Nicaragua Sailing Charters

Nicaragua’s vast blue Pacific ocean offers one of the most beautiful and unspoiled sailing destinations on the planet. San Juan del Sur, the base of our sailing charters, lies on a stunning half-moon bay framed by dramatic headlands pointing into the sea.

North and south the coastline combines the thrill of blue water passages with the serenity of sheltered, sandy bays and streches of silvery beaches. Our crewed sailing charters on Gypsy offer a unique way to explore this stunning coastline. Prepare to be enthralled!

We’ve listed our most popular crewed sailing packages below. But we can also build a sailing itinerary designed for you. Just tell us how many days you would like to spend sailing and we’ll do the rest. Want to a sailing charter with some Nicaragua surf? No problem. Just start by filling in your preferences on our custom vacation page.

Our most popular sailing packages:

Nicaragua sailing1 Day Sail to a hidden coastal bay An 8 hour sailing experience to a beautiful beach south of San Juan del Sur. Our guests swim, surf and explore the beach and there’s also the option for some fishing. But don’t worry about catching your lunch, we pack a delicious meal and refreshing drinks. On our return leg, we serve sunset cocktails on deck and watch the cliffs slowly turning pink as we sail into the bay. It’s the perfect way to round off your sailing adventure. Book your 1 day sail.

Nicaragua surfing and sailingSail the entire Nicaraguan coastline and surf all the major breaks This is the ultimate surfing and sailing experience. Over an action packed 7 days you get to see the entire coastline and surf it’s best breaks. We’ve selected 5 beautiful spots to overnight on shore. At each stop we’re welcomed by our road team ensuring that everything is taken care of. But there’s more than 5 stops along the way, we make sure we surf all the best breaks and chase down the swells. We offer this tour on only 2 dates each year. Register your interest in this ultimate adventure trip.