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Sailing Greece

For about as long as I can remember I’ve wanted to charter a sailboat and sail the Greek Isles. Since we were already over here we decided this would be the year. We just sent in our contract and deposit and I’m so excited. My friends and I got together and chartered a boat and a skipper for 7 days in July. With that you get your own cabin, breakfast, and lunch (dinners are eaten on land) and then you sail around from island to island. In a lot of ways its all the conveniences of a cruise ship: you don’t have to move your luggage around, you always have a place to sleep, meals are provided. But it is on a much smaller scale. There will only be 8 or 10 people on the boat, there isn’t bad food and we can stop at anytime to swim. My friend sailed around Italy and Greece a few summers ago and said it was so great because you would sightsee and explore all day and then the next morning you would sail to a different town so there was built in down time. You could relax and read on the deck of the boat. Sounds perfect to me! While I think it might be interesting to do with kids Paul’s parent’s will be staying with us and agreed to babysit so we’ll be leaving the kids home this time.

One thing that surprised me is how affordable it was. It is about $230/night total per couple and when you consider that includes two meals, some tour guiding, lodging and transportation its probably cheaper than if you took a train, ate in restaurants, and stayed in hotels.

Have you ever gone on a long sailing trip? Should we worry about sea sickness?

photo from Michiel_

  1. Helena - A Diary of Lovely

    April 11, 2011

    That's amazing! Im part Greek myself and always go back in the summer but have never done something like that. Everybody who has done it though speak wonders and come back very very excited!

  2. Jennifer

    April 11, 2011

    I haven't done it myself (lucky you!), but my girlfriend lived in dread of a sailing trip around Italy with her sailing-fiend husband because she often gets seasick…and she was completely fine! She had a wonderful time! Wishing you much the same. Enjoy!

  3. Where My Heart Is

    April 11, 2011

    I've always wanted to go to the Greek Islands so I can't wait to hear all about it.

  4. Chris

    April 11, 2011

    woo-hoo. My husband and I spent 3 weeks sailing around the greek islands with a group of friends many Mays ago. To this day, one of the most memorable trips ever. It was gorgeous, leisurely, and a new way to travel. I didn't get seasick but my husband did. It didn't last long. None of our group really had an issue with it but those seasick bands and a few meds could be good to pack just in case it strikes. Are you taking the boys?


  5. amy turn sharp of doobleh-vay

    April 11, 2011

    You will love it. I lived on Mykonos after college. I have friends there! Let me know if you plan to go and I will have you meet him! Locals are the best!xo

  6. sherri lynn

    April 11, 2011

    what an amazing trip! that water is so crazy blue. can't wait to hear stories and see pictures!

  7. Miss K

    April 11, 2011

    Do you have a life list? Because it sounds like you are making so many of them come true! Bravo!

  8. janis

    April 11, 2011

    This sounds like an absolute dream!

  9. meenal @ maison marigold

    April 11, 2011

    that sounds like a dream holiday..xx meenal

  10. LoGunns

    April 11, 2011

    This sounds wonderful! I got to go on a sailing with my friends family through theCarribean for a week when I lived in venezuela. Never got sea sick. I'm very excited for you!

  11. Kate

    April 11, 2011

    I sailed the Med with my family for 2 years. It's definitely an amazing experience and a great opportunity to see places and cultures normal methods of transportation won't give you access to. The waters in Greece are typically fair and the anchorages/harbors are usually well protected. If you think you may get sick, stay on the aft deck until you know for sure! Smooth sailing!

  12. communikate.

    April 11, 2011

    Oh man! Jealous! My family has talked this about doing this forever but have yet to make it happen! Hooray for you!

  13. Gina

    April 11, 2011

    I have done a few of these trips with my family to the British Virgin Islands and the Grenadines, Greece is next on our list. We didn't have a skipper because we sail ourselves but it is the same idea. We always rent through Barefoot Charters. You will have an amazing time. Like you said, it's the perfect mix of sightseeing and downtime. If you are worried about seasickness, there is this German gum called Superpep. I'm sure you can find it at a pharmacy over there (my aunt get's it from one of her flight attendant friends). I have no idea what is in it, but it is a miracle. Have fun!

  14. Bethany

    April 11, 2011

    It's much better to be prepared for seasickness than not. I'd suggest ginger pills, which we always had on hand for guests when we would sail in SF. Greece should be much smoother sailing, but you never know. Also, if you're feeling queasy, don't go below deck. Stay on deck and focus on the horizon. Driving the boat is the best way to get over it. You're vertical, you're focused on the horizon, and your mind is busy. Have fun!

  15. Nicole Marie

    April 11, 2011

    lucky lucky lucky!!!!!!!!

  16. Ashley

    April 11, 2011

    Jordan, how exciting! My fiance and I are getting married in late May and are off to Greece and the Greek islands for our honeymoon and cannot wait! YAY!

  17. Anonymous

    April 11, 2011

    is there a website to check out?

  18. The Parkers

    April 11, 2011

    What an amazing trip that sounds like! Really can't wait to hear all about it. I would LOVE to know what company you are using for future reference…..I want to do this to now!

  19. Sarah

    April 11, 2011

    Look at that water! So beautiful.

  20. kh

    April 11, 2011

    And if you have a chance to visit Turkey while you're in the area, DO. I just got home and absolutely loved it.

  21. Erin

    April 11, 2011

    How fun!! I agree with others above that you should be prepared with ginger (even candied), etc. I used to get pretty sea sick on the SF bay, so when I when we chartered a large catamaran in the Caribbean, I went prepared with cute plastic sea band type things that are also used for morning sickness (they come in different colors with little designs on them) that I got off Amazon and non-drowsy Dramamine that I ended up taking twice. I found laying on the front trampoline cured my seasickness best.
    What islands are you visiting?

  22. Alyssa Coberly

    April 11, 2011

    I have done a few dive trips where we were on sail boats – OH ITS AMAZING … just bring a nice wide brim hat since shade is usually hard to find on the boat – and going down below deck is not nearly has fun (and if you get sea sick that will be the place you get it) I didnt get seasick but I know some of the people wore 'the patch' ginger and peppermint essential oils work good too!

  23. Kasey

    April 11, 2011

    i'm starting to think you are independently wealthy;-)

  24. karen @ our slo house

    April 11, 2011

    My husband has wanted us to charter a boat and do this same thing for forever. We would go with certain family members (but only the ones that we could stand to be trapped on a boat with!) LOL, but I'm serious.

  25. Cindy

    April 11, 2011

    That sounds AMAZING! When I am on a cruise ship I get severely seasick, but when I'm on a smaller sailboat I don't. I think it has to do with seeing the water and seeing the movement that you're experiencing that is in part responsible. I think you'll be fine, but bring some seasickness/nausea pills just in case (: Have fun!

  26. Denise Laborde

    April 11, 2011

    Sounds wonderful! Friends did it last summer sans kids and loved it! Another set of friends did it with kids and liked it too. I think it would be fun with older kids (5yrs+) but would SO welcome the idea of leaving the kids at home. Score!

    More than worry about sea sickness, I would just prepare for it. Thoroughly.

  27. fanciful no.2

    April 11, 2011

    amazing. i know its not good to be jealous, but…
    i would love to get back to greece one of these days, and this looks like the perfect way to do it. can't wait to hear all about it!

  28. kelli

    April 11, 2011

    I'm with you- ALWAYS wanted to do Greece. (My husband's favorite vacation was Greece on motor scooters with his family.) I've sailed Turkey with my family and one other for a week and it was incredible. Fresh fish and salads for every meal. I love that culture. But yes- seasickness got me. I hope it misses you.

  29. Monica

    April 11, 2011

    I never get seasick so I've never had to worry about that. I've been to the Greek island of Corfu (beautiful) when I was 12 and have always wanted to go back. This sounds like my absolute dream vacation. Thanks for the idea!

  30. Funnelcloud Rachel

    April 11, 2011

    OMG – this is my dream! Can't wait to see pictures from your trip!

  31. Tawnee

    April 11, 2011

    Looks amazing! How how i romanticize sailing! Dream of it! then I go and can't stop being seasick (it is always worth it).

  32. likeschocolate

    April 11, 2011

    I have some friends who did this in Turkey and loved it. Have a blast.

  33. Sara

    April 11, 2011

    My husband and I sailed for two weeks in the Dodecanese Islands; can't recommend the experience highly enough. We especially loved this itinerary because the islands were mostly very small, and well off the standard American tourist track. We also did a day trip to Ephesus in Turkey; fabulous.

    Plan to go back someday with children in tow, as it would be a great destination for children.

    I get motion sick, though in cars worse than boats, and I was fine with a daily prescription pill (probably didn't even need that most days).

    And, genuine question here, not judgment: how do your kids do with you away for long periods at your age? My youngest are 5 and 18 mos; my 18 mo old is just now OK away for a night, but I think he'd struggle with more than a few days (and that's being left with daddy, who is clearly his favorite parent :) ).

  34. Moriah

    April 11, 2011

    that sounds amazing!! Something I would like to add to my own bucket list! That photo is breathtaking as well.

  35. Carrie

    April 11, 2011

    Sounds like you just helped me plan our next vacation. But unfortunately I struggle with motion-sickness. And the older I get, the worse it gets. I usually try to stick it out, but it is tough! On my last sailing trip, a veteran sailor with me said that he still gets sick almost every time he goes out…but that it was worth it!

    Have a blast and I can't wait to hear all about it!

  36. eva burns

    April 11, 2011

    Holy moly! That sounds amazing. I can't wait to see the photos and hear about your trip. BTW, I've been following your blog lately. I love reading about your adventures in Paris. Such an inspiring story!

  37. redmenace

    April 11, 2011

    Oh happy day, indeed! A dream come true. I'm thrilled for you!

  38. jordan

    April 11, 2011

    @Sara I know some kids get separation anxiety but so far neither of my kids have. (knock on wood) We've taken several week long trips and even took a 14 day trip to Brazil when Moses was 16 months. But after 10 days the trip starts not being fun because we missed him. It helps that Paul's mom is amazing with children. She can get them to nap when even I can't. We wouldn't be able to travel if we didn't know they were in safe trusted hands.

    In general I believe its healthy for moms and kids to have time apart. Kids need to learn that their mom will always come back.

  39. Julie Karatzis

    April 11, 2011

    Have you factored in the docking fees at each port? I've wondered about how much that would add onto everything else. So happy you're going to Greece though. My family is from Kefalonia and I will be there all of August, so ping me if you guys want a tour :)

  40. jess @ fushmush

    April 11, 2011

    I spent a week sailing around the Whitsundays in Australia with my husband. I suffer a little bit from motion sickness but found that I was fine on the boat.

    However, it was a different story when the week was over and we returned to land. I suffered from sea sicknesses on our first night back on land. The restaurant we went to wouldn't stop rocking!

    Might not be a problem for you though as you will be spending more time off the boat than we did.

  41. Christie in Jersey

    April 11, 2011

    Go to the island of Santorini! The village of Oia is absolutely breathtaking.

    Who are you using to charter your boat? That sounds amazing

  42. Alice Q. Foodie

    April 11, 2011

    My husband did this trip with some friends when they graduated from law school – he actually skippered it himself (he has a bareboat certification) but swears he wouldn't do it again. We also chartered a boat in Belize five years ago with some friends (hmmm….sounds like we're due!) and had an absolute blast. No seasickness there, but the water was like glass. Email me if you want some tips – I am sure he will have some for you!

  43. Sigrid

    April 11, 2011

    We have charted boats, manly in the San Juan Islands near Seattle where it is cool and a bit rougher water at times. I would imagine you will have smoother seas and warmer weather in Greece in July! You are spot on, sailing is greatly relaxing and nice to bring your bed with you. Nothing like it. In fact, sailing is actually our living in Europe plan. We are saving up to take a long summer, and 'live' in Europe by way of our own boat. Not such a wild idea ~ did you know about this ( Greece has always been our dream trip, can't wait to hear about your experience. Sounds divine!

  44. corinne

    April 11, 2011

    how totally exciting!!

  45. Christie Chase

    April 11, 2011

    How awesome! I sailed the BVI with 12 family members on a Catamaran last year, and it was such a unique experience. I think you are wise to leave the kids at home…it would be really stressful to watch them in such tight quarters, and there is a lot of climbing around that you do on a Catamaran. Those prone to sea sickness got a patch from the doc before setting sail. My husband is really affected by sea sickness and he wore the patch the entire trip and did great. It may be worth getting some patches from a doctor in the states if you have opportunity before you sail. Have fun!

  46. Geeta

    April 12, 2011

    That sounds amazing.. I'm Waters-of-Greece-Green/Blue with envy :)

  47. little t

    April 12, 2011

    This sounds amazing- I would love to do this!!

  48. Joydip

    April 12, 2011

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    April 12, 2011

    I did a similar 45 foot sailboat charter to get from Panama to Colombia in January! It was a 5 day trip and we hit rough seas the last two days which made that part miserable! I would definitely take at the least over the counter meds with you and you may want to look into a Scopolamine patch, which your doctor can prescribe for you. It lasts for three days and you don't have to worry about taking any meds while you have it on! You can read about my adventures on my blog:

  50. Corrie

    April 12, 2011

    That sounds truly lovely. Take lots of photos so we can live vicariously through you! :)

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