Sailing the Leeward Islands with Sunsail

I’ve been very lucky to visit a number of incredible destinations. As a result, people always ask me about my favorites. Favorite city. Favorite trip. Favorite airline. The truth is I don’t have many favorites… except one, sailing! I absolutely love sailing. A week on a boat, exploring islands with your best friends, floating in the ocean as the sun sets in the distance. It doesn’t get much better in my option.

sunsail yacht sailing travel photography sunset

Now I’m not talking cruise ships or yachts. When I say sailing I am referring to a 50’ monohull or catamaran, eight friends, one skipper, and the wide open ocean.

sunsail yacht sailing travel photography

I promise you, if you have not been sailing, now is the time! There are a number of companies, such as Sunsail through which you can rent a sailboat and chart your own course, or others such as The Yacht Week or Sailing Collective that organize highly curated group sailing journeys. I’ve tried them all and no matter which you choose you’re guaranteed to have an amazing adventure.

It had been a while since I was on the water so I organized a group of friends and decided to explore the Leeward Islands. We flew in and out of St. Maarten (SXM) and spent the week exploring St. Maarten, Anguilla and St. Barths. Each island was unique and stunning. The food in the Leewards is highly French influenced, and as a result, divine. We spent our days hopping from bay to bay, snorkeling and sunbathing. After sunset we’d escape to shore to dine and drink the night away.

sunsail yacht sailing travel photography

My time sailing the Leeward Islands was absolutely perfect! It was great to get off the grid for a week, relax in the sun, and explore new and exciting places. If you’re looking for a unique and adventurous vacation, sailing is the perfect choice!


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