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What are you looking to do and what do you enjoy? Relaxing? Food? Nightlife? City?
A few options (assuming in nyc):
Beach/Relaxing:
Azores (beautiful, great food and wine not the best time to go as not that warm)
St Lucia (or St Barths or many other Caribbean options)
Bermuda (short direct flight)
Puerto Rico (US so easier to get to)
Hawaii (long flight so need to spend some time there)
Good nightlife and food:
Miami (warm right now)
LA or San Diego (less nightlife)
any major European city (big fan of London and Paris, but Amsterdam is more affordable and also great) - risk is it may feel more like nyc
Hiking/Outdoors:
Maine (maybe too cold right now)
Northern California (and can couple that with Napa if you enjoy food and wine)
Arizona or Utah (great national parks)
would also recommend skiing but a bit late in the season.
I personally enjoying getting away fro 3-4 days to a beach at this time of the year (Caribbean or similar). How many days are you thinking?
Any skiing recs for south america/southern hemisphere? Trying to set up a summer ski vacay
Look into cat-skiing in Chile (Patagonia).
Gotta bump theATL's comment here, because he nailed it. All about what you prefer. Before you book a plane ticket or anything, just sit down and think about what you want to do. No, really - what do you want to do? Start with no limits - nothing financial, nothing social, nothing. From there, ask yourself: how do I combine this Utopia experience with a realistic plan? Work down from there. Brainstorm. Write a list of things you'd dream of doing, they don't have to be city-specific or region-specific - just think.
From there, you can begin to drop and add valuable points to each of those activities, and figure out what's realistic for you. Are these activities offered in a single metropolitan area? If so, which ones? Which ones seem the best? Which ones are the cheapest? Which ones are the best combination of value for their money, and value for their time? You see where I'm getting at here?
Does this seem like an unnecessary amount of effort for a vacation? Yeah, probably. It may sound stupid. But hey - since you asked, I'll tell you about the best vacation of my entire life while doing this exact formula, and have tried to replicate it ever since. I've evolved a bit since then, now grouping in my fiance with reason, but that original trip was the greatest thing I've ever done.
The Mojave West Solo Trip: June to mid-July, 2016. One month after I graduated from b-school. Had just gotten a first-year analyst gig at a REIT fund, but didn't get to start until August. Had two months to kill, was considering working a full-time service job to keep me chilling on rent - said fuck it, subleased my apartment two months early, and took off in my car. No regrets. Greatest trip of my life. Decided what I wanted to do and went with it.
In context, this didn't start off with the 'dream vacation' vibe I thought about, it actually came from a loss. Girlfriend of 3.5 years broke it off, was feeling down and out. At the time, I drove a 2004 Toyota 4Runner that I had thrown a 3" lift and a Thule rack on. Took my dog and just started driving. Figured out what I wanted to do. In no order of importance, it was: drive all of the Mojave Road in CA, get a 3840x2160 photo of the uninterrupted South Utah star pattern, go without non-emergency cell service for 10 days straight, and find out what really matters in life by virtue of spending those days with me and my Aussie Shepherd. Corny? Yeah. But rewarding? Holy fuck.
I can't tell you how much I enjoyed that trip. I've flown first-class internationally to five-star resorts in Dubai before. I've played at the most high-profile golf courses in the United States. But that trip... that one trip with me, my dog, and my 315,000 mile 4Runner was the greatest 39 days I've ever spent, arguably in my life. I got lost once. Genuinely thought I was going to die, and broke my ten days of cell service rule - thank God that AT&T decided to install a remote link tower in the middle of the fuckin' Mojave. But, I saw the stars and I got that photo. I woke up every day without my phone. I ate delicious Tui Chub that I fished in the Mojave River. I spoke with people of indigenous cultures, small-town business owners that had a different perspective on life, and got high as fuck with two chicks who wanted to see if their Ford Explorer could make it to Nevada - by the way, it didn't.
None of this is bullshit. This is the internet, so I don't blame you if you're like yeah ok buddy on this story. But I swear to you, it's entirely true. And those 39 days changed my outlook on life in many ways and allowed me to temporarily step away from the fast-paced finance world and let me just breathe. I have wanted to do a repeat of that trip with my soon-to-be-wife ever since. One day, I will.
Best of luck to you on your search. Remember - think about what you want. Go fucking do it.
This is phenomenal
God damn this made me emotional. Cheers to that man!
Solid
Never happened?
Have any recommendations for someone who wants to step away from the fast paced world of finance and just travel like this?
Easy, just go. Get a map (a real map) draw out a path you want to go, and do it. I did something similar for about 7 days traveling around Lake Michigan (circle tour). Pit stops were large cities along the way. Those were the days.
wolfofwso is right in a sense - just go. If you have the means, whatever they may be, then just go. However, we're on a financial forum, and this community is not representative of the typical 40-hour workweek. We don't have a lot of time, I get that. I got extremely lucky in my two-month hiatus, and although I wish it wasn't as big of a consideration as it was, that was a large part of why I decided to do that. That was six years ago, and in those six years, there has never been a time where I had nearly forty days of freedom to truly just do what I want.
On the flip side, however, some things ARE more important than work. I think that's a concept that's been respected on this forum in recent years. There are a lot of people out there that will say "dude no, you gotta be a beast and GRIND or else you'll never be successful" and that mentality has been engrained in the finance world since the 1980s. Investment Bankers will probably agree with that statement for the most part, and it's perfectly logical to decide that for the next 2-3 years you're going to put down your social life and emotional freedom to dedicate yourself to your job. 2-3 years of grinding seems like nothing in the long run, right? That one makes sense.
For me, it was different. It was something I had to do. I was not happy with where I was in life, regardless of the relationship thing. That came less from a career standpoint (I was doing great in the field, but that was the only thing that was going well) and more from a personal life expectancy theorem. I didn't have a lot of friends, I didn't like how I looked without a shirt on, I spent too much of my day wasting time and I was just boring. I hate boring people. Boring people have nothing to talk about, nothing to do, no ideas. That's who I was. This trip FORCED me out of my comfort zone and forced me to battle life through something else besides a computer with numbers on it. That's what made it so special.
I think that everyone in their life should have a trip like this. Maybe not the location I went to, the duration of it, and the content of the events. But everyone should have a period where they do something that isn't ordinary - not what they'd consider a 'routine vacation' with the typical beach/mountains/urban vibe that everyone else does. Yeah, those are sick and you should have plenty of those, but I also think that everyone should take some time for a solo trip filled with surprises. It allowed me to slow down, look around, and just fuckin' breathe some damn air. To the people that I met, finance didn't matter. No one gave a fuck that I worked for a Fancy Cool Real Estate Investment Trust Wow MBA Super Cool. It allowed me to be a different person for a bit, just another human who was interacting with other humans.
There are so many specific things that I could tell you about how that trip changed me, but I like to keep most of them for myself. This isn't to gatekeep or imply that I hold the 'Keys To The Great Happiness And Shit', but it's just a personal experience. An experience for me to keep and remember. I truly saw the world from a different perspective, corniness & cliches aside. All around great time.
Best of luck to you in your future vacation. If you got the means and the time, just go do it. You will thank yourself later, even six years post like I am now.
This gave me chills. Salute to you brother. I strive for this
Had a similar experience like this during a trip from California to Virginia in 2020 - I went through some amazing cities (Little Rock, OKC, Memphis, Nashville) then I hit Charlotte, Atlanta, Auburn, Shreveport, Dallas on the way back. Truly religious experience those ten or so combined days on the road, by myself, meeting people in different cities and enjoying a night together before starting over the next day. I hope everyone gets the chance to do something like this eventually
Why do you think flying first class and staying at 5 star hotels in Dubai didn’t make you as happy as your road-trip?
As I mentioned in my prior reply, that trip was just a different kind of vacation for me and benefitted me in so many ways. It was special because it was for me alone - I didn’t have to make any personal considerations for those around me. I'm not saying accomodating others on trips is a bad thing, but I just didn't have that kind of requirement set. I had a plan, I executed it. I let things come and go on that trip as they please. Everything I did was for ME, and other things came second.
The Dubai trip, for example, was a conference for some foreign clients last year that we were focusing on. There was an agenda - formal introductions, meetings, pressure, specific times, and places to be. I had people who were relying on me, and I had people I had to rely on to make sure it was successful. I had a fuckin' BLAST on that Dubai trip, but it wasn't one curated for my specific enjoyment. When I was in the desert, I was there because I wanted to be. All of my time was spent doing new things that I either previously wanted to do or was energetic to try. It was just beautiful in so many ways.
In addition, that trip really focused on the lack of the materialistic side. I've always been a pretty materialistic person - I can't lie, I like things. I have nice clothes, I have a nice car, apartment, etc. because they make me feel good. But they aren't the cure for happiness, even as cliche as that sounds. That trip was some time away from the materialistic world, the financial grind, the social norms, just doing shit that I wanted to do because I could. It let me look at people and the world in a different way. That's why I will maintain it's the greatest trip I've ever been on, and I'd love to think that I'll be able to do that again someday. Cheers!
Safari. Can be expensive but worth it
Kenya, went to a few different conservancies and of course the Mara. Could've stayed there for weeks on end
I’ve had a few fun trips:
- Surfing Lakey Peak in Sumbawa Indonesia
- Surfing Hossegor France
- Surfing Jeffrey’s Bay South Africa and meeting Kelly Slater and his girlfriend Gisele Bundchen
- Snowboarding boardercross in the national championships in NH and CO
- Surfing Sayulita Mexico with an Austrian model
- Surfing Bell’s Beach in Australia
- Playing poker all across the US and also at Crown Casino in Australia
- Scuba diving in FL (cave diving), offshore SC, Grand Cayman, Jamaica, Egypt (Red Sea)
Was this before she married Tom?
Yeah
Hawaii my man. Went their recently for 2 weeks with girlfriend and had the time of our lives. Expensive but worth it. AirBnb on the Big Island - everything you want to do, all on one island. Serene beaches? Check. Awesome views and cool wildlife? Yup. Volcanoes and lava tubes? You bet. Mountains that give you views of the whole island, Green sand beach, most southern point of the U.S. with 50ft cliff jumping into ocean, Kona coffee & beer, surfing.. list goes on and on. If you need an escape, that's the place.
I came here to say this, +1 DebtChug . Hawaii is unreal, and both the Big Island and Ohau are amazing. In 2021 I went to the Big Island with my GF and a few other couples and stayed at a massive Air BnB on 5 acres with our own pool, horse stable etc. It was much less expensive than you would think, and as we split costs six ways for everything, it only came out to a few grand a person. I would also recommend staying on the east side of the big island for a much more authentic experience. All of the tourists tend to stay on the west side of the big island island, and you feel like you are packed on top of one another. Definitely get a few friends to go and do an Air BnB over a hotel room too.
Had a week off in between jobs and took a solo trip to Miami on very short notice/minimal planning. It was truly awesome and I'm glad I did it.
Met a ton of cool people that were also traveling there that were my age, and even got shitfaced with another WSO user.
I would definitely recommend it.
Road trip with the boys through the South Island of New Zealand. Next level beauty.
.
Contrary to the people above who said to think deeply about what you want I’m a vacation, I usually just go with the flow and go to the first destination that pops up in my mind. A few of my best vacations though:
- Egypt: really great, lots of history, good wheather, good for snorkelling
- Tenerife (Canaries Islands): great nature, chill people, peaceful
- Peru/Bolivia: nice for a month backpacking, incredible sights in Macu Picchu, the Amazone, Salar de Uyuni, Sud Lipez
- Cuba: Really fun place to go
- Mexico: partying, pretty fun, nice beaches
- Yangshuo, China - saw some of the best sights in my life, especially rice terraces, top of the moon mountain, light and sound show
- Europe in general: Portugal for surfing, Budapest for baths and partying, Amsterdam for [ ;) ], Greece in the summer, Italy for history and food, Spain for chatty people and tapas..
- Philippines: Really relaxing, great islands with white sand beaches, Boracay for partying, Palawan I heard is the best
Thinking of going to Tenerife - any recommendations?
Yup, I lived there for a few months.
Don’t stay on the south like Los Cristianos, it’s too touristy feels like Nice. Go to the local places, San Andres near Santa Cruz is nice and has a great large beach (Las Tejita i think). La Laguna is the best town. Los Gigantes is nice too.
You will need a car. Visit the best beaches like Bolullo, Benijo, Los Gigantes, Medano (best for kitesurf), Ancon etc. You can stay anywhere as most places will be within 1-1.5h drive.
Go hiking in Anaga, the Teide park, and the Teide volcano itself (you need to start at 5-6am to see sunrise).
You should check out Masca (and the hike too if you can) as well, pretty magical
The local coffee “barraquito” with alcohol is the best.
My second time in Japan - went to Tohoku by myself for cherry blossom season. It was really soul cleansing and allowed me to focus on what's important in life. Also tried some amazing cider in Aomori (Apple capital). Then flew down to Nagoya and visited my friend in the countryside. Highly recommend visiting the off-beaten paths in Japan.
Maui, paragliding with a hot baby I was with at the time.
Has anyone been to BVI?
south of france/north of spain is awesome, san Sebastian is one of my favorite cities
Yeah San Sebastian is a nice city. I've also been to the end of the Camino de Santiago (Santiago de Compostela).
I've surfed the coast of France in Hossegor - one of the best surf trips of my life. Amazing waves - shore break.
Jackson Hole if u can skii and don’t mind dropping a few racks
Has anyone been to the Bahamas? We are going to The Cove at Atlantis for a week over Memorial Day and would welcome any comments for must-do's, recommendations, etc.
Grab some conch fritters and drink some Kaliks at the Fish Fry at Arawak Kay.
https://www.nassauparadiseisland.com/things-to-do/unique-tours/food-dri…
I went scuba diving in the Bahamas as well - would recommend if you're certified. They might have snorkeling or something if you don't want to scuba.
Utah national parks are great if you want something domestic/affordable and to spend a week outdoors in the next couple of months. Did it a few years ago and had a blast. Daily itinerary was basically do an unreal hike every day from like 7am-1pm then chill at the hotel pool or drive to the next park in the afternoon when its gets hot. The drives between the parks are also crazy scenic. Spring is a good time to go before it starts getting too hot. Probably the most polar opposite place to NYC I've ever been in the US.
you want happiness, go to Orlando
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