How do you plan a vacation?

[katespade]

I've never planned one before.
How do you usually start the process?

H and I have been talking about taking a trip somewhere later in the year, and I was thinking it might be nice to go somewhere for his birthday in October. What  I'd like to do is surprise him with a few different options and let him pick which one he wants to do. He doesn't like getting birthday presents, so getting to pick which trip we do could be his present instead.


We would probably want to do a short trip: 2-3 nights or so.
He's already said he doesn't want to go to California, so that whole area is out.
We've talked about spending a weekend in Seattle, but I feel like that would be a better summer trip. The weather will probably be not so great by mid-October. 

I want to be able to take a direct flight to wherever we go. Layovers suck. Also, Europe is farther than I'm comfortable going at this point, especially considering that I might be pregnant by October (eeeeeeeee!). 

Some of the ideas I've had:
Hawaii, Las Vegas, Austin, Denver, Montana, Orlando.


Any ideas? Recommendations on where to go? Places to stay away from?
Once you know where you're going to do, how do you start making decisions about where you're going to stay, what you're going to do, etc? There are too many choices. It's overwhelming!

[luv2rn4fun]

Personally, I would do Hawaii, Denver or Austin. Denver has a lot of great outdoor activities like hiking and also has great food. Austin I hear is great as well, especially food and touristy type stuff. Between all the choices I would definitely hands down pick Hawaii (we went to kauai for our honeymoon and I would love to go back there or to Maui or Oahu). DH doesn't really travel much outside of road trips so I could see him leaning more towards Denver or Austin.

We would research hotels, most likely on a site like kayak, and then yelp for restaurants. Google for activities. We would plan the activities in advance so we have a game plan and then decide on restaurants once we are there (unless we want to go to a special restaurant to celebrate an occasion in which case we would make a reservation before we left home).

[katespade]

suzv - I'm the same as you. I want to go somewhere beautiful and just relax for a few days. I mean, I'd like to do a bit of exploring, but I don't want to be on the run the whole time we're there. I would definitely be willing to spend a little more on the hotel/resort, knowing we would spend most of our time there.

[katespade]

luv2rn4fun - I have a friend who is in Hawaii right now, and her pictures are definitely influencing my decisions. lol. It just looks so wonderful! Especially thinking about going in October, when it's so miserable, cold, and wet here.

My brother lives in Denver, and it would be really nice to visit him. I haven't seen him since he moved away two years ago. He and H get along really well, too, so it wouldn't be weird for us to go visit him together. I'm guessing it would be really cold there in October, but I bet the snow would be beautiful. A different kind of relaxing than a beach.

Austin just seems fun. H has actually mentioned that he thinks it would be a cool place to visit. Similar to Portland, but warmer. Haha. I feel like it would be more fast paced than the other options, though. Less relaxing and more sightseeing.

[katespade]

Also adding to the list - Boston or New York.
I didn't realize it's less than six hours if you get a nonstop flight.

I want to take H to New York soooooooo bad.

[luv2rn4fun]

I went to Boston when I was 13 (my dad ran the 100th Boston marathon). We did Boston and D.C.. As an adult (not taking kids) I would totally combine Boston and NY!

[katespade]

luv2rn4fun - I spent a lot of time in New England as a kid, and I have a ton of family in that area. H hasn't met any of them (minus one aunt and uncle who came here when we were still dating), and I feel like it would be so much fun to show him all of the places I loved to go as a kid.

Again, though, that might be better as a summer trip. The weather will probably be not so great by October.

[pooh8402]

I wouldn't do Hawaii for just 2-3 days. I think y'all would like Denver best, and Austin is a bunch of fun--I love to go there for a weekend. It would still be warm in October.

[amaranth]

Since you asked how we plan, I'll answer that first.

1: choose amount of time we can be gone & max budget.
2: choose our priorities (hiking, relaxation, eating, etc. Almost every trip our priorities are beautiful scenery and good food).
3: narrow down locations to a few options that fit our time, cost, and interest criteria then research flights and lodging available at each.
4: finalize the trip based on what sounds best with actual costs, hotel, and flight schedules taken into account.

We have a huge list of future travel interests so usually we just see which of those options are possibilities for the current budget/season.

Of your list I love Colorado. We've gone 4x to different cities. Another option could be San Antonio.

[MrsMB]

New York in October will be amazing I spent about 4 days there jn September one year and it was a fun little jaunt

[katespade]

suzv - I think if we went to the east coast, it would be a longer trip. It wouldn't cost as much because we would only have to worry about hotels in NYC, since we could stay with my sister in Boston and my other family in New Hampshire. I would want that trip to be a minimum of a week. Maybe even closer to two weeks, if we could swing it.

[wanderingenough]

We generally pick a location and then I start doing research on trip advisor, etc. I like to know the best time of year to go to a certain location, so if it's not an ideal time we look for somewhere else we might want to go instead. When choosing a locale, we try to figure out whether we want to explore a new city, relax, or do something adventurous. I do lots of research on Yelp/Trip Advisor. I'm not someone that thinks we have to live by a plan, but I never want to be in a new place and end up wondering what to do or eating at a Chilis or something.

Of your list, I probably would save Hawaii, NY, and Florida for when I had more than 2-3 nights. Hawaii because I'd want more time to explore the various islands and NY/FL due to flight times from your place. I'd probably look at Montana, Denver, Austin, Vegas, etc. myself.

suzv - We stayed at the cosmo the last couple times in Vegas. It's my new FAV. Do it.

[HoneySpider]

I do SO MUCH research on everything. Probably too much. I'm an overthinker.

[wineandcheese]

We usually pick a location and time and plan from there. H is a planner, I'm not.

As for ideas. New York is pretty in October. We only live about 90 minutes from NYC but don't go there often.

I love the Orlando area. We've gone to Universal in October and the weather was awesome, plus Harry Potter lol.

I like Vegas but haven't been there in years.

Hawaii, you need at least 5 days.

The other area, never been to so can't help there

We love cruises. They are most of our trips now. No driving, no cell phones, just us.

[estrellita]

Coming from a family that flies standby, we rarely plan far in advance

For our own vacations, we start with picking dates. We both take the same week off. Then we start looking at destinations. I like road trips, so we try to pick somewhere within decent driving distance. We'll look at availability and cost of accommodations and that helps narrow things down (big reason why our plan for Yellowstone didn't work!). Once we decide, then we'll start booking. Usually a couple months in advance.

On your list I'd pick Vegas personally. It's hard to go there with kids (and I wouldn't want to!) so IMO go before you have kids!

[krystee]

I get analysis paralysis so we basically pick a place we've been wanting to go (so right now we'd choose between Seattle/Olympic National Park, San Diego, a Maine road trip and Key West), and then I look at Trip Advisor and ask about it on these boards. That's it. If I do too much digging, I feel overwhelmed. Also, we just like to plan a few must-do activities and then have some adventures based on whatever we see and decide to do when we get there.

[estrellita]

krystee that's a good point. I get overwhelmed planning too when I don't know the area or have a very specific thing to do in mind. I look at Pinterest but there's so much sometimes!