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Home » Blog » Sailboat Living

Setting Sail for Cuba

Posted: May2,2017 | Modified: April 9, 2022 | by Karen

Night Passage

sailing as the sun sets - heading to Havana
Headed to Havana on an overnight passage.

There is no deeper darkness than a night passage, sailing on a moonless night. We're 50 miles off the coast of Florida, with full sails headed to Cuba. It has been a while since I did a night crossing and I will admit to a certain nervousness when pitch black is all I see beyond the bow. Sitting alone at the helm with nothing but the glow of our radar, I can see that there are other vessels navigating these waters - distant lights on the horizon. Right now, I'm alone in the darkness.

I took the helm from Ben three hours ago…one more hour to go. The hardest part of this watch was getting up at 1 am and staying alert. So far I have only had to dodge an oil tanker and a cruise ship, all the other AIS (Automatic Identification System) signals on the radar are other boats in the rally headed the same direction as us - south to Cuba.

I can't help but wonder what Ben was thinking during his first solo night watch. When he was younger our family lived aboard a sailboat full-time and night passages were special. Back then, both of our twin sons, Ben and Jack, would groggily get out of their birth to help with a night watch. Our helm was exposed to the wind and elements, so the boys would wrap in a blanket and snuggle under our armpit, clutching a mug of hot chocolate, sucking on Hot Tamales, reading Emily Dickinson, talking. Those were special times indeed.

Our passage from Key West to Marina Hemingway in Cuba is 90 miles. We started across at sunset so that we could arrive in the light of the day. For our catamaran, Snowcat II, this crossing will take about 16 hours. The traditional monohull sailboats in the rally will take longer. This is a relatively short trip when compared to the 16 days that our family sailed crossing the Atlantic in 2002…but that's another story.

Our family has been intrigued with Cuba, ever since we heard the late-night cheers of Cubans setting foot on the beach of Dry Tortuga.  They'd made it to U.S. territory - eight people in a dilapidated boat - resilient people from a nearby country that we could only fantasize about.  Twelve years ago we had to navigate around Cuba as we sailed from Florida's Dry Tortuga islands to Honduras, but we always hoped to visit one day.

Our lives have changed since then.  We sold Snowcat after four years and 15,000 miles of sailing.  When we left on our adventure, the boys were seven years old, Dean had his own environmental law firm in Denver and I was teaching nutrition at a local college.  When we sold the boat in Honduras and returned to the U.S., the boys were in middle school and Dean and I were ready for a new life.  We didn't know if we could find jobs in Steamboat Springs, but we decided to throw out our anchor and see if it stuck...it really stuck!

Now we are sailing Snowcat II to Cuba.  The boys are in graduate school with busy lives of their own but amazingly they found a way to join us for a reunion of sorts.  All of the Massey's together for one more sailing adventure.  Cuba here we come!

Massys Sail Cuba -4-2
Massys Sail Cuba -3-1
Sailing-to-Cuba
Sailing on Snowcat to Cuba
Snowcat-at-Marina-Hemingway
Boat-Parada-Havana-Harbor
Massys Sail Cuba -85-36
Havana-Harbor-from-Hammock
Massys Sail Cuba -66-31
Havana-Harbor
El-Morro-from-Snowcat
Sailing-Coast-of-Cuba
Cuban Cars
Massys Sail Cuba -56-27
Massys Sail Cuba -34-14
Massys Sail Cuba -16-6
Massys Sail Cuba -12-4
Exploring Havana
Massys Sail Cuba -92-38
Cuban-Cuisine
Massys Sail Cuba -36-15
Massys Sail Cuba -37-16
Massys Sail Cuba -39-18
Horse-Power-Rural-Cuba
Masseys in Vinales
Plantains-for-sale
Massys Sail Cuba -49-23
Cigar-Shop
Cuban Cigar Maker
Cigar-Souvenir
« ‹ of 2 › »

2

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  1. RITA Taylor says

    May 13, 2017 at 5:51 am

    Karen,
    So wonderful your family is sailing together to Cuba.
    Enjoyed reading the posts.
    And seeing the photos.
    Loved the reminiscing of when they were younger.
    Your friend,
    Rita

    Reply
    • Karen says

      May 15, 2017 at 5:42 pm

      I'm so pleased that you found my blog! Thanks for your comment - you're right, the family sailing trip to Cuba was wonderful.

      Reply
  2. Jill Paradis says

    May 09, 2017 at 9:27 am

    Amazing and inspiring Karen! Thank you!

    Reply
  3. Laura von Boecklin Mulkey says

    May 04, 2017 at 6:19 am

    Thanks for sharing your adventure, Karen! I see a book in your future.

    Reply
    • Karen says

      May 04, 2017 at 6:44 am

      I'm not so sure about a book, but I do enjoy writing about our sailing adventures. Thanks for the comment!

      Reply
  4. Edie McSherry says

    May 03, 2017 at 8:32 pm

    Karen,
    Loved reading about and seeing photos of your family sail to Cuba! Looks amazing. Can't wait to hear more.

    Reply
  5. Jamey says

    May 02, 2017 at 12:54 pm

    Fabulous....I could almost feel the wind in my face as I was looking out at the night sky! Wow Karen, this is such a great adventure and I can hardly wait to read the next segment.

    Safe travels.

    Reply
    • Karen says

      May 03, 2017 at 9:08 pm

      Thanks Jamey! Dean is writing a post about the sailing aspect of the trip next.

      Reply
  6. Lyndy says

    May 02, 2017 at 12:24 pm

    Love going on life's adventures with you - in many ways! Cuba is an amazing country. Let's hope and pray that the relationship between our two countries continues to improve.

    Reply
    • Karen says

      May 03, 2017 at 9:06 pm

      I agree, Cuba is an amazing country with a lot of changes ahead. We particularly enjoyed the meeting the people.

      Reply
  7. Geri and Laurie says

    May 02, 2017 at 11:51 am

    Karen, Dean, Jackson and Ben!

    We are thrilled that you are headed out for a new adventure on Snowcat II. Of course, we are just a little jealous! We will look forward to your fabulous descriptions (and pictures) of your adventure. Besides perfecting mojitos, I am sure you will enjoy amazing Cuban cuisine. Have tons of fun!

    We wish you fair winds and smooth seas.

    Reply
    • Karen says

      May 03, 2017 at 8:59 pm

      Stay tuned...I've been working on a recipe for Mojitos for a Crowd. I'll post it after a few more batches.

      Reply
  8. Joy AKEY says

    May 02, 2017 at 10:05 am

    LOVED reading your post! What an exciting adventure! Hope you enjoy every minute of it!!

    Reply
  9. Jan DePuy says

    May 02, 2017 at 9:39 am

    The Massey's are off on another exciting adventure! Please keep these posts coming. I'm enjoying the trip along with you! Have fun!

    Reply
  10. Kaye Kasza says

    May 02, 2017 at 8:21 am

    Karen, I'm excited to hear about your trip to Cuba! What an adventure!

    Reply
  11. jstimson says

    May 02, 2017 at 7:25 am

    Wonderful. Thanks for bringing me along!!

    Reply
  12. Kristiana Petre says

    May 02, 2017 at 7:09 am

    Karen - what an amazing adventure for you all - I am sure it will be more than special. Did you know that Kenny is in Cuba right now?? How life has changed - all good too! Enjoy your adventure my friend - Kristiana

    Reply
    • Karen says

      May 03, 2017 at 8:55 pm

      Thanks for letting me know about Kenny. I'll have to compare notes with him because I'm already trying to figure out how to go back!

      Reply
  13. Nancy Mucklow says

    May 02, 2017 at 6:56 am

    Karen, this brought tears to my eyes! Such a special trip, amazing memories adding to amazing memories for you and your family! Thanks for sharing!

    Reply
    • Karen says

      May 03, 2017 at 8:53 pm

      Yes - it was a special getting the family together for one more sailing adventure!

      Reply
  14. Barb Parnell says

    May 02, 2017 at 6:50 am

    It sounds amazing! What a beautiful description.

    Reply
Karen and Dean hiking at Grand Targhee, WY

Hello - I'm Karen!

I live in Steamboat Springs Colorado, "The Boat" with my husband Dean. This blog is a place for us to share our love of sailing, food and life in The Boat.

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