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Warm weather is slowly starting to creep into New England. I’m embracing it, in love with it and hope it never goes away again. Oh, but it will. And there will still be awfully cold days and rainy days  from time to time.

When I start to think about all that dreary weather, my mind tends to wander to happier, sunnier times. I love visiting tropical escapes and can’t even fathom what it would be like to live there year-round. Sure I spent 6-12 months in southern Spain, but even they are slammed with rainy months and some miserable conditions occasionally.

I’m talking SUN. Sunshine and blue skies 364 and a 1/2 days a year. Give it to me, baby.

Sometimes I sit back and think I’ve done it all – which is insane. Then all I have to do is pull out a map and realize there’s countless countries and beaches and islands and world left to explore. Sure I love a good ski mountain, but I have only warm places on the brain. Here’s some of the top picks for my tropical bucket list. What’s yours?


Tomash Devenishek

Word for word, I can go through the entire movie of Cool Runnings. It’s hands down my favorite movie of all time, no matter how old I get and how irrelevant it gets. YES I know it’s silly and has very little to do with the destination, but I begged my parents for YEARS to let me go to Jamaica. This might be one of my more frivolous ideas because I know little about the island off the resorts. But I hear beaches are great, live music is fun and it’s well worth spending a week or two there exploring. Or bobsledding.


Jesus Eduardo Vasquez

A few years ago my parents made it to this colorful island and still won’t stop talking about it. They fell infatuated with the funky cuisine that seemed to be always fresh and the blue waters filled with diving and snorkeling opportunities. If I dream hard enough I can see me sipping something fruity after an afternoon swimming with the marine life.

The island is running some incredible accommodation and tour deals too right now which is making it all the more difficult not to grab my plane ticket. Go nuts with all their discounts on car rentals, diving excursions and even resort credits, presented right on the official tourism board’s website. It sounds way better than a boring cruise to me. Check out the offers here.


Shanawaz Sid

India. It’s so massive, so mysterious to me and a place I’ve always wanted to go. A few times opportunities have slipped through my fingers much to my devastation, but I hope it’s in the cards for me soon. I also want to reach the beaches of Goa before it’s totally commercialized and all the hippies have been scared away. There trance music scene and ideal, hammock-laden hostels sound like something I’d dig, big time.

If you’re looking for the BEST possible flight to India, I’d go with the ITA software from Google. For real. It’s industry-known and you won’t find ANY deal online posted for less, promise. It’s pretty easy to use too – try it out.

Greek Islands

Jordi Espel

This is another place that I’ve been dreaming of for  along time, probably ever since I read “The Sisterhood of the Traveling Pants” and wanted to find a hot Greek boyfriend. Well I landed a British one instead but my love for Greece hasn’t wavered. Wouldn’t it be magical to hop on a sailboat (OK chartered because I have no idea in hell how to sail) and just glide form island to island? I need to see it all for myself – some of those views don’t even look real, framed by blue domed roofs and endless miles of turquoise sea.


Author EileenCotterWright

Eileen Cotter Wright is a Boston, MA local and a former London, UK expat. Despite losing her passport the first day she left her home country, she's continued to roam the earth with gusto for more than 16 years. You can keep up with her hot mess adventures on Instagram @CrookedFlight.

More posts by EileenCotterWright

Join the discussion 18 Comments

  • Sophie says:

    I’ve totally go sun on the brain right now. My dream destination right now is actually a Greek island – any Greek island, I’m not picky!
    I’m lucky enough to have been to Jamaica twice on family vacations. We did a lot of resort-y things but we did also take trips out into nature a few times, and spent one amazing day at the Dunn River Falls – you essentially hike through this beautiful area and can walk in the water/swim if you like. Touristy for sure, but incredibly beautiful!

  • Taylor says:

    I’m really wanting to hit up the Greek Islands! Hoping it fits in my travel plans to do so 🙂 Good selections.

  • ben says:

    Jamaica is great. So many beautiful landscape 🙂

  • Find my post on Santorini; you’ll see how magical it is. If you do decide to go, be there around March when there aren’t so many people. Otherwise, the hordes of tourists would just ruin its beauty.

  • I’m seriously jealous of the dog in that picture! I’ve always wanted to go to the Greek islands, and I hope to make it there sometime soon. I’ve been to Jamaica lots of times since my husband is from Negril – we’re way overdue for a trip back next year. His cousin lives in Curacao seasonally, and like you, it’s long been on my list. I’ve heard great things!

    • EileenC says:

      So cute huh Dana?!

      I just got word today actually I will be heading to Curacao in a few week! I was hoping this post would send good juju my way 🙂

  • I would sign anytime for 364 and 1/2 days of sun a year. I can take a cold Canadian winters simply because they come with lots of sun (although very cold), but grey, cloudy days make me depressed. I’ve been to three out of four places on your bucket list (never been to Goa). Pure coincidence, as I too have still lots of countries to see. Thanks for linking up to the #SundayTraveler.

    • EileenC says:

      Thank YOU! I just got word about Curacao in a couple weeks so I’ll be checking one off really soon! Yes I do love the sun, but I love changing season too, so I’ve chosen Boston as my base – but I still can’t get enough of that sun&sand!

  • NZ Muse says:

    Oh, you simply cannot go wrong with the Greek islands. It’s impossible to overstate them!

  • Katrina says:

    Greece is on my “Top 5 Before 35” bucket list. The imagery of white-washed houses and azure water sounds SO delightful right about now! But instead I’ll have to satisfy myself with a quick trip to Boston in two weeks – not exactly the same scene but still beautiful! 😛

  • Christina says:

    Thanks for commenting on my blog bb! These are all on my list! xx

  • Krystle Cook says:

    I’ve been to Jamaica a few times. Very lovely waters but crazy drivers. The guy driving us on a one way cliff with cars passing was like we don’t drink and drive, we smoke and fly.

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