Winter Holiday

My boyfriend and I are planning on going somewhere hot in February. I’ve only been to the tropics once in 2007 when I went to Cuba with my last boyfriend. I’m not really sure where we are going to go on this trip. I’m kind of leaving it up to him since it was his idea to go. I would really like to go back to Cuba because I had a good experience there. But for the same reason, I don’t think my current boyfriend wants to go there. I think I would be comfortable going anywhere except for Mexico, which is where he wanted to go. I just hear so many horror stories from there. But I guess most people are fine when they go there.

What tropical places have you been to? Did you book through a travel agent or did you just book online yourself? Do you have any places/resorts you would recommend? I would really like to go to an all inclusive resort, which is what I did in Cuba. It’s so nice not having to worry about buying food, drinking all the free alcohol you want, and just lazying around on the beach.

Do you think it’s better to book the trip now or wait until February and find a last minute deal? I’m a planner. It makes me so nervous when things are not all booked beforehand. I’m trying really hard to be patient and just let things happen. Planning my life has backfired so far so I’m really trying to just go with the flow.


  1. I’m a big fan of Hawaii! Each island has its own personality, so if you’re looking for something tropical, I recommend Kauai or the Big Island. I found that Oahu (where Honolulu is) is way too touristy, but Kauai and Big Island are much quieter.

    I’ve been to Hawaii 3 times, and booked 2 of those trips with a travel agent who had been to Hawaii many times. We chose to use her because she had a lot of experience and great tips for Hawaii 🙂 Like you, I’m a planner and feel much more relieved when everything is booked ahead of time. Then all I have to do is wait! Good luck on picking a place to go!

  2. I always book everything online by myself, but I’ve only been to cities, never to any vacation resorts or anything. Furthest south I’ve been in this world is Bulgaria, but I don’t think that counts as tropical haha!

    Everyone I know who’s traveled to a resort has done so by booking a package via a travel agency, so maybe that’s the easiest way to go?
    It also seem that to get the cheapest price you have to either book waaaay early or really last minute. I’m a planner too, so I understand that waiting ’til last minute seem scary, but it could be quite an adventure too! Maybe you find a deal on some really cool destination that you haven’t even considered yet! 🙂

  3. Ooh a tropical vacation sounds lovely! I’ve never used a travel agency, I just booked my flight and hotel online trying to find the best deal. But I guess it depends on if you know where you want to go and the details about the place.

  4. I do hope you have a good time when you go, and figure out where that will be.

    I haven’t really traveled so I can’t offer any great advice. I like to plan things ahead of time. But, then you can get great deals last minute too. I guess it just depends on if you are set on a specific place or not.

  5. I guess you’ll need the tropics before or during the Canadian winter! The only nearly tropical place I’ve been to Gran Canaria. But Italy is actually much warmer, only thing is that it’s only warm in the summer, at the same time as it’s decent weather at home too. So for a hot winter holiday I’d need to go to somewhere much further away. If it wasn’t for the long flight and the spiders I’d love going to Australia. 😉

  6. Oh yeah, I’m definitely a planner too, so I’d hate doing the last-minute deals if it’s for some place far away. I’ve never gone to anywhere tropical… 🙁 But have always heard so many good things about Hawaii! Or the Carribbeans!

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