A unique idea for a date night, kick-off to a girls’ night or fun thing to do with family from out-of-town night!


Hey, adventure seekers! Looking for the perfect evening escapade? Look no further than Oak Bluffs, the charming coastal town that will steal your heart! Join us for an unforgettable journey as we sail through the sparkling waters and create memories to last a lifetime.

Picture this: a serene sunset painting the sky with vibrant hues, gentle ocean breezes caressing your face, and a drink in your hand as you travel with us. With Hy-Line Cruises, you’ll experience all this and more on your voyage to Oak Bluffs.

Upon arrival, prepare to be captivated by Oak Bluffs’ unique character. Its historic Victorian cottages, adorned with colorful gingerbread trim, will transport you to a whimsical wonderland. Explore the picturesque streets, indulge in delectable seaside cuisine, and browse the quaint shops brimming with treasures. There’s something for everyone!

Whether you’re seeking relaxation or adventure, Oak Bluffs has it all. Stroll along the sandy shores, feel the sand between your toes, and take a refreshing dip in the cool Atlantic waters. Or maybe you’re up for cycling through town and grabbing a great meal at one of the many local restaurants in town? The possibilities are endless!

Don’t miss the chance to witness the famous Flying Horses Carousel and the Gingerbread Cottages, enchanting visitors of all ages. And if you’re up for a bit of nightlife, there are cozy waterfront bars and lively entertainment venues waiting to add some sparkle to your evening.

So, gather your loved ones, pack your sense of adventure, and join us on a magical journey to Oak Bluffs with Hy-Line Cruises. Book your tickets now and embark on an unforgettable evening of beauty, joy, and unforgettable memories.

Depart Hyannis at 4:50pm and arrive in downtown Oak Bluffs in an hour. Depart Oak Bluffs, Martha’s Vineyard at *8:40pm that same night.

Experience an evening trip to the Vineyard for only $35 per person!  Your discount offer for an evening to the Vineyard is ONLY AVAILABLE BY CLICKING HERE or calling the ticket office.

Valid June 22 through September 1, 2024