A long weekend in Maui might not seem worth it, but with the right plan, you can experience the island’s most iconic and unforgettable attractions. From sun-kissed beaches to fragrant rainforests, breathtaking views, and volcanic landscapes, Maui packs a punch of adventure, relaxation, and natural beauty.
Let us help you make the most of your brief escape to this Hawaiian paradise.
First, tune into Spotify and make a Hawaiian Music playlist a few days before your trip to get you in the mood when you land. We suggest you pack lightly so you can get around easily.
THEN … review our suggestions and make a plan.
Day 1: Embrace the Classic Maui Charm
Morning: Sunrise at Haleakalā National Park
Starting your Maui adventure with an early morning drive to Haleakalā National Park is a no-brainer. Known for its stunning sunrise views, the summit of this dormant volcano offers a surreal landscape that will leave you speechless. You may experience a Hawaiian Chant welcoming the sun, which is the magic of so many cultural experiences you can have visiting the island. Make sure to make a reservation and plan to arrive before dawn to secure a good spot and enjoy the mesmerizing play of colors as the sun rises over the crater. Do not forget to dress warmly – temperatures can be chilly at this elevation.
Late Morning: Have your Breakfast in Upcountry Maui
After your sunrise experience, head to Upcountry Maui for a hearty breakfast. The charming town of Makawao is a great spot to start. Enjoy a delicious meal at a local café or grab some yummies at T. Komoda Store & Bakery, renowned for its freshly baked pastries and local vibe.
Afternoon: Explore the ‘Iao Valley
A beautiful drive from Makawao, the ‘Iao Valley State Monument offers that island forest vibe and a taste of Maui’s tropical beauty. The unmistakable ‘Iao Needle is a natural rock formation and is worth the effort to take in its beauty. A leisurely walk on the paved trails to soak in this sacred site’s stunning scenery and historical significance is memorable, and a few photos will remind you of this special place.
In Maui’s effort to preserve sacred and unique spots, you will need reservations to enter the park.
Evening: Relax at your Kuleana condo for a Gorgeous Sunset
The west side of Maui is the best place for Hawaiian sunsets most of the year. Sunsets are spectacular at our Kuleana resort, so make sure and book an oceanfront or ocean view condo. Tucked away between Lahaina and Kaanapali, the area is also a favorite spot for Hawksbill and Green Sea turtles. If you are staying on the south or central coast, you can head to Ka’anapali Beach for a classic Maui beach experience. Park at Whalers Village, and discover a beautiful stretch of sand, perfect for a relaxing swim, a walk along the shore, or simply lounging under the sun. You can always cool off at an air conditioned shop at Whalers Village. As the sun sets, find a spot to watch the sunset – the colors over the ocean are truly spectacular. You could pick one of the beachfront restaurants, like Leilani’s on the Beach, which offers delicious seafood and breathtaking ocean views, or grab something to go for your private sunset party near the ocean’s edge, or back at your Kuleana condo. You’ll find everything you need for cooking and dining in your home away from home, and the kitchen and bar are always open!
Day 2: Dive Into Adventure – Snorkeling in Maui is Unforgettable
Morning: Snorkeling in Molokini Crater
Day two should be dedicated to an underwater adventure, where a whole other world of Hawaiian wildlife exists. A morning snorkeling tour to Molokini Crater tops many bucket lists. Molokini is a crescent-shaped volcanic caldera just off the coast of Maui. The crystal-clear waters and abundant sea life are some of Hawai’i’s best snorkeling. You will encounter colorful fish, and maybe a sea turtle or manta ray. If it is whale season, you may see some gentle giants, and you will surely hear their singing. Note that each person should assess if they are healthy enough to partake in the ocean activity they book, and seek medical advice if unsure, or about any restrictions on ocean activities before or after flying. If you’re scuba diving, a general rule is to wait 24 before flying, or more depending on your diving profile.
Afternoon: Scenic Drive Halfway to Hana
After snorkeling, embark on the legendary Road to Hana. This scenic drive is epic, winding through lush rainforests, past stunning waterfalls, and along dramatic coastal views. But you don’t need to go all the way to get your rainforest vibe on. One stop, not too far from the official journey start at mile marker zero, is Twin Falls. Featuring an easy walk to two waterfalls, there is also a really amazing food truck with items made from fresh island fruit (plus some packaged food and drinks) and bathrooms. Another is the Ke’anae Arboretum, a free, state-maintained park containing a path that follows a stream past examples of many indigenous trees and plants. Around the corner is Ke’anai peninsula. This agricultural outcropping of land over the sea contains a smattering of local residents, a church, bathrooms, and usually a snack shack. But what is really outstanding is the views-
Day 3: Unwind and Explore
Morning: Relaxation and Spa Day
Return from road tripping and spend your final day in Maui indulging in relaxation. Na Alii Massage comes right to your vacation condo, offers luxurious massages, couples massage, and other pampering services to help you unwind and savor your last day on the island.
Afternoon: Whale Watching or Sunset Cruise
Depending on the season, consider a whale-watching tour if you are planning your trip between December and April. These tours offer a chance to see humpback whales in their natural winter habitat.
Alternatively, a sunset cruise provides a perfect way to end your Maui adventure. Enjoy the stunning colors of the setting sun as you sail along the coast, snacking on pupus and perhaps with a refreshing drink in hand.
Evening: Farewell Dinner
Conclude your Maui experience with a memorable dinner. It’s a perfect way to reflect on your short but sweet Maui getaway. See our Dining Guide for recommendations, from favorite cheap eats or exotic cocktails, to the best fine dining.
With a well-crafted itinerary, even a long weekend in Maui can be filled with memorable experiences. From exploring volcanic landscapes and snorkeling in crystal-clear waters to relaxing on stunning beaches and enjoying local cuisine, Maui offers something for everyone.
So, you have made the most of your time and savored every moment of your long weekend in Maui. Make sure to keep track of what you did and what you might want to do on your next visit. Your long weekend in Maui might be brief, but it will undoubtedly leave you with lasting memories and a desire to return.
