Captain Holly

With Flyaway Charters, the goal is simple: give you the best possible day on the water and a Virgin Islands experience you’ll remember long after you leave.

🔹Favorite Snorkeling Spot
Indians or Horseshoe Reef Anegada

🔹Favorite Lunch Stop
Sydney’s Peace and Love JVD
Coco Maya VG

🔹 Favorite Spot to Anchor and Chill
Fallen Jerusalem VG

🔹 Favorite Spot to take a First Time Visitor
Sandy Spit is always a beautiful and doesn’t disappoint.

🔹 Favorite Beach
Spring Bay VG

Originally from Athens, Georgia, where she began her career in real estate, Holly traded life on land for the sea and never looked back.

Her sailing career began aboard the 160-foot schooner Arabella, crewing throughout Newport, Rhode Island, and Martha’s Vineyard before sailing south to the Virgin Islands. Once in the Caribbean, she continued aboard Arabella, hosting term charters throughout the U.S. and British Virgin Islands.

Over the years, Holly worked her way from professional crew to freelance captain and has now called the Virgin Islands home for 18 years. With 12 years as a captain, she has extensive experience operating a wide variety of sailing and power vessels throughout the Caribbean.

Her years on the water have given her an exceptional knowledge of the British Virgin Islands—from iconic destinations to tucked-away coves, beautiful snorkeling spots, beach bars, and those special places that can turn a great day on the water into an unforgettable one.

As a captain, Holly brings together experience, local knowledge, safety, and genuine hospitality. She pays attention to the details and tailors each trip around her guests—whether that means adventure and snorkeling, exploring the islands, finding the perfect lunch spot, or simply slowing down and enjoying a beautiful day in the Caribbean.