Let me add we have been to aruba, curacao,turks & caicos -twice,barbados, puerto rico, cancun & playa del carmen in terms of beaches. We are open to other places in the Caribbean.Were also onsidering south of europe but doesnt seem right weather wise. We are open to alot of options that give us this same feel but so far considering maui or costa rica.Thanks for your time.

May I suggest Maui instead of Costa Rica. In Maui it's peaceful and more laid back and also luxurious, depending of course on the hotel you choose. I would opt for a Marriott, they are always fine hotels. I was in Costa Rica last year, it is a wonderful place for an adventurist holiday but not for a young child. when he's older he'd probably enjoy swinging through the tree tops on a high wire, but not at three. You could maybe think of hiring a Nanny and taking her along to look after your son while you go and do the things you like to do. Trecking through a rain forest in Costa Rica with a tired little boy would not be enjoyable. Maui has some beautiful beaches and plantations you can tour too. A few tips for traveling with a small child. always take along plenty of small items that can be brought out to entertain the little one. While traveling with me grand daughter I took along "Stickers" always a favorite( she stuck them all over herself) and they kept her busy. small things like dinky cars, farm animals, small books to scribble in and lots of colored pencils. and of course the favorite teddy bear, blanket ETC. hope this helps you.
I have traveled around the world many many times. Have lots of experiences with just about everything regarding travel.

It's not so much that you can't enjoy Costa Rica with a 3 year old, just that you will enjoy it so much more when he is 7 or 8.
3 year old's can be pretty content with a day at the pool or in the sand, take advantage of that and plan something where you can just relax and kick back. You'll hopefully have years ahead to tackle the gotta-plan-every-minute-to-entertain-him vacations.

Have you taken the kid on all those other trips? How does the kid travel? Does it have a passport?

The travel time to/from Maui and Costa Rica have to be fairly similar.

Maui would be much easier overall. With a 3 year-old, I go for easy. As above, save Costa Rica for when the kid is more independent.

Thanks for the replies, more are welcome.My 3 year old has traveled to Turks & Caicos twice & to India ( very long flight ) & to Barbados & Canada ( short flight ), he travels well as we plan things to keep him all right through these flights so flying more I thn=ink we can manage but he is not an easy baby once at the place due to his age.Yeah he has a passport. Maui seems easier as above but will I be able to do road to Hana & the crater with him? Also what shore in November in maui? Thanks again

Wouldn't do Haleakala due to the altitude and Hana due to carsickness.

South Maui will be nicer in November.

A lot of people with young kids like to go to Manuel Antonio. It's easy to get around, and there's lots of wildlife and a beautiful beach inside the park. Check out someplace like Tulemar Bungalows. That would work if you just want to relax and have some beach time. I'd save adventure activities and all that for when your child is a little older. Maui could work too. I think things would be easier to do there with a 3-year old - Haleakala, whale watching, beach time, Road to Hana, etc. Does your child get car sick at all? If so, some of the roads in Costa Rica can be pretty twisty and turny and not in the best shape.

Travel time from New York to Costa Rica is less than 5 hours, to Maui about 11 hours. Regardless, I agree that Maui would be much easier once you get there!

My son has never gotten car sick, I do but can take medication. Having said that would u advise road to hana & the crater?

Is it going to be whale watching season then maybe 16th november to 21/1/12? roughly.

Having traveled extensively in both places (my sister used to live in Costa Rica and my wife has been going to Maui since the 50's), I would recommend you consider the Northwest-Guanacaste-Flamingo Beach area of Costa Rica - and possibly flying into Iberia airport - vis a vis the main city of San Jose - if that is less flying time/overall easier for you.

Actually - the beach area at Flamingo Beach is super - check out the Flamingo Beach Hotel - http://tinyurl.com/42czv4x
and there are other/newer destination resorts up in that area - plus you can get into the rain forest with ease from there - but hey - we also love Muai.

Both would be great actually, just a matter of what works best for your.

As for driving out to Hana - you could go part way and see how it goes, as even part way - you experience some of the beauty of the Hawaiian rain forest/waterfalls, etc.

As for going to altitude with a young one - suggest you check that out more as Haleakula is up there. Seeing the sunrise is magical - but not if you have a sick child, eh?

Not sure about Costa Rica, but you can fly nonstop from Newark or JFK on a good, widebody plane straight to Honolulu, then hop to Maui. We do that most winters from Chicago, buying coach and upgrading to first. You just float through HNL without leaving security for the hop. We have also flown ORD-DFW-OGG(MAUI).

You are unlikely to see whales in November. Best timing is January - March.

Few small children enjoy the 12 hour trip in and out of a car that is Road to Hana. Haleakala is too high for some little lungs. (Even adults can develop altitude sickness up there.)Your Three would enjoy Iao Valley and the Maui Ocean Center. (Buy a longer pass.) You'll probably spend most time on the beach and in the tidepools. There are *wonderful* sitter services on Maui if the adults want more adventures and some 'date nights'.

I like South Maui -- and condos -- for families with small children. Wailea has some very nice condos and is home to Four Seasons, Fairmont (all suites), and Grand Wailea (too kid-magnet for me). I like this site for South Maui condos: www.mauiownercondos.com Look at Wailea Beach Villas, Polo Beach Club, Makena Surf, Wailea Ekahi and Elua. Hale Pau Hana is nice too.

With two weeks, you might split time between two islands or right on Maui. Kapalua has The Ritz and many nice condos. Do any touring from Wailea -- more convenient location and four-lane highway all the way.

We love Hawaii, but...I have to say that our DS celebrated his third birthday in the US Virgins -- SO much closer to home! (Although less to see/do while you're there. Maybe that's a good thing.)

Hawaii gets busy with families whenever mainland schools are out -- including Thanksgiving.

You'll need a rental car everywhere outside of Honolulu, an visitors DIY tour, unlike in some non-US tropical locations.

Hana and Haleakala will be no problem, unless your child is prone to car sickness. However, sunrise can be bitterly cold, cloudy, and driving up in the dark for the first time is no fun (sunset is nice, though).
Easily accessible tide pools, lots of gentle beaches, easy driving; IMO, Maui would be a great choice.

The Haleakala National Park warns against young children going to the summit without a doctor's clearance.

http://www.nps.gov/hale/planyourvisit/yoursafety.htm

A 3 year old will get nothing out of the trip to the summit, or to Hana.

With a 3 yr. old, I would pick Maui. I loved Costa Rica, but it is not known for it's beautiful white sandy beaches. Also, to really see the country, you need to move around a bit. We took our 12 year old and he loved it..hiking through the rainforest, seeing all the animals, zip lining, riding small boats down the rainforest rivers. I would save it for when your son is older. Maui's beaches are nicer, water clearer and caters to families with small children.

The warmest water I ever experienced in an Ocean was at Hermosa Beach - north of Flamingo - a beautiful sandy beach and my brother in law - originally from Nicaragua - though he had found nirvana.

You can fly from Miami, Houston - or even LA? - to San Jose, Costa Rica - and will check on flights into the more northern airport at Liberia.

Here is the webpage for Liberia airport. Although the Volcan at Arenal (by the village of La Fortuna) - may not be booming like it once was - it was a wonder to behold and easy to get to. http://www.liberiacostaricainfo.com/Index.htm

And here are some pics of Flamingo Beach. We rented a nice villa right on the beach - and had a great time, especially looking at the ocean from hot tub type pool on the front porch - while drinking Cuba Libres - Rum and Cokes.

http://tinyurl.com/6w39336

BTW - you can also drive from Flamingo Beach/Guanacaste area down to Manuel Antonio in about 5? hours - maybe a little longer. It's also very beautiful.

Here is a page for more Costa Rica beaches: http://www.anywherecostarica.com/destinations/habitat/beach

And here is a pic of Hermosa Beach:

http://www.anywherecostarica.com/destinations/playa-hermosa-costa-rica

http://www.buenavistaluxuryvillas.com/accommodations/tulemar-bungalows/ is the Tulemar property I mentioned.

Thank you everyone, I do see more people recommend Maui to be easier with a toddler.Another question please.If we cannot do Hana & the crater national park then is it worth the 13 hour flight to go to Maui for beaches, pools, ocean center etc or for that go to a caribbean isalnd we havent been to. So far we havent gone to Grand Cayman,St.Kitts,St.Lucia ( heard about sand flies,poor reviews for Windjammer), St.Martin, Anguilla. We are also fans of turquoise water, white sand ( who isnt ) but we have been going regularly to the caribbean & this time it wasnt exciting me as much but am open to it.I would comapre it to Maui although at this time.I like what tracy2cents mentioned right now my son will be happy with sand & water & I have to entertain him less. Let me know without Hana & crater national park highlights, does Maui still hold its charm over other caribbean isalnds I havent been to. I have been to aruba, curacao,provo - twice,PR,barbados.Thank you all once again.

I think either the Caribbean or Maui would be better for you than Costa Rica, but two weeks in any of these islands is going to be much much more expensive than Costa Rica, so if cost is a consideration, that might be the place. Though I'm not sure I'd want to spend 2 full weeks in Manuel Antonio, and it would be difficult to travel around with a 3 year-old.

This is hard. I'd find an island where you can rent an apartment-style unit for 2 weeks. St. Martin might be the place. You can easily hop over to Anguilla for the day.

There is so much more to do in Costa Rica than there is on some isle in the Carribean - or even on Maui for that matter.

No comparison.

Maui, for a 3 year old and anyone else who wants beach time.

I think it is a misconception that Costa Rica is cheaper, BTW.

And in November, aren't you still in hurricane season in CR and the Caribbean...

I was there in 2010 when Tomas closed virtually every major highway in the country.

http://www.crsurf.com/news/community/flooding-help.html

I like Hawaii and CR much more than I've ever liked the Caribbean, just more to do. For the most part, I don't think the beaches in CR are as nice as in Hawaii or the Carib. though, although Manuel Antonio is very pretty. We go to CR for the wildlife and adventure activities more so than the beach. You could do a combo of Arenal and Manuel Antonio. Did you take a look at The Springs Resort since you said you like luxury?

http://www.thespringscostarica.com/

In the Arenal area, you could visit Proyecto Asis animal rescue center and feed monkeys, sloths, and macaws. You could hike the Hanging Bridges, and you could hike the waterfall and swim in the crystal clear river below. The Penas Blancas river float is neat if you think your 3-year old could sit in a raft.

We used to escape winter in the Caribbean when we were tied to our DS's school breaks. After 'discovering' Hawaii, we have seldom returned.

There's nothing to DO on these tiny islands. (Probably why there are so many bars -- LOL.) If you only want beachtime, they are perfect. If you want a wide choice of modern condos and restaurants, etc. Maui has that. Hawaii does not have 'sugar sand' or 'turquoise water'. It does have fine swimming and snorkeling beaches, and you can go almost anywhere you want on good roads, drink safe water, be safe -- even find adequate medical care.

We've stayed two to four weeks on the four major Hawaiian islands. Now we winter on Maui in a large, low-rise, low-density condo with ocean view that is 'home away from home'.

You can't go wrong with either one - so do one now - and perhaps the other later.

Thank you everyone. Caribbean is out but still researching costa rica as maui I do have a fair idea.
In November,if we go to Maui we are thinking of splitting the 2 weeks between Wailea & Kaanapali. Maybe one hotel & one luxury condo.Any views about this? We are flying out of nyc so it would be a long flight.
Considering Fairmont in Wailea & anyone know of a luxury condo on the beach - 1 BR preferred as we have a 3 year old.

Also any suggestions about splitting the time in 2 areas or should we just stick to Wailea area.Thank you so much.

For a luxury condo in Kaanapali, look no further than Kaanapali AlI'i. It's between the Marriott and the Westin, excellent location. The units are individually decorated, but nicely. Also, the units are very large, a 2 bdr is upwards of 2000 square feet.

http://www.kaanapalialii.com/

We've stayed in Wailea and loved it. It's a very nice upscale area - very nice beaches there.

Maui isn't that big. I'd find a condo in Wailea and stay put. You can drive up into West Maui to piney Kapalua and stop to wantder Lahaina's Front Street. I prefer low-rise, low-density on Maui. Look at Wailea Beach Villas, Wailea Ekahi and Elua, and Makena Surf. Polo Beach Club is 'tall', but is on a great beach -- and you could easily walk to the Fairmont from there.

Shops At Wailea is a nice open-air mall. The whole area is more upscale than Kaanapali. Beachtown Kihei is just north, with small restaurants and carry-out places. The three Kamaole Beach Parks in South Kihei have large play areas, lawns, shade, restrooms and lifeguards.

I like this site for South Maui condos because the manager won't accept an ad until she has vetted the condo: www.mauiownercondos.com

I have checked out maui condos but they dont mention an AC only ceiling fans.I am assuming they all have AC's? Was looking at Wailea Ekolu village. Have never booked a condo before so I am unsure.

Do not assume they all have AC because they don't!

We've traveled to one of the Hawaiian islands every year for the last 7 years with our kids. (Now 7 and 2.) Here's what they love on Maui...

* Viewboarding with me @ the Sheraton at Blackrock.
* Night-time frog hunting at the Westin.
* Maui Ocean Center
* 'Iao Needle Hikes - very lush, lots of wildlife
* Watching the kite surfers from Mama's - then eating there.
* Hula & lei-making lessons at the hotel
* Swimming, swimming, swimming in the ocean
* Tidepooling at Ahihi Bay
* Whale watching
* Counting rainbows over Ka'anapali

I would argue against Hana and Haleakala at this age, simply because the reward doesn't come close to the cost. (We've done both with and without kids.)

We've stayed down in Wailea several times and keep coming back to Ka'anapali. We like the beaches and snorkeling better there.

With a three, I really recommend the pool and beach at the Sheraton @ Black Rock. The Westin's pool doesn't have a shallow end -- anywhere! (What were they thinking?!?) And, the Grand's pool can get a little crazy.

If you like the Sheraton, check out the Hale Moana Suites. They're apart from the main hotel towers and have a wonderful semi-private grassy area overlooking the ocean where my kids love to run around. Just past the grass and down the cliffs, you can watch the sea turtles hang out on the backside of Black Rock. And, when we go out on the grass at night, the light from the Sheraton is largely blocked, so the stars are out in force and we watch the night diver's glow sticks move around eerily under the waves.

Given your duration, have you thought about spending one week on Maui and the next on Kauai or Oahu? That might be just the ticket...

Katemac, thanks so much. I am sold on Maui. As of my research this weekend we have 2 options

1) Split b/w Oahu, we have been here years ago & love the Hilton Hawaiian village & I am a hilton honors member & then head to Maui for 8-10 days & stay at the Fairmont. My husband is keen on this.

2) I am keen on staying maybe 8 days at the Fairmont in Maui ( cant afford more ) & then staying at the Kanapali area but in something less then 200 a night to fit the budget.Cant find anything that is on the beach, with a separation from my son at night, has an AC & is under $ 200 but am still looking.
So far all the places that are lower priced in Lahania/kanapali dont have the best reviews especially the condos that are owned by an owner.So if the under $ 200 doesnt work out may have to do honolulu but I prefer doing just maui as from nyc I am not sure whether I will be visitng maui again.

All the stuff you mentioned is enticing & does draw me towards maui.Thank you.Any suggestions anyone?

Ekolu is nice, and AFAIK all units have A/C, but...it is not beachfront. If you don't have to have beachfront there are many other places in Wailea and South Kihei. Hale Pau Hana? Mana Kai Maui? The Palms? You might like our complex -- 3-star Maui Kamaole. (Look at the 1 BR plus Den units near the upper pool.)

Traveling with a child, I'd much prefer a condo for more *space*, washer/dryer, a full kitchen. I'd skip the expensive single suite at the Fairmont and pay more for a nicer 'home from home' where Mom and Dad have both privacy and a living room and lanai to enjoy after the child goes to bed. Any split stay appeals to me less with a child.

Well now that you've decided on Hawaii I will comment on Maui. I have stayed at Kea Lani and think it is a perfect choice as the suites are spacious and give a separate room for the evenings and nap time. It's been a few years, but the beds were heavenly.

Save Kea Lani for the end of your vacation. We once made the mistake on Kauai of staying at the then Princeville Hotel and then the Sheraton Poipu. It was a miserable transition downgrading.

We often move around when on Maui. That way you can leave your lodging for the morning or afternoon and still have down time with your child. And each area offers a variety of things to see and dining options.

I would start in Napili/Kapalua/Honokoai area. Try vrbo.com to search for rentals. So you begin in a condo, so with cooler in hand, you have a kitchen and some provisions.

I would then head to Hana for 2 nights, if you're child does car trips fine. They will have by then adjusted from the plane ride and you can plan the drive with their nap time in mind. Many will say that is the journey but for us Hana is the destination and there is plenty to see. Find a nice rental and with the rest of your provisions from the condo you will be all set.

Then head to Kea Lani and luxuriate in resort life. They have a lovely little provision store where you can get bfast items, sandwiches, gelato, wine . . . .

Well that's the way I'd roll! Good Luck with your plans.

Oh and in November I would not worry about ac on the west end or Hana at all!

1)

I have taken a 3 year old to Hawaii. I suggest you split your time between Maui (either Wailea or Kaanapali) and another island. A condo or suite works much better than a single hotel room for a child that age.

Check out kureiff's trip reports. She has several. Here's her Maui trip report when her little one was 4yo - http://www.fodors.com/community/united-states/kureiffs-maui-trip-report.cfm

Thank you so much.I checked out kureiff's trip report, she is funny especially with the digging in the sand part.Thanks starrs, it was informative.
Thanks Lookin Glass, I checked out vrbo, its confusing but will review it in more detail this weekend.Have never rented a condo before so will take time to get familiar with it.We will do Fairmont later - they are suites with a separation from my son while he sleeps so we are good with that.
ChiSue, I will check out those names you have provided for sure. So far on vrbo I have looked at Mariott ocean club, Lahania Shores, Ashton Kannapli shores. Still have to get a handle on it.Fodors is so so exciting that I couldbe here all day & I have a good time everytime I post or read here.Thanks so much everyone.Any preferences people have with condo develop - we are looking for beachfront with more amenities than just a condo if possible.Also do they have daily maid service? beach service? unbrellas & chairs? Sorry hope I am not expecting too much out of a condo but am open to knowing more.Thanks

Your question about condos is actually a very astute one. Some condos are just that - buildings owned in common by a bunch of people, some of whom rent out their units. Others are operated like hotels, and have all the associated amenities. I would say that daily maid service is probably unusual, although you can get it (for ex. at the Marriott Ocean Club) for an extra fee. As for the ones you mentioned note that some are on the main part of Kaanapali Beach (south of Black Rock) and others are north of Black Rock. I think they've built a path so you can now walk from north to south, but someone else will have to confirm that (unless you can wait until late September, when I'll be there LOL). If true, that makes the north part of Kaanapali Beach more desirable than it used to be - I wouldn't stay there before, because I like walking on the beach path at night, usually to Whaler's Village for a drink or dinner, or just to poke around.

I was also going to mention that you'd only want your 'dessert' (Fairmont) at the end of the trip.

*I* would just get a very nice condo and pay for a sitter when you want to go out to a spa or for an evening. Kids generally don't like 'moving house' once they've settled in, and you have two long flights at each end of your trip. Most condos have everything a hotel has except room service. If maid service is not in the rate, it can usually be arranged for a small fee -- as often as you want it. Most condos have a closet full of beach gear, including a cooler, beach towels, chairs, umbrellas, sand toys, etc. I'm not sure just what 'hotel amenities' you are talking about. Do you want valet service, a mint on your pillow, bar service at the pool, someone to spray you with Evian? -- LOL! (All of these come complete with palms outstretched, you know.) In Hawaii all beaches are public.

You need to decide WHERE you want to stay on Maui, then look for your condo. (I wouldn't choose Lahaina Shores -- plain, no beach, just off Front Street with its bars.) I like the 'ends' of Maui best: Napili/Kapalua and Wailea/South Kihei. Wailea and Kapalua are more upscale.

(I would not be walking all the way from north of Black Rock to Whaler's Village mall, certainly not in the heat of the day.)

Hi all. Thanks so much for above suggestions.I am more perplexed......I have checked VRBO website & condos are expensive too.Here is my question in November is it too rainy,windy to stay in Kannapali?Lahaina? As mentioned above we will do a 2 week trip mid november.The last week will stay at Fairmont but the first week I had asked for something under $200 & was rightfully directed to VRBO.After checking it out I know I would like a change in scenary, something more close to restaurants etc & was thinking of not renting in Wailea in the beginning.

1) Would Kannapali be fine for November? I am looking only at beachfront condos & hopefully something walking distance to restaurants, shops.5 min drive would also be all right.

2)Can anyone comment on Whaler at Kannapali & Ashton Mahana? These are fitting my budget from expedia but are more expensive on vrbo at the time.Its surprising but alot of the condo hotels are more expensive from the owner plus cleaning fee as compared to expedia.

3) Does anyone have suggestions for abeachfront condo in november for myself, my husband & 3 year old son? under $200 if possible.I also welcome any specific condos you have stayed at.Would love to have an ocen front condo where we can see dolphins, whales ( I know whales may not be there yet but sitting on the lanai with a view of the ocean is my dream.)

4)Sorry for so many questions, but is a trip to Lanai with a 3 year old worth it?for a day trip?Are the waters too choppy?

Thanks all so much

Oh and also Kapalua Villas - please comment if you have stayed there.Thanks again

Kaanapali will be fine, weather-wise. It's not my cup of tea, but take a look at this realtor's offerings for West Maui: Chase N Rainbows. (Sorry, I don't know their web address.)

No, I would not take a child on the ferry to Lanai. The returns are especially apt to be rough.

As for VRBO condos being more than Expedia, remember that all condos are owned by individuals. Some are much nicer than the ones in a rental pool. However you book a condo, you want to be able to see photos of THAT unit. Also, don't hesitate to ask an owner for a better price than he shows in his ad. You should not have to pay a cleaning fee for a stay of a full week either! (Well, we don't charge it.)

Thanks ChiSue any other condo suggestions?

Check this site for South Maui condos. The site manager has vetted the units before she will take an ad. www.mauiownercondos.com

The agency we employ to look after our guests rents its pool of condos. I would use their websiste to get a feel for some complexes, then try to rent a specific unit from its owner. www.crhmaui.com

If you were not splashing out on the hotel for a full week, you'd have a wider choice of beachfront condos. If you'd be all right with a condo NEAR a good beach, you'd find more in the under-$200 range -- in both Wailea and South Kihei.