Travel Tips

Planning an Over-the-Top Surprise Trip To…

Over the past six years, I’ve helped a lot of people book their dream vacations on points and miles. Whether it was readers, friends or family members, I’ve offered advice and booking strategies to anyone who’s asked. The one person who hasn’t benefited from all of this, but who absolutely deserves it? My older sister. She hasn’t been able to join us on any of our family trips for one reason or another. She’s traveled with her family to places like Hawaii and Mexico but she has yet to really go “abroad” (sorry Mexico, you’re too close to home for me to consider you “abroad”). 

View from the airplane flying over Chicago

I’ve decided to just ignore her excuses and force her to go on our next family vacation. She’s currently in the midst of a demanding coding bootcamp, she works as a loan officer part time, and takes care of three kids under the age of 6. She does all of this without losing her mind or burning the house down, which makes her Superwoman in my eyes. At some point (preferably December), I want to reward her for her efforts with an over-the-top vacation. Before you think I’m ruining the surprise – she already knows I’m planning something. She just doesn’t know where we’re going or when. In fact, I don’t really know 100% either.

The idea for this trip is to visit 2-3 somewhat kid-friendly destinations over at least two weeks and to fly in business class. My nieces are 3 and 5 years old while my nephew is turning 1 this year. The plan is for all of them to come along, plus my parents and siblings. Will the kids be flying in business class? I don’t know how realistic that is but if they end up flying in coach, I’ll let the adults sit up front while my younger sister and I babysit the kiddos in the back of the plane.

So now it’s really down to destination. I don’t know where to go. Ever since I mentioned Singapore to my 5 year-old niece (her response, “What’s that? Does it have a Starbucks?”), she’s always talking about it. Singapore is a very kid-friendly city and one that adults can enjoy as well. So I’d like to work that in. But now I’m stuck – I don’t want to repeat 2015 and go to Hong Kong and Bali. My parents have this aversion to visiting the same place twice. “There’s so much to see in the world. Why go back to someplace you’ve already been?” That’s what my dad always says. So I need some ideas. We don’t have to stay in the immediate area – we can go to the Middle East to change things up.

The bottom line is I need ideas for destinations that are kid-friendly, somewhat easy to get to (i.e. no seaplane transfers), and where the dollar goes further than, say, the Maldives. This trip is all about my sister, who is one of the kindest, most compassionate, and selfless people you’ll ever meet. I want her to have an amazing time and see the incredible experiences that points and miles can bring about. 

So if I can get some solid ideas from readers, especially those who have some understanding of the challenges involved in traveling with kids, I’d greatly appreciate it.

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  1. here are some ideas for easy kid-friendly add-ons to singapore:
    (1) bintan (45-minute ferry ride, nice resorts including a club med, visa on arrival)
    (2) ho chi minh city
    (3) langkawi
    (4) hoi an
    (5) brisbane/gold coast
    (6) cebu
    (7) phuket
    looking forward to hearing what you finally decide on — have a great trip!

  2. tom mccall

    Thailand and Burma,Thailand esp Phuket and Chiang Mia, I think you you can fly to Burma from Phuket, Burma is amazing, friendly and still relatively inexpensive, I have been there three times and love it, like going back in time. Hope you work something great out for your sister.

    • Thank you Tom! I’d love to visit Burma but is it good for kids? I’m looking for a place that has fun activities and things to keep them occupied, even if the adults end up going sightseeing.

      • tom mccall

        Your right at those ages Burma wouldn’t work But as others suggested you could do the whole trip in Thailand and have lots to do with the kids. I go once or twice a year and see lots of young families.
        I love Japan but its expensive, The Japanese are very family orientated, They have Disney Land right out side Tokyo, culturally its eye candy from the moment you arrive.
        1, 3 and 5 are pretty young so its going to be a challenge, where ever you go be sure they have a nice pool, that’s always a life saver with young children. good luck

  3. Elizabeth Houck

    The dollar to the pound is at an all time high. Why not the UK? LHR an easy hop non-stop from SFO; no language barrier, great fun with the double decker buses, London Eye, Tower of London; then head south to Portsmouth to see the Mary Rose and Nelson’s ship Victory is fun and educational for all ages. A bit north is Sundown Adventureland – an amusement park geared for kids under 10.

  4. Don’t cram in too many destinations (maybe just go to Singapore and a beach somewhere). Jetlag with little ones is awful. I personally find if you can book a flight leaving the US in the evening (Or get the long haul flight to be in the evening), to arrive at your destination in the morning you will be better. It’ll take a while for the 1 year old to get to sleep, but when they do, fingers crossed, they should sleep for 12ish hours. I find adjusting to the time difference travelling US to Asia (or Australia) takes about 4 days. Going back the other way takes about a week (but maybe thats because the fun was over??). You should offer to help your sister out on return. She’ll be very tired with 3 kids with jetlag, plus her own jetlag. FYI: My daughter is only 2 so I’m not sure how older kids travel.

    My personal preference with kids is beaches (although I have sworn off holidays because they are too much work). I personally don’t think sightseeing is fun with a small child. But everyone is different – what does your sister normally like doing on holidays with her kids? What do the kids like to do normally?

    If you’re definitely going to Singapore maybe just stick with another nearby Asian destination like Thailand. You could do Bangkok (looks of activities – water parks, aquarium, indoor play centres) and then a beach destination (I personally think a 1 hour flight to a beach/island is better than going by car or ferry to something closer to Bangkok). Phuket, Samui (maybe look at Shiva Samui). Also Khao Lak (JW Marriott is lovely with nice kids club, plus many others), Si Kao (Anantara), but these have longer transfers from the airport (which you need to consider…..) All the big hotel chains have great kids facilities so plenty to choose from.

    If you don’t go to Singapore go to Australia. Lots of nice beaches, zoos, kid activities, Australian animals etc.

  5. dawn smith

    Yerevan and Tblisi

  6. Not sure of the time of year, but why not a cruise around South America?
    Cruising is wonderful for kids, you will see several different cultures and lots of penguins.
    Early January the weather is nice and cruising rates can be very inexpensive

  7. You are such a sweet sister. It is refreshing to read how you express your appreciation, how truly you love and cherish your sister.

    Not sure you have been to Taiwan or Japan, but these two cities (Taipei and Shinjuku) are really fun to visit.

  8. Been to many places with my kids and I found out that as long as there is a pool, the kids have a blast. Singapore, Bali, Bangkok, Koh Samui (rent a car and drive around the island. Stop whenever you see a nice beach and have fun!), Ho Chi Minh (tunnels were fun for the kids and also the cooking classes we took), Costa Rica (Andaz Papagayo is awesome!), etc. I agree with picking 2 destinations and take it easy. Anyhow, have fun planning and enjoy the trip!!!

  9. Takhliq Khan

    I would agree with Elizabeth few comments above. London would be very good for adults as well as kids. Make that your base. Spend about 5 days there and then head on to Italy for the rest of your trip. Your dollar will get you lot of value in both places.

  10. I think Thailand. A few days in Bangkok to adjust. Off to Chiang Mai and see the elephants and then to one of the islands for beach time. Try Koh Samui
    What a great sister you are.

  11. Caroline Nguyen

    You’re so sweet! Having traveled with kids (especially three of them all under 7 years old), I would suggest somewhere that would ease the mind for your sister. Third world countries have less reliable hospitals, and their viruses and bacteria in the water and food is different. This might add to the worries, having to make sure all the utensils are clean before her kids eat, the water can be used to brush their teeth, etc. Maybe save those adventures for when the kids are a bit older, all above 6 or something…

    So, I suggest Japan. The kids might like sitting on the train. It’s easy to use points for hotels and flights on Japan Airlines. Hakone is great for “spa” like retreat. Kyoto is full of history and beauty. Tokyo is just amazing.

    Have fun planning!

  12. I will second Nancy’s suggestion – Thailand. It has something for everyone – you like the hustle and bustle of big cities? There is Bangkok. Like nature and adventure? – There is Chiang Mai. Want to chill on the beach? Phuket, Koh Samui and many other little islands around.
    Plus – great food, friendly people, wonderful massages, and your dollar would go a long way. Besides, December is a great time for Thailand – it’s much cooler then.
    Whatever you choose – have fun planning! You are a wonderful sister, your family should be very proud of you!

  13. Argentina…perfect weather in December. Go to Patagonia, see some penguins, walk on a glaciar, ride horses, go to Bariloche and it’s beautiful Llaollao hotel…they have a fantastic kids program, and the most beautiful landscapes I have ever seen.

  14. BKK -> SIN -> SYD. The Thai’s and Singaporeans love kids and there lots of things to do, and Sydney has the Beaches, Awesome zoo, great weather in December and easy, direct connections back to the US.

    You’re welcome 🙂

  15. South Africa on Emirates shower class?

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