From dazzling sunsets and blissful beaches to delicious dining and cozy cottages, here’s how you can plan a romantic weekend on Martha’s Vineyard.
A walk on the beach
Being that Martha’s Vineyard is an island, we are surrounded by many miles of shoreline and sandy beaches. Begin your romantic weekend with a walk on Lucy Vincent Beach, which is open to all.
Spend some quiet time together to see the sunrise and maybe catch a speckled gray and white seal appear from beneath the waves as it starts to fish for the day. Passes are required for Lucy Vincent, except in the offseason.
Book your romantic weekend on Martha’s Vineyard at Menemsha Inn and your pass to the highly coveted Lucy Vincent Beach is included in your stay!
Enjoy a romantic sunset at Menemsha Beach
What could be more romantic than to watch the sunset on another beautiful day on Martha’s Vineyard? And at Menemsha Beach, this is just the place to do that! Known for its beautiful sunsets, Menemsha Beach faces the Vineyard Sound and one of the most spectacular sunsets in all New England.

For direct access to Menemsha Beach be sure to book your romantic weekend on Martha’s Vineyard at Menemsha Inn. When it comes to exploring all the island has to offer, our location in Chilmark makes it easy to experience the best of Martha’s Vineyard. Our guests enjoy access to the famous private beaches of Lucy Vincent and Squiby. Enjoy a relaxing walk to Menemsha Beach and our 300-year-old commercial fishing wharf to witness the best sunsets on the island.
Plan a gourmet meal on the go
If you are spending time exploring the island’s beaches and trails, packing a picnic is a great option for lunch on the go. A centrally located place to outfit your basket is the Black Sheep, a gourmet takeaway and marketplace destination! From Grilled Lemon Honey Shrimp to Mac & Cheese, tasty offerings of the highest quality are always available.
Stroll the streets of Circuit Avenue
Spend some time, hand in hand, window shopping with the variety of shops located on Circuit Avenue in Oak Bluffs. Find everything from restaurants, ice cream shops, clothing stores, art galleries, and more along this quaint street. And don’t forget to take a spin on the historic Flying Horses Carousel, the oldest carousel in America.
Fine dining experience
After a day of outdoor adventures, top it off with a fine dining experience that surrounds you in the natural beauty of the island. Pull up a seat at The Woods, an award-winning restaurant at Lambert’s Cove Inn in West Tisbury. Known for sustainably sourced on-island ingredients, generous portion sizes and excellent service, the garden and grounds are quite beautiful, and the dining room ambiance is truly unique.
Stay in a romantic cottage
Complete your romantic weekend on Martha’s Vineyard with a stay at Menemsha Inn. We offer a variety of accommodations including vacation homes, but for the romantic couple we suggest a stay in one of our cottages. For ocean views, check out our Sea View Cottages, with one and two-story options. Plus, enjoy a plethora of amenities to complement your stay!
Or hop on over to our sister property, The Beach Plum Inn for cozy stays in our bungalows. Nestled throughout the property, the bungalows allow for privacy with sitting porches, water views, and unique island details.

