If you’re planning a multi-island Hawaii vacation and wondering how to split your time, this 10-day Hawaii itinerary covers exactly how we did it—starting in Maui and ending on Oahu. It’s a mix of beach recovery days, iconic sightseeing, honest travel opinions, and plenty of relaxation.

This post breaks down each part of the trip, where we stayed, what we did each day, and what I’d do differently next time.

Where We Stayed in Maui

We started our trip in Maui, staying at the Fairmont Orchid. It was the perfect place to ease into island life after a long travel day—beautiful grounds, great beach access, and close enough to explore while still feeling private

We also had friends staying at the Four Seasons, which worked out perfectly because we were able to walk over and enjoy their pool and amenities a few days.

Day 1: Travel Recovery + Beach Day

After a long flight to Hawaii, we kept Day 1 very low-key.

• Beach time at the Fairmont Orchid
• Walking over to the Four Seasons to meet friends
• Pool lounging and soaking in the views

This was exactly what we needed—no schedule, no pressure, just ate dinner at the hotel that night.

Travel tip: Don’t overschedule your first day in Hawaii. Jet lag is real, and a beach + pool day is the best way to start.

Day 2: Road to Hana (Honest Review)

We tackled the famous Road to Hana on Day 2. Our group rented Jeeps, which made the drive feel like an adventure right from the start.

Stops Along the Way

• Paia Bay Coffee Bar for breakfast (highly recommend)
• Several scenic pull-offs during the first few hours
• A waterfall stop
• Black Sand Beach (absolutely worth seeing)
  • A reservation is required to visit for all non Maui residents. Fees are $10 a vehicle and $5 per person

While the first half of the drive was beautiful, the return trip was rough. That was something I personally wasn’t prepared for- so I had to be honest with my people here LOL.

Would I Do the Road to Hana Again?

Honestly—no. After several blocked roads and a very long drive home, it became stressful instead of enjoyable.

My recommendation: Drive halfway, make a few stops, and then turn around. You’ll still see incredible scenery without the stress of one way roads and steep cliffs. The Shaka guide is a app you pay a small fee to download and it gives you directions and stop information along the entire route of the road to hana. We didn’t get this , but it may be something to look into!

Day 3: Snorkeling at Makena Landing + Karaoke Night

This was one of my favorite days in Maui.

The hotel recommended Makena Landing as the best place to swim with sea turtles—and they were absolutely right.(The Fairmont provided snorkeling gear- which was clutch.)

Evening Fun: Karaoke Night

That night, we went out and stumbled upon a karaoke bar, and it ended up being one of the most fun nights of the trip. We sang Spice Girls – Wanna Be . and it was iconic.

Day 4: Four Seasons Pool + Sunset Views

Our last full day in Maui was all about soaking it in.

• Pool day at the Four Seasons with friends
• Watching the sunset from the top—pure magic

It was the perfect way to say goodbye to Maui before heading to our next island.

Traveling to Oahu + Pearl Harbor

From Maui, we flew to Oahu and made a very meaningful stop at Pearl Harbor before heading to our hotel. Something I feel everyone should experience once in their life. Definitely worth it to me & book ahead!

Staying at Turtle Bay Resort

We checked into Turtle Bay Resort on Oahu’s North Shore, and the vibe was completely different from Maui—in the best way.

That first evening:

• Stopped at Sunset Point Beach Park
• Grabbed pizza and drinks
• Watched surfers while the sun went down. This is so memorable & one of Andrew’s favorite things!

It was relaxed, beautiful, and felt very “Hawaii.”

Final Full Day: Spa, Golf & Group Dinner

Our last full day was all about relaxation.

• Spa day at Turtle Bay
• The guys went golfing
• Pool time and exploring the resort
• Big group dinner to wrap up the trip

It was the perfect balance of rest and quality time before heading home.

Final Thoughts: Is a Maui + Oahu Trip Worth It?

Absolutely.

What I loved most:

• Maui’s beaches and snorkeling
• Turtle Bay’s laid-back North Shore vibe
• Mixing adventure days with full rest days

What I’d skip next time:

• Driving the full Road to Hana

If you’re planning a 10-day Hawaii vacation, splitting your time between Maui and Oahu gives you the best of both worlds—luxury, nature, history, and total relaxation. The biggest thing I tell people is that it is a very expressive trip, the cost of everything was just higher in Hawaii (because it is all imported), just something to be aware of, I was a littler shocked at first.

Hope you enjoyed! Make sure to save my NYC itinerary for your next trip!

Mary Margaret