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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.
Blog
Explore Gloucester’s Coastal Wonders: Halibut Point & Hidden Tide‑Pools
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
The One‑Legged Seagull and the Boat Captain of Gloucester
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, 2026Gloucester’s Fishing Legacy: A Storied Past Meets Oceanfront Luxury
Trace 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
Gloucester Summer Escapes: From Cozy Bookshops to Seaside Strolls
Discover local favorites—from independent bookstores to oceanfront trails—for a relaxing and enriching stay in Gloucester.
By k8 · June 8, 2026Discover Gloucester’s Coastal Charm: Hidden Beaches, Harbor Dining & Natural Wonders
Unwind 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, 2026Gloucester on the Water: A Local’s Guide to Seaside Charm and Practical Pleasures
From 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, 2026