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.
Fishing Charters
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.
Catch of the Day
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.
Relax and Unwind After Fishing
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.