Best Walking Tours in Cape Cod 2025

Cape Cod , Massachusetts

From $ 30.00

Formerly the Anne Hutchinson Tour of Provincetown, Lucinda Liphol has taken over the talking points. Her tongue is so sharp she can't close her mouth! She knows each and every fact old or new and simply can't wait to make you laugh using Provincetown's history. Though routes vary, 2025 tours start in the center of town at Bas Relief Park and are each about an hour in duration and a mile in distance. Offered daily. 20 people maximum on each tour. For a sampling of Lucinda's comedy, find her on social: @lucinda.liphol. IMPORTANT NOTE: Due to content, this is a tour for people 21 years of age and older. No exceptions. IDs required.

Cape Cod , Massachusetts

From $ 76.00

Toast to Provincetown’s vibrant past on a 2-hour history journey down Commercial Street, blending craft cocktails, local bites, and tales of bohemian spirit. Ideal for cocktail lovers and history buffs, this tour celebrates Ptown’s maritime, artistic, and LGBTQ+ legacy. Start at The Harbor Lounge sipping a cape Cod Blueberry vodka lemonade martini amid nautical relics and beautiful harbor views. Pass Lobster Pot, Gov. Bradford and the Old Colony Tap Room one of America's oldest bars. Stop at Spiritus Pizza, tied to the 1990 gays rights riot for two pipping hot slices. Pause at Lopes Square’s 1801 anchor. See Cannery Wharf Park’s harbor views. Catch UU Meeting House’s 1847 steeple. Pass Provincetown Library’s schooner. Wave at A-House (1798), loved by Tennessee Williams. Stop at a local favorite for a delicious fresh Espresso Martini. End at Boatslip Resort’s Tea Dance originating in the 1970" This uniques tour will make you wanting more!

Cape Cod , Massachusetts

From $ 98.00

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.

Cape Cod , Massachusetts

From $ 14.99

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. Buy once, use for one year! Ideal for extended visits and return trips over the next 12 months.

Cape Cod , Massachusetts

From $ 92.00

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!

Cape Cod , Massachusetts

From $ 12.31

Hey, adventurers and trivia masters! Let me introduce you to Let’s Roam—the ultimate scavenger hunt experience that’s as wild as it is educational! Imagine strolling through the city’s hotspots and uncovering secret gems while tackling brain-busting trivia and zany challenges. It’s not just a game—it’s a quest for glory and giggles! Team players, listen up: join forces to conquer the hunt together, or unleash your inner competitor and go head-to-head in a battle of brains and bravery! Whether you’re planning an epic birthday bash, a legendary bachelorette blowout, or a team-building extravaganza, Let’s Roam is your go-to for non-stop fun. And here’s the kicker—each player gets to pick their own interactive role with challenges tailored to their skills. So, gather your crew, download the app, and get ready for an adventure-packed journey where every step leads to new discoveries and unforgettable moments! Let’s Roam—where fun and adventure collide!

Cape Cod , Massachusetts

From $ 38.00

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!