Why I love All Inclusive Vacations.

I love travelling. Part of the reason that I resigned my old job and started working as a Business Operations Consultant was because I wanted to be able to travel more. They say be careful what you wish for because it might come true. Well, it did come true. For the first 6 months of my new role I was home a total of 35 days. I spent the rest of the time on the road.


Now, don’t get me wrong. I love flying, and airports and visiting new places, but visiting for work is different than visiting somewhere for fun. Back in 2009, my friend, Anita and I took off for Europe for 6 months. We backpacked our way through most of it. That was an adventure. Not knowing what hostel we were going to stay at when we got off the train in any given city was both exciting and nerve-wracking. But we had fun. We met some of the most amazing people on our journey, and I can say that I was altered by it. Europe, also, took a bit of planning, and we needed the time to create our adventure. Having a week off work isn’t the same thing. I can’t fly over to Germany and hang out for a week, it doesn’t work like that, and quite frankly isn’t in my nature. I need/want to explore the city, live with the locals, learn their ways. This is one of the reasons behind interviewing for roles in Argentina. I wanted to live there and feel settled.

The first time I travelled by myself was 2008. I had just broken up with my boyfriend of 2 years, been in a car accident that totalled my car, and might have been somewhat traumatized. I went online, found a trip to Cuba for the next evening and packed my bags. (My boss was kind enough to allow me leave after seeing pictures of my car, and the cuts on my face). The goal was to spend a week in the sun, get my tan on, and read. That was it.

I paid $490 taxes in for an all inclusive trip to Cuba. I know that I have a few readers from the States and flying to Cuba is a bit of a challenge, but let me tell you that it is worth it.

Since then I’ve been to every Caribbean country, and would still pick Cuba. Let me explain why.

I don’t go to Cuba for the food. That’s not the point of the trip for me. I enjoy the experience. I also love getting on a plane and knowing that my hotel, flight, food, is all taken care of.  I also like my cigars (I don’t smoke cigarettes). This is especially important to me since I have a limited amount of time for vacation, and spending the most amount of that on the beach is a priority. The majority of the trips that I’ve gone on are 7 day last minute ones. I have gone on the rare 4 day weekend trip to Varadero as well. The country just doesn’t disappoint.

For those who have issues with the food, I say suck it up. Cuba has some of the world’s best beaches, really friendly people and tourists(mostly Canadians), and its only a 4 hour flight from Toronto.  And, this being a personal finance blog allows me to point out that Cuba is most likely the cheapest destination for most Canadians. Where else are you going to find a flight, food and alcohol, ground transportation and hotel for that price? I can go to New York for 2.5 days and spend that and not get tanned, or go away for a week on an all inclusive vacation for the same price.

Cuba is a very close second to my favorite place in the world. And knowing that I get on the island for under $700 at any time makes me love it that much more.



  1. says

    Yeah they seem like a good idea but they are charging you like $200/day for meals.

    I don’t know about you but I don’t eat that much food. I went to San Juan a few years back and rented a condo.

    The owner helped me get everything I needed and the trip was WAAAAAAY better.

    I went to the local grocery stores and got my own food beer wine and had a great time and saved plenty money.

    I’m just saying.

  2. says

    Do people think Cuban food sucks? Maybe I’m spoiled, because I’ve never been to Cuba, but I’ve been to two awesome Cuban restaurants (out of about two). One, in (believe it or not) Louisville, is just absolutely fantastic, and it’s in a strip mall. We pulled up and I didn’t want to go in. Now I can’t wait to go back.

      • says

        I didn’t know about the food, I did all inclusive once in Dom Rep and it was fine, lots of fresh fruits and vegetables to make up for the junk food. I guess in Cuba there are some restrictions too. I have never had the occasion to go and would love to explore that country! It is pretty expensive to fly from Guatemala, strangely.

  3. says

    My wife and I found out the hard way that we LOVE all inclusives. We spent a week in Hawaii, and it was frustrating because we had to make TOO MANY money decisions, and since our funds were limited, kinda put a damper on the whole thing. Cuba does sound nice this time of year, especially since it 38 degrees and raining here…

  4. says

    We’ve never done an all inclusive vacation. Hearing the benefits of them though I really do want to some day. We’ve been to quite a bit of the Caribbean and would love to try Cuba, I’ve heard so many good things about it. I hope the US restriction gets lifted on it so we can go there at some point in our lives.

  5. says

    My friends and I did 2 weeks in Varadaro Cuba in Nov of 1998 and you are right about the beaches. So very beautiful. I love Caribbean beaches, but there was something so nice about the sand on the beach in Cuba. We did one bus tour while there to see Cuba itself. The rest of the time was spent at the resort. We met so many Canadians. The only drawback of the trip was the flight from here to there. We did Air Transat and via Toronto and we were packed in like sardines. So uncomfortable.

  6. says

    Wow that’s odd that you would pick Cuba over every other island in the Caribbean. I guess I’ve never thought of Cuba as real vacation destination. The only island I’ve ever been to was Aruba and I loved it. It had a certain peacefulness to it.

    I’ve never been to an all-inclusive resort but I heard they are a lot of fun. On the other hand I did stay at a Timeshare down in Aruba but I can honestly say I wouldn’t do it again simply because with an all-inclusive they cover all the cost from the drinks to the food which can save you a bundle.

  7. says

    Traveling for business is definitely different. I make a point to do one fun/personal thing while on a business trip, and it really changes things up. Like when I traveled to FINCON this year and rented a car to go to a natural hot springs an hour outside of Denver!

  8. says

    I do and I don’t like all-incluvies. The first trip I went on I loved, the second, well I think we just picked the wrong hotel. Plus because I’m usually busy in my normal life it takes me like 4 days to finally relax. I just don’t think I’m good at vacations really. But I do love that you can find some really great deals for all-inclusives.

  9. says

    The BF and I haven’t been on a vaca in a while, and we’ve not been on an all-inclusive vaca together. My last all-inclusive was in the Dominican Republic and it was great (all you could eat and drink, beaches, warm sun, what was not to love?) I like paying in advance and not worrying about anything but relaxing.

  10. says

    I’m well travelled myself and am one person that can’t stand resorts or all-inclusive but never on business. I prefer to hang out with the locals, travel around and mingle to learn what the culture is all about and throw myself into it. I want to meet the people, learn from them and maybe teach them a bit of where I come from. I’ve eaten some of the best foods in little run down shops, huts and side streets and long for it sometimes.I’ve been to a resort once and yes it was all fancy, boxed in like we were in paradise but it wasn’t for me. It’s one of those things that you either love or hate it. Glad to hear your all inclusive experience is one that you desire. :-)

    • Marissa says

      I do that too! Some of my best meals were from food carts and small stores in Turkey. I also venture out of the resort a few times, but I need more time to chill with the locals. If I need a break, the all-inclusive gives me that.

  11. says

    I’ve never done an all-inclusive, but it’s something I would like to try at some point. I imagine sitting on a beach in Cuba beats shovelling snow in February every time.

  12. says

    My in-laws love Cuba. My mother in law just got back actually. It is the beginning of some hunting season here and my father in law was planning on disappearing into the bush, so the MIL said forget it, I`m going to Cuba.

  13. says

    I`ve been to Cuba once, and it was with my family about 5 years ago. Even though I wasn’t expecting to like it – I always thought of myself as backpacker-explorer-type-of-traveler, it was a lot of fun. Usually our biggest decision of the day, was deciding what to have for dinner. I was also expecting the food to be so-so, but I really enjoyed it. Looking back, it was perfect for getting on a beach and doing nothing.

    BF and I have been doing self-guided tour trips, but we’re usually too busy to plan too much in advance, so it’s nice to take the work out of it. And let me know if there is a blogger vacation coming up!

  14. says

    We did an all-inclusive for our honeymoon and it was definitely worth it. We went to Jamaica and the beaches were beautiful. We loved that we could eat at any of the restaurants whenever we wanted (I seriously was NEVER hungry because I ate so much, I loved it!). We are going on a cruise in February but I would love to go to another all-inclusive sometime in the next few years.

  15. says

    Interesting. I found Cuba to be okay. Not sure if I would go back without a reason (like a wedding). Friends of ours who have traveled very extensively spent 3 weeks there backpacking/in resorts and ended up leaving early, they hated it so much. At the resort it was fine, but being actually in Havana was annoying.
    Two friends went on exchange there and one basically never left the apartment, he was so sick of being harassed. The one with a very dark complexion found it fine. ..I digress.

  16. says

    Brian and I have never been on an all-inclusive vacation yet and I’d really like to! I’m not sure where we would go, but anywhere warm, tropical and relaxing would be fine for me :)

  17. Audra says

    I love to taste different foods when moving to vacations. But, I haven’t tasted Cuban foods yet. Marissa, you are same as like me spending more time in road then in home.

  18. Mat says

    I’ve never been on an all-inclusive vacation before (in fact, any sort of vacation is rare nowadays). However, I think it sounds awesome to have everything taken care of and not have to spend as much time on day-to-day details and decision-making. Even the pre-vacation planning is not something I enjoy, so the package deal is attractive to me. I see the pros and cons, but I would imagine it really just depends on the particular resort and pricing as to whether it’s worth it or not.

  19. Vicky says

    Kind of late catching up with the blog and my fiest time writing.
    Just wondering what were you interviewing for in Argentina?
    Great blog always helping me trying to out my money in order lol

      • Vicky says

        Finally you decided to stay there? Its not a great economical time to be living in Argentina. We are having soo many issues, in fact we have to ask for permission to the Afip (something similar to the irs) to be able to exchange local currency to us dollars or any other foreign currency, and 95% of the times they dont allow you to exchange it. And saving in local currency (argentine pesos) with an inflation of 20% per year its kind of nit worth it… You might have dodge a bullet there lol. Btw I looove your posts, they are super interesting and helpful!! Congrats!

  20. says

    Who doesn’t love all-inclusive vacations? For someone who’d rather skip the bookings and all, I’d take anything that lets me do two things, make a single booking for everything and then have fun with my vacation.


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