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.
Discover Halibut Point State Park’s dramatic quarry‑turned‑coastal preserve and tide‑pool trails—just minutes from your oceanfront retreat in Gloucester.
By k8 · June 8, 2026
Discover the charming tale of Mentoni, the Gloucester boat captain whose one‑legged seagull companion perches on his shoulder—adding a touch of local magic to your oceanfront stay.
By k8 · June 8, 2026Trace Gloucester’s evolution from humble 17th‑century fishing outpost to an enduring maritime heart, all from your oceanfront retreat with panoramic views and private dock.
By k8 · June 8, 2026
Discover local favorites—from independent bookstores to oceanfront trails—for a relaxing and enriching stay in Gloucester.
By k8 · June 8, 2026Unwind in oceanfront luxury and explore Gloucester’s best—from tide‑pooling at Halibut Point State Park to waterfront dining and charming indie bookshops.
By k8 · June 8, 2026From hidden coves to local essentials, discover how to make the most of your oceanfront getaway in Gloucester, MA—whether you’re paddling at sunrise or stocking up at the Market Basket.
By k8 · June 8, 2026Hear first when this host opens direct rates or adds a new place.
