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Best Day Sail Destinations From Key West By Sail

Enjoying the Florida Keys from land is fun, but have you ever gone on a sailing trip from Key West? Chartering a catamaran from The Perry Hotel & Marina Key West is your gateway to explore the 3rd largest barrier reef in the world. And it’s right at our fingertips!

The Florida barrier reef extends 221 miles along the southeast coast, from Key Biscayne to the Dry Tortugas. The best way to explore the reef is to book a yacht charter from Key West and take your time exploring different islands and keys. Bluesail provides guests with sailing catamarans for bareboat or crewed charter in Key West. Each vessel has its advantages, but all offer an exclusive and relaxing escape to discover the best of the Florida Keys.

If you’re searching for things to do in Key West, here are the best destinations that you can travel to by sailing catamaran in one day. Don’t forget the sunscreen!

1. Boca Chica Sandbar

Turn up Jack Johnson and sail to Boca Chica Sandbar, 3 miles northeast of Key West. Pack a picnic, cooler, floats, swimsuit, and sunscreen before embarking on a peaceful cruise under the sun. It’s a quick and easy sailing trip to Boca Chica from Stock Island Marina. Once you’re there, spend a few hours splashing in the shallow waters or paddle boarding to explore the area. Warning: you’re not going to want to leave.

Charter by sail: 4+ hours

Activities: Swimming, paddle boarding

2. Sand Key Lighthouse

There are about 6 lighthouses scattered around the Florida Keys. But Sand Key Lighthouse is an ideal sailing destination from Key West. This 200-year-old lighthouse is built on a sandy shoal and surrounded by a colorful reef. After tying up your private catamaran charter to a mooring buoy, jump in the clear water for a swim or snorkel. You’re bound to see schools of tropical fish, nurse sharks, loggerhead turtles, and healthy coral. Bring an underwater camera to capture the fun!

Charter by sail: 6+ hours

Activities: Swimming, snorkeling

3. Ballast Key

Fun fact about Ballast Key: it’s the southernmost point of land in the United States. If you’re stretching your head because you may have visited an oversized buoy in Key West that reads “Southernmost Point In The Continental United States” then re-read the first sentence. Ballast Key is a 14-acre island about 8 miles west of Key West.

This former private island was donated to the Key West National Wildlife Refuge by David Wilkowsky in 2018. Ballast Key is home to protected wildlife and native plants; the clear, shallow waters surrounding the island are filled with a healthy coral reef ecosystem. Because it’s full of protective wildlife, you can’t actually set foot on the beach. But a day trip past Ballast Key by sailing catamaran is an excellent way to spend the day on the water and (even better) to watch the sunset.

Charter by sail: 8+ hours

Activities: sunset, sightseeing

Ballast Key Day Sail Destination in the Florida Keys

4. Boca Grande Key

Boca Grande Key is an uninhabited island about 14 miles off the coast of Key West. A charter aboard the 40-foot Fountaine Pajot sailing catamaran KAIMANA is the perfect way to cruise to this remote destination. Start your charter in the morning to enjoy a Key West sunrise and a leisurely cruise west toward Boca Grande. Once you arrive and are safely anchored, paddle through the mangroves. It’s an awesome spot to spend the day away from the crowds and in the sun.

Charter by sail: 10 hours

Activities: Swim, snorkel, paddle board, beach

Boca Grande Day Sail Destination in the Florida Keys

5. Woman Key

Woman Key has some of the best coral reef gardens and marine life in the Florida Keys. The water depth ranges from about 3-10 feet, making it the perfect spot to snorkel, kayak, or paddle board. It’s also home to a sandbar that’s safe for swimming. Add Woman Key to your Key West sailing itinerary to enjoy swimming, snorkeling, beaches, and sandbars in privacy. Keep in mind that the southeast side of the key is closed to visitors.

Charter by sail: 8+ hours

Activities: Swim, snorkel, paddle board, beach, sandbar

6. Pelican Shoal

Pelican Shoal was once a haven for native birds, but the island went through a few bad hurricane seasons and the land was destroyed. Still intact is an excellent coral reef that surrounds the shoal. Start your private charter from Key West bright and early for a 6-mile cruise east to Pelican Shoal.

Because it’s further away from shore, the reef has fewer humans and more fish. Snag a mooring buoy and jump into the cool water — you’ll see plenty of marine life including spiny lobster, sea sponges, grouper, parrotfish, nurse sharks, and yellowtail. Sailing to Pelican Shoal is a relaxing way to spend half a day in the Florida Keys.

Charter by sail: 4+ hours

Activities: Snorkel, swim, paddle board

Pelican Shoal Day Sail Destination in the Florida Keys

7. Cottrell Key

Cottrell Key is about 9 miles northwest of Key West and an excellent day trip by sailing catamaran. This mangrove-filled island and its surrounding reef offer exclusive opportunities for snorkeling, diving, or fishing. Because it’s on the Gulf side of Key West, the waters surrounding Cottrell Key are calm, making it an ideal snorkeling and sailing destination. Keep your eyes peeled for dolphins! They love to splash around this private location.

Charter by sail: 6+ hours

Activities: Snorkel, sandbar, dolphins

Dolphins at Cottrell Key Day Sail Destination in the Florida Keys

Set sail from Key West on a 4, 6, 8, or 10 hour custom sailing adventure to discover the world's 3rd largest barrier reef. Bluesail offers private luxury yacht charters from Stock Island Marina Village, including a 40-foot Fountaine Pajot Lucia (KAIMANA), a 44-foot Fountaine Pajot Helia (ROGUE ANGEL).

Each catamaran can accommodate up to 12 guests comfortably on a private bareboat charter with world-class amenities such as air conditioning, a full galley, cabins, and showers. All you need do is select your yacht, choose your preferred sailing duration, and lock in your dates. Then sit back and relax on your private luxury yacht charter.​

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