1. Oak Bluffs
2. Overview: Begin your adventure in Oak Bluffs, known for its whimsical and colorful Gingerbread Cottages, a true architectural marvel dating back to the mid-19th century. Stroll along Circuit Avenue, the island’s lively main street lined with boutiques, galleries, and eateries. The area exudes a vibrant, family-friendly atmosphere perfect for leisurely walks and people-watching. Rating: 4.8/5
3. Visit Duration: Morning until early afternoon
4. Must-Try Delicacy: Lobster Roll at Linda Jean’s Restaurant