Star Island Walking Tour & Harbor Cruise

Star Island Walking Tour & Portsmouth Harbor Cruise aboard the M/V Challenger

Discover hidden legends, centuries of history, and the breathtaking beauty of the New England coast.

Set sail on an unforgettable journey aboard the smaller, more intimate M/V Challenger, your floating front-row seat to the scenic wonders and storied past of the New Hampshire Seacoast. This unique cruise offers more than just panoramic views of Portsmouth Harbor and the rugged Atlantic coastline as it invites you to step back in time.

Your voyage begins in the bustling harbor of Portsmouth, where centuries-old architecture lines the shoreline and tugboats crisscross the river with old-world charm. As we glide down the Piscataqua River and into open waters, our seasoned narrator will bring to life the history and lore of the Isles of Shoals. These isles are a remote cluster of nine archipelago islands that once buzzed with fishermen, poets, pirates, and summer vacationers from America’s Gilded Age.

After a scenic 60-minute tour through the Piscataqua River and Portsmouth Harbor, we’ll dock at Star Island, part of the Isles of Shoals and home to a wealth of historical intrigue. Here, you’ll have approximately one hour ashore to explore this captivating island, either on your own or with our knowledgeable guide for an optional walking tour.

During the guided experience, you’ll stroll the grounds of the historic Gosport Village, a reconstructed 17th-century fishing settlement complete with rustic cottages, a peaceful stone chapel, and the echoes of a long-gone seafaring community. Hear tales of early explorers, including Captain John Smith, the English colonist of Jamestown and Pocahontas fame, who was granted the Isles as a reward for his service to the Crown.

You’ll learn about the pirates who once prowled these waters, Blackbeard and Captain Kidd among them, and the chilling story of the Lady Ghost of White Island, a legend whispered through the ages. The tour includes views of the Oceanic Hotel, one of the last grand seaside resorts still standing from the 1800s, and a visit to the Caswell Cemetery, where the John Smith Monument stands as the tallest gravestone in New Hampshire.

Prefer to wander solo? That’s just fine. You’re welcome to explore Star Island at your own pace & snap photos of rocky tide pools, peek into artist cottages, or simply sit and soak in the salty breeze and crashing waves that define this magical place.

The Star Island visitor fee is included in your ticket price, and there’s no need to print ticket! We’ll check you in by name as you board.

Whether you're a history buff, a nature lover, or just someone looking for a unique day trip with a salty splash of nostalgia, this cruise is one for the books. Families, photographers, and anyone yearning for a story-rich experience will find something to love on this unforgettable excursion.

Come aboard and let the past speak to you on the wind.

About the M/V Challenger

The M/V Challenger is our smaller, more intimate, single level vessel.  The Challenger is perfect for quieter sailings, scenic transfers to Star Island, and is flexible for private bookings. With an open design and shaded seating, it offers excellent visibility and a comfortable ride through Portsmouth Harbor and out to the Isles of Shoals. While smaller in scale, it retains all the charm of our coastal cruise experience and is frequently used for the outbound portion of our Star Island Day Trips. The Challenger can also be reserved for private charters, with limited availability throughout the season.

• No smoking or vaping allowed onboard, including e-cigs and pens
• Bags and small coolers are allowed on daytime cruises only
• No bags or coolers permitted on evening or 21+ cruises
• On-site parking available for $5 per vehicle
• Boarding begins 30 minutes prior to departure

Whether you're planning a casual day on the water or a high-energy group celebration, the Challenger offers the perfect s intimate setting with character, and one-of-a-kind harbor views.