Have you planned a surprise trip? Help & Hawaii suggestions

[carfar]

So, yesterday at Brunch with some lovely MMers, I came up with the idea to take hubs on a surprise trip to Hawaii for his 35th B-day in August. Neither of us has been.  I asked hubs what he wanted to do for his birthday. He said "a surprise". I thought this could cover that.
I think we'd plan to stay 4 days because I wouldn't want to do a surprise trip that was longer than that... and that length of time wouldn't really effect his PTO, and we're on the West Coast, so it's a fairly easy flight.  Questions: 

1) What island would you do for a first time trip?  

3) Any other tips/suggestions for Hawaii? We have a two for one voucher from our FF program that I'm hoping to use for the flights... hotels suggestions very welcome. Will we need a car?  

2)  Should I tell him I'm planning a trip, just not where? This way he can pack and ask for the time off himself? I could also  speak to the Admin assistant at his office to see if it's possible to arrange it completely without his knowledge?  



Is this a horrible idea? 

[ECB]

I would tell him you're going on a trip. Location a surprise, cool. But I think it would be odd for you to call work and get his time off for him. Especiallly if he doesn't know he's taking those days- what's to stop him from planning meetings or what have you for thsoe days? He needs to be able to handle his own schedule and not expect someone else to try and juggle this for him. I think that's asking WAY too much,

[konapoppy]

Fun! I agree about telling him you are going somewhere, or make it very clear he should mark off his calendar.

If you want beautiful and relaxing, I would go with Kauai. It is super laid back and naturally very beautiful. We have gone several times in the last few years. We are going to Maui next month- it has a lot more activities that I am sure others can speak to. Oahu is our least favorite island, so I would skip it it felt more like our normal life, just in Hawaii. Not as special.

[rootbeerfloat]

1. Any would be fine. Big Island is my fave, but you probably need a few more days. I'd choose one you can fly directly to.

2. You need a car.

Eta: Oahu often gets a bad rap, but it's a good first time island.

[spunkarella]

1) We did Maui and I thought it was great for a first trip.

2) No hotel suggestions, sorry. We stayed in a condo in Wailea. It was a very peaceful area if you are looking to get away. I might choose a different area closer to more restaurants, etc. for a future trip. We definitely needed a car, not sure if there are areas where you might not?

3) I would tell him you are going on a trip so he can plan work accordingly. Sounds fun!

[audry80]

Yay!

1. Maui- it's the perfect blend of relaxing with plenty of stuff to do

2. Hyatt, Westin, Kaanapali Beach Hotel or Sheraton on the kaanapali side. With such a short trip, you could get away with not renting a car. You can take a shuttle to and from the hotel. Kannapali has plenty of things within walking distance and most hotels have a shuttle that will take you to Lahaina.

3. Since he wanted to be surprised, keep it a secret!

[carfar]

Jul 13, 2014 23:14:21 GMT -5 @juno said:

We just went on our first trip there and went to Kauai. I despise crowds, and Kauai had none of that. But I thought the food situation really wasn't all that great. If you aren't a vegetarian, probably a good bit easier on the food front. Kauai required a car, at least where we stayed. We stayed at Koa Kea, which was nice, with one of the couple of restaurants I enjoyed. We did lots of kayaking and hiking. Very nature intensive, and I had to take a couple of showers every day because we were NASTY most of the trip. It was rainy in Feb., so it might not be so muddy at some other time of the year.

I might tell him he needs to take off X number of days but not anything else

Oh I like this! That way he can deal with work etc, but I think it will be more fun to not tell him much of anything. Hummm, now decisions must be made! 

[Deleted]

Maui hands down and you do need a car there. I'd tell him you will plan a surprise trip so he can plan accordingly.

[aurora]

You really need a car on any of the islands.

If possible, I'd try to do VRBO or similar instead of a hotel. Everything is really expensive in Hawaii, and we appreciate being able to cook at home. We've stayed in some good ones on various islands.

I guess it depends on your H's job, but I would absolutely want to know if H was planning a trip, even if I didn't know where. My admin just wouldn't be able to make the necessary arrangements for me not to be at work.

If you only have 4 days, I'd pick an island you can fly directly to from your city (probably the Big Island, Maui, Oahu, maybe Kauai). What kinds of activities do you enjoy? The older islands are further west (Kauai and Oahu) and tend to have more extensive reefs. The Big Island is the youngest and has an active volcano, which is pretty neat, but the island is less vegetated overall because of its youth. You'll definitely be able to find 4 days worth of activities wherever you go.

[Deleted]

Can you get a direct flight to any of the islands? I would use that to narrow the choices with only 4 days. I love Maui, but would really like to go to Kauai or the Big Island. We've stayed both at Wailea and north of Lahaina and I prefer Wailea. The Four Seasons there is very nice.

[ESF]

I've only done Maui, and we stayed in Lahaina, not Wailea.  We were not sure if we were making the right decision, but when we got there, we concluded that we definitely preferred  Lahaina (west Maui) to Wailea (south Maui).   The south is a lot of large resorts.  It's gorgeous, and quieter.  Lahaina has a bustling downtown area, lots of little restaurants, etc.  A lot of the sailing and snorkeling tours leave from there, so if you are into that, that would be more convenient.

We stayed at the Lahaina Shores Beach Resort.  It wasn't luxurious but the room was quite nice - modern condo-style, with an absolutely incredible view.  Not a good beach for swimming right out front, so if that's important to you, it's probably not the best choice.  Beach is fantastic for walking at night though - nobody's on it. It's right next door to a couple of great restaurants, including the Feast at Lele, a luau-ish thing, which I think you would like.  We had a blast there.    

Anyway, if you decide on Maui, I think you can easily do 4 nights and see a lot.  

Have fun planning!

[RoxMonster]

I don't think anyone has mentioned Oahu but that's what we did for our first Hawaii trip (on our HM). It has the perfect mixture of things to do and relaxation. You could stay in Waikiki and enjoy the shopping, nightlife, etc. or you could stay elsewhere on the island that is more relaxing and quiet. Oahu is not just Waikiki/Honolulu and is more than just a big city.

The North Shore is awesome--there is Turtle Bay Resort up there where my ILs stayed and said they loved it. There are lots of beaches and cute little towns to explore. You can go hiking, take surf lessons, beach bum, shop, explore some of the history the island offers (like Pearl Harbor), go to a luau. We loved it. And you're pretty much guaranteed a non-stop flight to Honolulu and you wouldn't have to fly to another island from there.

[MixedBerryJam]

Jul 14, 2014 11:14:58 GMT -5 RoxMonster said:

I don't think anyone has mentioned Oahu but that's what we did for our first Hawaii trip (on our HM). It has the perfect mixture of things to do and relaxation. You could stay in Waikiki and enjoy the shopping, nightlife, etc. or you could stay elsewhere on the island that is more relaxing and quiet. Oahu is not just Waikiki/Honolulu and is more than just a big city.

The North Shore is awesome--there is Turtle Bay Resort up there where my ILs stayed and said they loved it. There are lots of beaches and cute little towns to explore. You can go hiking, take surf lessons, beach bum, shop, explore some of the history the island offers (like Pearl Harbor), go to a luau. We loved it. And you're pretty much guaranteed a non-stop flight to Honolulu and you wouldn't have to fly to another island from there.

I KNOW! Oahu has a bad rep for being just Waikiki, but for a 4-day trip I think it'd be perfect. OP can do one day hiking Diamond Head, one day doing Pearl Harbor/Arizona (bonus if it's Sunday(?) and they can do the flea market the same day) and a day on the North Shore for some great hiking and secluded beaches, too. Oahu has a small zoo and aquarium, too; not world class my any means, but definitely worth seeing. My husband's weird work situation had us traveling through Hawaii twice a year for nearly 5 years and our last vacation was 10 days on Oahu and really we had a ton of fun.