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Update - and call out to Bostonians (Travel dilemmas - Chicago, Boston, Jekyll Island)
I know there are a lot of travelers on here and would love to get some feedback. Warning: I'm so wishy washy.
I need to complete about a one-week vacation before Sept. 30th or I get paid out for that vacation time. Originally, my H and I were going to go to Europe. Except we applied for our passports three months ago and my H has still not received his 
. He put an inquiry in 1 1/2 weeks ago, but it takes up to 3 before they will even respond. So I'm coming from a place of aggravation. We are probably postponing Europe until Spring 2017, unless a miracle happens and it both arrives and we can still book our flight/hotel without it being a fortune. But I feel like I need to get something booked and planned pretty soon, so I can give my work about a one month's notice. Not their requirement, but I don't want to be asking for a week of vacation at the last minute.
I want to use my vacation time to GO somewhere and preferably keep the airfare/hotel total under $1500. Less would be even better. Here are my thoughts:
- Cheapest option -- $600 total for flights (no hotel needed). Go home to CA and visit my family. It's been 3 years since I've been back. It would be fun and nice to catch up, but nowhere remotely "new" to visit...to say the least!
- Chicago -- $100 per for a r/t direct flight (nice!), great Groupon for $75/night (nice hotel) in the heart, about $800 total. I've been there and liked it, though it was 20 years ago, but my H hasn't.
- Boston -- Cheap flights ($340 total), but I couldn't find anything for hotels for the main part of the city under $250/night. This is where I wanted to go the most! But unless anyone has suggestions, it is just too much money for right now (over $2K).
- Jekyll Island, GA and Savannah -- Saw a Groupon for a Jekyll Island beach resort for $75/night. Don't know much about Jekyll Island, but it looks nice. Better/worse than FL Gulf Coast beaches (for anyone in the know)? We would drive with this option (9 hours each way), but could stop and visit my cousin for a day and maybe go up to Savannah for a couple nights also (90 minutes each way from Jekyll). Around $1,000, including gas. Food would be cheaper also, because there are kitchens in the units. I wanted to go to Atlanta too, thinking it would be on the way. Boy was my geography way off, lol. Jekyll Island is almost a straight shot from NOLA. Atlanta would meander us about 4 hours north (one way).
The Jekyll Island intrigues me because we would get to visit two places, plus visit my cousin (which would break up the trip). But I've become less enamored with road trips as I have gotten older. And just for the usual airline hilarity. I looked into flights to Savannah, which would also require a rental car, and they were $360/per. Boston is WAY further and less than half that.
I don't especially want to go back home to CA, but I feel guilty because it's been a long time. It's just such an especially boring option (for me) after the let down of Europe that I am not sure I could stand it. I've been debating going more in November and save September for somewhere new. However two trips within a few months, plus going to Europe next year, is so out of character for me. I've been trying to get out of my "no travel rut", but it is tough loosening those purse strings, lol.
Re: Update - and call out to Bostonians (Travel dilemmas - Chicago, Boston, Jekyll Island)
Personally, I used to just let my company cash me out. Then I'd toss it in my Roth IRA....
Although I don't have a specific recommendation, I'd also look at anything in the Harvard Square or Central Square areas of Cambridge. Both will be a quick T ride to the city. Harvard Square is cool; you can walk through Harvard Yard and there are loads of great restaurants. If you end up booking there I'll get you a list! Central Square was a little gritty when I lived there 7-10 years ago but is likely not anymore.
There was a Holiday Inn on the Green Line in Brookline where all of my OOT friends' parents would stay when they visited in college that is supposedly not too bad. Coolidge Corner is a nice neighborhood with fun little places and good T access. Anything on Commonwealth Avenue between BU and BC also wouldn't be too far out there if you really want to see Boston.
You could also check Air BnB.
If you're going in the fall, look at spending 3 days in Boston and 3 in VT or NH. Leaf peeping is a stereotype but if you haven't been to New England in the fall before it's really worth doing. Those areas can also be done much more cheaply. Best way to get there would be to rent a car.
Are there any Groupon/Travelzoo/etc last minute getaways that look good?
All of your options sound good except maybe Boston since it is more $$.
The Jekyll beach is fine, but it's Atlantic and not Gulf. The Gulf coast beaches are the best in the continental US, IMO. If you are really just looking for beach, then stick to some place on 30A in north Florida. It's also a lot closer for you. Jekyll and/or Savannah would be a haul for you guys.
I would not detour through Atlanta unless you are interested in sitting in traffic. Last time I was there we left the city at 6 AM local time on a Monday and hit traffic.
Of the places you listed, Boston is definitely my favorite, especially if you are thinking of going in the early fall right as the leaves are changing. That would win for me, even with the budget stretch.
EDIT: NOT St. Simons - I meant Tybee. Whoops
Now I wish we'd expedited our passports! But there should have been plenty of time. I'm assuming my H's stuff got lost somewhere. Ironically, NOLA is one of only 13 cities that has one of those special passport offices. But the big caveat is you have to have travel, already booked, and are leaving within two weeks. That's just too much dice rolling for me.
Even to expedite it now would still take up to 6 weeks. Plus, I don't know if my H has an extra birth certificate. They've never sent back the one that was turned in with his application.
Thanks for the recommendations! I'll check out the hotel options, because I've heard so many great things about Boston and it is definitely on my bucket list.
New England is one of the few areas of the country I have never been to. I've pretty much only seen pictures of leaves changing color, lol. In So. CA, we only had palm trees where I lived. In NOLA, some trees do, but not the majority. That's a good suggestion to possibly check out some other areas.
I don't know, but I always forget about AirBnB types of options. I've even been an AirBnB hostess a few times and I still forget, lol.
When I was a kid my parents planned a family vacation up there where we focused on famous places for American authors. We spent a few months reading some of the books/poems, and then we visited Walden Pond, Emerson's house, Louisa May Alcott's house, the Mark Twain house in CT, etc. We had a blast, and in retrospect it let my parents book less expensive places to stay.
Someday H and I plan to do a similar trip, but next time I would like to visit Providence and maybe stretch ourselves to get to southern Maine.
You would need a car to do something like that though.
Ugh, Groupon tricked me again with their supposed low hotel rates. This is the hotel I had been looking at:
https://www.groupon.com/deals/ga-bk-warwick-allerton-hotel-chicago-10
There is not one day in September that is the advertised $93 rate. There is one week where the rates range from $99-$189, depending on the day.
This is a Red Roof Inn, but it is downtown on the Mag Mile. Saturdays are higher, but most of their days are around $88-$119.
https://www.groupon.com/deals/ga-bk-red-roof-inn-chicago-downtown-magnificent-mile-12
I would also recommend NOT detouring to Atlanta. Traffic ain't worth it.
A friend of mine recently vacationed to Jekyll and stayed in a condo or an airbnb type of rental that she really liked. I'll see if I can get the link from her and share it here. Whoops, she actually stayed at Tybee Island. It's much closer to Savannah!
Even $189/night is a really good rate in downtown Chicago. I'd also look down in the Loop... I'd almost prefer to stay down there as it's closer to the museums and has better El/subway access to all the lines, vs just the red line when you go up to Mag Mile. The Orange line goes to Midway and the Blue goes to O'hare.
AirBnB for any of the cities you mention might be a great option for you too. By doing it by the week, you can probably get a discount, and you'd have a kitchen to prepare some meals yourself.
I could but, if I am going to spend the money for plane tickets, I'd rather just go for a whole week. I understand why some people would like having vacation time paid out, but I would literally sit at home before I did that, lol. I already work a lot.
It is a long time. Which is why I was thinking about taking a second trip in the winter. Confession time: I love my family, I love to see them, we get along well...but we also aren't that close and I don't miss them that much.
The second bolded did give me another thought. Maybe we could do a couple closer long weekend trips, go to CA for a week in Nov. And I will swallow my disappointment about Europe and just be PATIENT that we will go early next year. I want to take my 40 hours of vacation that would put me over the "pay out" line, but it doesn't have to be taken all at once.
Thanks for the input! That's what I was worried about, that Jekyll Island would be a lot farther to go and not as nice/the same as the closer Gulf Coast FL beaches anyway. If we go this route, I'll take your suggestion and focus more on Savannah and maybe a couple nights at a beach closer to that city. I have always wanted to go to Savannah.
I only suggested it because it seemed more like you were taking the time just to prevent being paid out versus actually having somewhere to go. I use my time when I have somewhere to go, but I don't force a trip just to use time.
I wish my current company cashed out. It's all use or don't accumulate here. So I take days and end up sitting at home which to me is a waste of a vacation day.
They are within striking distance of DC and Baltimore.
Honestly, I could (maybe) see Hawaii beating 30A for best beach, but it also might not. I think the 30A area has a better beach than most of the Caribbean islands I've visited.
Frankly, that part of Florida is why H and I don't travel to the Caribbean very much. It's kind of hard to justify a flight+resort cost when one of the best beaches in the world is a 4 hour drive from us. When we have vacationed in the Caribbean it's been more for the AI or cruise experience, and not so much about the beach.
Totally agree! I've been to Hawaii a number of times, though not since I was an older child, and I do like the beaches in the FL Gulf as much, if not better.
I grew up walking distance to the beach, but the Pacific. It's cold and often has big waves. Great for surfing, but not so great if you are more of a paddle around in the water person, like myself. FL Gulf is hands down better (for me).
If you're coming in the fall definitely plan to head up to Vermont if you can - the foliage is great, the people are great, and they really know how to do good food and beer.
The loop, Mag mile, river north, millennium park, south loop/soldier field?
This is very true, lol. BUT I've accumulated so much vacation time because I'm always saving, saving, saving it...for all those trips I never plan and always have "better" things to spend the money on. I'm trying to get out of that rut and start traveling more. So, while the timing is not perfect, if I'm going to take the time, I might as well use it to go somewhere.
I did want to add that my company only pays out anything in excess of 160 hours by 9/30. And I'll have close to 200 by then if I don't use them. But I'll still come out at the end of September with about one month of vacation time accumulated.
As an aside, I used to track employee vacation time at a previous company for about 80 people. It was very interesting! Just like money, most people were either vacation "savers" or "spenders". We accrued vacation time with each pay period (same at my current company) and some people would use it almost as soon as they got it. Other people, obviously I am in this category, would use very little of it or...if they did...it was only in a big chunk because they were going somewhere on vacation.
Haha, that's where my H is from...but the other one. All the way across country in Oregon.
Not a deciding factor, but a bummer that Boston is not getting rave reviews on food or its price.
I looked online quickly, and you might find a good deal on a hotel in late September.
Another factor for Providence (and I bet Portland too) is that the cheap rent is attracting a lot of really talented young chefs who trained in Boston, NYC, etc. but want to strike out on their own. My favorite restaurant, for example, is owned by a former sous chef from Momo Fuku (I probably spelled that wrong).
Anyway, @short+sassy, if you do pick any of the New England cities let me know and I'll share my favorite restaurant suggestions. I love all of the food.