girl is all about traveling on a budget – I’ve dedicated several posts to just that, but when you’re alone it’s also important to treat yourself a little bit. I had one dinner alone on the roof a beautiful (expensive) restaurant at sunset, ordered a nice glass of wine and allowed myself to reflect on how grateful I was to have the ability to take a trip like this. Save your money buying souvenirs that will end up in your drawers and in your friend’s garbage cans, and treat yourself to a nice meal, or a massage, or something that you might hesitate doing at home.

Be Present

The most important of aspect of a solo trip is that you have no one to entertain, you have no one else’s schedule or needs to accommodate, and you can just take the opportunity to have a little introspection. It is so rare in our busy lives to be able to truly disconnect and fully enjoy our experiences. As much fun as the adventures were, the down times inbetween spent dining alone, or walking around town gave me the opportunity to really reflect on everything going on in my life. I came back feeling super in tune with myself, and I’ve been doing my best to maintain that.


Favorite spots to eat:

Breakfast: Leoda’s Kitchen and Pie shop – get the fried chicken and waffles. The best I’ve ever had, and I’ve had A LOT of chicken and waffles. You won’t regret it.

Brunch: Merriman’s was beautiful outdoor seating and great food (get the French toast).

Lunch: Leilani’s – right on the beach with great, healthy options.

Dinner: Fleetwoods had a great rooftop and fresh fish (like everywhere else in Maui).

  • I also loved Choice Health for acai bowls and green juices in the mornings.
  • Everyone raves about Mama’s FishHouse, which is by far the most popular spot on the island. It was booked up when I was there (so if you’re dying to go, make a res in advance), but to be honest I don’t feel like I missed out on anything.

Things to see:

Paia: Very cute little beach town that has a hipster vibe with little shops and cute restaurants

Makawao: Right next to Paia, this “cowboy” town has more cute shops and bakeries – you’ll walk the entire thing in about 45 mintutes, but very cute and worth seeing.

Road to Hana: This was my MUST. At first I was worried about taking the long drive around the circumference of the island alone, but it was one of my favorite days of the trip. The entire drive is through lush rainforest. Download the Road to Hana App – it used my GPS and worked without cell service (since you won’t have much), and lets you know what stops are coming up, what they entail, and what is worth seeing. My favorites were the Black Sand Beach, and absolutely Haleakala state park with the 7 sacred pools and a giant waterfall that is worth the 2 mile hike (partially through a bamboo forest – magical).13567051_10157155410220241_5509459474853951622_n

Haleakala Sunet/Sunrise: Another MUST for Maui. I personally enjoyed sunset more than surise, because it was much warmer and I had more time to linger and appreciate it. You are elevated on top of the clouds, and it is a surreal experience.13439154_10157128427450241_5681018475770362088_n

Things to do:

SURF LESSONS: I was connected with the absolute best surf instructor on the island, Bully’s Surf School in Lahaina. This guy not only got me up and surfing, but was able to explain surf etiquette (it can be rough out there for a novice), as well as how to read the waves so that I can maybe, maybe, surf solo someday. This was absolutely worth the money, and he also serves as an incredible guide. Get in touch with him to see all that he offers (including day trips).

13532850_10157155410190241_1755544001023105228_nSnorkle: Get on an early morning boat with Trilogy to Lanai, an island about 45 mintues from Maui, for some incredible snorkeling. I also rented a snorkel for $7/day and checked out Honolua Bay (amazing coral) and Kapalua Bay (I literally swam next to a giant sea turtle).

Beach: My favorite beach was Kaanapali. You’ve got shops and restaurants right on the beach, the water is crystal clear and beautiful, and there’s cliff diving.

You’ll never regret taking adventures, and you will absolutely never regret taking them alone. It’s a luxury I promise you’ll appreciate.


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