Top Cape Cod Private and Luxury

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.

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.

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.

Step into Cape history with a visit to Highland Lighthouse—Cape Cod’s oldest and tallest lighthouse, proudly standing watch over the Atlantic since 1797. Once a critical beacon for mariners navigating the Outer Cape’s treacherous shoals, it remains an active aid to navigation and a beloved symbol of maritime heritage. Join us for an unforgettable stop in Truro, where you’ll have time to: - Climb the lighthouse tower for sweeping coastal views - Explore the keeper’s house and onsite gift shop - Visit the Truro Highland Museum, featuring local maritime history, Edward Hopper’s Cape Cod connections, and stories from the area’s earliest tourism - And enjoy a scenic drive to and from the Lighthouse Whether you’re a lighthouse aficionado or simply love coastal history, this experience offers a rare glimpse into the life and legacy of Cape Cod’s rugged shoreline. Lighthouse and museum admission included in the tour price.

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!

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.

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.

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.

Upgrade your drive through scenic Cape Cod with a self-guided tour that you can conveniently download onto your phone. The audio narration plays based on your location, and you can start, stop, and skip stops whenever you like. You’re in charge of your time, unlike traditional tours, and can explore at your preferred pace.

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.

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.

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.

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.

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.

Explore the highlights of Cape Cod’s seashore, starting from Pilgrim Landing and later into the Beech Forest for a guided hike on this small-group tour. This is an intimate group, so you can ask any questions from your knowledgeable tour guide, and learn all about the area’s history as you explore together. Drive for part of the tour, and then be prepared to walk around one mile (1.6 kilometers).

Dive into Ptown’s culinary and cultural treasures on this 2-hour Anthony Bourdain centric stroll, savoring a lobster roll, Ice Cold Beer, and a Portuguese malasada (all of his favorites) while uncovering tales of Bourdain and seaside lore. Pass the Lobster Pot, its neon sign glowing, where Bourdain toiled in the 1970s. Roll by the Old Colony Tap, a 1937 dive bar Bourdain loved. Stop at Spiritus Pizza, a 1971 haven that sparked the 1990 riot and housed Bourdain. Savor a malasada at the Portuguese Bakery. Slow at Lopes Square, with its 1801 anchor from the 1873 railroad. Admire Cannery Wharf Park’s harbor views. Catch the UU Meeting House’s 1847 steeple. Pass the Provincetown Library, with its schooner and Bourdain’s archives. Wave at the A-House, a 1798 tavern of Tennessee Williams and Billie Holiday. End at the Boatslip Resort’s Tea Dance, a 1965 LGBTQ+ disco tradition!