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4 islands…6 friends…12 days

I’m getting ready for my summer sailing trip. My husband and I will fly St. Martin, where we will charter a sailboat from the Moorings. With four friends, we’ll sail the clear blue water around St. Martin, Anguilla, St. Bart’s, and Saba.


Living on a sailboat for over a week is a life changing experience. The bathrooms are small, the air conditioning may not work, and the only way to get to most islands is to swim or take a dinghy. It’s not a glamorous endeavor.

But on what other trip can you get rocked to sleep by the gentle roll of waves? Or drink a glass of wine with sea life below you and the Southern Cross above you? Ah, life is so simple when all you worry about is where you left your book, which sunscreen to apply, and whether it’s time for a boat drink. It’s nothing short of magical.


With all that said, having six people on a boat for twelve days can create a few questions about what to pack. We’ve sailed other islands before, including two trips around the British Virgin Islands, so I’ve had a few opportunities to overpack, under pack, and pack all the wrong things.

With all this experience, I thought I’d share with you the right things to pack. Here are a few highlights of what I’m taking this time around ~

  • 2 TERVIS TUMBLERS WITH LIDS. The boat is stocked with some essentials like silverware and plastic dinnerware but there are no Tervis Tumblers. Keeping my drink cold on the sailing trip is one of my only responsibilities, so I take it seriously.
  • 2 WINE THERMOSES. I bought these at Nordstrom rack. They hold an entire bottle of wine and the airtight, screw top makes them ideal for travel. An added benefit is that they keep beverages cold all day. I’ll use them for water and the occasional vodka and soda.


  • SUNSCREEN. These days I like Sun Bum for my body. It has fewer bad chemicals and the smell takes me back to my Hawaiian Tropic filled teenage years. I’m taking a variety – lotion, sprays, 15, 30, 50. For my face, I use something with titanium dioxide and zinc oxide and a 50 SPF.


  • 4 BEACH TOWELS. The Moorings provides bath towels but not beach towels. There’s no washer or dryer on board, so I’ll bring 2 for me and 2 for my husband. Depending on how often  we use them, we may have to wash them at a laundromat on one of the islands.
  • POLARIZED SUNGLASSES. Polarized lenses protect your eyes from the sun and enable you to see color variations better than regular lenses. The water is even more beautiful when seen through the right glasses.
  • VIBRAM  5 FINGER SHOES. These shoes are a game changer. They are like gloves for your feet. The idea is that your feet are healthier when you engage each toe. The hard rubber bottoms also protect your feet while snorkeling and walking in the water. When on vacation, I exercise in them. Not having to pack running shoes saves me a lot of space in my suitcase.


  • 2 PAIRS OF SANDALS. 1 casual. 1 dressy. Dinner at an upscale restaurant in St. Bart’s or Anguilla will require a fancier sandal with a little bling.
  • 5 BATHING SUITS. I’m taking mostly solids so I can mix and match for different looks.
  • 6 COVER-UPS. When sailing and island hopping, you spend most of your time in bathing suits and cover-ups. Think laying around reading, jumping in the water to cool off, and snorkeling. I take more cover ups than anything so that I feel stylish and fresh without much effort. And a chic cover up is essential for an island lunch.
  • 2 FUN NECKLACES. What makes a simple sundress chic? The right accessories. Here’s one that I’ll be packing to wear to a fun, island dinner.


And last, but not least…

  • 2 BOOKS. Everything Asian by Sung J. Woo. A reviewer said that it’s a charming tale about a Korean immigrant family. I’ve read a short story by Woo. He has a masterful way with words. And my second book is Beautiful Ruins, which I’ve been saving just for this trip. 

10walter "Beautiful Ruins" By Jess Walter

Life on a boat is the perfect mix of solitude and bonding with friends. Some of my favorite memories were born on starry nights on the back of a sailboat. Sailing is also a perfect reminder that less is more.

So whether you’re sailing or flying or driving or walking…travel light.

Life’s too short to get weighed down.


Karena Kilcoyne

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