So this is somewhat (although not exactly) how I did part of my time in Maui, in January and February 2020.
For this trip, I had about one month in Hawaii, flying into and out of Maui. The plan below outlines the general plan of what I did into a 2 week Hawaii itinerary, all on Maui, with an option of a day or 2 on another island.
The BEST part about visiting Maui during the winter months?
Maybe that seeing whales became a pretty normal thing!
I mean, it was always still exciting to see a whale, but I feel like I saw a ton of whales from shore (out in the distance) without even trying!
Winter is whale season in Hawaii. Maui is considered to be the best Hawaiian island for whale watching.
The WORST part about visiting Maui during winter months?!
Well, specifically, visiting Maui in the middle of February.
It was not a good idea to be in Maui without accommodations booked ahead of time.
If you’re planning a trip to Maui around Valentine’s Day, book in advance!
I ended up beach camping on Lanai because I couldn’t find anything reasonable on Maui.
The cheapest accommodation option on Maui that I found cost $500+ searching a few days before.
Well clearly max occupancy for Maui hotels is no longer the case in 2021. And as I think back to being in Hawaii in February 2020, I feel so happy for all my fellow tourists who were there at that time as we were blissfully unaware of what even just a few weeks out into the future would be like… It’s like everyone was able to have one last trip. But anyway I digress… 😜 Back to present day…
Outdoor activities on Maui
Even though I was there during peak tourist season (as was indicated by the nearly full occupancy of hotel rooms on the island!), for most of the things I did on Maui I don’t really feel like I was overwhelmed by crowds at all. The vast majority of things that I did were outdoor activities and I’d say I had plenty of space. That is just the type of place Hawaii is! There’s a long list of outdoor activities to do!
And so, seeing as how even during peak tourist season I had space, most of the things on the list below can actually be perfect to do even in this “new normal” that we live and travel in now.
Where to stay when you have 2 weeks on Maui
If you’re looking for a few beach days along with activity days, then West Maui (Kaanapali, Kapalua) and South Maui (Wailea) are considered to be where Maui’s best beaches are located. These are the areas of the Maui’s best beach resorts as well.
And as you will see below (listed is the general area of the island each day’s activities are located), there are many activities in both West Maui and South Maui. So, if you don’t want to stay in just one spot for your whole 2 weeks, these could be 2 areas to split your time between.
Be sure to see more to help you decide how long want to spend in each area:
Aside from that, since you do have more time than the average Maui tourist, you’ll also want to consider if you want to spend more time on the Road to Hana! It’s very common to do this Hana Highway drive in one day, but since you have the luxury of time, if you look at the list of things to do on the Road to Hana and it seems very interesting to you, then it’s worth spending at least one night on the Hana Highway to take things at a slower pace!
The best of Maui
If you’re looking for the best of Maui in a (much) shorter time, also see this Maui itinerary for the best of Maui in 3 days!
To do the best of Maui, you do need a car. But, with 2 weeks on Maui, it might not be necessary to have a car the whole time. See more to decide how many days to rent a car on Maui for.
Another “best of” list to look at is this list of best hikes on Maui. You could plan out your days so that you do one hike a day, and the rest of the day is chill time!
Also see the best snorkeling spots on Maui.
More below for ideas on how to spend 2 weeks in Hawaii!
Here's some info on Hawaii trip prep!
- Best shoes for hiking in Hawaii
- The perfect type of shirt for swimming in Hawaii
- Do you need water shoes for Hawaii?
- THE top things to pack for Hawaii
Save the Maui video playlist to watch on youtube later!
Explore the outdoors all over Maui:
- Driving to the top of the Haleakala summit
- Things to do in West Maui with amazing views
- How much time do you need in Waianapanapa State Park?
- Where to see Maui lava fields
- One day in the West Maui mountains with amazing views
- The big list of 50+ things to do on Maui (mostly free and outdoors!)
What to do with 2 weeks on Maui
Some ideas below of things to do on Maui! There are tons of things to do on Maui for FREE!
I started off my Maui trip by staying in a hostel located in the town of Paia for about a week or so. Paia is pretty close to the airport, so it made it a convenient spot to arrive to as there was a direct bus from the Maui airport. I was without a car for the first few days, and then I rented a car.
Day 1: Paia
Day 2: South Maui
- Oneuli Beach (kind of black sand, with red sand too)
- Jawz fish tacos food truck
- Maluaka Beach (aka Turtle Town)
- South Maui Hawaiian church
Maluaka Beach (aka Turtle Town snorkeling spot)
Day 3: Road to Hana
- Keanae Peninsula
- Waianapanapa State Park (black sand beach)
- Hamoa Beach
- Wailua Falls
- Back road to Hana (back side of Haleakala)
I was staying at a hostel on Maui that offers a free group tour on the Road to Hana. (Tips $ appreciated.)
There are definitely sooo many things to do on the Road to Hana, and doing it on your own is really the best way though, I think! There are tons of waterfalls, a few unique beaches, a famous bamboo forest, and MORE!
If these kinds of things interest you, then definitely look into doing the Road to Hana over a few days, instead of just one day, especially if you have 2 weeks on Maui!
Driving the back road to Hana is something to look into before you do it. It can be considered an unsafe road at times and Maui rental car companies may not cover your car if something happens to it when you’re driving this stretch.
Back road to Hana (back side of Haleakala)
Day 4: West Maui’s rugged coast
- Olivine Pools
- Ohai Loop Trail
- Nakalele Blowhole
- The previously heart-shaped rock
- Honolua Bay (snorkeling)
On the morning of this day, I took a bus from Paia to the airport, and then picked up a rental car.
So West Maui was my first “trip” with a car. And the views of far north area of West Maui were AMAZING! This is a great scenic drive.
Honolua Bay (snorkeling)
Day 5: Haleakala National Park, summit area
You will want to bring extra layers of clothing on the day you go to the Haleakala summit! Being at higher altitude means cooler temperatures!
Day 6: Central Maui / West Maui mountains
- Waihee Ridge Trail (one of the best hikes on Maui)
- 13 Crossings Trail (waterfall hike)
- Iao Valley State Park
Day 7: South Maui
See the South Maui list.
La Perouse Bay
Ahihi Kinau natural reserve (snorkeling)
Day 8: CHILL DAY
We’ll call this a chill day for the purposes of this 2 week Hawaii itinerary, but I actually spent one week on the Road to Hana! My accommodation on the Road to Hana was a mix of tent camping, dorm-style cabin, and private cabin. These were all locations that had campgrounds with ocean views! There’s a national park campground (Kipahulu) and a state park campground (Waianapanapa). At the time I went, there was also a YMCA campground (Keanae) but at some point during 2020/2021 it changed management and it’s unclear if it’s going to continue to operate as a camping spot.
Day 9: Lahaina, West Maui
On the last day of my Road to Hana trip was my last day with a car on Maui, and it was basically a day of getting from the Hana Highway to Lahaina. I stopped by Hookipa Beach (turtles and seals) and the Hookipa lookout once again. I drove to Lahaina to drop off my luggage so I wouldn’t have to carry it all with me on the bus. Then I drove to the airport to drop off the rental car, and then I took a bus to Lahaina.
Driving all the way to Lahaina from Paia and then back to the airport did “waste time” as it would have been quicker to go straight to the airport. But I made this day about just getting to Lahaina which meant that I had time!
Day 10: Day trip to Lanai
I didn’t actually go to Lanai as a day trip (explained in the next day) but doing a day trip from West Maui by ferry is a popular way to visit the neighbor island of Lanai.
There is a ferry from Lahaina to Lanai. The views as you sail across the ocean are amazing!
And speaking of day trips to neighbor islands, in normal times it can be reasonable to do a day trip to the Pearl Harbor national memorial. This is on the island of Oahu (the island with Honolulu and Waikiki), and you’d fly there.
Day 11: CHILL DAY
Once again we’ll call this a chill day for this 2 week Hawaii itinerary, but I actually spent a total of around 1 week on Lanai spread across 2 trips. (The second trip because of that thing of a lack of accommodation on Maui during busy season.)
In total, I did camping on Lanai at Hulopoe Beach for 3 nights and camping at Shipwreck Beach for 1 night. I stayed in the town area of Lanai City for 3 nights – bed and breakfast and hotel. (Although not in that order.)
One of those nights was because my ferry back to Maui got canceled due to rough seas (as well as all remaining ferry departures for the day – cancellations are an increased risk for winter months) so I spent an extra night on Lanai.
If you have 2 weeks on Maui, you may consider a day or 2 on Lanai. Be sure to see the basics to know about Lanai.
If you would consider camping, then also see about what to pack when you’re flying to your camping trip.
See pictures from the boat ride:
Day 12: Kapalua, West Maui
I went to Kapalua by bus from Lahaina. Kapalua is a resort area of West Maui. See the Kapalua list.
Kapalua Bay Beach
Day 13: Kaanapali, West Maui
- Kaanapali Beach
- Black Rock (snorkeling)
- Kaanapali coastal walk
I also went to Kaanapali by bus from Lahaina. Kaanapali is the big resort area of West Maui.
Black Rock (snorkeling)
Kaanapali coastal walk
Day 14: Wailea, South Maui
- Ulua Beach (snorkeling)
- Wailea Beach
- Wailea coastal walk
Wailea is the big resort area of South Maui. See the South Maui list.
Ulua Beach (snorkeling)
Wailea coastal walk
And those are some ideas of how to spend 2 weeks in Maui!
Also be sure to see: how many days you might want to rent a car on Maui for.
For the list of mostly free things to do on Maui that’s more so organized by area of the island, see:
- Things to do in West Maui
- Things to do in South Maui
- Things to do in East Maui
- Things to do all around Maui
Here’s the 3 day Maui itinerary to take a look at with a few more details!
Also see more Hawaiian islands:
- How to spend 7 days on the Big Island + best Big Island hikes (ocean views!)
- How to spend 3 days on Oahu + best Oahu hikes (ocean views!)
- How to spend 2 weeks on Oahu
HAPPY 2 WEEKS IN MAUI!