Gloucester · St. John

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.

Local Delicacies Await

Dive into the culinary treasures of Gloucester and St. John. From fresh seafood markets to local artisan shops, discover the best places to stock up on delicious provisions that highlight the unique flavors of each destination. Whether it's local fish for grilling or tropical fruits for refreshing cocktails, your culinary adventure starts here!

Preorder Provisions

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.