Wanting to propose in Italy

You can't go wrong in Italy for romantic places. Some consider Venice to be a place high on romance. Others don't care for it. James Bond took Vesper there (or maybe Vesper took James there), and although things didn't end romantically for them, that wasn't Venice's fault.

lock up your love and throw away the key, into the Tiber. Lots of people do. http://www.nytimes.com/2007/08/06/world/europe/06rome.html

I guess it would be helpful if I mentioned what she enjoys. Unfortunately, I am not known to be much of a romantic, so the information will not be that helpful. She does enjoy the outdoors and she always enjoys when I plan little picnics for us. She also loves flowers and the theater...at least she does in the US. She is very much a practical person, so I don't think she would care for anything on the "frilly" side of things. Hope that gives you a little more information.

"Unfortunately, I am not known to be much of a romantic." You're taking her to Italy to propose to her - I think that means you've become a romantic.

Dude, you're in freakin' Italy! ANYWHERE you propose to her it's going to be romantic! :-)

It's really wonderful that you're putting so much thought into your proposal. I like the idea of a picnic - in Italy, there are many small shops with delicious foods - cheeses, breads, olives, fruit, wine, etc. Find the perfect setting - maybe somewhere in Tuscany or the Cinque Terre. On the other hand, perhaps too much planning could be stressful. Maybe spontaneous is best - it's possible that you'll know it's the right moment to propose when it happens. Best Wishes!

What do you mean by "following the itinerary from Rick's Italy travel guide"? What cities? I would imagine someplace with a stunning view at sunset would be pretty great.

I'm with Kent on this. I think Venice is the most romantic city anywhere.

I'm thinking that proposing anywhere along your itinerary is going to seal the deal. But since you asked.......having gelato, sitting on a fountain in a quiet piazza is pretty romantic. It doesn't have to be a big production.

I agree with many of the others that Italy gives you plenty of scenic options for the proposal. Canal-side in Venice, sitting on a hillside in Tuscany, or beside a fountain in Rome are all great options. I have one question for you and the others who might know. I assume you are taking an engagement ring with you? I assume you'll want to it upon entry to avoid any problems or tariffs if it is somehow discovered. Perhaps someone on these boards has experience in this. If I am right and you should the ring, you'll want a plan to be sure you can tell the customs agents both in the U.S. and Italy without revealing it to your fiancee-to-be. I helped a friend take a diamond ring to his girlfriend in the Peace Corps in Cote d'Ivoire once. He opted to hide it rather than bring it to the attention of authorities. It worked for him, but I am not endorsing the idea. (It was probably the only time a diamond was ever smuggled INTO Africa!)

I'm with Kathy on this one. Guys nowadays seem to feel this need to make some grand, specatacular production in order to propose - scoreboards at sports games, skywriting, etc. (I work just under the Space Needle here in Seattle and I can't tell you the number of times I've seen an airplane fly by with a banner that reads "(name here), will you marry me?".) Things like that come across as trying too hard to impress others, not the woman you're proposing to. The production and spectacle doesn't matter to her as much as you think. What does matter are the words you chose. Think about what your going to say before hand but don't talk as if you're reciting from memory or reading off a cue card. Speak softly. Look her in the eye when you tell her how much she means to you and how much she's changed your life. Resist the temptation to make some over-the-top Hollywood movie style speach. Use your own words. Above all, speak from your heart. This is not the moment to hold anything back. Trust me. This will mean more to her than where you happen to be standing at the time (well, she'll be standing, you'll be on one knee).

Cicero, I'm somewhat out-of-touch with what's "romantic" these days, but I'll try to offer a few suggestions. First of all, it would help to know which of Rick's Itineraries you're following. That will provide a list of the cities you'll be visiting. I agree with Kent that Venice would be a good choice. With that in mind, there are a couple of possibilities. > A Gondola ride, perhaps around sunset, preferably with a singing Gondolier. Pre-arrange the details with a Gondolier (discreetly ask the Staff at your Hotel if they can help with that - Italians love this sort of thing, so I'm sure they'd be happy to help). Having some flowers or Champagne "hidden" in the Gonodola might be a nice touch - don't forget glasses. Don't forget a gratuity for the Gondolier (and perhaps for the Hotel staff). > A romantic dinner at a nice restaurant, preferably along one of the Canals at a secluded table. Again, ask the Hotel staff to help pre-arrange this, also with flowers and Champagne. Just tell your girlfriend that "the Hotel suggested a nice restaurant", so you made reservations. It might be a nice touch to have a local performer sing at your table at some point in the evening (perhaps with a Violin or other instrument). Either choose a song that both of you like or one of classic Italian romantic songs. This might be a possibility, although I don't know what it would be like without the orchestra: www.youtube.com/watch?v=fJxQ8bdYUrk (If you read the comments below the video, you'll note that someone used this song for renewing their vows - it might appear that they're "lip syncing" but that's not the case - I watched the live performance on PBS) Don't forget the gratuities! There are lots of possibilities in Italy! Happy travels!

another reason for not making a big production out of it http://www.youtube.com/watch?v=ZvdZJvmAfws

Without knowing which itinerary you're following, I'll take a stab at a rec. Again, you're in italy, so you can't really go wrong. Of course, Venice is the perennial favorite. Me, I'd head to San Gimignano for an overnight stay. Have dinner at La Vecchia Mura (make reservations for a railside patio seat). Take your time at dinner, linger for the people to thin out, get some gelato in Piazza de la Cisterna, then casually wander through town while heading to the castle ruins on top of the town. Lean over the crennellated tower walls while the sun sets over Tuscany, and voila! You've got romance. But, what do I know, I'm a self proclaimed unromantic guy, so take all of this with a grain of salt

Bob's advice is so on-target.......follow it!!! Make sure what you say is genuine, not "stiff or fake." She will remember what you said and how you acted forever....so be the "real you" and have it come from the heart. And, my one original piece of advice to be sure to have a pre-paid phone card (that works in Italy....buy an AT&T one at Walmart) in your pocket so she can call home and tell her parents, friends, etc. the next day. The personal conversation will be much better than email or a facebook posting, etc. Then, BE SURE to introduce her as "my fiance" from that point forward. And, beforehand be sure to keep the ring in your money belt where it will be safe and not likely to get lost.....also a good way to get it through airport security, since money belts need to come off to go thru security. Put the ring in the small pocket section of your RS money belt and put a few coins in with in to disguise it in case there is any remote chance she would see the image on the screen when it goes through the airport screener. But don't act weirdly nervous about it...just act like it's your deep storage money, etc. going through security (which requires some carefully timing putting/guarding anyway when you put it on the belt to scan).

Please, do not proposein a resturant. You are in Italy, make it very memorable. Maybe the Spanish Steps in Rome, a hill town in Tuscuny at a picnic, a spot she will remember forever. The name of a resturant she will forget, the spot - never.

Follow Bob's advice... personal, private and from the heart...all the rest of the 'typical' proposal sites seem so contrived. Take an ordinary place in Italy and make it extraordinary for her....

Hi Cicero: congratulations on your upcoming proposal! It's very sweet and I wish you and your girlfriend all the best.
The place that came to my mind for a beautiful site is this: when you are in Florence, take a trip up to FIESOLE (1/2 hr bus ride from the city center)....go near sunset when the gold and pink light is shining and burning down on FLorence. The vista is breathtaking and you can be in an open air ancient amphitheatre built by the Etruscans. Fiesole has garden retreats, a little museum, a few restaurants...and all of FLorence, laid out below. It's not expensive and it is romantic, soulful, meaningful, poetic and gorgeous. Good luck!

Don't stress Cicero...all of Italy is very romantic and she'll be overjoyed! I think I'd just "go with the flow" & be spontaneous & just do it when the time seems right. I personally think Venice is super romantic & might be a nice place to propose but really do what feels right when you're there.

I would highly recommend the Plaza Michelangelo in Florence – it worked for me five years ago!

Be sure to make a printout of this and give it to her....it would make a great momento for a scrapbook to see the thought you put into it and how many people all over the world are giving you advice!

Don't wait too long to propose or you will be so stressed out you won't enjoy your trip. You could even do it on the plane over and have the pilot make the announcement!!! You will probably even get free drinks.

The sons of friends of mine did this last year. He told his parents and his GF's parents and asked them to come to Italy to be there when he proposed on her birthday, but to keep it a secret. He waited as long as possible before telling the GF that he was taking her to Italy for her birthday. The parents and a few Italian relatives were waiting for them on the Rialto Bridge in Venice. She was thrilled to see the family and before she had a chance to think, he had the ring out and was proposing. I just had to share the story. I agree, anywhere in Italy is good, but for me, Venice is the most romantic place. Footnote - for their honeymoon, they went mountain-climbing in New Zealand, he's in training to climb K-2 next year. She will wait for him at the base camp there.

Cicero, please us when you return from Italy & let us know how you ended up proposing! By the way, I love Gail's idea of proposing on the plane!

The video Otariidae posted brings up another very important point - in order to try a proposal such as this you have to be VERY certain (or as certain as you can possibly be) that she will say yes. If she doesn't say yes (god forbid a million times) then your remaining time in Italy will be pure hell. Are you fairly sure she'll say yes? If not, and she says no, will you be able to travel together, eat every meal together, sleep in the same bed, etc, etc, for the next several days (or weeks) without going crazy or wanting to jump off the nearest bridge? If you're not 99.5% certain of getting the answer you want, reconsider doing this in Italy.

Dear Cicero, Congratulations! I have been to Italy a million times (approximately) and agree with others that you probably won't go wrong. If you are more of a relaxed type, I'd just wait for a beautiful place that's not too crowded. If you want to plan, here are some tips from a not too frilly girl. Towers/Views: Italy is full of charming little towers with beautiful views. The Mangia tower in the main square of Sienna overlooking the city and cathedral is lovely, for instance. The top of the Duomo in Florence also springs to mind. I think any tower with a nice view would be romantic, but NOT if it's crowded with other tourists. For instance, the clock tower in Venice is a veritable train station of business and would not be intimate. Piazzalle Michelangelo has a great view of Florence and would be a nice place for a picnic or evening snack.

(continued) Rome at Night: I think Rome at night is amazingly romantic. You could get a glass of wine on Tibertina Island which is very nice in the summer (they have bars and shops and outdoor movies there), eat dinner outside in the Ghetto area, walk through the Portico D'Ottavia to the Campidiglio. I suggest actually proposing overlooking the Roman forum as you descend the stairs from the Campidoglio (If you came up the large stairs, the route to the forum should be on your left). There are little landings and places to sit and you can see the forum lit up and the Colosseum below. Again, this will only be romantic at night. If you are a champagne drinker, you could also try to sneak a celebratory bottle to open and drink afterward (polite public drinking is well-accepted in Italy). Whatever you do, as someone else said, make sure to tell all the Italians you meet the rest of the trip that you just got engaged. In general, Italians love this sort of thing and will be very friendly to you and very pleased you asked her in Italy. Good Luck,
Rose

By the way, I totally agree with GGBridge. Fiesole would be a perfect place. Sunset in the amphitheater would be romantic and fairly private.

The thing to keep in mind about going up bell towers, is that sometimes those bells start ringing while you're up there, and not in a good way. It can be deafening. And, yes, the view of Florence from Fiesole at sunset is stunning. I'm still curious as to what cities the OP is visiting. I see he hasn't responded to any of the requests.

Everyone, Thank you so much for the ideas. It has put at ease to have so many suggestions. Also, I apologize for the delay in responding but have been busy with work. Since, several of you have asked, here is the itinerary: Milan, lake Como ( varenna), Bolzano, Venice, cinque Terre (vernazza), Florence, Assisi, Orvieto, Siena, sorrento, Rome.
Thanks again.

Hi Cicero. I'm assuming that you listed the cities in the order that you are going to visit them. I'm guessing you'll probably want to propose towards the beginning of the trip. I would therefore choose Varenna/Lake Como. I absolutely loved Varenna; it's quaint and relaxing and has a charming promenade. I would suggest going for a pre (or post) dinner stroll on the lakefront promenade and stopping along the way to propose. We were there in mid-Sept and the town wasn't very crowded (especially in comparison to Venice & some of the other places you're going to visit). I found Varenna to be very peaceful and enjoyable. Have a great time & remember to let us all know how it went when you get back!!

I second the idea of the promenade in Varenna. It is very romantic and beautiful. Much nicer to be someplace a little private rather than in the midst of tourist mobs.

...or at a picnic site on the hiking trail just above Vernazza.

I was already married when I went to Italy with my husband, but we talked about how much fun it would be to get engaged on a trip like that! I asked him where he would have done it and he said Ostia Antica (ruins outside of Rome). I thought that was a really cool and original idea...it was so peaceful and beautiful there. There's also an amphitheatre there that is very cool...you said she's into theatre and my theatre friend who we were traveling with said that was one of her favourite parts of the trip.
Best of luck, wherever you do it will be amazing!

It wasn't a formal proposal, but it sealed the deal. This was back when you could still put locks on the Ponte Vecchio.
For which I had brought a lock , just for this occasion. She didn't want to marry me then. But I put the lock on anyway, and told her she was the one... cause it meant something to me. Then, tossed the only key in the Arno. A little later, while riding a motorcycle and climbing up the hills out of Florence on the 222 to Siena; is when, later, she said that this was the moment she decided to marry me.

Trevi Fountain at night. Pay one of the photographers to take your picture. Walk her right down in front. Get down on one knee with the photographer there. I am pretty sure you will get a loud round of applause from the crowd and she will never forget it.

Cicero, I agree with Fiesole. In the Rick Steves guide there is a spot at the top of the hill across from a restaurant that looks down on olive groves and Florence. As the sun sets and it starts to get dark, the lights from Florence and the Ponte Vechia shine down on the river. So beautiful I almost proposed to myself. Then either eat at the restaurant there (it's got an incredible view of Florence but may not be open) or have dinner at Pegasus at the bottom of the hil. Good luck!

If you find yourself on the Amalfi coast, there is a spectacular hike to be done between the towns of Positano and Bomerano. It's called The Path of the Gods and it's well worth the name. Take a bus to the town of Amalfi. From there, take a bus to the town of Bomerano up in the mountains. Once in Bomerano follow the signs and make your way down to Positano. You'll have spectacular views of the sea and the cliffs as well as see old shepherds' huts and grazing sheep and goats. You can find a map for the hike at the Amalfi tourist office. The hike can be done within 4 hours. During a two week vacation in Italy, that hike was possibly my top experience there.

I proposed to my now-wife in France last year. Two things I learned: 1) do it early in the trip! I spent the first three days freaking out over whether she'd find the ring, and she spent the first three days wondering why I kept swatting her hand away from my backpack. I don't really remember much from the first few days of that trip! 2) Do it some place a bit more private, because you're doing this for her, not for any onlookers. You mentioned she's an outdoorsy type so I'd suggest doing it on a hike or a walk through some beautiful scenery... perhaps in the mountains near the start of your trip. Good luck!

I agree with proposing at the beginning of your trip, and you couldn't pick a much more beautiful setting than Varenna on Lake Como. You'll have the lake in front of you and the mountains behind the lake. Stunning. There's a lovely little park area as well as the promenade. Then you'll both have the rest of the trip to enjoy your newly engaged status. Plus, Varenna will be one of the coolest (least hot) places you'll be visiting, so take advantage of that as well. Happy travels, you romantic son-of-a-gun. :-)