Our May 2008 Maui itinerary was packed with snorkeling, beaches, scenic drives, surfing, volcanic landscapes, and some unforgettable adventures by air and sea. Over seven days, we explored as much of Maui as possible while also making time for one incredible day trip by airplane to the Big Island.
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Our trip to Maui in May 2008 was one of those vacations where we wanted to see as much as possible. Rather than spending the entire week at the resort, we filled our days with snorkeling excursions, beaches, scenic drives, hiking, surfing, and exploring some of Maui’s more rugged landscapes.
The trip began with a long journey from Florida before we settled into our Maui routine. We stayed at two different hotels during the trip, with the Fairmont Kea Lani becoming our home base for most of the vacation. From there, we explored both the South Maui coast and some of the island’s most scenic areas, including ʻĪao Valley, the northwest coast, and part of the Road to Hana.
One of the things that made this trip especially memorable was how much variety we were able to fit into one week. We snorkeled at Molokini and Turtle Cove, took surf lessons in Lahaina, explored beaches and lava fields near Makena, drove along Maui’s rugged northwest coast, and even took an airplane tour over the Big Island to see its volcanic landscape.
Getting There
Our trip began at Southwest Florida International Airport in Fort Myers, Florida. Getting to Maui from Florida in 2008 required a long travel day with one or more connections on the mainland before continuing west to Hawaii.
Once we arrived in Maui, we picked up a rental car and used it to explore the island throughout the remainder of the trip. Having a car gave us the flexibility to fit in scenic drives and spontaneous stops instead of being limited to organized excursions.
Best Time to Go
Maui is a year-round destination, but spring and fall can be especially pleasant times to visit when temperatures are comfortable and outdoor activities are enjoyable. Summer brings warmer weather and excellent beach conditions, while winter offers the added possibility of seeing humpback whales around Maui.
For an itinerary like this one, having several days available is important. Many of Maui’s best experiences are spread across the island, and a rental car makes it much easier to combine beaches, scenic viewpoints, hikes, and longer drives into one trip.
Day 1: Travel to Maui
Travel from Florida to Maui
Our Maui adventure began with a long travel day from Southwest Florida International Airport in Fort Myers. The journey included a couple of connections through mainland airports before continuing on to Hawaii.
We left Fort Myers early in the day on May 15th, but due to the long flights, layovers, and time differences, we didn’t arrive in Maui until about midnight. But, to us, that felt like about 6am. We were exhausted! We stayed overnight at Maui Seaside Hotel to get some rest before starting our first full day in Maui.
Jennifer looking out the window at the first dark view of Hawaii
We were sooo tired when we finally got to Maui!
Darrell looking at the map at our first hotel
Day One Map
Day 2: Arrival and Big Island Volcano Tour
Arrive in Maui
After the long journey from Florida, we arrived in Maui and picked up our rental car. We checked in to our first hotel, the Maui Seaside Hotel.
This was a short stay because the next part of our day was a much bigger adventure: an airplane tour over the Big Island. Then we checked in to our hotel for the remainder of the stay: Fairmont Kea Lani.
VIP Air Adventure Volcano Tour
One of the most memorable experiences of the trip was taking an airplane tour to see the volcanic landscape of the Big Island. Rather than spending the entire day driving around the island, we experienced it from above, giving us a completely different perspective on Hawaii’s enormous volcanic landscape.
The tour was a highlight of our first full day in Hawaii. We got on a small plane that seated about 12 people, and my dad was chosen to be the copilot and sit in the cockpit! This tour took us over key places on Maui, then over the Big Island. The best part was seeing the flowing lava from a recent volcanic eruption on Big Island. While the steam made the rest of the tour hazy, it was so neat to see real lava!
Fairmont Kea Lani Hotel Checkin
After the flight, we returned to Maui and checked in to the Fairmont Kea Lani Hotel. This became our home base for the rest of our Maui vacation.
When we arrived, we were greeted with real flower leis for the women and kukui nut becklaces for the men!
Staying in Wailea put us in a convenient location for exploring South Maui while also giving us a beautiful place to return to after our busy days exploring the island.
Beth and Stephanie on the plane for the volcano tour
Looking out at the rugged Maui coastline
We loved getting to see an active lava flow!
Day Two Map
Day 3: Molokini, Turtle Cove and Wailea
Maui Magic Snorkel and Turtle Excursion
We started the day with the Maui Magic Snorkel and Turtle Excursion, one of the biggest highlights of our Maui vacation. The excursion took us out on the water for a day of snorkeling and exploring some of Maui’s best-known marine destinations.
The excursion departed from the Māʻalaea Harbor area. From there, we headed out toward Molokini before continuing to Turtle Cove for more snorkeling and the opportunity to see sea turtles.
Molokini Island Snorkeling
Molokini is an extinct volcanic crater located offshore from Maui, and snorkeling there gave us the chance to experience Hawaii’s underwater world rather than simply enjoying the island from the beach.
Unlike snorkeling from shore, getting to Molokini requires a boat trip into the open ocean. Once we arrived, we could get into the water and explore the reef and tropical marine life surrounding the crater.
Turtle Cove
After snorkeling at Molokini, the excursion continued to Turtle Cove for additional time in the water. This was another opportunity to explore Maui’s underwater environment and look for Hawaiian green sea turtles.
The combination of Molokini and Turtle Cove made this a full day on the water and a great way to experience two very different snorkeling locations during the same excursion.
Stephanie and Tricia on the boat ride excursion
Stephanie snorkeling at Molokini Crater
One of the many turtles we saw while snorkeling at Turtle Cove
Day Three Map
Day 4: Lahaina and South Maui
Surf Lessons at Royal Hawaiian
We began the day by driving from Wailea to Lahaina for surf lessons with Royal Hawaiian. Learning to surf in Hawaii was a memorable way to experience the island beyond sightseeing and snorkeling.
The surf lesson gave us the chance to get into the water and try something completely different from the other activities on our itinerary. After spending the morning in the ocean, we continued exploring Lahaina.
Lahaina Jodo Mission and Great Buddha
After our surf lesson, we visited the Lahaina Jodo Mission and its Great Buddha. The massive Buddha statue is one of the most recognizable features of the mission and provided a peaceful contrast to our active morning of surfing.
This was one of several stops that allowed us to experience a different side of Maui, adding cultural and historical interest to a day that had started in the waves.
We had no clue that this was here, but the surf instructors told us about it, so we decided to make it a side quest.
Stephanie in front of the large Buddha statue
Mākena Landing
After returning to the Fairmont Kea Lani, we decided to head out again and explore South Maui. Instead of turning left from the resort like we had become accustomed to doing, we turned right and headed south toward Makena.
That spontaneous decision led us through a series of beaches, coves, volcanic landscapes, and scenic stops that became one of our favorite stretches of the trip. One of those stops was Mākena Landing, where we explored the rugged shoreline and surrounding landscape.
Mākena State Park
We continued south into Mākena State Park, one of the area’s best places to experience Maui’s beaches and volcanic scenery.
The park includes several different landscapes and gave us another opportunity to get out of the car and explore the South Maui coastline. It fit perfectly into our goal of seeing as much of the island as possible.
Mākena State Park
Oneloa (Big Beach)
Oneloa, better known as Big Beach, was another stop along our South Maui drive. The expansive beach is surrounded by the dramatic volcanic landscape that makes this part of Maui so memorable.
We were able to take in the scenery and continue working our way farther south, where the landscape gradually became more rugged and less developed.
Puʻu ʻŌlaʻi and Little Beach
From Big Beach, we could see Puʻu ʻŌlaʻi, the volcanic cinder cone separating Big Beach from Little Beach.
The area around Puʻu ʻŌlaʻi added even more volcanic scenery to the drive and gave us another perspective on the coastline as we continued toward the ʻĀhihi-Kīnaʻu area.
Oneuli Black Sand Beach
We continued south to Oneuli Black Sand Beach, also known as Naupaka Beach. The dark volcanic sand made this beach noticeably different from the lighter-colored beaches earlier in the day.
It was another quick but memorable stop as we continued exploring the increasingly rugged South Maui coastline.
ʻĀhihi-Kīnaʻu Natural Area Reserve
Our drive eventually brought us into the ʻĀhihi-Kīnaʻu Natural Area Reserve, where the landscape becomes much more rugged and volcanic.
This was one of the reasons our spontaneous decision to turn right from the resort turned into such a memorable adventure. Instead of simply spending the afternoon at the beach, we found ourselves exploring a completely different side of Maui.
Kanahena Cove
Within the ʻĀhihi-Kīnaʻu area, we stopped at Kanahena Cove on ʻĀhihi Bay. The rocky coastline and clear blue water provided another beautiful contrast to the sandy beaches earlier in the day.
The cove was part of the sequence of coastal stops that we reconstructed from our photographs, making it one of the confirmed locations from this South Maui adventure.
ʻAʻā Lava Field
We continued toward the southern end of the road, where we reached an ʻAʻā lava field. The rough, jagged volcanic rock created an especially dramatic landscape and was a fitting end to our exploration of this part of the island.
After reaching the southern end of our drive, we turned around and headed back toward Wailea. What started as a spontaneous afternoon drive ended up becoming one of the most varied days of our entire Maui trip.
Day Four Map
Day 5: ʻĪao Valley and Northwest Maui
ʻĪao Valley State Monument
Day five took us from the dry, volcanic landscapes of South Maui into the lush mountains of Central Maui. We drove from Wailea to ʻĪao Valley State Monument to experience one of the island’s most beautiful landscapes.
ʻĪao Valley is known for its dramatic green mountains and the iconic Kūkaʻemoku, commonly called the ʻĪao Needle. The contrast between the lush valley and the rugged coastline we had explored the previous day made this another completely different Maui experience.
ʻĪao Valley State Monument
ʻĪao Needle Lookout Trail
We walked the ʻĪao Needle Lookout Trail, the main trail through ʻĪao Valley. The short paved route provides views of Kūkaʻemoku and the surrounding valley while also passing through lush tropical vegetation.
The trail was an easy way to experience the valley without spending a large portion of the day hiking, which made it a natural stop before continuing toward the northwest coast.
Nākālele Point
After ʻĪao Valley, we continued toward the northwest coast of Maui. One of our confirmed stops was Nākālele Point, a rugged coastal area known for dramatic volcanic scenery and ocean views.
The landscape here was a sharp contrast to the lush greenery of ʻĪao Valley. The northwest coast gave us another opportunity to see the wilder side of Maui, with rocky shorelines and exposed volcanic terrain.
Olivine Pools
We also visited the Olivine Pools area along the northwest coast. The pools are located in a rugged coastal setting where volcanic rock meets the ocean.
After exploring the northwest coast, we headed back toward Wailea and the Fairmont Kea Lani.
Day Five Map
Day 6: Part of the Road to Hana
Drive Through Central Maui
For our final full sightseeing day, we headed toward the Road to Hana. We left the Fairmont Kea Lani and drove through Central Maui toward Pāʻia before continuing east along the Hāna Highway.
We did not complete the entire Road to Hana on this trip. Unfortunately, there was some construction going on and the southern portion of the road was closed so we couldn’t complete the loop.
Hoʻokipa Beach
Hoʻokipa Beach was the confirmed highlight of our Road to Hana drive. Located along Maui’s North Shore, the beach is known for its beautiful coastal scenery and powerful waves.
We stopped at the beach and overlook before continuing farther east along the Hāna Highway. Even without completing the entire drive, this gave us a taste of one of Maui’s most famous scenic routes.
Partial Road to Hana
From Hoʻokipa, we continued along part of the Hāna Highway and made additional scenic stops.
We eventually turned around and returned to Wailea. The drive was still a great way to spend our final full day because it allowed us to experience part of one of Maui’s most famous routes without trying to force the entire journey into a single day.
Day Six Map
Day 7: Departure from Maui
Check Out of the Fairmont Kea Lani
Our Maui vacation came to an end on May 21. We checked out of the Fairmont Kea Lani and loaded up the rental car for the drive to the airport.
After returning the rental car, we began the long journey back to Florida. Because of the distance and time-zone change, the exact arrival date in Florida is uncertain and may have been May 21 or May 22 depending on the flight connections.
Fly Home to Florida
After a busy week of exploring Maui and one unforgettable adventure over the Big Island, it was time to head home.
Looking back, this trip packed an incredible amount into just a few days. From snorkeling at Molokini and Turtle Cove to surfing in Lahaina, exploring ʻĪao Valley, driving the rugged South Maui and northwest coasts, and taking an airplane tour over the Big Island, we experienced a huge variety of Hawaii’s landscapes and adventures in one trip.
Stephanie and Tricia with a large tiki statue at the airport in Maui