Thanks everyone for your help along the way. I've gathered ideas from old posts and new suggestions alike. I'm trying not to overplan this trip...and just relax, go with the flow and soak it all in. Having said that, the type A in me has to have some sort of plan...please let me know if you have anything else to add or if I'm missing something not to be missed!

4 nights Waikiki, Hawaiianna Hotel
Day 1
check-in, unload, stroll down to the beach to sink my winter tootsies in the warm sand and hug the turquoise waters. Sit down someplace nearby for dinner and drinks (any suggestions? I'll be on my own at this point...)
Day 2
early morning jog on the beach, check out the area/play on the beach, meet my friend in the afternoon, go someplace for sunset, drinks and food. ??
Day 3
Pearl Harbor USS Arizona tour first thing in the morning. Take a swim, maybe surf and/or catch a ride on an outrigger canoe. 7:30 dinner resies at Alan Wong's, chef's counter...suggestions for nearby sunset & cocktails place prior to dinner?
Day 4 - Valentine's Day
Hike Diamondhead early morning. Chinatown and potentially explore other sights around Honolulu. Dinner at Dukes, Tikis or ???
Day 5 - check-out day
Picking up our car and heading north via windward side. Plan to take our time and make plenty of stops. Have gathered plenty of ideas from Driving & Discovering Oahu (but if anyone wants to give me their top 3 windward experiences, that would be fun!) Stop for breakfast at Boots and Kimos, shrimp truck for lunch, and will hopefully arrive at our place on the n.shore by 6:30pm. 6 days of yoga, surfing, hiking, relaxing and exploring to follow....

Thinking about a whale watch boat trip while staying on the south shore? Would appreciate any advice or recommendations. Anything special going on in the area from Feb.11-15 or on the n.shore from Feb 16-21? Also any ideas for breakfast/lunch would be great too.

Aloha!

The last time we were on Oahu it was over President's Weekend and they had a marathon in Waikiki on that Sunday. I think it is an annual event but I'm not sure if it takes place the same weekend every year.

Check out this whale tour- www.sailhawaii.com 808-306-7273 $95

Drinks on the beach- Sheraton Moana Surfrider.

Duke's for breakfast rather than dinner.

Aloha Tower for drinks and food.

Brunch on the beach on Feb 15th - Sunday!

Pyramids for great Greek Food and bellydancing.

Cabanas at Kahala Mandarin for the view and experience.

Kailua- Maui Tacos, Lani Kai beach and Haliewa Joes in Kaneohe for a drink.

You know, I'm not so sure about whale watching on the south shore. I think the whales travel mostly on the east shore. I have an incredible view of the south shore and don't get to see whales. They are supposedly best seen at the crack of dawn, though.

Is Feb 14 a Tuesday?? Maybe you can take one of PakePorkChop's Chinatown tours!

Thanks everyone!

Islandmom - I'm going to check out that link and take your recommendation for Duke's for breakfast and drinks at the Moana. Any other Oahu picks this week? Any of those yummy bars left at Starbuck's?? ;-) We probably won't make it to brunch on the beach on Sun. -trying to get an early start that day.

MelissaHI - I'd love to take the Chinatown tour...but I'm only in Waikiki Wed-Sun and Feb.14 is a Saturday.

Thanks for all the responses!

Moose McGillicuddy's or Leonard's Bakery (fabulous malasadas) for breakfast.

p.s. do you normally jog on the sand? If not I should warn you that it can be tough on the calves and arches. No worries--if you decide not to jog on the beach, you can jog on the sidewalk over to Kapiolani Park, then up Diamond Head. The jog from Kap Park and up & around the base of Diamond Head is about 4 miles. The view is great! If you jog at the crack of dawn, you can see the silouette (sp?) of the other islands when you are at the lookouts on the base of Diamond head. MAYBE you can see whales.

Often you can see whales when you hike Makapuu. I've done the whale boats from the south shore and really think somewhere closer to the northshore would see more.

I'm staying down there that same weekend and think there may be a marathon..... Saturday I hope to go to Farmer's Market at KCC.

You sound like someone who would like to kayak Kailua Beach to the islands too.

It is the Aloha Run Weekend. There will be many activities and Waikiki will be busy.

20TH ANNUAL GREAT ALOHA RUN (Oahu) Hawaii's largest participatory event raising monies annually for numerous local charities, encouraging a healthy lifestyle, promoting physical fitness and bringing people from all over the world together. This 8.15 mile Run/walk starts at Aloha Tower in downtown Honolulu (with entertainment along the route) and ends in Aloha Stadium (home of the NFL Pro Bowl.) Prior to the Monday, Presidents' Day race every year, is a 3-day Family Fitness & Sports Expo, Senior Citizens Fun Run/Walk and a Keiki (Children) Fun Run & Circus Party. Entry Fee.

Picks this week...hum...trying to think what I did this week.... Went to a fair at the Blaisdale. Bought zoo passes - $25 for a family for 1 year. Went to Dixie Grill in Aiea twice so daughter could play in the sand while we have a big meal. Thumbs up for meatloaf and mashers! I'm still trying to get into the Cheesecake Factory - the lines are too long. Thumbs up for Auntie Pasto's off King Street- good and cheap. The Waikiki one changed owners. Yummy juice at Thirst Quenchers in Ala Moana food court. I also like the Garden food spot...forget the name... for salad and a potato. You can tell I'm pregnant, all I'm doing is eating. LOL! Daughter went to The Children's Discovery Center and pretended to be a judge. I like photo developing at Photo Trends in Windward Mall. Kodak 100 film. Tried to get into Tiki's but the line was too long. Ended up at Wolfgang Puck's again which we love. Went to the Korean Festival. Ate $1.99 pizza at Costco. Also, they sell those boxes frozen pb&j sandwiches for $6 which you could throw a package into your bag and they would still be fresh for a snack or meal 8 hours later. Our next big adventure is hunting for sunrise shells. Some sell up to $3,000. www.pukahawaii.com

Your itinerary looks good! A few other recommendations for you:

When you're on the eastern side of Oahu, be sure to stop at Laie Point. It's right near the BYU campus. We almost cruised right by it-- it's down a side road. I thought that this was one of the most beautiful places we saw on Oahu and I really recommend it.

We did the USS Arizona tour and definitely enjoyed it. Afterward, we toured the USS Missouri and found it really interesting as well. It costs like $12 or something for access to the USS Missouri.

In Waikiki, our best find for good, not-hideously-expensive food was the Shorebird (right on the beach at the Outrigger). Be sure, at some point, to have a salad with a local papaya-seed dressing. We loved it so much we brought home a couple of bottles.

Have fun!

Wonderful information! Thank you all.

I checked out the sailhawaii link and it sounds spectacular...however, the logistics are just not working out for us. So, I found one through Deep Ecology on the north shore. Any scoop on that operation?

p.s. thanks Melissa for the run tip. I do okay running on the sand, where's it's firm near the water's edge.

Hi Bogart,
Just a note on your planed stop at Boots and Kimo's in Kailua. We just returned from Oahu and had a very early breakfast there based on a recommendation. It was not nearly as good as some say. We were told we couldn't have o.j. 'cause the person with the key to unlock it (?) wasn't there yet. (Okay....) My side of bacon was mostly fat and tasted distinctly of fish. The macadamia nut pancakes (plain pancakes with a mac nut sauce) were fine. My French toast (not even a wedge of pineapple with it) was very simple, nondescript, but okay. Our waitress was the only exceptional part - she was perfect. However, when trying to pay with a traveller's check (same as cash) the cashier (manager?) didn't even look up at my husband and said a flat out no, she wouldn't take it. When asked why, she still made no eye contact, and gruffly said no, she wouldn't take it. She was surprisingly rude. It made the entire experience unpleasant.

As an aside, try Teddy's Bigger Burgers in Kailua. They're great! (Gotta have them with their special sauce though.) Their fries are almost too salty, but still good.

My favorite side of the island is Windward side. That is just a 20 minute hop over the pali into waikiki.

So gorgeous over there, check out byodo temple, Kailua beach park, Lanikai for photos.

I have not had good house renting experiences on Oahu but I only did it one year so I am not a judge. It is a bit more expensive than the outer islands but of course you have a lot more activity.

Diamond head sound excellent for that time of year. But I have been on Oahu in April and did not find one side rainer than the other. Check out Kailua, lanikai for rentals.

Sarah-
where did you stay when you rented a house in Oahu? We are going in April and renting a house. What was the weather like in April?

Lanikai but I can not suggest a realitor we had a bad experience. Loved being on that side of the island. It was removed yet close to honolulu.

I lived on Oahu for three winter seasons and never stayed away from Kailua during any season. I find that it is a bit over cast sometimes but then again sometimes that is a nice break from the strong Hawaiian sun.

Sarah-
Who is that realtor you know of?

Thanks

I was working and living on Oahu during the winters I spoke of. I rented one week in August 01. I am not going to bash the realitor now. It was only a week and for all I know the realitor has sold the business and maintained the name.