The Deal Mommy

When The World is Too Big: Help Me Decide Where to Go!

As this is a first world problem, I owe a Kiva loan.

A rare downside of traveling on miles and points is that most destinations cost the same to visit. Assuming you can find a ticket, the world is open for you to explore. How is that a downside, exactly? When you are trying to decide where to go! I’m currently finding the World is TOO big and could use your help.

My Christmas (and birthday and anniversary and Valentine’s day and…) present this year (and every year) is two weeks solo travel on the even years while Deal Dad takes the kids to visit Grandma and Grandpa.  So far I’ve explored Panama, Tenerife, and Italy  and am now planning for Camp Mom Solo 2016. Even using my destination checklist isn’t helping as too many destinations fit my criteria.

Here’s what I have so far:

  • Do I want an active trip or a restful one? A mix. Definitely some culture/great food/history. Ocean views a plus.
  • Urban, Rural, or a mix? Leaning towards urban as I’ve learned I don’t love a lot of driving on solo tips. 
  • One destination or moving around? With solo travel moving around is easier than with kids. Definitely not a city a day but 3-4 in two weeks would be ok. 
  • Luxury or simplicity? Flexible, although with solo travel I appreciate details more in hotels. Willing to fly coach. 
  • 1st World or 3rd? Definitely not the middle of nowhere if developing, more hustle-bustle.
  • Am I limited by the calendar? Yes, firm first two weeks of August.
  • By current events?: Possibly. Leaning against some European capitals and much of Africa b/c of security concerns. (Not so much my own security as closings/protests/etc being disruptive). Also not sure how I feel about some parts of Central/South America solo. Much of Brazil out due to Olympics. 
  • By the climate or the seasonsPossibly as some parts of Asia and Caribbean are in hurricane/monsoon season. 
  • What is my cash budget? As low as possible.
  • What is miles/points budget? 75K Starwood, 75K Hyatt, 60K each UR and MR, 25K Delta
  • Are there any sweet spots in my miles/points programs that fit the above criteria? Too many, which is why I’m stumped!
  • What about other promotions? (Skyauction, Luxury Link, EVR, etc.) Weekly rental always an option but nothing specific.

Here’s where I’ve been lately:

  • Canary Islands (Tenerife and Gran Canaria)
  • Spain (Madrid, Costa del Sol)
  • Salzburg
  • Paris
  • London
  • Japan: Tokyo, Osaka
  • Vietnam: Hanoi, Danang
  • Hong Kong
  • Ireland: (lived in) Dublin, Belfast, Galway
  • Mexico City (2x)
  • Caribbean: Turks and Caicos, Bahamas, St. Maarten
  • Panama City
  • Canada: Montreal, Quebec City
  • Hawaii: Big Island
  • Italy: Rome, Naples, Matera
  • Cuba: Havana, Veradero, Trinidad (pre-USA restrictions lifted)
  • Thailand: Bangkok, Ko Samui, Phuket, others (has been a long time but lived there)
  • Australia: Melbourne and Victoria state (has also been a long time but lived there)
  • China: Beijing (has also been a long time but lived there)

Here’s what’s made the list so far:

  • Portugal (weather/crowds?)
  • South coast of France (ditto)
  • Morocco (heat/security concerns)
  • Northern Germany/Copenhagen/Scandinavia/Poland (Not sure there’s enough in Germanic/Scandinavian culture to keep my interest for two weeks.  Cash outlays as not a lot of points options.  Also a lot of transit)
  • Santiago/Mendoza/Buenos Aries/Iguazu/Easter Island (a LOT of transit)
  • Columbia/Ecuador (too ambitious for solo?)
  • Asian circuit: possibilities include Siem Riep, Seoul, Chiang Mai, Singapore, etc. (Heat and Monsoons! Also did a month in Asia last year so may be burnt out)
  • South Africa (loooong flight, enough for two weeks?, cash outlays if add on safari)
  • ?????????

Help!

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24 thoughts on “When The World is Too Big: Help Me Decide Where to Go!

  1. April

    I’ll be on Rapa Nui for a week in June. Not sure whether we’ll also hit Santiago or another connecting city on the way down. If you decide on that route then I can give u my input when I come back. Ditto for Germany and Poland after March. (And if you get bored in Europe, I hear the Paris Vendome is highly recommended…)

  2. Christian

    If you do somewhere in Europe, you might consider combining with Crete. Heraklion, the capitol, is cheap, lovely, has great food, pleasant people, gobs of culture, English is widely spoken, Americans are welcome, and has wonderful day trips available. You would be away from the flow of refugees, so that wouldn’t be an issue. My wife and I went last year, and had a lovely time. We’re going back this Summer for a graduation trip with two teenage girls, which we assuredly wouldn’t do if we felt there were safety issues.

    1. thedealmommy Post author

      Hi Christian,
      Thanks for the info- Crete could be a good option as I’ve just remembered a have a few Aegean air miles floating around!

  3. Brandi

    When the husband and I do get to travel without the kids we try to do things that we couldn’t do with the kids. Makes the trips more meaningful and keeps us from constantly thinking ‘oh the girls would love this!’. We take the motorcycle on long trips, do winery tours, snorkel, etc. I know you’re traveling solo, so I would suggest think of something YOU want to do that you can’t really do with the kids. Or can’t do with them for a few more years. Personally, I would head to Argentina and just cut your list down. I would relax and take the time to leisurely enjoy a few of those areas, drink a lot of good wine, and immerse yourself in the culture.

    1. thedealmommy Post author

      Hi Brandi,
      Santiago-Mendoza-Buenos Aries would be doable. You’re right: save Easter and Iguazu for another trip.

  4. DaninMCI

    Looking at your lists. I would suggest Puerto Rico, Costa Rica, a cruise (Med, Euro River or Caribbean) or Germany. Fiji or Australia would also be on my personal radar.

    1. thedealmommy Post author

      Hi Dan,
      Puerto Rico would be on my list if it weren’t August- too risky with hurricane season. Germany is rising higher.

  5. Nancy

    How about Guatemala? Lots to see there, travel within the country can be a little rough…but it has beaches, cities, ruins.

  6. Pat

    Since you’ve only been to the Big Island in Hawaii, I go back and do Maui and island hop to Oahu and other islands. Only costs 5k between islands if you use AA points and I’ve personally stayed at the Westin Maui and highly recommend it. You’d be able to use your Starwood points and transfer some to aa to fly Hawaiian airlines from island to island. Easy flights from island to island and so worth it. I’d only spend a few days in Oahu but go see Pearl Harbor while there.
    On the other hand I’d go do the southern part of Italy and visit Sorrento, the Almafi Coast and Cinque Terra. Easy to get around by train so you don’t have to worry about driving. I’m sure you’ll have a blast whatever you decide.

  7. Nickelfish

    We’re hitting Croatia, Bosnia and Montenegro this summer. Montenegro seems cheap!
    I highly recommend Slovenia and northern Croatia. Slovenia is the bomb-diggity! Ljubljana is terrific…kinda like a hipper Amsterdam in my opinion…and loop in places like Lake Bled or Porec where you can chill for a few days without being overly active. Or take a catamaran from Porec to Venice if inspired. Or stop off in Trieste or a day trip.

      1. Phil

        Just back from DBV and kotor, side trip to ostrog monastery, couldn’t recommend it more. Summer will have crowds, but all of Europe will. Hilton DBV has a great location

        1. Nickelfish

          Phil-were planning a three day base in Kotor. Any other recommendations? Have two 16 yr old with us…anythjng teens would get a kick out of?

  8. Lourdes

    If you did Canary Islands and did not visit Fuerteventura and Lanzarote, you are missing out. No Hyatt though! But if you have Avios the flights in between the islands are cheap or take the ferry, cheaper and more fun. You can combine it with Barcelona. My husband and I used Avios in all inclusive hotels and stretch the money a lot. When visiting Puerto Rico, go to Vieques also. Starwood has a nice hotel there. Good luck! Have Fun!

  9. Mark D.

    As previously mentioned, I like the idea of the rest of Hawaii as well as the idea of the Croatia-Montenegro area. I don’t know how you feel about the continental 48, but it could be a good time of year to drive through the NE states (I know you said not a lot of driving) or even just spend some time in Maine which is supposed to be great that time of year.

    1. thedealmommy Post author

      Hi Mark,
      On a related note, I was considering a road trip through Eastern Canada to Newfoundland. Thanks for your help.

  10. Becky

    I think the South America options you listed are going to be more hectic than it feels like you want, unless you truly settle in just ~2 cities for a week each and dig deep into those places.

    I think you’d love your own suggestion of Portugal – you could easily spend a week to 10 days there, wouldn’t have to drive (unless you want to), and so many places are accessible as day trips from a major base that you don’t have to pack up and move all the time unless you want to. Plus costs there are reasonable compared to most of western Europe.

    Throw in a quick stopover somewhere else in Europe (you know how easy it is to get around!) and you’ve got a great trip. The concerns about crowds in France, heat in Morocco, eventual boredom in Scandinavia, etc. are all manageable if it’s only a portion of the trip as a whole.

  11. icicle

    I’ll throw this into the mix.

    1) How about a road trip from Vancouver to San Francisco? That sounds like a really awesome trip. Or start in Juneau (or thereabouts) and go south to Vancouver. Or just Vancouver/Victoria/Seattle? I love Vancouver and Seattle.
    2) Scotland. Highlands. *sigh*
    3) P.E.I. A tour of the island while reading Anne of Green Gables. Seriously, I’d love to do this. With a side trip to Newfoundland or Saint Pierre and Miquelon. Not sure I’d do it alone though.
    4) The Outer Banks of N.C. Ooh, starting with Chinoteague, VA going down to Charleston, SC. Awesome trip!
    5) New Zealand. Just because it is New Zealand.
    6) Finland. Because no one really goes there but doesn’t it sound like a really cool place?
    7) Wales. Because most people don’t go there either but why not?

    And I just realized that my list is heavy on English speaking places. Except for Finland. And Saint Pierre and Miquelon. The Finns have a really good ice hockey team…but that knowledge won’t help you in August. And Saint Pierre and Miquelon is kinda remote. LOL

    As a Floridian, I always advise people to avoid cruises or travelling to the Carribean during August, September, and October.

    1. thedealmommy Post author

      Hi Icicle,
      Love these ideas! I do think a road trip screams “girlfriend getaway” though, so eventually will have to drag someone along.

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