Top Cape Cod Private Sightseeing Tours

Last season I launched Cape Cod’s first walking food tour in Chatham, and thanks to amazing guests and local partners, Chatham Food Tours earned Viator’s Badge of Excellence in its very first season. Now we’re bringing that same recipe for success to Provincetown. But Provincetown is entirely its own experience — with different stories, personalities, history, art, and energy. We’ve partnered with fantastic local establishments to create a tour blending great food, local storytelling, waterfront culture, and the unique spirit that makes Provincetown unforgettable. Seafood lovers will enjoy authentic Cape Cod flavors, while non-seafood options are always available as well. This relaxed walking tour is designed to feel personal, welcoming, and fun — with plenty of opportunities to stop, explore, and take in the beauty and personality of Provincetown along the way.

Skip walking and sightsee while seated with a guide to provide commentary and recommendations on this private pedicab Provincetown tour. Board your open-air pedicab with your bicycle-pedaling guide and glide around the Pilgrims’ First Landing Park and Commercial Street where you’ll feel the town’s vibe in a way that’s difficult from inside a vehicle. Then, visit dune-backed Herring Cove beach before a drop-off near the Long Point shuttle—handy for continuing your sightseeing. A souvenir Polaroid photo is included.

Ready to taste Ptown? Lace up for a 2-hour trek through history and coastal rebel lore. You’ll track the footsteps of Anthony Bourdain and dive into the bohemian scene that made this fishing village the birthplace of modern American theater. Find out where the Provincetown Players launched, where an undiscovered Eugene O’Neill staged his first plays. Alongside O'Neill, trailblazing writers like Susan Glaspell, Edna St. Vincent Millay, and John Reed fueled the town's creative fire. Over the decades, icons like Tennessee Williams, Norman Mailer, and poet Mary Oliver drew inspiration from the salt air, while acting legends like Marlon Brando and Bette Davis graced local stages early in their careers.End your journey at Vorelli's Restaurant, a beloved local classic. Sit back, relax, and reward your feet with the ultimate Cape Cod feast: a massive, chunky lobster roll, a rich, creamy cup of New England clam chowder, and a refreshing non-alcoholic beverage of your choice and a ice cream cone

Experience the best of Cape Cod in your own time without overlooking any sights with this self-guided driving tour. Download the app with its GPS map, audios, and text, and hit the road from the Cape Cod Visitor Center. Follow the route to see and learn about the peninsula's lighthouses, beaches, and sights, and take optional detours to relax, hike, or delve deeper into the cape's history. For lifetime access, you can dip in and out whenever you wish.

A private crossing focused on observing gray and harbor seals at a relaxed pace, with only your group aboard. With time to linger where conditions allow, this trip is guided by tide, weather, and respectful distance from wildlife. Ideal for families, photographers, and anyone who wants a quieter, more personal seal-viewing experience. Up to 6 passengers total.

Join Your guide Cathy and embark on a captivating journey through Provincetown’s West End, where the sands of time meet the tides of history. This unique walking tour weaves together the stories of ancient homes, weathered wharves, and steadfast lighthouses, all nestled along the shimmering edge of Provincetown Harbor. Designed to feel like a step into a living museum, this tour blends maritime grit, pilgrim lore, and bohemian charm, offering a soulful exploration of Cape Cod’s northernmost tip. This 90 minute walking tour covers about .5 mile along the West End of Commercial Street. Each stop pulses with Provincetown’s unique blend of history, art, and seafaring spirit, making this tour a love letter to a town that’s both timeless and ever-evolving. After the tour, opt for a Pedi-cab back to the center of town!

Upgrade your drive through scenic Cape Cod with this private self-guided tour you can download onto your phone. The audio narration plays based on your location, letting you start, stop, and skip stops whenever you like. You control your time and pace, enjoying a personalized experience without the constraints of traditional tours.

Provincetown’s charming seaside facades hide a sinister past soaked in blood, betrayal, and supernatural terror. On this chilling self-guided walking tour, you’ll discover the dark underbelly of Provincetown’s history, from bloodthirsty pirates and treacherous mooncussers who lured ships to their doom. I’ll also tell you about the restless spirits that continue to haunt the town’s historic buildings and picturesque streets. Starting at the infamous American Horror Story house, you’ll journey through Provincetown’s most haunted locations. You’ll explore historic cemeteries where smallpox victims lie in unmarked graves, and pass by former funeral homes that now operate as quaint inns. Along the way, you’ll discover how this seaside paradise earned its ominous nickname “Helltown” after centuries of maritime tragedy and malevolence.

Enjoy complete flexibility and explore the parts of Massachusetts that most interest you with this collection of self-guided walking and driving tours. Receive 10 different itineraries and choose the day and time to use any of them. Use offline with GPS and learn about each place as you travel through.

Discover the culinary scene of Hyannis on this walking food tour that takes you through the charming waterfront and historic streets. Sample a variety of freshly prepared dishes from local favorites stopping only at locally owned and operated restaurants and shops . Sweet and savory tastings! All while enjoying fascinating stories from expert guides. Ideal for food lovers, families, and couples looking for a unique dining experience. Comfortable walking shoes are recommended for this appx 3-hour tour covering about a mile. - Enjoy a diverse selection of local foods from Hyannis' best eateries - Guided tour featuring insights into the area's history and culinary culture - Perfect for families and couples, small groups seeking a memorable outing - 2.5-3 hour walking tour with a route that includes both indoor and outdoor stops

Explore Provincetown's rich history with this self-guided walking tour! Discover the charm of Commercial Street, admire the towering Pilgrim Monument, and visit the bustling Beachcombers at Town Hall. Stop by the historic Adams Pharmacy and Whalers Wharf. Take in the architecture at 2 Masonic Place and the Martin House. Experience the legacy at the former Zora's Fish Market and Railroad Wharf. Pass by the Seth Nickerson House and the home of Jack Tworkov. Conclude at the stunning Land's End Inn and Pilgrim's First Landing Park. After booking, check your email/text to download the separate Audio Tour Guide App by Action while connected to WiFi or mobile data. Enter the password, download the tour, and enjoy it offline. Follow the audio instructions and route from the designated starting point. This isn't an entrance ticket. Check opening hours before your visit. New, Lifetime access, no expiry. Use it anytime, on any trip, as many times as you want.

Download GuideAlong's Cape Cod audio tour to discover what “summer” really means. Drive the iconic “bent arm” between Barnstable and Provincetown, with side trips to striped lighthouses, sandy beaches, and historic Pilgrim landmarks. Along this 60-mile route down Route 6, we’ll detour to discover everything from quaint coastal towns, gorgeous salt marsh hikes, and hidden histories. Don’t miss the highlights: Nauset Light, which once guided ships past the treacherous Cape shores, Pilgrim Monument, with its gorgeous ocean views, and the thrilling rocky causeway at the very end of Provincetown. Enjoy the freedom to explore offline at your own pace, spending more time at places that interest you and bypassing any that don’t. Stories, tips, and directions play automatically based on your location Travel at your own pace Tour offline using GPS. No cell service or WiFi is needed Suggested itineraries for half, full, or multi-day use No time limits or expiry, and free updates

Explore the charm of Cape Cod on the Old Kings Highway, a scenic drive along Massachusetts Route 6A. This self-guided tour reveals centuries-old villages, picturesque landscapes, and historic landmarks from Sandwich to Provincetown. Discover the stories of early settlers and maritime legends as you meander through colonial homes, cranberry bogs, and art-filled towns. Perfect for history enthusiasts and leisurely travelers alike, this tour offers a unique perspective on Cape Cod’s heritage. Plan for a full day to soak in the sights, whether you’re drawn by summer sun or fall foliage. - Scenic self-guided drive through Cape Cod’s historic Route 6A - Visit charming towns including Sandwich, Barnstable, and Provincetown - Discover colonial homes, art galleries, and cranberry bogs along the way - Ideal for all travelers seeking history and beautiful landscapes

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.

Herman Melville said this city was perhaps the dearest place to live in, in all of New England. On this tour you will explore the streets that inspired Melville's tale, showcasing the city's nineteenth-century architecture and the landmarks that played a crucial role in both the whaling industry and Melville's masterpiece. Go at your own pace, anytime. The tour is location aware and plays as you walk guiding you step by step through the streets. Stop anytime, and listen again later anytime.

Discover P-town's LGBTQ+ sites, oldest gay bars and historic stories. Go at your own pace, anytime. Explore the rich history and cultural significance that have made Provincetown the gayest town in America. Go at your own pace, anytime. Go at your own pace, anytime. The tour plays automatically as you walk making it a hands free heads up spooky experience. The tour is all outside. You can go anytime, 24/7/365. It does not enter any buildings :)

Discover Provincetown from a new perspective with our Private Open-Air Pedicab Tours. Relax in comfort as our knowledgeable guides lead you through the charming streets and scenic coastline of this historic town. Enjoy unobstructed views and personalized insights into local history, culture, and hidden gems that only a pedicab can offer. Whether you're captivated by the natural beauty or intrigued by Provincetown's rich heritage, our tours provide a unique and eco-friendly way to experience all that this vibrant destination has to offer. Unlike large bus or group tours, pedicab tours provide an intimate experience with a knowledgeable driver who can tailor the time to your interests. You can ask questions, engage in conversations, and make specific requests. Pedicab tours can be customized to your preferences and schedule. Choosing a pedicab tour contributes to sustainable tourism practices and minimizes your carbon footprint.

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.