Set Sail to Woods Hole
During your stay at Woods Hole Inn, don’t miss the opportunity to experience Woods Hole from its most breathtaking angle—out on the open water. Woods Hole Island Tours offers unforgettable scenic boat tours to the nearby Elizabeth Islands and Martha’s Vineyard. This is perfect for travelers looking to discover the hidden beauty, coastal charm, and maritime history of Cape Cod’s surrounding islands.
Led by local experts Captain Donny Estes and Captain Stacey, each island boat tour is packed with fascinating stories, historic landmarks, and panoramic ocean views. You’ll cruise past windswept beaches, historic New England lighthouses, and the unspoiled shores of places like Penikese Island, Cuttyhunk, and more, many of which can only be experienced by boat. Whether you’re new to the Cape or returning, this is a must-do Woods Hole activity.
There are two memorable ways to experience the Woods Hole waters:
Private Island Boat Tours from Woods Hole
For a fully customizable trip, book a private or custom charter tour. Set your own pace, ask questions, and even make special requests—like stopping for a swim or exploring a favorite island. These private boat tours offer a personalized way to connect with the water, the crew, and the stunning surroundings. Ask our front desk for assistance or click here to book your private island boat tour. Add our hassle-free Picnic Package to enjoy!
Woods Hole Sunset Happy Hour Cruise
If you’re looking for something more laid-back and social, the Woods Hole Island Tours Sunset Happy Hour Cruise around Woods Hole Harbor is the perfect option. This is limited and available first-come basis. Bring your own beverage and food (BYOB/BYOF), or let us pack a “Picnic Package” for you to enjoy on board. It’s a relaxing, fun-filled way to watch the sun dip over the harbor while enjoying good company and great views. Whether you’re here to explore Martha’s Vineyard by boat, tour the Elizabeth Islands, or simply enjoy the ocean breeze, Woods Hole Island Tours delivers a truly Cape Cod experience.