Maui rewards an early start. Most tours and outdoor activities are at their best in the morning, when the wind is lighter and the water is calmer. These articles cover the island’s biggest days out and smaller side trips: whale watching, ziplines, luaus, golf, pickleball and an Upcountry loop, each with our candid take on what’s worth your time and money from a Wailea home base.
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Is the Road to Hana Worth It? Our Candid Take for 2026
Personally, we’ve driven the Road to Hana many times, including during the pandemic when it felt like we had the entire world to ourselves. Things are different these days, and that’s why you need a solid plan before jumping in the car. It’s a bucket list experience to be sure and we highly recommend that…
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Best Maui Ziplines: Our Top 7 for 2026, Ranked Mild to Wild
In 2001, there were only 10 commercial zipline operations across all 50 states. Now there are 400, and 7 of them happen to be on Maui. That leaves you with plenty of options to zoom through the tropical canopy during your Maui vacation, although these adventures don’t come cheap. That’s why it’s worth doing some…
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Candid Maui Luau Guide: 2 Shows & 1 DIY Option
Here are the only two Maui luaus worth booking: Old Lahaina and Te Au Moana, or make your own free DIY luau night in Wailea.
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Maui’s Public Pickleball Scene Unpacked
You’ve traded the backhand volleys for beach views, but that doesn’t mean your favorite activity needs to take a vacation. Maui offers a friendly and accessible public pickleball scene that welcomes visitors from the mainland. Here is your comprehensive guide to the best spots for a quick dink during your island escape. 1. South Maui…
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Pride of Maui vs. PacWhale: Which Whale Watching Tour to Book in 2026
When it comes to Maui whale watching, two names pop up again and again: Pride of Maui and Pacific Whale Foundation (PacWhale). Both are icons, both get solid reviews, but they offer very different vibes once you’re on board. Whether you’re the type who wants a laid-back afternoon with a plate of BBQ and a…
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Maui Whale Watching: Best Tours, Season & Shore Spots (2026–27)
Whale season in Maui isn’t just a sightseeing activity. It’s a full-blown spectacle. Every winter, thousands of humpback whales swim roughly 3,000 miles from Alaska to the warm, shallow water off Maui to breed, give birth, and raise their calves. From December through April they turn the channel into their playground, and the only real…
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Upcountry Maui Itinerary: Best Stops, Scenic Views & Local Charm
If you’re on Maui for more than a handful of days, you might want to get out and see the countryside a bit. Landlubbers like us can only handle so many hours drinking original mai tais in the hot sun before we start to melt into tropical oblivion. An “Upcountry” day offers the opportunity to…
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2026 Maui Golf Guide: Birdies in Paradise
Oahu may have more golf courses, but Maui’s are easier to get on and a lot less crowded. From one of the country’s first munis (Waiehu) to a longtime PGA Tour venue (Kapalua Plantation), there’s something on Maui for every hacker, Spackler, and aspiring tour pro. Fore! Here’s what you want to know about every…
🏝️ Host Insider Tip
Everything on Maui starts early, so build your days around the morning. Book the first whale watch raft from the Kihei Boat Ramp, about ten minutes from Wailea, or a morning zipline slot when the wind is usually lighter. You’ll be back at the pool by early afternoon with the rest of the day to yourself.
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