Santorini, Greece - Photo: Pedro Szekely | FlickrCC

Santorini, Greece – Photo: Pedro Szekely | FlickrCC

I am going to be a bit selfish here, but I think for good reason!

I recently got married (yay) and we wanted to wait a bit to plan our honeymoon; we didn’t want to be planning a wedding AND a trip at the same time. My new bride and I both want to go some place we’ve never been before. While we think we are set on a destination, there are so many fun options to get there and different things to do; I thought I would try to see if any of you had some swell ideas.

I’ve never done something like this before, so I’m not sure if it will work. But it can’t hurt! My idea is to give you all some of my thoughts so far, and see what you think. Maybe I will get 0 comments and be sad, or maybe I will be overwhelmed and no better off, but I am hoping to get a gem or two out of this little experiment! Here we go:

The Big Picture

  • We plan to spend the majority of our time in Santorini, Greece. It’s place she has wanted to visit and neither of us have been.
  • We are not fans of places with a million tourists.
  • Being native Washingtonians, we don’t like hot weather.
  • Shooting for late April to mid May, but would do late September to early October if needed. 
  • Wanting to do about 10 days total, but would expand up to 14, if it made sense.
  • Being this is our honeymoon, we are cool spending a bit more on where we stay, the food, etc, if it has a good ROIOF (return of investment on fun — acronyms are fun!). Obviously we have a reasonable budget, but I don’t want it to hold back any ideas.

There is the Santorini Airport – Photo: Andres Alvarado | FlickrCC

Getting to/from Santorini

  • We will be departing out of Seattle. Unless it is a big enough difference, we don’t really want to go to YVR or PDX. (Editor’s note: what about PAE?)
  • Getting there, I am looking at getting creative. Maybe do something like flying into London, Paris, or Rome and take trains/ferries down to Athens for the final ferry to Santorini? Maybe stop for a night once or twice on the way down? Been reading up on options, but wonder if it would be more of a pain than it is worth. 
  • Coming back, I think we would just want to fly as quick and cheap as possible, but not more than 18 hours for a total trip. Looks like some airlines like Condor and Norwegian have options, but not every day, so need to play with dates. 
  • Even after 10 years of writing this site, I am still a miles noob. As I write this I have 35,000 Alaska miles. After a basic search, that can get me a one-way ticket to LHR or FRA. Not a requirement to use, but that would save a few $. 
  • Since we have our miles with Alaska, it would be nice to earn miles with them on tickets that we pay for. 
  • My awesome wife is game for me doing a story or two out of our adventures, so if there is a unique airline/aircraft type or if I can pitch an airline for a story/experience, that is a bonus. That said, she wouldn’t be game taking 36hrs, flying the wrong way across the globe to try a bunch of different airlines.
Santorini... the beauty, the height, the water - Photo: Wolfgang Manousek | FlickrCC

Santorini… the beauty, the height, the water – Photo: Wolfgang Manousek | FlickrCC

While we are in Santorini

  • I end up spending more time figuring out how to get to/from a place, the flights, the boats, the trains, etc., and sometimes I forget about planning what to do once I arrive. Guessing maybe some of you can relate? I normally like to have some ideas of things to do, but not all the days scheduled.
  • Once there, I’m looking at probably renting a car. Looks like there are taxis and buses, but not the best, plus we always have fun adventures with driving around on our trips.
  • Looking at things like boat or jetski tour, the hot springs, taking the car to explore the island, relaxing.
  • Want to stay on the Caldera side. Guessing a few nights in one of the nice hotels with amazing views, and a few in a more reasonably priced hotel. Just depends.

Okay, so this ended up being longer than I expected, but there are a lot of moving pieces. Please leave your suggestions/questions in the comments and let’s see what happens. Thank you!

EDITOR-IN-CHIEF & FOUNDER - SEATTLE, WA. David has written, consulted, and presented on multiple topics relating to airlines and travel since 2008. He has been quoted and written for a number of news organizations, including BBC, CNN, NBC News, Bloomberg, and others. He is passionate about sharing the complexities, the benefits, and the fun stuff of the airline business. Email me:
For Alaska Airlines, Business is Booming

I am a former Airline employee without flight benefits. So, I have learned to work the angles on reduced fair and free flights! First thing… Get an Alaska Airlines BofA credit card. If you already have one then get your sweet fiance to get one! 40,000 free miles toward a flight on AS for each new credit card holder! This will go a long way toward free flights to Europe. Since you are a writer, it is time to contact airlines and travel companies to see if you can get free airfare or hotels in exchange for a nice article about your travel experience! If you can get free airfare, maybe BOGO (buy one get one.. free)
Best of luck! Chuck H

Hey Chuck,

Thanks for the comment. The bad news is even though I am a mileage noob (my wife too), we both have the Alaska card and have made use of our miles (and free companion pass — although that was for US flights only). Not to toot my own horn, but I have pretty darn good credit and already have a lot of old credit, so opening up more cards isn’t my favorite thing to do right now (and just bought a house and car in the last year). But yes, I am for sure thinking about story angles. Typically is it not as easy to pitch an airline for a free ticket (especially two), but more of paying for economy and pitch for an upgrade to do a review (although two is much more difficult and you know who will be up front if I only get one 🙂 ). Of course I would love to find something that works, but I also don’t just want to weasel my way into something, I want to make sure it would be good/interesting (or at least not bad) content!


Tom Rowell

If you are going to be in that part of the world, Southern Italy is really pretty and in May /September it won’t be too crowded. Tropea and Scilla in Calabria are really nice, my wife and I went there for our honeymoon this past May and the weather wasn’t too hot and it wasn’t too crowded.

“wasn’t too hot and it wasn’t too crowded…” talking my language Tom :). Thank you for this, I will for sure look at these as we head on south. Much better than just looking at the big attractions in the big cities!


Michael Moscaritolo

One thing I would note is when I fly to Europe, I avoid LHR/LGW as my points of entry. No. 1 their border is really horrible … very slow and long. (last two times it was two hours the first time and nearly an hour the second time). No. 2 … not being part of the EU you will need to clear border again where you end up. Going into Paris, CDG border crossing is faster (it was when I went a few years back) and once you’re there, you’re in the EU and everything from that point is domestic travel so to speak.

Hey Michael,

I think I have been lucky when flying to LHR. Although I have never flown to LHR and to another destination. Probably the longest I was held up is when I flew American’s 777-300ER to review it and went from JFK-LHR for just a few hours before turning around back to JFK. The border folks asked a few follow up questions since I will admit that looks a little suspicious. Nope, just an airline nerd doing his airline nerd thing :).


Hi David! Congratulations on your wedding! So nice to hear that…. I wish you and your wife a lifetime of marital bliss!

blair kooistra

Last two trips from US to LHR (in April and September this year) couldn’t have been more smooth through T5 and British Airways. No longer have to fill out a customs form from the US. Automated customs intake. A 10 minute line. Didn’t even speak to a human being–scan your passport, get your picture taken, and you’re done.

Hey Blair,

Well, you are speaking my language — not having to wait in lines. When I did some basic airline pricing searches BA were some of the lowest. I actually have never flown them and when looking deeper into their pricing there seem to be a lot of additional cost “options”. Of course when I nail down the dates a bit more, I will do my thing and figure out all the actual costs/benefits.

Cheers, David

Gordon Bowker

Congratulations, David-

Here’s a thought: Trieste. It’s an amazing place, with Italian, Austro-Hungarian, Slovenian, Croatian, and other cosmopolitan influences. Hardly any tourists (at least for the moment, except possibly in high summer.} Fantastic architecture (Piazza della Repubblica, Castello Miramare). Seattle-like climate. Incredible shellfish restaurants. Amazing literary history-James Joyce, Italo Svevo, Claudio Magris, Umberto Saba, many others. Incredible coffee. Here’s the thing: everybody gets off the train, ship, automobile in Venice, an hour away, but get to Trieste before it’s too late. Sadly, the ancient Opicina Tram that winds up the Corso to Slovenia is out of service.

Fly Condor through Frankfurt. There should be a good connection. Earn or spend Alaska miles. Then make your way down to the sunny Greek Isles. Return? You’re on your own

Hey Gordon,

This is great! I will for sure need to look into Trieste. You are describing pretty much everything I was looking for, plus some good coffee! And with the stick shift rentals — that is a bonus for me :). Stick shift convertible Mini Cooper putzing around Santorini sounds like a fun adventure.

Thank you much, David

Gordon Bowker

Transmissions: Forgot to mention: FYI, probably 98% of cars in Greece and much of Europe are stick shift. Automatics are very difficult to find, even if the agency promises.

William Bevers

We just returned from Santorini. Our favorite 2 days were one spent at Seaside Beach club. The other day four of us chartered a catamaran for the day.

Hey William,

Did you just charter the boat for you and your party? I have been looking at the boat options and I really don’t want to be on a boat with 200 of my closest friends and all go swimming at the same time. Probably chartering a boat just for us two would eat too much in our budget, but there are some that are about 20-30 people and seem a bit more of a reasonable compromise. And I will have to look at the Seaside Beach club, haven’t done that yet.

Thanks, David

William Bevers

Yes David we chartered about a 35 foot cat for 4 of us for a half day. The boat was operated by a couple. They made a fantastic Greek lunch for us. The cost was about $1200 total plus we gave them a tip. It was money well spent. One of our favorite days while in Santorini.

blair kooistra

From what I can gather, flying out of the Northwest–from SEA or PDX–is certainly cheaper than flying from the hub airports where I live, in Texas. I found both DFW and IAH to be particularly pricey when flying to Europe. Much cheaper for me to fly to LHR out of DEN or Orlando or anywhere on the east coast–even with a connecting separate flight out of DFW. I flew recently to London non-stop out of Austin and it was several hundred dollars cheaper than out of DFW. . . guessing perhaps because there isn’t the upward pricing pressure of being a hub city that IAH and DFW gets from United or American–or perhaps because of the downward pricing pressure that comes from Norwegian flights?

Hey Blair,

I was just looking last night about where we might want to fly into Europe. Now looking more into Milan or Rome, which SEA doesn’t serve direct, so was looking at going through New York and damn, there are some cheap flights… like $238… of course on Norwegian. And it is a red-eye. But that is so, so cheap and I end up in the quandary that many before me have been in before.


Mike Butorac

Just spent three nights in Kamari before Athens Flying Week last month. With a short time and wanting to make the most of it, we chose a custom tour through Kimkim. More expensive that way, but well worth it for us. While the scenery is very beautiful, the primo locations are quite crowded. Food and wine was excellent. However, not flushing TP (putting it in a bin) was very weird for us. If you are set on Greece, I’d spend some time in Athens. We went on a evening (8pm start) food and drink tour – amazing. Made me want to come back and experience more of the city. If you’re open to suggestions, I’d try Lanzarote (Canary Islands) because: less crowded, more to see, more varied scenery, really good aviation museum, easier to get to, better wine, better plumbing system – lol.

Hello Mike,

Aviation museum AND plumbing?!!? I am sold :)! But in reality, thanks for sharing that about the bathroom times. So few places talk about that sort of thing and it can be pretty surprising for folks who have never experienced it. Heck, first time in Japan and my toilet had a remote, I thought it was some hidden TV and boy was I surprised!

Thanks for the ideas and heads up!


Mike Butorac

BTW, Santorini transit system does work well and is very inexpensive, so you can save some money on a rental car.

Gary Bisbee

We did a Southern Italy tour in May, 2018 and it was Hot. I would imagine Greece would be the same. We are from the Portland Oregon area and share your comments about heat.

Nick Nellas

Honestly if you don’t want a hot climate and a crowded place then Santorini is not for you.
I’m greek and a travel agent, trust me although you’re considering travelling during late April early May it might get hot, september-october is the same thing, however, it’s a very beautiful place, a bit pricey for my taste, you will be able to swim easily during the seasons that you selected (especially september october), the transportation system is relatively inexpensive, you can hire an automatic car but you have to request it (don’t forget about it) gas is a bit expensive there.
Consider staying in Athens for 2-3 days, it’s a pity that you’ll be here and not visit the Parthenon and the Acropolis museum.
I’ve taken the liberty to check also for the flights, I think it’s better if you arrange your tickets with AF-DL-KL-AZ as they are well connected with ATH (also any star-alliance company) I wouldn’t include the ATH-JTR-ATH as you can either issue some cheap tickets with OA (if you decide to come with star-alliance they will also check your bags through as they are star-alliance also) or use any ferry that costs about 80 euros roundtrip fare (but the trip to santorini is about 5 hrs with the fast ferry and about 8hrs with the slow ferry), the flight to and from ATH is about 45 mins.
Hope this helped

Best Regards

I think this place is perfect for the honeymoon. But I don’t like so much crowed.
Visit for news

Hello. I have never been to Santorini, but believe me no one could have browsed through as many information as i did. For, honeymoon, undoubtedly Santorini is the best place. Don’t allow any other idea to influence your decision, as you are going to spend life best moments there. Take care. Have a Joyful trip.

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