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So me and the misses are planning our 3rd year anniversary and are narrowing down our search to a couple of cities. My wife originally wanted to go to an all inclusive resort in Jamaica but because of other expenses in our personal life, going to a top notch all inclusive resort in Jamaica is just not an ideal situation for next year. So she still want's a romantic leisure trip. Me on the other hand want an urban adventure in a city where we can get around easily and only rely on public transportation. That's why we've combined those 2 wants in narrowed it down to these specific cities. We're looking for good weather, fun things to do, romantic things to do for 4 nights and 5 days in mid to late April.
Oh and i'm trying to keep our budget under 2,000 for the total trip. Wherever we go we'll be staying in an Airbnb so neighborhood and proximity to the cool spots is very important. With that said here's our list of cities. Please tell us which one would be ideal for you and if so why. Thanks in advance.
If you want to come close to replicating the weather you'd have in Jamaica, San Diego is the only choice. The rest may be comfortable, but they also run the risk of being pretty cold that time of year. Transit in SD is probably the worst of the bunch, however.
Montreal would be my top choice. Not only will you get good bang for your buck because of the exchange rates, but it's an incredibly romantic city. Old Montreal is beautiful (I'd stay there and use it as a jumping off point) and the entire island is easily navigable between being transit and walking. It's also arguably one of the best cities for bikes in North America too. You'll have easy access to the outdoors via transit as well. Mont Royal is in the city center (and has views extending to the mountains of Vermont and Upstate New York), and there are a ton of parks across the city and along the river.
Montreal is very safe and is a culinary mecca. Because of the exchange rate, you should be able to keep within your budget too. Restaurants are plentiful, and if the sun is shining, you should have no problem getting a seat outside (even in April). I can't emphasize the food enough Quebecois cuisine (more than just poutine) is unique and excellent. It's also an incredibly diverse city, so you'll have no shortage of ethnic options. Make sure you hit the food markets and explore the neighborhoods outside of the city center. If you stick to the Old City and downtown, you won't get to see or feel what makes the city a truly great place. Thankfully, it's easy to branch out. You also don't need to know French, but knowing basic greetings and please/thank you certainly helps.
Also, mid-April should be in/toward the end of sugar season. See if you can't find a sugar shack to pop into. It's absolutely worth the experience. Also, it's a little far, but Quebec City might be worth a single overnight or long day trip. If you're looking for romance, there's really no beating it. The Old City is one of the most charming places in North America. I just checked and saw nights at the Chateau Frontenac for under $200/night in mid-April. It's not beaches in Jamaica, but it's very romantic in a different way.
For that time of year I think San Diego is your only option. The rest of those cities might not be fully out of winter by then, and could be rainy or even snowy.
If you pick San Diego, transit options would be easier downtown than at Coronado, though be sure to at least visit Coronado.
I feel Chicago might be the cheapest overall.
Personally, I don't mind weather much and would chose Montreal. It's the most unique of the cities listed, and there's plenty to do inside if the weather isn't ideal. I'd strongly suggest you take a day trip by bus or train to Quebec City if you haven't been there before, though that will add to the cost. Montreal will probably be the most expensive option.
If you're open to other options, you might also consider Charleston/Savannah.
For that time of year I think San Diego is your only option. The rest of those cities might not be fully out of winter by then, and could be rainy or even snowy.
If you pick San Diego, transit options would be easier downtown than at Coronado, though be sure to at least visit Coronado.
I feel Chicago might be the cheapest overall.
Personally, I don't mind weather much and would chose Montreal. It's the most unique of the cities listed, and there's plenty to do inside if the weather isn't ideal. I'd strongly suggest you take a day trip by bus or train to Quebec City if you haven't been there before, though that will add to the cost. Montreal will probably be the most expensive option.
If you're open to other options, you might also consider Charleston/Savannah.
Me personally, as long it’s not heavy rain/sleet/snow storm or freezing temps than I’m perfectly fine with whatever option offers the most for our experience even if the weather isn’t ideal or similar to Jamaica. And I know my Wife eventually will be ok even if it isn’t sunny every day. As long as we’re on vacation she’ll be fine.
With that said, one of my main reasons for picking San Diego was specifically for the weather and beaches. I know San Diego has a ton to do for tourist but we’re not super big on doing touristy things on a couples trip. A few tourist traps here and there but mostly go where the locals go.
My Wife might be the least excited about San Diego as well but that’s just cause she doesn’t know what all the city has to offer outside of a couple of YouTube videos.
We’ve been to NY before but mostly Manhattan and we stayed in New Jersey when we did visit. Btw, that was a family trip and was somewhat of a mix bag of fun and frustration mainly because people were not use to all that walking. (were from Texas)
Never made it past Dumbo though so we said if we go back just me and my Wife well stay in Brooklyn.
Out of all the options I am leaning towards Montreal though. Never been outside the country, me and my wife have been to most major cities in America as is and the culture alone has me very interested.
As far as Charleston or Savannah, my Wife already ruled those 2 out. Lol, she say’s she doesn’t want to go to a city this year that has a similar vibe to New Orleans next year. I know both have their own charm and character but we go to N.O. twice a year so she wants a different scenery for 2020.
Out of all the options I am leaning towards Montreal though. Never been outside the country, me and my wife have been to most major cities in America as is and the culture alone has me very interested.
I would also lean towards Montreal out of the listed options. Given that you've never left the U.S. you'll feel the most "abroad" in Montreal, which feels much more European than most U.S. cities. It will be a very romantic atmosphere!
San Diego in April, I would say Chicago but April is a risk for Chicago. Weather may turn out fine, it may not though. The other person who suggested Charleston/Savannah was a good option too, although the OP seems to want bigger cities than those two.
Those are all great cities (haven’t been to Montreal yet, but want to), but like others have said you run the risk of getting washed out a good portion of your trip, maybe the whole trip, unless you go to San Diego. Nothing can put a damper on a vacation like rain can.
So my Wife pretty much laid out to me after looking over with me that the weather in late April in Montreal is not ideal for her. Montreal was our #1 option up into this point but after doing more research and of course taking advice on here, the thought of possibly experiencing slightly cold temps mixed in with some rain is unappealing to her. Wherever we decide to go we're booking 2 months in advance so she doesn't want to take the risk especially considering she had her sights set on Jamaica. So unfortunately, Montreal probably will have to be taken off the list.
Also looking into Chicago during the same months. The temps don't seem as bad but it's seems somewhat similar to Montreal as well. I was told by a friend from Chicago that the end of April isn't bad but it still is windy. Still tolerable for the most part. My wife hasn't ruled out the thought of visiting Chicago but she did briefly mention "How much walking will we have to do if it's that windy?"
Which I guess leaves me with Brooklyn and San Diego. So far it looks like it's coming down to those 2.
With Brooklyn, even though she's been to Manhattan twice and wants to visit somewhere new she does like the idea of going back to NYC with just me and her and staying in Brooklyn. I see the weather around that time in NYC is better than Chicago and Montreal. Weather is not the end all be all just as long as it's tolerable.
And last but not least San Diego. Clearly has the best weather out the bunch. My wife just isn't that excited about the city itself in comparison to the others. However she's not ruling it out. I'm thinking about surprising her with a day trip to Guadalupe Valley or Los Angeles. She just needs to be really sold on a trip to San Diego
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