Hey there, my husband and I are coming to Hawaii for the first time and will only be able to visit Maui island during this trip. We have 3.5 days and 3 nights for our stay and are seeking the tropical locales, unique experiences and the chilled vibe of Maui to celebrate our 1st wedding anniversary (and 15th Valentine's Day) in advance. I've jotted down a ton of ideas for things we'd like to see/do (there's a ton we want to cover) but would like recommendations on a sensible itinerary for our stay. Happy to leave some parts of the day open/unplanned, just want a rough plan to go by as a guide.

Arrival - Landing in Maui on 30th Jan (Monday) at 2.00 pm

Departure - Flying out of Maui late evening on 2nd Feb (Thursday) at 9.40 pm or 11.15 pm

Stay

- Will likely end up at the Ritz Carlton in Kapalua or Kapalua Bay Villas (pending confirmation)

- Second option is Andaz or Hotel Wailea along the Wailea beach

- Equally love Travaasa and may consider splitting our stay with 2 nights on the west coast and 1 night in Travaasa when we do the road to Hana but need your guidance here if this is a good idea at all

Here's a list of things we'd like to cover. Not all may be feasible in our short trip so we'd like some suggestions on a smart (but not super hectic) itinerary. We've rented a car for our stay. Would love your suggestions on how we should organise our days and what would be stupid to do/miss during our short trip.

Must-Do (don't want to skip at all if possible)
- Haleakala Crater (sunrise/sunset)
- Napili, Kapalua, Kahana, Honolua Bay
- Beach town of Paia and the quaint historic village of Makawao
- Road to Hana, Wai'anapanapa State Park (was thinking we can spend the third night at Travassa at the end of the day - would that be silly?)

Would like-to-do (can consider skipping)
- Zipline (reccos for companies?)
- Dolphin/whale watching (is Hawaii Ocean Project the best for this?)
- Helicopter Tour (reccos for companies?)

Good-to-have but can easily be skipped
- Sailboat to Lana’i
- Sunset cocktail cruise

I know Road to Hana and Haleakala and Kapalua are all A LOT to cover but I'd like your tips on a few things -
- Should we split our stay between Hana and the west side or just stay put in one place and do the Road to Hana as day trip?
- Between Kapalua (our first choice) and Wailea, is one location better than the other for the things we want to cover?
- Would it be better if we stayed in/around Paia to cover everything we want to?

Here are 2 potential itineraries that I'd like to get your input on (could be totally off here so please tell me if it's a crazy plan).

OPTION 1
- Day 1 (30 Jan) - drive from airport to Travaasa potentially with stops along Paia town for a meal, Honomanu Bay/Wailua Valley and Pa‘Iloa Beach/Wai'anapanapa State Park - we don’t need to rush any of this and can get to Travaasa around 7-8 pm if that makes sense. Stay the night at Travaasa in Hana. Any stops we should skip/add? I guess it’s a lot to cover but I rather we drive through and soak in the scenic beauty without many stops than not do it at all.
- Day 2 (31 Jan) - drive from Travaasa to Haleakala for afternoon and sunset (via Ohe'o Gulch) and drive late evening to Kapalua/Wailea (depending on where we decide to stay)
- Day 3 (1 Feb) - Zipline (reccos for companies?), Dolphin/whale watching (is Hawaii Ocean Project the best for this?) and Helicopter Tour (reccos for companies?). Not sure if all can be done in a day - happy to skip something.
- Day 4 (2 Feb) - Spend the day around the beaches of Napili, Kahana, Kapalua and Honolua Bay before heading to the airport (we are booked to fly out at 11.15 pm)

OR

OPTION 2
- Day 1 (30 Jan) - airport to hotel in Kapalua/Wailea (depending on where we decide to stay). Chill by the pool/beach and head out for cocktails and dinner to Merriman’s at night.
- Day 2 (31 Jan) - Zipline around Kapalua and Dolphin/whale watching (is Hawaii Ocean Project the best for this?) or Helicopter Tour (reccos for companies?) or all depending on time and energy
- Day 3 (1 Feb) - Head to Haleakala for sunrise, enjoy a relaxing breakfast, make a slight detour to Paia and head over to the road to Hana to stay the night at Travaasa.
- Day 4 (2 Feb) - Relaxing breakfast in Travaasa, drive to the west again and spend the day around the beaches of Napili, Kahana, Kapalua and Honolua Bay before heading to the airport (we are booked to fly out at 11.15 pm)

If not any of these, can you suggest a more sensible itinerary for things we want to cover? We can stay in 1 hotel for all 3 nights or split, whatever makes more sense.

Sorry if this is too much info but I thought it'll be best to put it all out there and get your suggestions on how we should plan our trip to this tropical paradise. Thanks a ton in advance for helping us plan our trip.

With your very limited time, I wouldn't move hotels - it takes up a lot of time that could otherwise be spent vacationing. Also, how much of your time to you want to spend in a car? You have a couple long drives (Hana, Haleakala).

Personally, I think drawing up an itinerary like this is a waste of time and will tempt you to spend the whole time rushing from place to place. In general, I choose one special activity per day, and otherwise use the time to relax and connect with my sweetie,

I would totally drop Hana in winter, it rains a lot there and the beaches are not that great. Took a look at the website for that hotel and if you stay AI they charge $675 per night and that does not include tax or any alcohol.
I would keep Haleakala trip and spend a few hours or half a day in upcountry including Paia.
Then spend the rest of the time on the beach, eating, etc. I have heard the Lanai daytrip is pretty nice, not sure if you have time.

This January? In a week or two? Sunset in Hana is around 6pm so you will spend a hefty tariff to barely get a taste of Travassa. The dining room will likely be empty and after your relaxing breakfast you will not have experienced the charm of a stay as you head out to explore and move on.

With three nights choose either Hana or Haleakala - not both. Although I am an advocate of staying in Hana, perhaps with only 3 nights I would just stay in Kapalua and do a long day trip.

I'd skip ziplining and do a whale watch.

I do have fond memories of Merrimans at sunset.

Awesome tips, super helpful. Thank you all. If we were to skip either one of Hana or Haleakala by road/in person, I am thinking we do Haleakala by helicopter and Hana by road as we'd like to enjoy that drive with pitstops along the way. Only thing I'd be gutted about is not seeing the Haleakala sunrise or sunset - are there helicopter rides that cover either?

We were originally keen on doing the West Maui and Molokai helicopter tour but may consider one for the whole island or just Haleakala & Hana now. Is there a full island tour that would include Molokai as well? Couldn't find one on the Blue Hawaiian site.

Torn between Hawaiian Ocean Project and Pacific Whale Foundation for the whale-watching tours. Any tips to pick one over the other?

Jamie99, are you suggesting that we skip the road to Hana and just do the Haleakala trip and spend a few hours or half a day in upcountry including Paia? That sounds fun too. I guess we can keep one day open for either Haleakala or Hana (depending on the weather with the latter being our top pick just for the drive). What do you think?

Here's what I am thinking for our itinerary now. Thinking that we may stay in Wailea just for the proximity to different sites though Kapalua is still our first choice for its vibe. What do you think?

Day 1 (30 Jan) - Chill by the pool/beach and head out for cocktails and dinner to Humuhumunukunukuapua’a Restaurant or Four Seasons

Day 2 (31 Jan) - Helicopter Tour and Zipline and/or Whale-Watchining

Day 3 (1 Feb) - Road to Hana or Haleakala depending on the weather

Day 4 (2 Feb) - Drive to Kapalua and spend the day around the beaches of Napili, Kahana, Kapalua and Honolua Bay before heading to the airport (we are booked to fly out at 11.15 pm)

Thank you guys for all the help!

Well, both my husband and I were not all that thrilled with Hana and the drive there, we went in mid November and it was pretty rainy off and on. Maybe we had been spoiled by having spent time on the North Shore of Kauai but Hana was just "meh" IMO. Others love the place so who knows, maybe I am in the minority.
I would do Haleakala and whale watching, you can zipline just about anywhere. Really like your Day 4 plan.