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.
Provisioning
Your Essentials for an Unforgettable Stay
At Anchor & Isle, we believe that a truly memorable getaway starts with thoughtful provisioning. Explore our curated selection of local markets, gourmet shops, and all you need to make your stay seamless and enjoyable, whether you're savoring fresh seafood in Gloucester or tropical delights in St. John.
Gourmet Groceries at Your Fingertips
Find nearby gourmet grocery stores that offer a range of organic produce, specialty cheeses, and locally-sourced goods. With everything from homemade jams to freshly baked bread, you can create a delightful home-cooked meal or pack a picnic for a day by the water. Enjoy the convenience of quality ingredients just a short drive away.
Sip and Savor by the Sea
Enhance your seaside experience by stocking up on regional wines and craft beers. With stunning views as your backdrop, enjoy a sunset toast on your private dock or balcony, savoring the tastes that reflect the essence of coastal living. Our tips for local beverage shops will help you find the perfect pairings for your meals.