Does winter actually exist in Hawaii? We have visited Kauai and Maui in May before, and the weather was a bit warmer compared to this trip. However, we were fortunate to have perfect weather during our stay, and I never felt uncomfortably hot. But let me tell you, the real reason to enjoy winter in Maui isn’t for the weather. It’s for the unforgettable opportunity to go whale watching! During this time, humpback whales migrate from Alaska to mate and give birth. It’s a truly astonishing sight to behold. If you’re planning a Spring Break trip to Maui, don’t worry, you won’t miss the whales! They’re around all the way through April!
We also enjoyed snorkeling, breathtaking scenic drives, and indulging in some of the best food on the island. Check out our 6-day itinerary for our winter trip to Maui, Hawaii.
TRAVEL DAY
Living in the Midwest, it takes us roughly 11 hours to fly to Hawaii. Add in the 2-hour drive to the airport and the 2-hour layover in Dallas, and we’ve got ourselves a decent little travel day! We got into Maui on time and ended up Living in the Midwest means we have quite the journey to reach Hawaii, with roughly 11 hours of flight time, a 2-hour drive to the airport, and a 2-hour layover in Dallas. However, we did arrive on time in Maui; we had to wait on the tarmac for an additional two hours due to a broken-down airplane.
It was certainly a long day of travel. But once we secured our rental jeep, we made our way to the west side of the island. Despite having to navigate grocery shopping and finding our condo, we couldn’t resist stopping at a fish taco food truck. Let me tell you; it was hands down the best meal of the week. (Hooked Food Truck – Ka’anapali Food Truck Park)
HERE ARE MY TRAVEL ESSENTIALS!
DAY ONE – SUNRISE WHALE WATCHING
While obsessively researching Maui, I found out you want to book your whale-watching tour early in the trip. Because if you don’t see a whale, they’ll rebook you on another day. I’d recommend avoiding my mistake of booking for the very first day of your trip. You’ll be exhausted after traveling the previous day.
We had an unforgettable experience with Ultimate Whale Watching Co. during their sunrise humpback whale-watching tour. As soon as we arrived, we witnessed a fascinating scene: eight or nine male whales engaged in a heated competition to win over a female whale who led them around (hilarious, right?). To our amazement, the whales swam incredibly close to the 15 ft long raft we were on and even went under it. According to the crew, the average length of a female whale is around 50ft! I couldn’t resist taking shaky videos and screenshots to capture how close they were. But the surprises didn’t stop there. We were also lucky enough to have playful bottlenose dolphins keeping us company for a long time. We were told that this was a rare occurrence, making our adventure even more special!
This tour took so much out of us as we were already tired. However, nothing was going to keep us from walking the beach at sunset! I’m so happy we did because we witnessed the most stunning rainbow!
DAY TWO & THREE – SCENIC DRIVE + SNORKELING
We drove up this windy road similar to the Road to Hana “up north” to see the famous blowhole (not that interesting) and this giant mountain cliff. I’m pretty sure we met a famous golfer who took our picture.
To save money, we always go grocery shopping and grab random food for lunches or dinners. *grocery store sushi on the beach*. Since we grabbed ice cream 100 times on this trip, all the saved grocery store money went directly to the ice cream shops. 
Every morning, we would catch sight of whales right outside our condo and couldn’t resist recording the experience, even if the videos didn’t turn out great. While the snorkeling wasn’t ideal during this time of year, Ben had an incredible encounter with a massive turtle. As for me, I found myself hyperventilating and opting to stay onshore.
DAY FOUR – BEACH + SUNSET WHALE WATCHING
Can you believe we hadn’t had an acai bowl yet!? Because of this tragic error in judgment, for breakfast, we drove back to Lahania to try the Bayan Bowls food truck. I’d recommend it if you are nearby and be sure to call and order ahead to skip the line.
After indulging in a satisfying lunch, we cruised down to Big Beach in Hawaii, eager to soak up some sun and the quintessential “big beach” atmosphere. However, we were in for a rude awakening as the waves were incredibly aggressive – I thought I was going to meet my maker! Winter in Maui definitely brings some crazy waves with it. Thankfully, the initial shock dissipated quickly, and we dashed to the nearest public shower, which happened to be located at a stunning church. I regret not taking a better snapshot of it! We spent a good twenty minutes attempting to remove sand from every nook and cranny before rushing to our sunset whale-watching expedition just in the nick of time.
Embarking on a whale-watching tour, I was immediately entranced and forgot about everything that had happened before. Firstly, there were so many whales! Not only that, but the males were engaged in a heated fight, and we were completely surrounded by their massive bodies. Suddenly, one of the whales surfaced and bumped our boat, spraying water all over us. It was truly an awe-inspiring experience. If you’re thinking of spending some of your winter in Maui, this experience should be your reason!
But the most unforgettable moment was watching the sunset over a Hawaiian island, with whales slapping their tails between us and the sun. I simply cannot put into words the beauty of that moment.
DAY FIVE – RELAX DAY
On day five, we decided to fully unwind and indulge in some R&R. We couldn’t resist another serving of delicious pineapple whip and then stopped by Lahaina for lunch. Although the food we tried was only okay, we stumbled upon an outlet mall down the street where we passed the time exploring a used bookstore. Of course, the breathtaking sunsets from our condo made for a perfect end to the day.
DAY SIX – TRAVEL DAY
You wouldn’t believe how much I attempted to pack into this day! I had not yet seen a sunrise that wasn’t at our condo. The night before I had googled where the best sunrise was on the island. Most are way on the other side, down the road to Hana. I found there is a good spot up north where we had been on that first day. We drove up to a trail called XXXX with our donuts and coffee in tow.
I had some outfits I just couldn’t let go to waste, so we set out to explore a nearby coconut farm. We then visited a small aquarium, which admittedly charged a steep admission fee, and grabbed some delicious bites from the food trucks located near the airport. As luck would have it, I even ran into one of my close girlfriends while we were there. We had been trying to meet up for a few days, so it was a serendipitous moment.
Beautiful photography and I’m saving your itinerary for my own trip someday!