Top Cape Cod Seasonal & Special Occasions

Enjoy a private seal-watching crossing with only your group aboard. We’ll explore at a relaxed pace, with time to linger when conditions allow and observe gray and harbor seals from a respectful distance. Each trip is shaped by the tide, weather, and wildlife, making every outing a little different. A great choice for families, photographers, and anyone looking for a quieter, more personal experience on the water. Up to 6 passengers.

This private guided walking tour of Provincetown's majestic Pilgrim Monument, , is led by expert local guide Cathy from Cathy's Cape Cod Tours. Cathy, a knowledgeable historian and storyteller, specializing in blending Provincetown's maritime grit, pilgrim lore, bohemian charm, and artistic legacy into engaging narratives. Based on her popular West End History Tour, Martinis & Mingle Tour & The Local Legends & Lobster Roll Tours, The Pilgrim Monument Tour is customized for a private experience, this tour centers on the iconic Pilgrim Monument and Provincetown Museum, incorporating a scenic ride on the inclined elevator, museum exploration, tower climb, and park grounds. It's designed for small groups or individuals (1-8 people) for a personalized touch.

Experience true local wines with a tasting at Plymouth Bay Winery, where talented vintners and chefs create wines, wine jellies and wine sauces from fruits that are native to the northeastern United States. Sample the entire collection of wines, and learn about using the jellies and sauces in your home cooking. Finish the tasting with an etched, commemorative glass from this unique winery in ‘America’s Hometown,’ just a stone’s throw away from historic Plymouth Rock.

⭐ Top-Rated Vacation Photoshoots 2025 We’re not just photographers, we’re storytellers capturing your holiday exactly as it feels. With over six years of experience photographing travellers around the world, our small team specialises in authentic, natural photography that truly reflects your trip. In Cape Cod, we combine creativity with local knowledge to show you hidden gems, secret angles, and the best light. You’ll not only get beautiful, professional photos but also insider tips to make the most of your time here. We’re proud to be recognised among the top-rated photography tours of 2025, trusted by travellers worldwide for our relaxed style and stunning results.

Embark on a privately guided journey through Truro’s soul, where history, culture, and breathtaking landscapes converge. This tour weaves together three iconic Cape Cod landmarks: The Highland House Museum, Highland Links Golf Course, and the historic Highland Light. Begin at Highland Light, Cape Cod’s oldest lighthouse (1797). Ascend 69 steps to the lantern room for panoramic Atlantic Ocean views and hear the thrilling tale of its 1996 relocation. Next, step into the Highland House Museum, a 1907 farmhouse-turned-hotel-turned-cultural gem. Once a haven for literary giant Henry David Thoreau, who penned parts of Cape Cod here. Explore rooms inspired by Edward and Josephine Hopper’s artistry. Stroll along the Highland Links Golf Course, America’s first 9-hole links course. Nestled amid rolling dunes and windswept grasses. Available June-September only.

Explore the vibrant history of Provincetown, America's LGBTQ+ haven, on this engaging 2 hour tour which includes a cocktail and a show! We'll Uncover the stories of the artists and activists who shaped the town's legacy of drag artistry and queer freedom. After your tour, enjoy a drink at Brewhouse before experiencing the hilarious SCREAM KWEEEN drag show at The Art House. Tour includes: History of Ptown's LGBTQ+ Community One Cocktail per person before the show VIP Entry to Scream Kween. A legendary drag performance by Miss Conception. SCREAM KWEEEN is a hilarious live-singing parody that slashes its way through the most iconic horror films of all time. From masked killers to possessed prom queens, nothing is safe in this fast-paced comedy spectacular where the screams are big, the wigs are bigger, and the jokes come faster than a horror movie body count. Packed with camp, nostalgia, and spine-tingling fun.

See Provincetown from a viewpoint that most visitors never experience: through the eyes of the infamous 17th-century Anne Hutchinson on this walking tour. With a costumed guide who plays Hutchinson with a gender twist, see the town's landmarks as you hear both traditional and irreverent “heretical” accounts of its history—the latter inspired by Hutchinson’s challenging of the Puritanical mores of her time. With commentary reflecting the “licentiousness” Hutchinson was accused of, the tour content is suitable for adults only.

Experience Cape Cod on a different level with this fun-filled scavenger hunt. Part tour, part detective hunt, this immersive experience centers on a smartphone digital quest and remote host who guides you around the cape by self-drive car. Check in at scenic destinations like Truro Vineyards, interpret art, history, and culture clues; complete challenges, meet locals, and score points to compete on an international leaderboard.

Capture long-exposure images of Cape Cod at night by prebooking this private one-on-one photography tour with an experienced photographer. Night photography is a specialized skill, and working with a full-time night photographer is a great way to improve your shooting technique. Book in advance to secure one of the limited spots available, and bring home an included matted print and night-photography course material.