Solo to Hawaii
 

I'd love some advice. I'm off to Hawaii in October for a few days of work and would like to add on a couple days. I am a 40 year old woman and will be traveling by myself.

I have been to Oahu and that's where I'll be for work, but would like to explore another island. I'm afraid what I have in my head might not exist -- a resort in a less commercialized area. As I will be alone, I think I would prefer a resort over a condo, because I assume there will be more people around, dining options, pool side bar, etc. I, however, would like to be in a more quaint area -- something not so commercialized. I'd like to grab breakfast at a cool coffee shop before heading off on a hike or eat "street food" from a shack after a day of snorkeling. I'm not into shopping, but would like to have art/craft shops to explore before heading to dinner at a local restaurant.

I'm willing to rent a car.

Thanks for your help!

Lanai has the four seasons resort, which is quite expensive, but may offer what you are looking for. Lanai is less commercialized than the other islands and has some great hiking and such.

Maui has some great stuff in Wailiea (Marriott resort is fairly reasonable) and the Westin has a resort north of Kaanapali. If you want to get further out of the commercialization of Kaanapali, Kapalua has the Ritz (pricey) but away from the hustle bustle.

Kauai-The princeville resort is nice and somewhat pricey too-but near some great hiking along the Napali Coast. There is also the Sheraton and Hyatt in Poipu, which is very nice as well.

stayhawaii.com

konaweb.com

my fav rent a car bop around

circumnavigate the islands safe tonnes of fun...

Kona Kohala Coast best base for least rain

See TerraForming in action a do not miss at Volcanoes NP

Truly AMAZING!

priceline.com great Hapuna Prince deals with a car in the past

princeresortshawaii.com from $1k/wk inclusing air car room

lots cheaper for you from HNL

Do consider rain issues Kohala Coast usually driest in fall

They do the Ironman there in late October

so be sure you do not go then unless a fan...

It will be chock a block with nearly naked triathletes

in speedos eating touring everywhere...

the Germans are the worst from personal experience X 3

followed closely by the swiss.

Just rent a car and travel a little bit around. Hawai is great. There are some little sharks at the whater, but no worries, the bigger ones usually dont come to the coast. But still listen to the news. Hawai is a great place for surfing and you really should make a course there. Have fun.

All the above suggestions are good ones but they are not what I would call " quaint" as you mentioned being what you are seeking. I don't know if their are any areas of Hawaii that I would call "quaint". I would call Victoria, Carmel by the Sea, and Solvang quaint. I would call the resorts in Hawaii beautiful, tropical, and scenic.

If you're planning to go to Volcanoes National Park, then the Kilauea Lodge is really charming and has a good restaurant. Not sure if that's more isolated than what you're looking for. It's not commercialized and is very pretty. We stayed in a charming little cottage there and loved it.

Either:

Hanalei in Kauai. Wonderful little town to kick around in, great beaches. Quaint in an expensive hippie way.

or

Visit The Big Island and spend lots of time visiting Hawaiian Volcanoes National Park.

In Hanalei, check out www.hanaleisurfboardhouse.com

Terrific location, fun decor and a really fun owner.

On The Big Island, I love Hapuna Prince Beach Resort so I can take lovely long walks on that sand in the morning and spend my time playing in the water.

I just think some of your wishes are contraditory. It's going to be hard to find a "resort" with "poolside bar" in a non-commercial and not touristy area. Coffeeshops, arts and crafts stores, even local style restaurants are more likely to be in a town, not an isolated area.

As long as you have a rental car, I think you can find the experience you're seeking in an overall (if not specific) way. Either Oahu or Maui could work. On Maui the town of Lahaina is fun for shops, theater, restaurants (yes it is "commercialized" but I also think it's pretty cute/quaint). On Oahu going outside Honolulu/Waikiki and around the island there's lots of more out of the way places.

If you stayed on the Big Island at Mauna Kea, Mauna Lani, or Hapuna Prince you could drive about a half-hour north to Hawi, a little town that has a fun coffee shop that also sells Tropical Dreams ice cream, my favorite. I hardly touch ice cream while at home, but can't get enough of Tropical Dreams while in HI. hawi also has the Bamboo Restaurant, a kitschy place with local Asian-Hawaiian style food and friendly staff. On weekends they have live Hawaiian music. There's a good sushi restaurant there. There are some arts and crafts stores there, too. I believe there are also a couple of pricey smaller resorts in the area. You could Google "resort Hawi, Hawaii" and see what comes up. (Hawi is pronounced hah-vee, with the accent on the second syllable.)