It’s always summer in the Hawaiian Islands! Maui arguably has the best of each of the 4 Hawaiian Islands. Sandy beaches, great hiking on the rugged coastline and dormant volcanoes, surfing, snorkeling, and amazing culinary experiences ranging from healthy vegan options, and roadside hidden gems to exceptional farm-to-table dining. Whether you are a newbie or a Maui pro, mix it up with some beach days, some day trips, and immerse yourself in local activities - like a picnic or surfing at a local beach and eating at a local hidden gem.

In this 7-day itinerary, your home base is West Maui. Start your trip by easing into the Island life (take advantage of Jet lag!) the first day or two. Enjoy Kaanapali Beach and relax in the resort (we stayed at the fabulous Westin Kaanapali Ocean Resort Villas). Next up, hit the roads for the incredible Haleakala Sunrise at the Summit for a half-day trip and the breathtaking Road to Hana for another full-day trip. Slow down and for the next 3 days, just explore and enjoy the Old town of Lahaina, the hippie town of Paia, and Haiku and do snorkeling in nearby Honolua Bay. The day before departure just stay at the resort, rent an umbrella and chairs and spend the day at the beach, sipping Mai Tai’s into the incredible Sunsets!

Tip -  As you vacation, recreate responsibly. Respect the local culture, people and the island. 

Trip Highlights

Duration - 7 Days

Places - Maui, Hawaii

Best for - Family Adventure Vacation

Travel Pace - Active

Season - Summer (July 4th Weekend)

Experiences - Haleakala Sunrise @ Summit, Road to Hana, SUP Cruising, Snorkeling in Honolua Bay, Sunset grilling, Exploring hippie towns of Paia and Haiku, Hiking Pipiwai Trail, Exploring uncommon local eateries, and Staying at the oceanfront resort Villas.

Trip Cost - $385/day/person excluding airfare. Cost includes 1 Bedroom Oceanfront Villa at a 5-star resort; Jeep Rental + Gas (prices were high due to shortage from the pandemic); Food and Drinks (assumes at least 3 dinners cooked in the villa). National Park tickets and passes. You can trim this budget by choosing alternative accommodations or non-resort condo rentals and renting a car vs a jeep or just renting for the days you need (Availability is risky though!)

NOTE: In Maui suggest staying at a fully furnished (w/ kitchen) villas, like the Ocean Front Villa at this Westin Kaanapali Ocean Resorts

Trip Route

Itinerary

DAY 1 ALOHA! EASE INTO ISLAND LIFE

No matter where you are flying from, getting to Maui is in the middle of the Pacific Ocean is a long flight. Start with easing into the island life the first 2 days relaxing on the beach, indulging in some water activities (paddling and snorkeling) just enjoying the beautiful Westin Kaanapali Ocean Resort Villas.

Most flights either arrive late mornings (11ish) or evenings (after 5 pm). If you arrive mornings as we do, check-in is not until 4 PM, so suggest making a quick stop for refreshing Acai bowls and cold coffee at the Choice Health Bar and pick up some groceries and supplies (local store or a Safeway) for the first few days as most resort villas have full kitchen and grills. If you arrive in the evening, then check-in, grab a drink and quick bite qt the poolside bar, take a walk on the beach and then settle into your comfy Villa beds for a good night’s sleep!

Tip -  Call ahead and rent your Standup Paddle board and Snorkeling equipment. They will deliver to your resort villa!

Duration: Flight Time (5+ hours)

Good To Know: Westin Resort Villas can properly store your groceries in proper boxes while you hang out at the beach till your villa is ready for checking in.

How to get there: Rent a car from the airport if you plan to go around the island a lot. Else take a rideshare to the resort and rent scooters or a car locally for the days you want to get around.

Note: you can get a 30% from Avis if you are an owner at Westin Ocean Resort Villas.

DAY 2 HIT THE BEACH AT KAANAPALI!

With jet lag looming in, start early with a fresh and healthy Acai bowl or smoothies at Choice Health Bar and 5min drive from the villas. Its a full day of enjoying the beautiful Kaanapali Beach, SUP cruising, some snorkeling in the Hawaiian blue waters taking the nap under swaying palm trees, and eventually wrapping up the day with BBQ grilling on the Westin Kaanapali Ocean Resort Villas lawns and enjoying the beautiful sunsets and fireworks (Yes we happen to be there on July 4th) while sipping Mai Tai’s!

Tip: Your SUP boards can be stored overnight in the board racks available in the resort. In case you forget to rent from ahead, you can always rent by the hour at the beach.

Duration: Full Day

Activity Level: Easy

Good To Know: BBQ grill in the resort is very popular in the evenings and is a first-come-first-serve basis. So plan to avoid disappointment.

Morning

Afternoon

Evening

DAY 3 SUNRISE AT HALEAKALA SUMMIT

Haleakala Sunrise at Summit is a Maui travel bucket lister. The experience is surreal. Seeing the sunrise above the clouds at 10,000 feet is one of a kind and the red glow on the surface of the crater gives the feeling of being on Mars!

Start your day early - very early, like 2:30 AM! The drive from West Maui is about 2.5 hours to the summit. You want to arrive at least by 5 AM to get situated - find a parking spot, set up a camera (especially for time-lapse). Take some pictures but do take time off the camera to enjoy the sunrise⁠ above the clouds. Walk around the top of the crater and enjoy the early morning views⁠. There are some amazing trails (3-5 miles) if you want to spend more time exploring.

By 7:30 AM head back down and make a must-have stop for great coffee and pastries at Sip Me in the town of Makawao⁠ - it is literally on the foot of Haleakala. Once back at the resort, suggest catching some sleep or hang out at the beach or the pool and wrap up the day with an early dinner at Whalers Village.

Tips: Remember it can get cold up there even in summer! Pack a wind jacket, a beanie and tech pants. 

Duration: Half Day

Activity Level: Easy

Good To Know: 1. You need a reservation specifically for the sunrise at the summit. Book your entry pass first on recreation.gov, 30 days before your desired date. There are usually only 50 or passes available per vehicle. 2. The Haleakala NPS pass is separate and you can use that when you visit Hana within 3 days!

How to Get There: Drive via HI-30E for about 65 miles. Will take 2+ hours. Early morning is generally slow as it’s dark to drive!

Morning

Afternoon

Evening

DAY 4 HIT THE ROAD TO HANA

Continue the excitement from yesterday to have a full day exploring the scenic road to Hana. It is another top Maui bucket list item. With amazing waterfalls, lush green forests, bamboo groves, black sand beaches, quaint small towns, and amazing roadside food stalls, it can get tempting to stop everywhere! However, it will be a long day of exploring (10-12 hours!), so don’t plan anything else! In this full-day itinerary, there are both common and not-so-common stops. Nonetheless all worth it! Keep your plans flexible. Remember, you want to save some for future trips too! The whole experience is the beautiful drive and the stops along the way. There is nothing magical about Hana. It's a very small town :)

After a long active day, relax back at the resort villa and grab dinner at the poolside bar or back in the comfort of the villa and have a good night’s sleep.

Tip: I strongly recommend renting a jeep and driving yourself to manage your own pace versus a paid tour! Start early - say 5:30 or 6AM so you have enough time at your last stop at Pipiwai Trail (will need 2 hours to hike)

Duration: Full Day (10-12 hours)

Activity Level: Moderate

Good To Know: 1. Eat some ginger candies, if you feel dizzy on the windy roads. Back seat passengers suffer most! Also, consider an open-roof SUV or rent.

How to get there: Take Hi-30E and then HI-360 all the way to Hana and beyond to your last stop at Seven Sacred pools. It’s about 87 m

NOTE: Read details of each stop on this separate post for Road Trip to Hana

DAY 5 HEAD TO NORTH SHORE - PAIA AND HAIKU

Head to North Shore and enjoy a relaxing half-day in the chilled hippy and hip town of Paia. The streets are lined with trendy restaurants, famous natural food stores, art galleries, spa and wellness centers, and of course beaches. While some do a dinner stop on the way back from Hana, I strongly recommend dedicating a separate half-day to really enjoy Paia as it is only a 30-40min drive from many of the famous resort areas of Kaanapali and Wailea.

Today, start the day at Paia Town around 11 AM and grab healthy Acai bowls, coffee, or other organic plant-based meals at the awesome Choice Health Bar (this is their other popular location besides Lahaina). After that stroll around town shops. Plan to stop at the Great Paia Peace Stupa, and Mana Foods for interesting organic food treats. Wrap up the town trip in about 2 hours and then drive few minutes to the wonderful Ho’opika Beach Park. Enjoy watching amazing Kite-surfers from the bluff and take a walk on the green pastures (you will see cute cows grazing around!) and down on the beach, soaking in the sun and gentle, tropical breezes. Late afternoon spend some time relax in your resort villa and then grab dinner at the old-time favorite - Leilani’s in Whalers Village

Tip: You can visit the Twin Falls in Haiku if you missed that in the Road to Hana. Haiku is just 25 min drive from Paia town center. Suggest doing a short hike in Twin Falls area before spending time in Paia.

Duration: Half Day

Activity Level: Easy

Good To Know: 1. You can rent bikes from Maui SunRiders right in Paia and explore the town or if feeling adventurous then ride on Baldwin Avenue (its Paia’s Main Street) all the way to Makawao town and back. Roundtrip about 2 hours! 2. For dinner, several restaurants do take walk-ins. It’s worth the wait if you are in Whalers village or Lahaina Town as you can walk around the beach or stroll the streets to browse quaint shops.

How to get there: Drive from West Maui on HI-30 and take the same road towards Hana. It’s about 30-35 min from the Westin Kaanapali Ocean Resort Villas

Morning

Afternoon

Evening

DAY 6 SUP AND SNORKEL

On the last day before heading home, plan to stay back in West Maui and spend relaxing time exploring around Kapalua Bay and Kaanapali Beach. Enjoy a short hike and snorkeling in Honolua Bay and roadside eats (there is a hidden gem - keep reading below!

The rest of the afternoon spend time SUP cruising back on Kaanapali Beach at the resort and wrap up the day with burgers and beer dinner at Pailolo Beach Bar at the resort.

Tip: Request a late check-out if you can, especially if your flight is in the early afternoon. Gives you time to pack early AM!

Duration: Half Day

Activity Level: Easy

Good To Know: Honolua Bay gets pretty busy and parking is hard to find. Alternatively, you can go back 2-3 miles to DT Fleming Beach Park and enjoy swimming instead.

How to get there: Drive West on Hi-30 (Honoapiiiani Road) towards Kapalua Bay. It’s a short 20 Min drive.

Morning

Afternoon

Evening

DAY 7 HEAD HOME - MAHALO AND ALOHA!

On this day of departure, plan some final fun activities based on what time your flight is. If you are flying in the morning then, you could squeeze a quick beach walk. If early afternoon departure (we had a 1 PM flight) then, pack and head to the airport but make a stop at Choice Health Bar in Lahaina for one last taste of the incredible Acai Bowls and take to go the awesome cold game (The Game Changer). If flying in the evening, then you have the full day. Pack and have the front desk store your bags (no cost :). Head to "Bad Ass” coffee (5 min drive) and plan to rent an e-bike from Boss Frogs (adjacent store) and cruise on the Lower Honapialani road (it runs from Kaanapali to Kapapula Bay) and enjoy the coastal road and the area around Plantation course in Kapalua Bay.

Tip: If you rented the car from the airport, you can fill up gas before returning at the Aloha Gas station. Few minutes to rental car return from there. No sweat! 

Before You Go

1. Book your Haleakala Sunrise at Summit Pass on Recreation.gov 30 days before the date of arrival. You will also need to pay a fee for entrance to the park which you can use within 3 days to visit other parts of the park, especially for Road to Hana (for access to Pipiwai Trail + Seven Sacred Pools)

2. For Road to Hana, you will need to reserve a daily parking ticket for Waianapanapa State Park prior to your trip. It gets sold out quickly. Here is the link to reserve. Note: On this itinerary, we decided to skip as we had enough stops and also we did not reserve in advance as we did not know!

3. Pack - Plan to take some warm windbreaker and beanie for early sunrise at Haleakala - yes it’s at 10,000 feet and even in summer gets pretty windy and cold between 5 and 7:30 am!

4. Gear - If you have snorkels, take them with you as during COVID-19 we were not keen to rent!

Map It!

Recommended Alternatives

Here are some helpful alternatives to add /swap on this itinerary.

1. Full-day snorkeling trip to Molokini Crater. This is a partially submerged crater, creating perhaps the best snorkeling site in Maui. Consider doing this on Day 6 in the above itinerary.

2. A round of golf at either the plantation course at Kapalua Bay or the oceanside course at Kaanapali Golf.

3. If you love road biking, consider renting from West Maui Cycles and explore several challenging loops in West Maui. They can provide several route maps to help.

4. If you are a foodie, then highly recommend trying local hip restaurants like Lineage, Star Noodle, Paia Fish Market, the new Tommy Bahamas Restaurant in Lahaina Town, or all-time favorite - Mama’s Fish House in Paia

5. For more recommendations read my post on Top 10 Things To Do In Maui

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Plan Your Trip

Take this itinerary as is or if you like to make some tweaks you can consider swapping with the recommendation additions above. If you have less time 3 or 5 days, then pick and choose from the plan above to personalize your trip. If you have questions on planning your trip or have feedback on this itinerary, leave us a comment below.

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