Just A Weekend: Maui / Wailea – Just Hit Send Gifts

Just A Weekend: Maui / Wailea

Just Hit Send is here to make your life easy; our city guides are a curated experience for the perfect weekend in a new city. With up-to-date recommendations for 2021

To clarify, this city guide might be more of a long-weekend, unless you're coming from California -

But if you’re itching for a real, relaxing vacation, it’s more than worth the trek across the Pacific to experience beautiful, tropical Maui!

If you’ve ever experienced Hawaii, you know that upon arrival you’ll feel truly transported; the lush landscape & laid back vibes, native Hawaiian music, & friendly locals will have you forgetting all about to-do lists in no time.


Follow this guide for a magical escape to the beautiful Maui, Wailea area:

  • Stay:

Andaz Wailea

It doesn’t get better than the Andaz Wailea; a welcoming boutique vibe meets five-star, Hyatt service. Add to that the best cocktail lounge (Lehua lounge) & sunset views in the area, and even friendlier staff for a must-stay in Maui.


  • Eat + Drink:



One of the best places for a buzzing vibe on this quiet island is at the Four Seasons, specifically their Spago restaurant. Go for fresh fish & decadent steak entrees, and feel like you’ve had a night on the town. 

The Restaurant at Hotel Wailea

Reserve this spot for a special occasion (but aren’t they all when in Maui!) and expect a unique, five-star, three-course experience with their prix-fixe menu. Topped off by panoramic views of Wailea, for a very special night.




Café O'lei at the Mill House

The Tropical Plantation turned destination is our top pick for lunch! Enjoy fresh mahi mahi and a pina colada, then tour the local market & diverse tropical landscape after lunch.




Monkey Pod Kitchen

Your go-to from lunchtime, to happy hour, to late night! Monkeypod Kitchen is the chill (but still delicious) option when you want to grab a bite or a drink (they’re famous for mai tais) & make some friends at the bar.



Bird Cage Bar

For a more high-end cocktail experience, opt for Bird Cage at Hotel Wailea. Lofty ceilings & interesting interior décor are paired with a fancy cocktail list for a big-city vibe that still feels relaxed. 



  • Things to Do:

Hike Iao Valley

The Iao Valley hike is one of the shorter & more simple hikes to choose, and the views give you a real Hawai’ian experience – from lush hilltops to rushing streams & exotic flowers, you’ll feel like you’ve stepped inside a movie set.



Sunset Cruise

While there are plenty of outdoors activities on Maui, a sunset sail is a must-do! Sunsets from the water are breathtaking, the whole family or group can experience it together, and you may even see a whale.



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