Mai Tais & Mile High Views: A Maui State of Mind

Morning

• Arrive in Maui and check into your accommodation.

Afternoon

• Settle in and start unwinding. Explore your nearby beach or take a short stroll through town to get familiar with your surroundings.

• Sweet welcome treat: Stop at Ululani’s Shave Ice in Kihei to cool off and indulge in your first taste of paradise. Their ultra-fine shave ice and bold tropical flavors are a must. Don’t forget to add a snow cap (sweetened condensed milk).

• Pro tip: Walk right across the street and enjoy your treat with a relaxing ocean view — this is Maui magic at its finest.

Evening

• Embark on the Deluxe Ka'anapali Sunset Sail with Sail Trilogy. Enjoy plated appetizers like BBQ chicken skewers and Kalua pulled pork sliders, complemented by a variety of beverages. Gotta have the Mai Tai!

All day

Head out in the early morning for the legendary Road to Hana. If you prefer the flexibility of stopping when you want, driving yourself is a great option. Be ready for a full day of winding roads, waterfalls and jaw-dropping scenery. If you don’t want the stress of driving, a day excursion is a must!

Highlights:

• Stop at Twin Falls for a refreshing waterfall walk.

• Visit the stunning Waiʻānapanapa State Park with its famous black sand beach (make reservations up to 30 days in advance).

• Explore charming Hāna Town and grab a bite from a roadside stand or food truck.

• Snap photos at Wailua Falls, one of the most photographed waterfalls in Hawai'i.

• For dinner, stop in Paia Town on your way back and enjoy specialty pizzas at Flatbread Company. I love the Mopsy’s Kalua Pork Pie!
  
  

Morning

• Head upcountry to explore Maui’s cooler, lush slopes:

  • Start at Maui Wine in Ulupalakua for a tasting and stroll through the historic grounds.

  • The pineapple wine is a must-try — light, tropical and totally unique to Maui!

  • Make your way to the Ali’i Kula Lavender Farm.

  • Must try the lavender scone and lemonade — both are light, fragrant and perfect for a mid-morning treat.

  • The farm is full of beautiful photo ops with sweeping views, vibrant flowers and charming gardens.

Lunch

• Dine at Kula Bistro, a local favorite known for its hearty portions, Italian and Hawaiian-inspired comfort food and cozy, laid-back vibe.

Afternoon

• Treat yourself to a luxurious afternoon at Ho'omana Spa Maui, nestled in the rainforest.

• I personally had the Lomi Lomi Massage and honestly, I woke up a new person — it’s incredibly restorative and deeply rooted in Hawai'ian tradition. The setting alone is worth the visit.

Evening

• Keep it easy with a relaxed dinner at your resort or Head to Maui Brew Co. Enjoy live music nightly from 6:30-8:30 pm or trivia on the first and third Tuesday of each month while enjoying refreshing brews!

Early morning

• Arrive at Haleakalā National Park at least an hour prior to sunrise to secure a good spot and witness the breathtaking sunrise from the summit. It’s an early start, but the view is absolutely worth it! Be sure to book your entrance ticket in advance, as access is limited.

• Dress warmly! Temperatures at the summit can drop, even in the summer months.

Morning

• After the sunrise experience, head back down the mountain. You might want to grab a breakfast snack or enjoy the drive back to your hotel.

Afternoon

• Spend a relaxing afternoon at Wailea Beach Park. This picturesque spot is perfect for unwinding by the ocean, whether you want to take a walk along the beach, have a picnic or just soak in the scenery.

• Lunch: Grab delicious sandwiches from 808 Deli and enjoy a laid-back lunch by the beach.

Evening

• After a restful afternoon, consider a casual dinner at Nalu’s South Shore Grill, known for its great food and killer Mai Tais.

Morning

• Start your day at one of Maui’s charming local farmers markets. Depending on the day of the week, check out:

  • Kihei Farmers Market – ideal for tropical fruits, fresh smoothies and handmade island treats.

  • Upcountry Farmers Marketin Pukalani (if it’s Saturday) for local produce and artisanal finds.

  • Pick up some fresh snacks or baked goods to enjoy later by the beach.

Late morning to afternoon

• Spend your last full day relaxing at one of Maui’s beautiful beaches — Big Beach (Makena) for wide, sweeping views or Kamaole Beach Park III for a mellow, family-friendly vibe.

• For lunch, grab a to-go meal from Tin Roof Maui in Kahului. It’s a local favorite serving Hawai'ian comfort foods that pack perfectly for a beach picnic.

Evening

• Close out your Maui trip with a sunset dinner at the iconic Mama’s Fish House in Paia.

• Known for its fresh catch of the day and unmatched oceanfront views, this is one of the most memorable dining experiences on the island.

• Reservations are essential, so be sure to book ahead.

• After dinner, enjoy a final stroll on the beach and toast to an unforgettable Maui adventure.