Top Cape Cod Sightseeing Tours

Taste your way through the heart of Cape Cod on a relaxed, flavor-packed food tour through Chatham’s most iconic streets and hidden gems. Led by a local expert, this 3-hour walking tour features multiple tasting stops with hand-picked seasonal bites from beloved local spots. It’s a delicious way to explore the area, whether it’s your first visit or your summer tradition. Along the way, hear the stories behind the food—tales of tradition, local legends, and the people who make Chatham so special.

RideAway Adventures has been awarded the best tours on Cape Cod 12 years in a row. We have the only fully ACA certified guide staff on Cape Cod. Our tours stay at low numbers so that it is a fun and unique experience for every participant. Our equipment is always top of the line and this area is perfect for all levels of kayakers.

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!

Taste your way through the vibrant streets of Provincetown on a relaxed, flavor-packed walking food tour blending local bites with rich cultural history. Led by a local guide, this 3-hour experience explores one of New England’s most unique seaside towns, with multiple tasting stops at locally loved eateries and hidden gems. Provincetown is unlike anywhere else on Cape Cod—known for its thriving arts scene, maritime roots, and its role as one of the most welcoming LGBTQ+ destinations in the country. As you explore iconic spots like Commercial Street, you’ll enjoy curated tastings while hearing the stories that make this town unforgettable. From waterfront views to lively streets filled with character, this tour offers the perfect mix of food, history, and local insight—whether it’s your first visit or a return to a favorite escape.

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

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.

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.

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.

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.

RideAway Adventures has been awarded the best tours on Cape Cod 12 years in a row. We have the only fully ACA certified guide staff on Cape Cod. Our tours are small and intimate so that it is a fun and unique experience for every participant. Our equipment is always top of the line and this area is perfect for all levels of kayakers. RideAway Adventures is the highest rated outdoor company on Cape Cod and we are committed to creating ocean ambassadors through education and active environmental awareness.

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.

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.

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 :)

Learn about Plymouth through games on this interactive scavenger hunt. Using your smartphone as your guide, visit different locations and solve puzzles with your team. Enjoy the route at your leisure, as only puzzles are timed. As you enjoy the sights of Plymouth, unlock educational riddles to figure out where to go next.

Get ready for an unforgettable day along the stunning Outer Cape! Whether you're a foodie, an art lover, or just eager to soak in the best of what the Outer Cape has to offer, we'll work with you to create the ultimate itinerary! Our expert guides are here to take the hassle out of your adventure. Let us handle the driving while sharing fascinating insights into the Outer Cape’s vibrant history and culture. And if you need any personalized recommendations along the way, we’ve got you covered! What to Expect: • Once you book, we'll create a personalized itinerary just for your group. • Plan for up to 5 hours of Fun! (Can be longer if you want) • Self-Purchase: You’ll be in charge of buying your own drinks and goodies, but we’ve teamed up with some awesome businesses to offer exclusive perks for you to enjoy. • Convenient Transport: We’ll pick you up and drop you off anywhere on Cape Cod, so you can relax and enjoy the ride!

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.