Anchor & Isle
Distinctive Seaside Stays
Anchor & Isle is a curated collection of premier vacation properties bridging the historic shores of Gloucester, Massachusetts, and the tropical paradise of St. John, USVI.We connect discerning travelers with handpicked waterfront retreats designed for seamless, elevated living. Every property features spectacular coastal views, thoughtful design, and direct proximity to the water.
Water Toys
Explore Our Exclusive Water Toys Collection
Dive into adventure with our selection of water toys perfect for your seaside getaway. Whether you're looking to paddleboard, kayak, or just lounge by the dock, these experiences will enhance your stay at Anchor & Isle, where the ocean is your playground.
Kayaking in Gloucester’s Coastal Waters
Experience the breathtaking beauty of Gloucester from a kayak. Paddle through tranquil waters while enjoying stunning views of the coastline and local marine life. This unique vantage allows for unforgettable memories and picturesque moments, whether you're gliding alone or with family.
Relax at Our Private Dock
Unwind at The Dock House’s private dock, where relaxation meets stunning coastal views. Enjoy a peaceful moment in the chairs, drink in hand, as you watch the sunset paint the sky in vibrant hues. This spot is perfect for soaking in the tranquil ambiance of Gloucester’s waterfront.