Hi There.

Limitless San Francisco is more than a lifestyle blog--it's a love letter to The City.

2019 Update : Maui Travel Guide

2019 Update : Maui Travel Guide

Maui Travel Guide 2019

2019 has been full of ups and downs. I’ve spent almost a month on-island this year, and even though it wasn’t all vacation, Maui is still just as beautiful a place as ever. I thought I’d update my 2017 post and include some more places to go, things to eat and dos and don’ts. I love giving recommendations, so let me know if you have any questions or are planning a trip! Mahalo!

We still spend most of our nights staying in Wailuku with my boyfriend’s mom. Wailuku is the county seat and is located in the geographic center of the island. It's an old plantation town that used to be full of pawn shops, but new business, coffee shops and stores are breathing life back into it. The brightly colored homes were all built between 1910 and 1940. Wild chickens wander around, and it seems like everything is in bloom or fruiting.


Since it's in between the West Maui Mountains and Haleakala, you can pretty much decide where in the island to go based on the weather you can see from Wailuku. If it was dark and rainy on the north shore, we headed towards Kihei or west to Lahaina or Kaanapali. The best thing about Maui is the size. It's big enough that there are plenty of things to do, but small enough that you only need a short drive between adventures.

I’ve now been to Maui in winter, spring and summer. Winter is whale season, the dry side is green, and it's easy to find off-peak prices. There are turtles resting on North Shore beaches, and plenty of room at bars and restaurants. The weather is mostly warm and sunny but there are rainy days and some chilly nights. You should pack a light jacket to wear in the evenings and mornings, and keep in mind that the further up the mountain you go, the chillier it will get. Winter is the best time to see rainbows. I love spending evenings on the beach, watching the sun set and listening to the waves crash. BYOB and just remember to clean up after yourself.

Spring is lovely. Warm days and nights, some hot days balanced out by cooler mornings and evenings. Even more plants than normal are in bloom, and days aren’t quite so hot. The beaches have way less people and we managed to get really good rates at some of the island’s best hotels including the Andaz, which I think is easily the nicest hotel on the island. Airbnbs are plentiful but do fill up quickly.

There’s never a bad time to visit Maui, but summer was not my favorite. It’s hot—very, very hot. And humid. We got to attend our friend’s beautiful wedding and spend time with lots of my boyfriend’s high school friends, but the weather in December/January/February is much better. Days are hot, nights are hot and it can get windy in the afternoons at the beach. If you’re planning a trip, try to go to the beach in the morning and then move inland or to the pool in the afternoon.

Maui sunset
Ho'okipa Beach Maui
Waikapu Store Drymein and Kaohu Store Poke
Maui Brewing Beer
XIX Palms
Maui Upcountry Lavender Farm
Best Beaches in Maui


The North Shore is still my favorite part of the island to explore. Ho'okipa is breath taking. In the winter, there’s practically a perpetual rainbow, 30 resting turtles, and plenty of local surfers (moms with kids out in the big waves!) to make for good people watching. The sand is more coarse, but so comfy. If you're up for an off-road adventure, there's a dirt road that leads to the famous Jaws lookout. It wasn't breaking big when we were there, but the ride was fun, and the view was pretty.

The tourist mecca of Wailea is probably my other favorite beach to hang out at. If you’re staying at one of the resorts, a day on a beach chair is a must. There’s also a public beach with restrooms and grills.

If you’re in the Kaanapali area, head north through Napili to Flemming Park Beach or Honolua Bay. Honolua Bay is perfect for snorkeling but please use good judgement and be on your best behavior. When you park, don’t leave anything visible in the car. The walk to the bay takes you through a beautiful old Hawaiian garden and a series of sacred and culturally important sites. Stay on the path, keep your voices down and be respectful. The beach has no facilities or lifeguard, so come prepared. Please do not apply spray sunscreen (which is bad for kids and the environment), only wear reef-safe sunscreen, and wear physical sun protection like a rash guard when possible. Bring your own gear, be careful on the slippery rocks, and remember to take everything with you when you leave.

edited DSC_1311.jpg
proteas maui flower farm
proteas maui
best burger on maui upcountry maui wine
O'o Farms Coffee tasting and tour

Upcountry : Lavender Farm, Wine Tasting + O’o Farm Tour

I love Upcountry. The air is less humid and cooler, the views are spectacular, and everywhere you go the food is amazing.

The Ali'i Kula Lavender Farm has breathtaking views, tons of blooming flowers, and an exotic collection of Proteas from around the world. Sure, it's a lavender farm, but the Proteas were the best part. And the view! You can literally see the whole of Maui spread out before you. 

For lunch, continue up Route 37. When the yellow line ends and the road gets a bit rough, keep going. There's a cattle ranch and winery about 35 minutes up the road. We had the best venison burgers for lunch at Ulupalakula Ranch. They were juicy, perfectly cooked, and came in at just under $12. There were tons of locals grabbing a lunch and taking in the view. All the meat is from Maui, and is all grass fed, free range. The burger was way better than most of the burgers in SF. Across the road is the tasting room for MauiWine. The little winery offers three free tastings, and an optional tour for $10. The grounds are beautifully landscaped and are full of ancient trees, historic structures, and breathtaking views. We did the tour, but I'd suggest skipping it. Maui's world-famous pineapple wine is produced here, as are several other varieties. Be sure to ask questions--not all the grapes are grown on the island, and the staff is quite knowledgeable. 

If you’re interested in local agriculture, permaculture, are a foodie or a coffee snob, O’o Farms is a must. The farm practices sustainable agriculture and grows a big variety of fruits and vegetables on about 10 acres. The morning tour features breakfast, a coffee tasting and tour of the farm. The food is fresh and healthy, the coffee tasting was informative and the guide is an expert in permaculture.

paia hawaii
paia nourish bar and cafe
paia maui things to do
maui flowers
paia fish market maui things to eat


Located at the beginning of the Road to Hana, Paia is a little hippy town that has turned into a hipster/tourist/shopping destination. The town is still really cute, but really commercialized. The stores are cute, but not cheap.

The Paia Fish Market is much better in Paia than in Kihei. If you stop in Paia in the morning, you’ll be able to grab a coffee and breakfast (and parking!) before the stores open and still have time to wander around before it gets too hot.

Makawao Town

Makawao is a historic cowboy town in Upcountry, and home to some of the cutest boutiques on island. It’s on the way to most of Upcountry’s best destinations, so it’s an easy stop in the morning or afternoon. Boutiques are definitely more high-end, but I love supporting local businesses and artisans. Most stores carry a ton of local labels and are expertly merchandised. I literally freeze my spending a few months before we go to Maui just so I can spend freely here. Driftwood Maui, Pink by Nature, HOMME by Nature, Holoholo Surf and The Mercantile are all amazing.


Maui is full of amazing food, but poke and plate lunches are staples. Be prepared to try something new.

In Wailuku, the historic downtown is seeing a resurgence. The coffee shop is solid, there's an acai bowl place that's tasty but expensive, and Umi Sushi is a fun BYOB spot. Outside of town, the Tropical Plantation is a great place to stop for a touristy snack or morning coffee. Kaohu Store in Wailuku has the best poke and masubi, but they sell out daily.

The plate lunch at Sam Sato's was really good, as was the drymein and the under $4 hamburger. The spam masubis at Minit Stop are tasty, and are under $2. Foodland has a big selection of prepared food including chicken katsu masubi, spam masubi and poke. Waikapu Store, located on Route 30, has amazing plate lunch. For a fancy dinner, Sansei is my favorite. It’s some of the best sushi I’ve ever had.

If you’re staying somewhere with a kitchen, a trip to the local Foodland, Safeway or Whole Foods will actually save you a bunch of money. Try some local fruits and get a gigantic avocado. Things like lettuce, kale, fresh herbs and imported milk and meat are more expensive than on the mainland, but exotic things like dragon fruit, papaya, star fruit, guava, mangoes, passion fruit, etc. are all much cheaper. Pick up some Spanish rolls for a quick breakfast and a few malasadas. Fish is also much more affordable and plentiful than in California, and you’ll see lots of people with coolers at the airport.

I’d stay away from chain restaurants that you can easily find at home. Lahaina, Kihei and many of the touristy shopping areas feature mainland chains and subpar food. When in doubt, hop on Yelp and find somewhere with good reviews.

O'o farm tour breakfast coffee tasting
shave ice maui
poolside lunch maui
o'o farm breakfast maui things to do tour foodie
happy hour on maui

Whale Watching

November through April is whale season in Maui. Humpback whales travel thousands of miles from their feeding grounds in Alaska to give birth and breed in the warm, Hawaiian waters. Up to 60 percent of all Pacific Humpbacks come to Hawaii in the winter, and make the long journey solo. From beaches you can see them spouting and splashing. If you swim out past the break, and stick your head under water, you can hear them singing. But, the best way to see the whales is from a boat.

There are tons of whale watching tours, but I highly recommend choosing the Pacific Whale Foundation. They're a conservation and education focused non-profit, and the tours run about $40/person.  All proceeds help their cause, and the naturalists on board are extremely knowledgeable. We went out on a sunrise tour on our last morning, and it was breathtaking. Leaving from Maalaea Harbor, we were out for a couple of hours and saw dozens of whales. None breached super close to the boat, but hearing their songs and seeing mom's and calves together was magical.

We left the harbor in the dark, with an inky sky dotted with stars. Soon, the sky began to lighten, and the sun rose over Haleakala. As the sky grew lighter, it was easier for our captain to spot the tell-tale spouts, slaps and dives. We saw plenty of tales, and watched slick, huge bodies move across the surface.

I'm so happy we chose the Pacific Whale Foundation, since conservation was at the heart of their mission. If you're interested in science and biology, there's also an aquarium at Maalaea that is a great way to spend a rainy or windy day. 

Iao Valley Maui

Things I’d Skip:

As much as I love Maui, there are definitely some places and things I’d avoid.

  • Chain restaurants and shops

  • Eating “American” food at every meal

  • Going to the mall or any of the touristy shopping destinations

  • Road to Hana (it’s pretty but I’m just not convinced it’s worth the time/effort/crowds)

  • Daily breakfast buffet at the resort (unless it’s included in your room rate)


  • Try new foods

  • Get out of your comfort zone

  • Be friendly and embrace the Aloha spirit

  • Remember to take your shoes off if you visit someone’s home

  • Go to the beach, but swim at your own risk

  • Show respect to the land and sea


  • Don’t drive the Road to Hana if you’re a nervous driver

  • Don’t forget to honk if you’re coming around a blind curve on a one-lane road and keep your window rolled down to listen for oncoming traffic

  • Don’t speed

  • Don’t litter or disrespect cultural sites

  • Don’t forget to leave your resort/condo and explore the island!

Maui Hawaii Travel Guide
Den + Guest Room Make Over

Den + Guest Room Make Over

Film Photography + The Joy of Surprises

Film Photography + The Joy of Surprises