Hi, sounds like you are open to making the most of your trip to Kauai....wonderful! So here are a few helpful hints and feel free to ask any specific questions you might have.
Best time of year: NOT summer!! Too crowded with tourists and too expensive. September and October are great if you like hot weather (hottest time of year on Kauai...~88 degrees) but early November is wonderful weather and the ocean is still quite warm, the plumeria are still blooming and smelling sweet, airfares are cheaper. In the winter, April has cool, less humid weather, but the ocean is a bit chilly and there can be rain. Still, April and May are beautiful.
Where to stay...if you want a big hotel, split your time between the St. Regis and Grand Hyatt. The St. Regis is on the north side of the island, the most beautiful part of the island, but typically rainier. Gorgeous views of Hanalei and Bali Hai. The Hyatt is really gorgeous, maybe the nicest large resort in Hawaii. Spectacular lobby and pool area, comfortable rooms. In the winter, Poipu is warm and dry, so more time for beach than the northshore.
If you still want to stay in a hotel but more limited budget, stay in Kapa'a, on the east side of the island. There are a few smaller properties there, on the beach, that offer nice accommodations, beach locations at a far lower price. I like The Islander...a great inexpensive place to stay.
For B&B, nothing beats Mahina Kai. Just north of Kapaa, it is a Japanese-inspired estate across the road from the beach in the Aliumanu area. Beautiful, full of special energy, a little pricey but nice.
Regarding airlines, Hawaiian is the best way to get to the islands, but lets face it. Flying to Hawaii is not too exciting and nothing beats shortening the trip. Flying United, American or Useless Air (I mean US AIR), you can fly directly to Kauai from the mainland, typically in 757's. Kauai smartly decided to never expand the runways to accommodate jumbo jets.
Hope this helps. You are going to the most beautiful place on Earth and the best way to enjoy it is CASUALLY. Hike, swim, snorkel and leave the helicopter trips to others. If you want to do a Napali cruise, see if any are leaving from Hanalei rather than Port Allen. If not, at least get on a smaller boat to enjoy. Try EVERY beach...Kauai has more beaches than all the other Hawaiian islands combined...but be careful and listen to ocean reports. NEVER turn your back to the ocean.
Thank you for thinking about traveling to Kauai! It is a beautiful island and a great place to explore the outdoors. There are several hikes in Kokee State Park where you feel like the first explorer to discover this lush tropical rainforest. If you go to this website: www.kokee.org, there are several hikes listed with directions and brief descriptions of the hikes.
In addition to the Hotels suggested by the previous post, another option for a Hotel on Kauai is the Kauai Marriott Resort. It has a complimentary airport shuttle available for easy arrival and departure. The bellmen run the shuttle so you can leave your luggage with them and they'll deliver it to your room for you so you can start relaxing immediately. The Resort is centrally located on the island so it is easy to experience the island of Kauai. It is about 45 minutes to Princeville, 25 minutes to Poipu and a little over an hour to the Waimea Canyon.
If you like the outdoors, the Marriott also has the largest single-level pool in the state of Hawaii with 5 full-size jacuzzis separated by waterfalls, each in its own gazebo. Two of them you can walk up to but the three in the middle you have to swim up to. It makes it a lot of fun! The beach is also a great beach to swim, relax or learn how to surf at! The Kauai Beach Boys can teach you how to stand up paddle surf or surf traditionally. After one lesson with them you'll be able to rent a board and surf on your own on Kalapaki Beach!
There are also 6 restaurants on-property to choose from. Duke's Canoe Club is open from 11am - 11pm for Lunch and Dinner. They have consistently good food and service and wonderful frosty drinks. Kukui's on Kalapaki Beach has a wonderful Prime Rib and Crab buffet the first Friday of each month. Cafe Portofino with Northern Italian cuisine, Aupaka Terrace for Kauai Coffee and continental breakfast, Kalapaki Grill for lunch and food & beverage service poolside and Toro-Tei Sushi Bar with views of Kalapaki Beach.
For Airlines, Kauai has several direct flights available, depending on where you are flying from. From LAX there are direct flights to Kauai on United, Delta and American.
Not so certain if I would recommend the Marriott so highly. Certainly convenient and I love eating at Duke's downstairs, but its an old property sitting on a commercial bay, near the Lihue airport flightpath. Many of the rooms were converted to time-share, and it has a laid back vibe, but its the only highrise on Kauai...so not a great place, but certainly far less expensive than the Hyatt or St. Regis.
There are alot of great places to stay on Kauai, hotels, resorts and condos. It depends on your interests and budget. Anytime is a great time to visit Kauai, but prices are best in Sep., Oct and early Nov. Also, the 1st two weeks of Dec. Depending on where your trip originates, airline choices are American, United and USAir. Hawaiian Air is also an excellent choice, if you live in a city that Hawaiian Air operates from. I would be pleased to give you more detailed info. You can contact me directly at firstname.lastname@example.org.
We like April to October. Prices tend to be more reasonable if you avoid June 15 Aug 15, although this year is certainly an exception if you are considering the more upscale properties. The resort area of Poipu tends to get the most sun. The coconut coast area near Kappa is greener, and Princeville is greenest. The north gets the most rainfall, but has spectacular scenery. Regarding airlines, know that all flights from the mainland are either on single aisle 757's or smaller 737's. If you like larger aircraft, connect via Honolulu. Billy of Rainbow Voyages