Are we suggesting you fly all the way to Hawaii just to lock yourself in a dark room? Yes, yes we are. If you know us, you know this is always our first stop on the island.
October may not be peak whale watching season, but we highly recommend the Sunset Cruise on Sail Trilogy. Take a 2-hour sunset cruise inclusive of cocktails and pupus (appetizers) to relax and unwind after a stressful day on the beach.
You might think a comedy magic show sounds cheesy, but don't be fooled, you will have a great time at Warren and Annabelle's. A very unique experience, we highly recommend it!
We would be remiss if we didn't provide some dining recommendations. Tin Roof-head here as soon as you land as it is right near the airport. Order the Mochiko chicken and garlic noodles. You'll thank us later. Lineage-if you're looking for fine dining, Lineage is probably one of the best restaurants on the island. It's located in Wailea, a 30 minute drive from Lahaina. Star Noodle-the third restaurant in the Chef Sheldon lineup (chef at Lineage and Tin Roof). Located in Lahaina a great hawaiian/asian fusion. Mama's Fish House-it's a bit of a drive, but the views are worth it. The restaurant is located right on the ocean and they do their own fishing daily. Try to get there for sunset if possible. Miso Phat Sushi-super casual BYOB sushi bar. MaLa Ocean Tavern-a great little restaurant right on the Ocean in Lahaina. Great seafood.
There are tons of great hikes on Maui so you really can't go wrong. There are tons of great websites out there so google away, but here's a great starting point to help you out.