What to Do on Your Second Trip to Maui: Hidden Gems & Fresh Adventures
What to Do on Your Second Trip to Maui: Hidden Gems & Fresh Adventures
It’s fairly easy to pick your activities for your first trip to Maui, you’ve already experienced the Road to Hana, watched the sunrise from Haleakala, visited Iao Valley and enjoyed a traditional luau. Now you’re headed back to the Valley Isle—lucky you! Your second trip to Maui is the perfect chance to go beyond the “must-dos” and dive deeper into the island’s local culture, hidden gems, and lesser-known adventures. In this guide, we’ll help you rediscover Maui with fresh eyes—whether that means exploring a new side of the island, trying a surf lesson, or uncovering small-town eats that tourists often miss.
We are here to help with a
Top Ten List of activities for your second trip to Maui
1. Zipline
Experience a thrilling blend of adventure and education with Skyline Eco-Adventures, the first commercial zipline operator in the United States. Since launching in December 2002 on Maui’s historic Haleakala Ranch, Skyline has expanded to include the Kaanapali Skyline Adventure, opened in 2007 as Maui’s second zipline course. But Skyline is more than just adrenaline-pumping fun—it’s also a journey into Hawaiian history and culture. Each guide receives extensive training in environmental stewardship and cultural knowledge, including Hawaiian language basics, traditional customs, and the history of the islands. Guests learn about Hawaiʻi’s past—from the reign of King Kamehameha to its annexation by the United States and beyond—gaining a deeper appreciation for the people and stories that shape this place. At Skyline, the goal is to make every zipline experience not just breathtaking, but meaningful. Whether it’s your second trip to Maui or your tenth, there’s always something to learn with the incredible crew at Skyline.
2. Visit Upcountry
On most people’s first trip to Maui, they focus on the beaches and the oceans, and rightfully so, but Maui’s upcountry area is teeming with fun adventures that are only slightly off the beaten path. Is it weird to put a top ten list inside a top ten list? We’ll try it …
- Shop in Makawao
- Watch a Polo Game
- Visit Surfing Goat Dairy
- Enjoy live music while watching the sunset at Mahalo Aleworks
- Catch the Rodeo
- Cruise through the Lavender Farm
- Take a horseback ride at Triple L Ranch
- Take a tour at Maui Winery, Ocean Vodka, Haliimaile Distillery or Waikulu Distillery
- Dine at a variety of places from casual food trucks to fine dining experiences. If you are upcountry around dinner time, put these places on your list to check out: Marlow, Casanova, Kojima or the Cafe at Ocean Vodka
- Eat the donuts at Komoda’s (not open on Wednesday or Sunday, and get there early – before 10am – for the best selection)
3. Sail to Lanai
Maui is beautiful with some incredible beaches, but we’ll be honest, the best beach in Maui County (which includes Maui, Molokai and Lanai) is Hulopoe Beach on the island of Lanai, and the best way to get there is with Trilogy Excursions. Their full-day sailing adventure combines world-class snorkeling, stunning coastal views, and warm Hawaiian hospitality. Guests can expect a scenic catamaran ride, a chance to spot dolphins, and time to relax or explore Lanai’s secluded beaches—all with delicious meals and attentive service that Trilogy is known for.
4. Take a hike
There are so many great hikes on Maui, but if you want to not have to worry about where to go, where to park, how to check the weather conditions, safety, trespassing on private property or anything else, go with a guide! Check out the various options provided by HikeMaui for family friendly excursion on your next trip to Maui.
5. Spend the day in Paia
Paia has great shops, awesome restaurants, and great beaches! There is free street parking and a free parking lot on Hana Hwy, and enough souvenir shops to keep the whole family entertained. You really can’t go wrong with any of the restaurants, but Flatbread, Cafe Des Amis or Paia Fish Market are perennial favorites. You can take small kids to Baby Beach, bigger kids to Baldwin Beach, or everyone up to Hookipa to watch the surfers and look for turtles (just follow the crowds).
6. Go Snorkeling
You probably got in the water on your first trip to Maui, but it’s Maui, so you might just get in the water each day while you are here! You can rent from any of the snorkel and dive shops, and make sure you sign up for the daily Snorkel Report! If you want to go with a guide, check out The Ocean Project, or Shoreline SNUBA if you are up for a new adventure!
7. Take a surf lesson
Surfing might seem like an extreme sport, but with Maui Surfer Girls, it’s all about fun, safety, and confidence in the water. Our expert instructors, beginner-friendly gear (including rash guards and booties), and uncrowded surf spot make it the perfect place to catch your first wave—or finally cross it off your bucket list. If you didn’t try surfing on your first visit, your second trip to Maui is the perfect time. Just be sure to book in advance, especially during holidays and peak family travel seasons—we fill up fast!
8. Learn more about Hawaiian culture!
We get asked about it all the time, so we wrote a blog post specifically about Maui’s best cultural museums and activities – click here to read it.
9. Give back to the local community
Especially after the fires, so many people have wanted to know what they can do to help. Hands On Maui is an incredibly helpful resource that not only includes volunteer opportunities for visitors (and residents) that are wanting to help, but also has an awesome calendar of upcoming events that are searching for volunteers! Or if you are just looking for casual ways to help the island while you are here, we suggest picking up trash on the beach, and always tipping your servers and guides, as those in the visitor industry were (and still are) among the most impacted as a result of the fire devastation and loss of visitors during the recovery phase.
10. Relax, recharge, and just go with the flow!
When we posted an Instagram story asking this question – What to do on your second trip to Maui? we overwhelmingly heard – just relax! And we can’t agree more. Your first trip to Maui probably had at least one activity listed for each day you were on Maui, and several dining, shopping and snacking lists! While there’s still so much to explore, so much of the beauty is in just taking it one day at a time, enjoying the year-round perfect weather, and in finding places to explore that we never even on your list! We would definitely suggest either alternating days with plans vs no plans, or planning out the first half of your trip and leaving the second half unplanned! Leaving some flexibility in your schedule means you can move things around if the weather happens to go awry (rare but it happens) or when you learn about an entirely new activity or location to explore!
Not a Sponsored Post.
As Maui Surfer Girls celebrates our 25th anniversary, we are just highlighting other established Maui companies that have excellent customer service and records. And all of our suggestions are just ways to help you discover and plan for your next trip to Maui, whether you have never been, or have been dozens of times!