This post may contain affiliate links and Corporette® may earn commissions for purchases made through links in this post. As an Amazon Associate, I earn from qualifying purchases.
Here's an odd question for today, ladies: How do you find your preferred type of vacation? How do you find the type of vacation destination that's right for you, as well as the vacation activities and vacation budget? A few dimensions to think about as we begin discussion:
- Do you prefer to tag along or plan your own vacation? At what point in life do you change from taking family-led vacations (or friend-led vacations) to choosing your own destinations? For example, I know a lot of people who in their early 20s were still going off to the beach house for a week with their nuclear family, and many who at the same time were deciding to tag along with friends on various trips
- How often do you “repeat” vacations, like going to the same beach town (maybe even because you have a timeshare) for your “vacation” for the year? How did you find what timeshare situation you wanted, how often do you go, and do you try to mix in “new vacations” with the repeat destinations?
- How much of your “vacation time” have you spent during the last year in supporting friends in milestones like graduations, engagement parties, bridal showers, marriage/union ceremonies, baby showers, and other celebrations?
- How varied are the “types” of vacation you take — and how many times do you try a new kind of vacation (say, cruising) before you say it's not for you — versus chalking it up to specific circumstances around that trip?
- Have you ever been surprised by how much you liked (or hated) a vacation?
For my $.02, I think vacations can be expensive and time-consuming to research and plan — and I'm sad to say I definitely do not excel at this. In my 20s I feel like I missed a lot of travel opportunities — I graduated college at a weird time (two quarters earlier than my friends) and I was already working by the time they all graduated, so I never did any major trip to celebrate finishing college. Then there was just no money for travel … and then I went to law school, where I was so exhausted from shuffling from school to internship that I mostly used what downtime I had decompressing at my parents' house. Then (by my late 20s) we hit the “every day of preplanned vacation time is spent going to weddings” phase.
I think I thought I would travel in my 30s, and my husband and I did travel a bit before the kids came — but not a lot, and family vacations are a thing unto themselves, which we're talking about over at CorporetteMoms today.
So I've repeated a few vacations out of laziness (been to Paris 4x for shopping, eating, cultural sightseeing!), but aside from my honeymoon I never really took beach vacations before the kids.
I've never been on a cruise, or glamping. I went to a spa resort for a friend's 30th birthday, and that was something I did not think I would like at all — I was firmly anti-massage before that, in fact — and I loved the resort and the vibe and, yes, massages.
Another vacation I was kind of surprised by was Miami — I never would have thought Miami would be the kind of city I would be into, but we were down there often to support a good friend (engagements/weddings/visits), and the energy of the city and activities (like boating! I like boating! who knew?) really surprised me.
Speaking of boating, I never in my entire life would have thought I would enjoy kayaking — I'm not an outdoorsy person at all and hate things like hiking — but when we were last visiting my mother-in-law at her lake house, I finally went out in her kayak and was shocked how peaceful and beautiful and calming I found it.
So… let's talk, ladies. How do you find the type of vacation destination that's right for you? Do you prefer to travel to different corners of the globe for different kinds of trips, or do you repeat vacations often? Related questions: Do you enjoy traveling with friends? For those of you who are partnered, have you had to negotiate the type of vacation destination that's right for both of you?
Stock photo via Stencil.
Anon
I’ve been to NYC 6 times and I’m not tired of it yet! Every time I see something new.
Anonymous
I’ve been planning my own vacations since college. I’ve been to London a few times but otherwise rarely repeat. I refuse to spend my limited vacation time on most friend milestones- I think I’ve take 2 Friday’s off for stuff in the last ten years. If I can’t make it flying out Friday after work, you get a card and regrets.
In general I like to wander around cities, soak up some history, shop, eat great food, and enjoy museums. I was really surprised that I loved Costa Rica which was the opposite of all of that but lush, beautiful, and relaxing.
BabyAssociate
+1, particularly to the friend milestones. I tack a couple days onto every holiday weekend and then usually take 1-2 week long trips as well. I’ve been to a few places more than once (Paris, London, Puerto Rico), but typically prefer to visit somewhere new, there are just so many places to see! I always plan my own trips and always at least 4 months in advance, 6 is preferable. Tag alongs are welcome, but I don’t like waiting around to see if others will commit to plans, so I always anticipate going alone.
Cb
We try to mix it up. We’re trying to make an Easter European city break a tradition after a wonderful trip to Berlin this year. But when we just need a rest, we go to the Lake District in the north of England. It’s spectacularly beautiful but also easy – we do some hillwalking, eat lovely food, etc.
FFS
As a child, my family went on the exact same vacation in northern Wisconsin every year because my dad and grandpa fished. I do not fish and so I hated it after three days by the time I was in high school, and stopped going by college. The rest of my family (and my siblings’ new children) kept going and I went again the first year I was working after law school, but I regretted using my PTO for it. The rest of my family still does that every few years, but they have other vacations mixed in there. I’d like to take my kids to experience that type of vacation once with their cousins, but I wouldn’t repeat beyond that. There are definitely places I’d visit again, but I also want to try out new places now that we’re financially in a position to do so.
AttiredAttorney
This was my family growing up too! Except replace northern Wisconsin with obscure tiny beach town in South Florida. The whole purpose of the vacation was to give my dad a chance to fish, and it was the only place we ever vacationed to while I was growing up. Now my dad has retired to said tiny beach town, which means it continues to be a place I have to visit.
Anon
We’ve repeated vacations to places where we have family or good friends, and that eats up a pretty sizable chunk of our vacation leave. I don’t think I’ve ever repeated a vacation where we didn’t have family reasons to visit the place, although I traveled a lot with my parents as a kid and would definitely love to go back to some of those destinations because I think I’d get so much more out of them now.
Anon
Yes, similar, although at this point it’s only planning to return. If we add in side trips near the international cities where my in-laws live, I feel like there is still a lot for me to see!
Leatty
Growing up, my family went to the same small town in the mountains every year for a week. I wasn’t a fan of taking the same vacation (which I found very boring) every year. As an adult, there are only two places I’ve vacationed more than once: Denver (which we love and where we have some good friends) and San Francisco (once combined with a trip to Napa and once with a trip to Carmel). The rest of the time, we go to different countries (or at least different cities in different countries). IMO, the world is too big to visit the same place all the time.
Vicky Austin
I love vacation traditions. Our annual family roadtrips to visit my mom’s family and to go berry-picking in the mountains remain my absolute favorite memories, and I want to have something similar, some sort of constant, with my own kids. My husband’s family does a week in someplace tropical every other Christmas, and I love that idea too for creating a tradition that also mixes it up a bit. (Plus I’m just really psyched to join them this year!)
Abby
With my family, we always did big trips to the same country (parents home to see relatives) and all domestic trips were different. My husband and I don’t like to repeat vacations unless it’s skiing or going to visit family/a family’s vacation home, which we usually do as long weekends to save vacation days. We prioritize traveling and don’t repeat different countries, he really likes to dream and plan vacations so it’s pretty easy for us to do and we definitely like to be the ones planning and making decisions, instead of tagging along. I haven’t had to use any vacation days on other people yet, which is nice. Into more active vacations vs laying on a beach for 7 days. Exploring new cities, I’ve been to more national parks in foreign countries than the US, trying the authentic cuisine. We prioritize countries that aren’t as family friendly to visit before we have kids.
Belle Boyd
Most of my vacations have always centered around going to NASCAR races (when my family was into racing) or to concerts. Repeat trips included Myrtle Beach in the fall (for a concert) and northeastern Alabama (also for a major concert). I’ve also gone on trips to visit friends in other states. Because I spent 10 years taking care of my mom, I really didn’t take any kind of vacation – we have a camp about 3 hours north of where we live that I try to get to as often as I can and consider my weekends away a mini vacation of sorts and I’m content with that.
The last vacation I took was 2 summers ago when my bestie’s husband sent us to Nashville/Memphis for her 50th birthday. It was a blast and I’ll definitely go back to Nashville because we didn’t see everything we wanted to. I also definitely want to go back to Memphis because seeing Graceland decorated for Christmas is now on my bucket list. My job makes it hard to travel since I don’t have anyone to cover for me and I need to process payroll every week, and being the lone single of all my friends and not having anyone to travel with isn’t a lot of fun. I’d do it, but it wouldn’t be as enjoyable as having someone to share the experience with.
Anonymous
We do a beach vacation to the same spot every year. My siblings and their families try to come most years too. My kids absolutely love this and look forward to it all year long. We also do typically two other trips–a winter vacation over Christmas break and then a trip over spring break. These vacations we go to different, new places and try for at least on international trip a year. My kids still love their summer beach trip the most and it is usually the cheapest vacation of the year because they literally just want to go to the beach all day every day.
cbackson
I do repeat vacations with my family – we’ve rented the same beach condo three times, and gone to the same resort in the Appalachians twice. But I haven’t typically repeated my solo travel…there’s so much I want to see. That said, I’m about to go back to Iceland and I’m super excited about that. I went in the winter before and there was a lot I couldn’t see or do.
DCR
I’ve never repeated vacation destinations, with the one exception of going to visit a friend in London last year when I had been there when in college. Very different trip with over 15 years in between, so I’m not sure that really counts. But my trips are pretty typical – travel to some remote location to see amazing nature and wildlife. I’m not really a city travel person.
There are just so many places I want to visit that I can’t convince myself to go back somewhere I have already been. But there are some places I would like to go back to, and haven’t yet – the Serengeti and the Galapagos Islands are the top of that list. Maybe I will go back some day when I have kids that are teenagers. And I want to take any kids back to places like the grand canyon and the badlands.
Anon
I’m doing fifty states, fifty half marathons, so the entire point is to *not* repeat vacation destinations. :)
CPA Lady
My goal would be 1 international trip to a different location each year and 1 or 2 domestic trips either somewhere new or somewhere repeatable. Repeatable options would include going to visit family in California, or going to either the beach (the gulf) or Disney world. I would probably branch out and visit different beaches.
I have a kid and up until now we’ve held off on international travel, but she’ll be 5 soon and I think that’s going to be a great age to get her started. I wanted her to be old enough to remember it.
I also want to take her to see all the major state parks. My family went on a epic road trip the summer between my 8th and 9th grade year and drove all the way across the country and back in a huge loop. On the way we saw the badlands, mt. rushmore, yellowstone, yosemite, monterrey and the California coastline, the salt flats, the grand canyon, the petrified forest, the meteor crater, the Arkansas hot springs, and all sorts of other random stuff along the way. I really really hate road trips, but it was an awesome way to see a lot of the country. We’ll have to see what I can force myself to do. Maybe someday we’ll repeat this trip, or maybe we’ll do it in a couple of batches.
givemyregards
My goal/philosophy is very similar, although I don’t have kids. My SO and I try to go on 1 big international trip a year (big to me = a week or more) somewhere new, 1 purely vacation domestic trip somewhere new (a few days in napa, or similar), and 1 repeatable trip a year (long weekend once a year at my favorite beach town that’s just a few hours away. All I want to do for that long weekend is sit on the beach, read a book, and drink wine in the evenings – going to the same place year after year helps make it a truly relaxing experience). Usually we each separately go on one trip a year with just our individual friends as well (my guess is this will eventually get reduced as more of our friends have children).
We also travel a decent amount to visit friends/family, go to weddings/other events, tag along on each other’s work trips, etc. etc. and those trips can be to either new/repeat places, but that travel gets lumped in a different bucket, mentally, for me.
Senior Attorney
I love to repeat and I also love new things, so we try to mix it up.
Lovely Husband has a longstanding (12 years plus) tradition of taking a cycling trip in Europe every year, so that is a thing we do. This year will be a repeat for him of the last trip he did before we started vacationing together, but it will be new for me. Those trips are largely “tag alongs” for me because he takes the lead in planning.
There are certain places I love to repeat — I’d go to NYC every year if I could swing it, and we are going to London for New Year’s this coming year after having done it and loved it a couple of years ago. I’ve been to Cambiodia, of all places, twice. And we have a few standard weekend getaway places including the California Central Coast and Palm Springs. But we also love new things so we try to mix it up.
One thing we have found ourselves repeating is train vacations with a certain set of friends — we rent a private train car and hitch it to the back of an Amtrak train and go on an adventure. This year we will be doing it for the third time. (Looking for a fourth couple if anybody is interested in a great late-October fall foliage trip featuring stops in D.C. and New Orleans — hit me up at seniorattorney1 at gmail!)
Yeah, types of vacations are quite varied: road trips, train trips, cycling trips (the last one was combined with a river cruise and that was great), city long weekends, country long weekends, Europe, Asia, Canada, various U.S. cities, some fancy and some not. The only thing I haven’t been able to convince Lovely Husband to try is an ocean cruise but I’m optimistic that will happen at some point.
The most surprising vacation was my first trip to Southeast Asia — I absolutely left my heart there and that was a big surprise. I’d go back again in a red hot second.
Senior Attorney
Oh, not much “friend milestone” travel at this stage of life. But we and a bunch of our friends traveled to New York for my milestone birthday last year and that was pretty great.
cbackson
Where are you guys going on your cycling trip???? I did a Belgium trip for the Spring Classics last year and it was so fun. I have Spain and Italy on my cycling bucket list…
Senior Attorney
We are doing Innsbruck to Verona (super easy because I am not a great cyclist and DH is recovering from a bad accident): https://www.mondobiketours.com/tours/view/innsbruck-to-verona-bike
And the one with the river cruise was Trek Tours Nuremburg to Budapest, which was divine!
cbackson
Oooh, that looks lovely. I was in Innsbruck for Christmas this year and it is a really beautiful and fun city if you haven’t been before.
I’ve traveled with Mummu Cycling which is all event-specific (so Tour de France, Giro, Spring Classics) and can highly recommend them if you guys ever want to do any race tourism.
I hope your husband’s recovery is going okay!
givemyregards
Did *not* know that renting a private train car was a thing and now know what I’m going to spend my lunch hour researching.
BabyAssociate
Ummm yeah, agreed. New Life goal!
FFS
Same. That is so cool!
Senior Attorney
OMG you guys it is the super best thing ever. We got into it because a friend of ours is into it.
Imagine this: There are 200-300 passengers on the train from L.A. to Seattle, and just two of us are sitting out on the viewing platform on the very last car on the train, watching Mt. Hood get smaller and smaller in the distance.
Super. Best. Thing. Ever.
This is the one we are taking this fall: http://www.sierrahotel.com/
Vicky Austin
Bookmarking this for the Super Future!
Anonymous
Senior Attorney continues to amaze and inspire. Definitely going on my bucket list.
anon
I definitely repeat vacation destinations. We have a very limited vacation budget, and every year we spend one week with my parents at Disney (which they choose and pay for), and one week at a family member’s beach condo a few hours’ drive from home. Before we had a kid, DH and I mostly took short trips to visit family or friends or for friends’ weddings or bachelor/bachelor*tte parties. We’ve actually seen a lot of the US thanks to our friends and extended family!
Next year will be our 10-year anniversary, and we are planning our first “just for us” vacation (not visiting family or friends, not traveling for a wedding or other milestone) since our honeymoon. We’re planning to go to Hawaii and leave our son with my parents!
Cat
We have one destination we repeat each year bc it’s our beach happy place. Otherwise, we like trying new places.
Fortunately hubby and I have similar vacation styles (there needs to be relaxing outdoor time involved or it feels just like our normal home city life), so even on Europe trips we either build in a few days in a coastal town, or choose a destination like Paris where walking around/lingering outdoors at a cafe is half the fun. We’ve also agreed that a giant cruise is on our “NEVER DOES NOT APPEAL AT ALL” list as we’d rather stay in one place and get to know it well, and the idea of visiting a beach/town at the same time thousands of other people are disgorged upon it is… a big nope.
Anonymous
We try to alternate a busy vacation exploring a city with a chill beach vacation or cruise. We take a 7 day cruise that goes from NJ-Bermuda every other year.
This year we tacked on a 3 day weekend in Dc to a work trip. We also spend about 5 vacation days yearly on travel for our families.
New Traveler
Where would you all suggest someone who is new to international travel go? Single female in late 30s and I’ve never been out of country. A solo trip is most likely since it’s hard to get friends to join (they all have kids/spouses) and no S/O in the picture. It’s my goal to plan and execute this first trip before end of year.
As for domestic, I’ve really only traveled for milestone events of friends/family or for work. Would love a couple of great suggestions for solo trips to do as well. (Preferably not in FL or Northeast as I’ve lived both places)
Thank you!
anon
London. Lots to see, good public transportation system, you’ll already know the language. But it’s different enough that it’ll be cool.
Senior Attorney
If you’re in the U.S., you could dip your toes in by going to Canada — Quebec City is like France without the long plane flight. And Victoria is like England without the long plane flight or the language barrier.
Other than that, I’d say London!!
InfoGeek
Ditto to London.
I was there for most of 6 months for work and I enjoyed doing things by myself — shopping, going to historic sites, going to West End shows and the ballet, wandering around, etc.
anon
For a 1st time international trip, I would think about something easy, but different enough. What about England, Scotland or Ireland? Fall would be a lovely time to experience. Barcelona, Spain might be something to investigate as well.
For domestic, not sure where you are located. Some options that come to mind: Midwest – Chicago, Madison. Southwest – Santa Fe. Southeast – Charleston, Savannah. West – Montana and California.
So much to see !
Use all your vacation time. There is no gold star given to those who don’t take all their allotted vacation time.
Work will still be there when you return, you need to recharge your batteries and refresh perspective.
editrix
Amsterdam! Totally different and easy to navigate in English.
Anonymous
Japan/Korea! The language won’t be the same AT ALL, but it is very different, and very tourist friendly as a solo female. If you are polite to the locals, they will be super polite back to you, and helpful. Also, Naver/Kakao Maps in korea runs like a dream, and you basically won’t have to ask for directions if you plan to bring a battery pack and get a good wifi.
J
London or Edinburgh would be fantastic. Both are super easy with the language and helping gain confidence. I’ve done both and they were largely stress free because things weren’t that different. London was a bit harder because I don’t have transit like it back home but Edinburgh was condensed enough that I could literally walk everywhere. My first international trip was Barcelona and it was also very welcoming. Paris was just a touch harder but I felt much more confident having been to London first.
Not an attorney
London or Edinburgh would be fantastic. Both are super easy with the language and helping gain confidence. I’ve done both and they were largely stress free because things weren’t that different. London was a bit harder because I don’t have transit like it back home but Edinburgh was condensed enough that I could literally walk everywhere. My first international trip was Barcelona and it was also very welcoming. Paris was just a touch harder but I felt much more confident having been to London first.
Mrs. Jones
Girls’ trip to the same beach every Memorial Day.
Girls’ trip to the same resort spa every couple of years.
I go to different destinations with immediate family.
I haven’t traveled for “milestones” in a while.
I am up for pretty much any vacation except camping.
Senior Attorney
Oh, man, I am with you on the “no camping!”
I went to a youth leadership camp a month or so ago and had to stay in a dormitory/bunkhouse with 16 women, 4 sinks and 2 toilets. No, no, no to that and a HUGE no to tent camping!!
Anon
A friend has a condo a few blocks from the beach, so we go there for several long weekend each summer, but I don’t count that as “vacation”.
When I actually use a significant amount of PTO and it’s just me and the spouse, we like to get in the car and just leave. We definitely do not repeat destinations that way, but we also live rough compared to what a lot of posters are saying. We take camping gear, spend most of our time in the wilderness, and focus on landscape/wildlife photography.
Good friends are constantly inviting us to cruise, but that doesn’t appeal to either of us. All of our friends seem to prefer vacations that focus on alcohol, night life, and shopping, but those things are just not our style of recreation.
Anonymous
Depending on the cruise and the length you might enjoy it. A nice break from reality.
JB
I’m with you. Give me peace and quiet. I want to hike and be in nature. A cruise sounds like a nightmare, because I live in a big city so I can have all the night life and shopping I want everyday. Vacation is the opposite of your daily reality.
Anonymous
As a child, my family always spent a week in the same beach town. I loved it! My parents still go back most summers, and my siblings and I occasionally join. My husband and I also take repeat trips, usually long weekends, to places where we have family or close friends, mainly Florida, Texas, Pennsylvania, Mexico, NYC and DC.
We also take longer vacations (a week to 10 days, or sometimes longer) to new places. Destinations we’re discussing for the near future are Hawaii, Pacific Northwest, Italy (I’ve never been), London (I studied abroad there but my husband’s never been), Vienna/Budapest/Krakow (we have friends getting married in a small town nearby) and Palm Springs/Joshua Tree National Park in conjunction with a few days in San Diego.
A
Team non-repeater here. The closest we’ve come to repeating is to go on two Danube river cruises- one through Czech Republic, Germany, Austria, Slovakia, and Hungary, and the second trip through Hungary, Croatia, Serbia, Bulgaria, and Romania. We love learning about other cultures, histories, and food.
My SO and I do 1-2 “big” 1-2 week trips per year. Up until now they’v all been international, but his visa is running out next year. Therefore, we’re going to Alaska in July and Arizona in August since they’re on his US bucket list. I’m lucky enough to have unlimited vacation. Also, we do have the advantage of speaking English, French, Dutch, Mandarin, Thai, and Japanese between the two of us.
Anon
I don’t think my husband or kids appreciate how much time and energy I spend on planning our vacations. We typically take 3 a year – Spring Break, late June and Fall Break. The October trip is usually always to the beach because it’s easy and relaxing and the weather is PERFECT and we stay in the same area so everything is a no-brainer (where to eat, where the liquor store is, etc.). It’s also nice that we have traditions from the trip that we always repeat (where we stop to eat on the interstate, a bike ride every morning, junky cereal for breakfast). We did a lot of beach trips when the kids were small, because it was so easy and there’s not a ton you can realistically do with toddlers in tow. But beach and pool were always a hit.
Now that they’re older, we have a lot more variety in our spring and summer vacations. Our budgets are also better since we’re not paying for daycare anymore. Last year we went to Cancun (it was our kids’ first time out of the country) and then to Colorado in the summer. Both were great. This past SB we had to unexpectedly cancel our planned trip to Arizona and repeated one of our favorite vacations (don’t laugh, but Dollywood is amazing). I have no idea what we’re doing in June! In years past we have been to SoCal, Kiawah Island, a different part of Colorado and Disney.
Planning vacations is a total pain, for real. We used a travel agent for our Cancun vacation and it really wasn’t worth it. She kept trying to steer us to resorts that were out of our budget. We ended up staying in the first hotel (JW Marriott) we had picked ourselves before I called her.
ggg
Nearly all our vacation time is taken up by visiting one family (across the US) for a week at Christmastime, and the other family (overseas) for two weeks every other summer. I would love to go somewhere else, but there is not enough time off, and flying a family of four to the “required” destinations eats up all the budget anyway.
Once during spring break we were able to take a short road trip with the grandparents, which was nice, but we don’t have the time off to be able to do that every year.
Drago Cucina
My husband is anti-beach and while I love it the time and energy is best put into a trip to Europe. If I want to veg I go to Vegas where there is either a cheap hot dog or fabulous fine dining options and a swimming pool. A Caribbean cruise is our idea of vacation hell, but have been on European cruises. Not 2000 drunks on ship, not over planned, but some great scenery and food.
Kristin Vincenzo
Great questions! As a kiteboarder, I’m always looking for new spots to see and kite. I’m lucky because my sport is done in some of the most beautiful spots in the world, but I definitely have my favorites. I’ll generally plan vacations to new spots when I’m in the driver’s seat, but I’ll tag along to places I’ve been before if I’m not feeling inspired to do the research but I want to have a good time!
Clark
I try to travel somewhere each month. I try to spend 4 weeks out of the year with my family: we take a weeklong family trip each year and I visit them for a week in the summer, at Thanksgiving, and at Christmas and I make it a goal to take 2 international trips each year: one trip to the northern hemisphere (usually more sightseeing-oriented) and the other to the southern hemisphere (usually a more casual surf or yoga retreat). The other months I try take short weekend trips, but unless there’s a “reason” (bachelorette party, wedding), I’m not so great about following through on these.
Jamie
In a way I do both. I take the same one week trip to the same low key beach in North Carolina plus a big week and a 1/2 (or so) vacation to a new location as a road trip. Last year we went to Colorado Springs/Pikes Peak and Yellowstone (staying in the park and hiking parts of it – Amazing!) This year we are road tripping to Niagara Falls and Bar Harbor, ME (Acadia). We going to take a long weekend to Nashville the weekend before Christmas and catch two shows at the Ryman. I love planning trips!
Laura
My family repeated the same vacation year after year when I was a kid. Maybe it’s not for everyone, but I liked it because it was like a home away from home for me. I find that when you’re going somewhere new it feels like there’s more pressure to go do and see things than there is when it’s somewhere you’ve been before.