Day 1
Ease into your romantic escape by exploring Martha's Vineyard’s quintessential towns and their vibrant arts scene, soaking in coastal charm and creative energy together.
Stroll Through Edgartown’s Historic Streets
Begin your getaway by wandering tree-lined streets and exploring beautiful whaling-era homes in Edgartown. Take in the charming shops and quaint cafes that showcase the town's rich heritage and relaxed coastal vibe.Browse Local Art Galleries in Oak Bluffs
Experience Martha's Vineyard’s artistic spirit at galleries like Alison Shaw Gallery and Featherstone Center for the Arts. Enjoy diverse works from local artists and consider picking up a creative keepsake.Sunset Cocktails on the Harbor
Relax with a pre-dinner drink at a waterfront bar, such as The Atlantic or The Port Hunter in Edgartown. Toast to your romantic escape while watching the sun set over the sailboats in the harbor.Live Music at The Ritz Cafe
Cap off your first night at The Ritz Cafe in Oak Bluffs, a local favorite for live music and a lively, laid-back atmosphere. Check their events schedule for bands or open mic nights!Walking Tour of Gingerbread Cottages
Take a self-guided tour through Oak Bluffs’ famous Gingerbread Cottages at the Martha's Vineyard Camp Meeting Association, marveling at whimsical Victorian architecture and vibrant colors.