Anchor & Isle
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.
At Anchor & Isle, our hospitality philosophy centers on creating memorable experiences through attentively curated spaces. Each property in our collection, from The Dock House in Gloucester to Cocoa Tea Villa in St. John, is equipped with premier amenities designed for relaxation and comfort. We prioritize our guests' needs, providing seamless access to both luxurious living and the beauty of the surrounding environments.
+ $250.00A romantic afternoon or evening escape, curated by our private chef in one of our recommended locations, or a location of your choosing. Your host will coordinate with you after purchase to discuss your preferences. Beverages, charcuterie, and ambiance supplied.
+ $100.00Enjoy paddleboard rentals during your stay for a flat fee.
Explore the Waters of Gloucester with Fishing Charters
Set sail from The Dock House on unforgettable fishing charters that bring you face-to-face with the rich marine life of Gloucester. Whether you're a seasoned angler or a novice, our local guides ensure an exhilarating experience on the water, surrounded by stunning coastal views and the charm of New England's fishing heritage.
Hook into an array of species, from striped bass to bluefish, in the bountiful waters just steps from your stay. With knowledgeable captains at the helm, you'll learn tips and tricks to make your fishing adventure a success while enjoying the breathtaking views of the coastline along the way.
After a day of fishing, return to The Dock House to relax on the private dock, soaking in the stunning oceanfront views. Enjoy the tranquility of the sunset as you recount the day's adventures, making it the perfect end to your fishing escapade in Gloucester.
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