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Help Me plan proposal trip for my gf!!

wheretopropose

Rough_Rock
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Jan 6, 2015
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3
I am posting with an alias, as my girlfriend already knows my Pricescope name (We have been planning the ring together).

I have gotten such great advice on Rockytalky for the ring, and I'd love some more outside unbiased opinion on the next matter:

"The Proposal" is a big deal to my girlfriend. I know she wants it to be a total surprise (as opposed to the ring selection). I know that she wants it to be "very special" -- She's a bit of a diva but not over the top I promise.

Anyway, we live in the midwest and I would love to take her on a trip somewhere great and propose there. She started her first job (after masters degree) in September and hasn't had a single vacation day yet. I know that she gets 2 weeks for 2015, but I'm not sure how it works (IE: I think she might need to get advanced authorization to take the specific day?)

I have a LOT of frequent flier miles from business travel. Enough to fly coach or biz class anywhere in the world several times.

My first ideas: Hawaii (she's never been), Disney World (we've been), somewhere in the Caribbean, maybe Europe? etc etc

Only thing is the trip would have to be 4 days max (fri-mon), so not sure Europe would really make sense with the hours of travel involved...

I want this to be in mid to late Feb or early March.

I'm thinking maybe email her boss, explain that I want to take her on a 4 day weekend somewhere, and would there be a good Fri/Mon to take off somewhere in that time frame, and could she authorize it and not let her know?! Or is that a weird thing to do?

Would love to hear your thoughts
 

JulieN

Super_Ideal_Rock
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Apparently it takes the same amount of time from Chicago to Hawaii or to Europe. (9 hrs)
 

Gypsy

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Four days is WAY TOO SHORT for a ten hour plane ride. Even 6 days including a weekend is way too short. No way.

Why? 10 hour flight means 12 hours of travel minimum by the time you drive to the hotel, then drive to the hotel. And if you add custom's to that. FORGETABOUTIT.

You want her to have a great time and be relaxed and happy. That means 5 hours flight or less (keep in mind that's 7 hours not including customs).

Does she have a passport? I'd go to Mexico and go to Puerto Vallarta. And if you can afford it, stay here: Oof...honestly it looks like one of those fake websites someone sets up to scam others. While I like the clean look he's going for, the way it was executed looks very cheap and not something I would really trust...
Not sure how to say that delicately though! Don't want to hurt feelings for something that I am sure was a labor of love. But it looks like something I could build in 15 minutes using a basic drupal platform.

It's a 4 hour 15 minute direct flight.

If no, she doesn't have her passport, then US Virgin Islands (although this is farther than I would go in 6 days), San Diego CA (stay that the Del if you can afford it), Martha's Vineyard, Napa if she likes wine.


Please remember. The occasion will be special and unforgettable because you are going to propose. So don't try to push it over the top and take her to "this place" or "that place". Especially if it means too much travel. That will make it unforgettable in a bad way.
 

zoebartlett

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I think it's sweet for you to want to plan a special trip for your proposal. I'd try to go somewhere closer though, given the 4 day restriction. I'll come back if I think of any specific places to recommend.

I'd caution you against contacting your girlfriend's boss. I just wouldn't get involved with that. I've heard of people doing that, but I think it's when the couple have a close relationship with the boss. Given that this is a new job for your girlfriend, I don't know how it would go over. Maybe others have a different take on it, but that's how I see it.
 

Mayk

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New York City? I also like the idea of Napa...
 

VRBeauty

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As Gypsy said, you have to factor in travel times. Travel to Europe or Hawaii will kill one day each way, leaving you with only two days to enjoy the locale. Of course you'll be traveling with someone whose company you really, really enjoy, but still...

I think one key question is what do the two of you love to do? Would her dream day involve a sparkling ocean and drinks on the beach, or exploring museums/stores/architecture/four-star restaurants and great coffee shops? Would her dream day include snorkeling or shopping?

On the beach and balmy front, you might consider the Mexican Caribbean (Playa del Carmen, Tulum, Belize). The area is beautiful and wonderfully relaxing, and there have been PS threads about some of the very romantic resorts in that area. But you're still going to run into the travel time issue. Puerto Rico is another Caribbean option - I've only had a few hours to explore there, during an unexpected layover, but a friend who spent a week there lately loved it - and I don't think you have to deal with customs returning from PR. I think there have been threads here about resorts in the Dominican Republic too.

If an urban, "sophisticated" vacation might appeal, consider New York City, Boston, or a Canadian city (Montreal?). Or consider the West coast : San Diego/Los Angeles, San Francisco, or Seattle/Vancouver. Not as exotic as a tropical locale, but you can enjoy top-knotch accommodations and restaurants, and maybe take in a play or two.

Also consider the Southwest. I also have a friend who loves to travel to the Santa Fe - a great locale if she likes art and shopping for jewelry! Sedona Arizona is spectacularly beautiful. Either can offer luxury resorts etc.
 

madelise

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You might not want to post this on PS. If she knows you're on this forum, she will find this post. You've given enough details for her to know it's you.


Good luck with all your planning. Gypsy gave great ideas.
 

ame

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I wouldn't make it a surprise trip. Go on A trip together, to relax, and you can propose right before you leave, or right when you get there.
 

telephone89

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ame|1420652092|3813011 said:
I wouldn't make it a surprise trip. Go on A trip together, to relax, and you can propose right before you leave, or right when you get there.
I like this.

I also wouldn't go somewhere too far, based on time restrictions. Personally I always like trying new places, but it really matters what she likes :)
 

wheretopropose

Rough_Rock
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Jan 6, 2015
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Thanks for your advice. You are 100% right about >5 hours each way of flying (more with connections from where we live) not being worth it for a 3 or even 4 day trip.

We went to Cancun about 6 months ago with family and really enjoyed it. She loves the beach.

I'm thinking now more along the lines of San Diego, Key West, maybe Puerto Rico or some easy Caribbean destination easily reachable on Southwest.

She is definitely more about beach/relaxing than urban or shopping trip

There's basically no way she finds this post I think. I've really only showed her a few of the ring posts I made, while on my laptop. Probably could have used my real username but just wanted to be safe
 

VRBeauty

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If you're looking specifically for relaxing on the beach, you should probably take those west coast locales of the list, especially for a February/March trip. We do tend to get a week or two of warm weather during this period, but it's not predictable and west coast beaches will generally be anything but balmy during this time period. Any of the cities I mentioned earlier are great places to visit and offer plenty to do and explore in a short vacation there, but - balmy, they're not. I'm sorry I led you astray there. :doh:
 

blackprophet

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Umm it might be a stretch but something you might not have considered is Iceland. Its only a 4 hour flight from NY, I'm assuming you are not more than an hour flight from there. Truly amazing country, and 4 days is more than enough. They have deals this time of year for 4 day trips too. Proposal under the northern lights... :naughty:

I am biased because I am getting married there in May, but Montreal is pretty awesome. It has a very European feel in an accessible location.

Another option is a cruise. You could fly to FL and take the boat from there. And squeeze in the Caribbean. And I don't think you need a passport for those (if I remember correctly). Not sure what the weather is like though.

You might want to investigate what is in driving distance too. You could be surprised. My FI and I took a drive through the finger lakes region, and thought it was awesome. We didn't even know it would be that beautiful before we got there.

Could do something in town as well. One of my friend's wore a suit for a whole weekend to throw his girl off, and then proposed on the Monday morning after she figured he was just toying with her. I took my FI around my city on a "this is my life!" tour of all the places I grew up. A chronological walk through my life. Which ended at the moment/place we met. I proposed there. "Special" doesn't necessarily have to mean get on a plane.
 

wheretopropose

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Jan 6, 2015
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Wow Iceland sounds awesome! I am reading about the Blue Lagoon thermal waters --- wow!
 

blackprophet

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The blue lagoon has too be seen to believed. Its not the beach, but its pretty awesome.

And because of the geothermal activity, Iceland is pretty temperate, considering its latitude. At that time of year, you are not getting all that much sun though.
 

diamondseeker2006

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I agree with Gypsy and others that Friday to Monday is really too short to go anywhere far, and definitely not Hawaii or Europe. That's just two full days at the destination. Are there not any upscale resorts within a couple of hours of where you live? If the wedding is to be later in 2015, I would not want to waste any vacation days at this point because she might need them for a couple of days before the wedding and the honeymoon.
 

Garnetgirl

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Dec 7, 2014
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Replying a bit late, but still before your proposal, I believe.

I don't have much to add to what all the others have said. But here's my 2 cents. I also think with only four days, you shouldn't travel too far for home.

Just one other thing. You said you want the proposal to be a surprise. If the two of you often fly together on short vacations, then some of the suggestions above are lovely. But if it's something you rarely do, just suggesting such a trip to your GF will make her suspicious and probably spoil the surprise. In that case, I would suggest taking her out to a romantic restaurant, proposing there, THEN telling her about the rest of your plan to fly away for the weekend.

Best wishes for whatever you decide.
 
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