Hawaii Travel Guide

I recently went on an AMAZING trip to Hawaii with my sister and it was nothing short of pure magic. We started on Big Island and then went to Maui. Details all below!

I booked this trip in March, 3 months before departure date. We left on a Wednesday and returned on a Thursday and the round trip ticket from Boston (direct flight) was $650. We flew to Oahu (Honolulu) and then took direct mini flights to each of the islands. All flights were through Hawaiian air!

We went in June, 2021, so we did need COVID tests 72 hours prior to departure. Also of note, Interisland travel ALSO required an updated COVID test. We did not know this prior to going to Maui, and thought our original tests would suffice. They (very regrettably) did not. So we had to quarantine in Maui for a night, fly back to Honolulu the next morning, get a new test, and then fly BACK to Maui. Truthfully, it was a very expensive misstep (I cried). At the time of writing this, Interisland travel is permitted without updated COVID tests. Also regarding COVID tests, Hawaii is very particular and it has to be an NAAT test performed by an approved partner. More on that here. Further, you have to note every detail of your trip prior to leaving, found here.

Renting a car

We rented a car in both locations. I absolutely love having the ability to drive in a new place. Allows such a greater understanding of the area and nice to not be on someone else’s itinerary. If you’re thinking of renting a car, BOOK EARLY! I booked right in March and was glad when I did. After COVID there was a shortage of cars so if you’re considering, book early. You can always cancel. I rented through Discount Hawaii Car Center.

The key to planning travel

What I do on all my trips is plug in the places I want to go on Google Maps. Then I “star” those places and plan the itinerary days based on proximity. Things in Hawaii are booking SO SO EARLY. If you know you want to eat somewhere, DEFINITELY book a few months in advanced (at least!!). For example, my Google Maps looks a little something like this.

Big Island

We really wanted a balance of active adventure with relaxation on this trip. And by we I mean me because my sister prefer to lay on a beach all day every day. So Big Island was our compromise to get a little exploration and activity in.

Where we stayed:

The location:

We wanted to stay on Kona side, as it had easier access to beaches and food. It’s definitely the more touristy side. So we stayed near Captain Cook and the location was perfect. A short drive from lots of amazing food options and about 30 min to Kona (west side of the island). However, we really wanted to be able to explore Hilo side (east side) for a day, which is ~2 hour drive from Kona. Note: the volcanoes are on the east side! Rather than having to drive all the way back, we booked a later flight out of Hilo and flew out of that airport. It actually ended up being cheaper for the rental car, too. Win win.



We stayed on a Mango Farm, found here. The price was $188 a night when we booked, and it was a 2 bedroom. There is also another unit on the property found here for $134 a night. The property itself was gorgeous and the host was great. However, it’s open air and very shaded. This translates to: A LOT OF BUGS. If you want a nature immersed experience and know that going into it, this is the place for you. With that being said, my sister counted 104 bug bites on me by the time I left. The bedrooms were netted, though so when I was in my room, I felt okay. The mornings reading were so peaceful looking over the treetops. You’ll wake with the sunrise, birds, and roosters. This worked for us given we were jet lagged and 6am Hawaii time was noon Boston time.

With it being open air, anyone could walk into your property. The mango farm itself is very secluded, but there’s no front door. There are “locks” on the rooms but they were not very secure. The property is also “locked” at night, though to unlock it you don’t need a code. You simply lift the chain off the gate. The bathroom was also a walk from the property and also open air. Somewhat terrifying when you have to pee in the middle of the night. Looking back, while the pictures were beautiful, we wouldn’t stay there again. Instead, I think I’d go for something like this that’s indoors. Big Island has little pockets of rain nearly daily, so it’s pretty damp and therefore buggy.

Things to do:

  1. Late night manta ray snorkeling. We booked this through Kona Style, with tickets at $109 each. Not only did we see TONS of manta rays, we also swam with a dolphin! The trip is slotted for 3 hours total, but we finished in about 2.5. You start with a 20-30 min boat ride, and then the guides bring you out to water where you’re floating with others in the group. You’re with the guides the whole time and if you don’t see a manta, you get a free trip to come back! We saw SO MANY!!! And they come up so close to you, literally centimeters away if not touching you. It was such a surreal experience. Of note, the trip starts at 9pm and we did this on our second night in Kona. This means it was 3am Boston time. We were so beyond jet lagged and we STILL didn’t regret the experience. Definitely book early because these experiences book up quickly!
  2. Hiking Captain Cook monument: This is a nice half day experience. While the hike itself isn’t all that long, don’t be fooled! There’s parking on the side of the highway. You then cross the street and start by hiking down. The way down took us ~40 minutes, way up ~45-50 minutes. The bottom reveals access to the ocean with amazing views of mountains in the distance. It was so surreal. You go through so many different terrains while hiking – lush greenery, tall reeds, volcanic ash, and ocean. We even saw some goats! Definitely bring water, snacks, and snorkeling gear. The snorkeling at the bottom is not to be missed!!
  3. Exploring volcanoes at volcano national park: if you can, park at the lava tubes. There’s a 4 mile hike that takes you through the lava tubes as well as down to kilauea iki crater trail.
  4. Akaka Falls: a STUNNING waterfall that’s a drive ~40 min from Volcano national park.
  5. Go on a coffee tour! We went on one in Kona called Greenwell Farms and had 100% Kona Coffee. We did a little coffee tasting and the tour afterwards. Educational and energizing!! Lasted ~45 minutes.
  6. Head to the beach: We went to Manini’owali beach and it was absolutely breathtaking. Definitely get there early otherwise you’ll have to park a bit of a walk away. AND bring an umbrella if you have one. It’s beautiful, but not much shade.
  7. Explore volcano caverns. Kula Kai caverns is ~45 min drive from Kona. You must call beforehand for reservations – more information here. $30 per person.
  8. Star gazing at Mauna Kea state park: you can book tours that include sunrise and sunset here (7.5-8.5 hours in duration and $230 per person). If you want to go yourself, I’d advise calling first. More information about self-guided tours here.

Places to eat:

  • Umeke’s: we went here straight from the airport and it was DIVINE! They do take out, so if you can’t get in with reservation you can always quickly get take out and sit on the picnic benches they have outside.
  • Da poke shack: also AMAZING poke. So fresh.
  • Dakine Coffee: great açaí, lattes, and baked goods! Really close to our Air Bnb so we loved it.
  • South Kona fruit stand: on the way from Kona driving south to the volcano taverns. A little side of the road stand! So cute.
  • Kaya store hawaii: my FAVORITE spot for breakfast on big island. So many amazing baked goods, kombucha on tap, and an egg sandwich that my sister said was the “best she’s ever had.” It’s the one with vegan tempenade and egg sprouts.
  • Basik cafe: açaí bowls right in the heart of Kona, we went on our way to the beach. So good!
  • Loko wraps: island style Mexican food featuring local, organic, seasonal and vegan versions of Hawaiian and Mexican faire.
  • Ultimate burger: casual spot with grass-fed beef burgers, fresh-cut fries, beer, and tea.
  • Cultivate Good Food: cold pressed juices, wraps, salads on the go.
  • vibe hawaii: a great place to grab a quick bite before heading to the airport in Hilo
  • Merriman’s: also available in Maui. Definitely need reservations before, which we weren’t able to get.
  • Broke da mouth: neighborhood nook preparing hearty portions of locally sourced Hawaiian & Filipino staples. closed when we tried to go 🙁
  • Rebel kitchen: Hawaiian-inspired burgers/sandwiches, salads & plates with homemade hot sauce & a bright exterior. Fresh Hawaiian food, BIPOC owned – heard great things, though unfortunately was closed when we went.
  • Pele’s kitchen: breakfast/lunch spot on Hilo side
  • Vibes Hawaii: vegetarian restaurant on Hilo side very close to the airport
  • Other recommendations from readers:

Our itinerary

  • Day 1:
    • arrive at Kailua-Kona airport
    • eat at Umeke’s
    • drive to air bnb
    • sleep because SO JET LAGGED
  • Day 2:
    • Breakfast at Basik cafe
    • Greenwell Farms coffee tour
    • stop at South Kona fruit stand for snacks
    • Drive to Kula Kai caverns
    • Stop at Da poke shack for lunch
    • Back to air bnb for change in swim gear + get snorkels
    • Hike Captain cook monument + swim
    • Dinner at Ultimate burger
  • Day 3:
    • Breakfast at Basik cafe
    • Purchase lunch at Loko wraps to bring for beach
    • Beach day! (Manini’owali beach – kua bay)
    • Dinner at Broke da mouth or Papa kona
    • walk around Kona – cute area with lots of places to pop in for a drink for happy hour!
    • back to air bnb for rest / nap
    • late night manta swim with Kona Style

  • Day 4
    • SLEEP IN
    • Breakfast at Kaya store hawaii
    • Drive to: volcano national park – kilauea iki crater trail
    • Lunch at Pele’s kitchen
    • Check out akaka falls
    • Get Vibes Hawaii for dinner before airport
    • late flight out of Hilo airport


Where we stayed:

The location:

We decided to stay near Paia, as it was in a cute little time and decently central. Our original plan was to do the road to Hana, so we wanted to be right in Paia to get an early start. We didn’t end up doing the road, and opted for all beach days instead, as we were pretty tired and just wanted to relax. But Paia is the cutest little time and wasn’t as crowded as other places like Lahaina. Definitely recommend.

Staying in Paia meant we were very close to the airport (~15 minutes), but had a bit of a drive to get to the more popular beaches. Wailea was ~35 minutes and Lahaina was ~45 minutes. I absolutely love driving to get to know a new place better so I didn’t mind this! But if you want more of a beach vibe, I’d go with the Lahaina area. There’s a bustling and touristy town nearby, and everything is within quite a smaller radius of distance.


We LOVED our AirBnb. It was so comfortable, a few steps to a local beach, and basically in the back yard of Mama’s fish house. It came equipped with the BEST shower head pressure AND snorkeling gear/beach chairs + towels!  It’s also steps from the most marvelous little cafe that I walked to every morning for coffee! AND on the road to Hana, AND 15 minutes from the airport. Win win win win win. We weren’t able to make reservations beforehand at Mama’s but because we were located so close, we checked in on the first night and asked for cancellations and were able to get right in! I truly can’t recommend this little oasis enough. So many sunsets visible right from the couch!

Things to do:

  1. Head to a Lavender Farm: home to approximately 55,000 lavender plants and 20 different varieties of lavender. Open Friday, Saturdays and Sundays, 10am to 4pm.
  2. Do a wine tasting: make sure to make a reservation first!
  3. Go to the beach: we loved Makena beach, but Kaanapali Beach in Lahaina was our favorite. We brought snorkeling gear and even happened to stumble upon sea turtles! Literally swam with sea turtles for free just by being on this beach!
  4. Take a drive through the Road to Hana! Head to Heleakala national park, walk down the pipiwai trail, and take a dip in the hot springs (seven sacred pools). It’s a full day adventure and takes ~10 hours total. Take the tour yourself, or you can purchase a guided tour.
  5. Swim / snorkel with the turtles in Molokini: tons of opportunities to book tours through different websites, like this one.
  6. Take a helicopter ride over Maui: we didn’t end up doing this, but it came highly recommended.
  7. Watch the sunrise at mt haleakala: If you plan on doing this, you HAVE to make a reservation. Sunrise reservations from Recreation.gov are required at the Summit District from 3 am to 7 am. Reservations can be made online up to 60 days in advance and are only valid for the day reserved. These tickets are released at 7 am HST. Some “last minute” reservations for any given day will be released 2 days (48 hours) in advance.

Places to eat:

note: tallies next to restaurant names are the number of times they were recommended by readers. Included a star next to the places we went to.

  • Mama’s Fish House* (OVERWHELMINGLY #1 recommended): this 100% LIVES UP TO THE HYPE. This may have been the best meal I’ve ever eaten. From start to finish it was just perfect.
  • Star Noodle* (IIIIIII): this also came highly recommended. We ordered the pad Thai and garlic noodles because we were ordering take out. The thought of hot ramen after a long hot beach day wasn’t entirely appealing. I was overly impressed with the food – definitely good! But not quite worth the hype. I think maybe we just didn’t order the right things off the menu. Apparently the chicken wings are life changing!
  • Tin roof* (IIIIII) – can order take out here. LOVED this place and tons of locals waiting in line, too! 100% go with the machiko chicken – you won’t be disappointed!
  • Monkey pod kitchen (IIIII) – The mai tai’s here came highly recommended! We weren’t able to get a reservation, but I’d definitely aim to go here when I come back to Maui!
  • Ululani’s* (III) shaved ice: Okay, I was skeptical about shaved ice. REAL skeptical. But after a long hot day in the sun, this is one of the most refreshing things I’ve ever experienced. I got mango, watermelon, and passion fruit and I was in LOVE. Don’t skip this!! There’s one in Paia and Lahaina (and a few other locations, but we did the majority of our stay in these two spots). We tried shave ice from other locations, but we liked this place the best!
  • Leoda’s pie* (best banana cream pie) (III): we stopped here after a day in Lahaina (it’s on the way from Paia to Lahaina) and everything was sold out. EVERYTHING!!!! So if you’re gonna go, make sure you go in the morning! Or order online! The location is also next to a cute juice truck and a little outdoor market with dried fruit, produce, and coconuts. Don’t get the coconut water. We did and its was not good.
  • Feast at LeLe luau in Lahaina (II): We REALLLYYYY wanted to do this but reservations went quick. There was nothing open during the time we were there so if you want to do this BOOK EARLY!
  • Kihei cafe* (II) (banana Mac nut pancakes with coconut syrup!). The banana Mac nut pancakes omg. You just have to. Proof here.
  • Fleetwood’s (II): Menu looked pretty average, but some recommended it. Great waterfront view!
  • Lahaina grille (II): Lots of top ratings. We didn’t go, but some recommended it!
  • Merrimens (II): Locations in big island, too!
  • Mala tavern (II): You can order online! Drinks look soooo good. Definitely regret not being able to go here.
  • Choice health bar: locations in Maui and Paia – quick stop for a healthy bite! All plant-based.
  • Paia fish market: locations in Paia, Lahaina, and Wailea.
  • Paia Bowls*: GORGEOUS açaí bowls! See here.
  • Paia coffee*: loved this place for coffee (vegan coconut caramel macadamia nut milk latte was divine) and organic eggs for breakfast! They also have live music, happy hour, and food at night!
  • Kuau store deli + market cafe*: Right on the road to Hana with so many grab and go options. TONS of plant-based, vegan, paleo snack options as well as organic wines, kombucha, beer, and everything in between. I went here every morning!

Other recommendations that I didn’t get to: 

Our itinerary

  • Day 4: arrive at night and drive to AirBnb
  • Day 5:
    • breakfast at Kihei cafe (banana Mac nut pancakes with coconut syrup!) – breakfast
    • tour a Lavender Farm (Friday, Saturdays and Sundays, 10am to 4pm
    • Makena beach (parking available for a fee or you can drive down the road and park for free)
    • lunch at Paia fish market nearby Makena beach.
    • dinner at Mama’s Fish House*
  • Day 6:
    • breakfast/coffee at Kuau store deli + market cafe, also grab snacks and lunch materials from here to bring with you!
    • I walked to Kuau cove from the market and SAW SEA TURTLES JUST HANGING OUT. Unplanned just stumbled right into them. Bliss.
    • Road to hana:
      • heleakala national park
      • pipiwai trail
      • hot springs (seven sacred pools)
    • dinner at Tin Roof Maui (take out – definitely get the Machiko chicken!!)
    • stop at Ululani’s for shave ice on the way back for shaved ice in Paia! So refreshing!
  • Day 7:
    • breakfast at Paia coffee bar
    • stop at Leoda’s pie on the way there to reserve pie for the way home or order online – they sell out fast!
    • chill beach day in Lahaina – highly recommend Kaanapali Beach in Lahaina. Bring snorkeling gear and you may just see some turtles!
    • lunch Choice health Bar
    • dinner at Star Noodle
  • Day 8:
  • Day 9:

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