I’d posted a few months back and got great suggestions when our trip was supposed to be to the Big Island. Well, because of the tsunami damage, our hotel wil be closed for repairs, so we’ve been moved to Maui. We’ll have a car, and like to drive…so we’re up for anything. We’ll be in Wailea (Four Seasons) for four days, then Lahaina for 3. I also need some running/swimming suggestions for both places.
Thanks!
If you’re going to be at the 4 Seasons Wailea for 4 days, don’t bother doing much other than enjoying what has to be one of the most beautiful properties on the planet.
If it’s just you and a significant other, enjoy the Serentiy Pool, really peaceful, stunning views. The beach is nice too. Don’t bother with the regular pool unless you have kids. You can run leaving the property, take a right out of the driveway and head towards McKenna Beach (where Xterra Worlds are hosted). When you get back valet will hand you a bottle of water and a cool, damp towel. Or enjoy the gym at the 4 Seasons, all the cardio equipment is in an open area areas overlooking the ocean, it makes treadmill running pretty cool.
With only that much time, I am not sure I wouldn recommend driving to the top of Hailekala (sp?) to see the sunrise. It’s cool, but a huge time committment and freezing cold. Driving the Road to Hana is cool, we only made it halfway to Hana and still saw a ton of cool stuff with plenty of time to get back and hang by the pool in the afternoon. The last big town on the way out Pa’ia, or something like that, is a neat little town with a great brick oven pizzeria.
The 4 Seasons doesn’t hose a luau, but the property next door did, and you could book it through the 4 Seasons, we did that one night, it was cool. A few good restaurants right at the 4 Seasons and then some other good ones at some of the other nearby resorts.
Enjoy, we were thinking of going to the Caribbean next year, but are considering going back to the 4 Seasons.
With only that much time, I am not sure I wouldn recommend driving to the top of Hailekala (sp?) to see the sunrise. It’s cool, but a huge time committment and freezing cold. Driving the Road to Hana is cool, we only made it halfway to Hana and still saw a ton of cool stuff with plenty of time to get back and hang by the pool in the afternoon. The last big town on the way out Pa’ia, or something like that, is a neat little town with a great brick oven pizzeria.
Ha! and I recommend just the opposite. Hailekala requires getting up before dawn - but as a triathlete you should be used to that 
Just a very cool experience - something I’ve never seen the likes of again - almost 20 years ago. Back at the hotel in time for a nice b’fast then crashed by the pool for few hours. Awesome day!
The road to Hana was kind of cool but Hana it self is nothing. Literally. Anti-climactic. The ride back is just boring as you’ve seen it all on the way there.
Go to Moose Mcgillycutty’s for a burger and beer! Oh, and as stated it was 20 years ago, but Eric’s Seafood Grotto was one of the best, freshest seafood meals of my life.
Enjoy. I’m jealous. Lots of fond memories.
great run is to exit the hotel and turn right on Wailea Alanui Drive…run out to the lava fields…beautiful run in early AM.
great swimming in front of Makena.
check out the ziplines above Maui Tropical Plantation in Waikapu on your way to Lahaina.
enjoy.
Albert
I’d take a shot a surfing (I do every year when I go there for the Xterra). Boards are easy to rent, there at lots of places that have lessons as well.
Also, gotta do some snorkeling. Great turtles, fish, dolphins, etc.
I really recommend the Hike Maui “Hike, Bike, & Kayak” trip - it was awesome. Our hike guide was Kahi & his family has been on the island for a very long time - he had awesome stories and could tell you absolutely everything about the flora, fauna, and local folklore.
There isn’t a whole lot to do other than relaxing and enjoying the peace and quiet. The two big things are Haleakala and the Road to Hana. Both are kind of big time committments–Hana more than Haleakala. I usually tell people to drive half of the road and then turnaruond. Like the other poster said, it’s very anti-climactic at the end and on the way back you’re just dying to get back home.
Not much in terms of running options. There’s really just one main road on each side of the island.
o Go to Lahaina Friday night early and stroll through the galleries and enjoy the free wine and cheese
o Go for a ‘performance sail’ or ‘sunset sail’ on America II. It’s not expensive and it’s a lot of fun. A great way to see the water between Maui and Lanai
o Whale watching cruise with Lahaina Cruise Co - like watching National Geographic channel live if it’s the right season
o When snorkelling, dive down and listen for whales. You may hear a male singing.You can rent snorkleing gear from Snorkel Bob’s in Kihei up the road from Wailea
o Snorkeling at Molokini is fun. There are cheaper, and possibly better options, up the NW coast, but this is fun. Go out in a sailing catamaran if you can – catamaran from Maui Prince Hotel just south of Wailea
o The ‘road to hana’ is okay. Nothing too great. If you do go, see the 7 sacred pools and take the hike inland to the waterfall. The waterfall is the most worthwhile part
o Take a kitesurfing/windsurfing lesson in Kihei. Lots of activities here.
o Enjoy Kaanapali beach
o Rent kayaks at Wailea beach
Paia is a cool, funky little town not far from the airport. The casual Paia Fish Market has the best fish sandwich I’ve ever had. The mahi mahi burger is a must when you’re on the island. You’ll share a table with strangers but the food is totally worth it.
Matteo’s near the Four Seasons has awesome thin crust pizza for dinner and is reasonable for Maui.
**Pacific O **in Lahaina, is literally right on the beach. We watched surfers and paddle boarders and a group surfing lesson as we ate. The food and drinks were outstanding. I highly, highly recommend the fish tacos.
Dinner at Mama’s Fish House in Paia is expensive, but worth every penny. There is a private beach and gardens to stroll as you watch the sunset if you time it right. All the fish is caught by local fishermen employed by the restaurant. The menu is printed twice daily and the fisherman who caught your fish is listed on the menu next to each dish. Get the Kuau Pie (chocolate mouse on a layer of caramel in oreo cookie pie crust) after dinner. Drinks here are amazing but don’t fill up too much 'cause the food is plentiful and sensational.
For swimming, you have Wailea beach or Ulua beach right there.
There is a ton to do on Maui. Enjoy the trip!
Agree with whoever said be a lounge lizard at the 4 seasons. It’s amazing - never stayed there, but have been to the Grand Wailea next door, where we got married.
Haleakala - if you want to avoid the 4 am wakeup, go up and do sunset. It’s the same, just in reverse. 
Stop at kula lodge for a bite to eat.
Road to Hana - long, full day, pack a lunch, but worth it. At the end, park in the parking lot and follow the 2 mile trail uphill to Waimoku Falls.
South (?) of you, i.e., right turn out of the resort, drive all the way to the end throught the "mini kina lavafields,’ hike a bit of the King’s Highway to the edge of the island. remote
We did the Hana Highway a few weeks back and 95% turn around in Hana and head back the same way…DON’T DO IT…go all around to Kaupo and Pukalani. They say the road is bad but it is not as bad as they want you to believe…we drove a convertable Mustang and had no problem getting around…its a day trip but definately a highlight and AWESOME senery! Another awesome drive is around the north part of the Island from the airport to Lahaina…a lot of it is narrow and winding but again an awesome and beautiful drive! Whale watching on the Hula Girl is cool…we must have seen 100 whales!!!
You said swimming/running suggestions, but by any chance do you like to bike?
If you are interested, the ride up and down Haleakala is epic. I think it’s about 35 miles from sea level to the summit over 10,000 feet high. I did it with www.gocyclingmaui.com . They offer supported rides w/ bike rental, or you could just rent a bike from them. There’s not many places you can ride that much elevation differential in such a short distance.
I was just there a couple weeks ago. We were at Makena Beach though, I’m not quite baller enough for the Four Seasons.
Running is easy. Just step out the door of your hotel and go. The road between Wailea and Makena has nice wide shoulders and is great for running. You’ll see a ton of other runners/walkers out and about if you go in the morning.
Wailea beach is pretty decent for swimming too. The water’s calm and there are a ton of people around. Just get out a couple hundred yards from shore and parallel the beach for as long as you want. If you’re feeling a little more adventerous and your schedule allows, there’s a local group that does open water swims from Makena beach Sunday mornings at 9. They meet on the south end of the beach fronting the Makena Beach Resort (where Xterra worlds is). Look for the guys in the pink speedos and let someone know you’re visiting and want to swim with the group. I swam with them twice while I was out there and they were super friendly. There were a fairly wide range of abilities in the group, but if you want to hang with the lead group good luck. They are hardcore. My first swim with them I got on the back of the lead group and just hung on for dear life. We ended up WAY out in the channel, maybe halfway to Molokini and had to fight a wicked current on the way back. I ended up spending 2.5 hours in the water. I later found out that that group has gone all the way to Molokini and back before. It’s something like 6 miles round trip. There are also 50m pools in Kihei and Lahaina if you want to go that route.
The road to Hana is way overrated IMO. It felt like a waste of a day. But I absolutely hate driving, so you may love it. The scenery is certainly pretty.
Go the the top of Haleakala, but don’t be a pussy and drive up. Do it on a bike. Check out Maui Cyclery in Paia for rentals. They also do fully supported rides where they have a couple guys riding with the group and a truck following for SAG support. The owner and mechanic are both ex-pros and are a blast to ride with.
Four Seasons at Wailea!?! I am SO JEALOUS! I suggest you take me along as your tour guide. This happens to be my favorite place on the planet and I can show you where to SBR. I look like Brooklyn Decker in a bikini and I can fly direct from the west coast and meet you there. Can’t wait to meet you and your wife!
At the 4 seasons, get the outdoor couples massage…it is amazing. Have dinner one night at Roy’s, the best seafood place. We drove along the north shore, got lost in the back roads, stumbled across a tiny village and had dinner with the locals there. I paddle outrigger so jumped on a practice session with Lahani Canoe club, surfed 4 foot waves in a six man. Just generally relaxed the entire time. Enjoy!
We got back from Maui a week ago. I really enjoy the ride from Kaanapali through Kapalua and out along the coastline. There are many good climbs and descents after you get past Kapalua. I ride out to the first cattle guard and return in about 1:45. This ride is the highlight of the trip for me. There is one climb that is just short of the turnaround that is an 18% grade and long enough to make anyone work. One of the TDF teams trained out there and nicknamed it “the wall”. I’m sure that is not the most original label, but, it gets the message across. I usually bring my bike. But, West Maui Cycles in Lahaina has pretty reasonable rental road bikes.
Running isn’t as great in this area from my experience. We do run along the boardwalk and further toward Kapalua, but, the traffic is not so easy and that is definitely not as much fun as the biking.
We swim from the Westin resort over to Black Rock and back and that is pretty nice. If I haven’t been clear, the biking is better.
Roys is a great restaurant in the kaanapali area as is Lahaina Grill and Sensai.
Have a great trip. We try to get there once a year and are never disappointed.
Aloha Mixed Plate in Lahaina. Patio dining right on the water, fish and mixed drink special every night, good Hawaiian beer selection, and if you go around sunset free music from the luau place next door. Inexpensive and fun. Kailua pork ummmm.
Also, visit Pa’ia - it’s a nice little place to knock around. Mama’s Fish House is out there (just past town) and Willie Nelson’s Pizza joint is right in town.
A little tip on the Haleokola sunrise thing - it is very cool, but yes a long trip. Do it the first morning you are there - your body clock will be off and you’ll be up early anyway.
I knew I could count on you guys to hook it up with the info. Awesome suggestions!
This trip is a corporate retreat type deal from my wifes company. They take a dozen or so people and their families once a year, and this year my wife got picked. They usually have it at the Big Island 4 Seasons, but they’ve shut down as of 2 days ago to repair damage from the surges. We’re bringing the 5 and 8 year olds, but leaving the baby with grandparents. The great part is that it’s a all-inclusive type deal, so everything is covered…including the couples massage, and the daily kids camp to keep the offspring occupied.
We were really stoked on the other Four Seasons, but the Maui complex looks pretty damn nice too…and I ain’t gonna complain. Second half of the trip we’ll be staying at the Ka’anapali Beach Hotel. We had reservations at the Hilton Waikaloa, but oh well. We’ll probably use those days to do our exploring.
Doubt I’ll get a chance to rent/ride a bike as it will probably eat up too much time. It’ll only be 12 weeks till CdA, so I will definitely be getting some swim/run time in though.
Thanks again for all the suggestions!
Here’s some (some already mentioned)
We really liked the drive to Hana from Kihei, but there’s too much to do in one day. We set aside 2 days for it, 1 to drive there and stay overnight and another to explore past Hana. On day 1 there’s beautiful scenery, but you need to stop occasionally to see it all. Several waterfalls including the twin falls, Keanae peninsula, the Garden of Eden arboretum, lava caves and Wainapanapa beach. We camped in the state cabins on Wainapanapa beach. The next day, breakfast at the Hana Hotel, then on to Kipahulu and Kaupo, the 7 pools and the awesome Waimoku falls after a good 2 mile hike through bamboo forests and amazing views. Drive back and have dinner at Mamas Fish House.
Haleakala sunrise experience depends what the weather’s like. When there’s a low cloud layer, it’s pretty incredible, with clear skies, it’s ok. Skies were clear for us and we were a little underwhelmed. The views up there are amazing though, almost like you’re on another planet. Lot’s of hiking in the craters. Coming back, go south on state hwy 377 instead of north and go through the upcountry area - Kula and the botanical gardens. Keep going and you get on hwy 37 for a gorgeous winding countryside drive to the Tedeschi vineyards and wine tasting. They ship to your home.
Hiking down around La Perouse bay was fun with very few people encountered.
If you’re in Wailea, you’ve gotta do little beach on Sunday at dusk, it’s right next to you and very fun - as long as you don’t mind boobies and fire dancing. Be careful climbing the rocks coming back after dark and a few drinks.
Ahihi Bay has lots of sealife, but pretty busy with people.
The Maui Ocean Center in Wailuku is pretty good.
We only went to the west side of the island twice. Friday night in Lahaina, which was fun and a day in Kaanapali/Kapalua for the zip lines and Fleming beach. Fleming beach was disappointing, there’s much better around Wailea, the zip lines were fun, but nothing special if you’ve done them before, plus your shoes are permanently red after hiking in the red dirt.
I’d try and hit up the Xterra course, it’s right by your hotel in Wailea. That would be awesome, but it may not be open to the public.