Cape Cod is a place that invites exploration—whether it’s capturing the region’s breathtaking night skies, sampling local wines, or wandering along historic streets. Its diverse landscape and authentic charm make it ideal for a wide variety of tours. I personally love the Private Guided Night Photography Tours for their personalized approach and expert instruction, especially if you’re eager to improve your astrophotography skills (more details here). For a relaxed taste of local flavor, the Wine and Wine Jelly-Sauce Tasting offers a fun, flavorful journey into native fruits and regional wines (more details here). Whether you’re into outdoor adventures, culinary experiences, or cultural tours, Cape Cod’s got something for all.
Quick Overview
Our list covers a broad range of tour types, including private photography sessions, food tastings, kayaking adventures, self-guided driving tours, and historic trolley rides. Whether you want to capture the night sky, sample local wines, explore Cape Cod’s natural beauty, or dive into the town’s history, there’s an experience for you. Here’s a quick snapshot:
– Night Photography: Private sessions with expert tips (see more)
– Wine & Food Tastings: Authentic local flavors (see more)
– Walking & Food Tours: Discover Chatham’s culinary scene (see more)
– Outdoor Adventures: Kayaking and boat trips (see more)
– Historical & Cultural Tours: Trolleys and self-guided walks (see more)
1. Private Guided Night Photography Tours on Cape Cod (for one photographer.)
At number 1, this private night photography experience is perfect for those eager to improve their skills with a seasoned photographer. The tour lasts about 4 hours, during which you’ll visit the best spots on Cape Cod for capturing long-exposure images of the night sky, whether under moonlight or starlight. It’s a tailored experience, with one-on-one attention that helps you learn techniques like light painting and astro photography. The instructor, Tim, is highly rated for his clear explanations and ability to adapt to your skill level. The package includes an included matted print and course material to take home.
This tour appeals to serious photographers or curious amateurs who want a personalized, hands-on experience. Since spots are limited and book well in advance, it’s best suited for those who plan ahead. The price is $375 per person, which reflects the exclusivity and expert guidance. Reviewers emphasize how much they learned and the quality of the images they took, calling it “a fantastic experience” and “a whole new way to look at photography.”
Bottom Line: If night sky photography is your thing, this is a rare chance for expert guidance in an intimate setting.
2. Wine and Wine Jelly-Sauce Tasting on Plymouth Bay
Number 2 on our list offers a delightful tasting experience at Plymouth Bay Winery, where you can sample wines made from native northeastern fruits. For just $13.18, you explore a collection of wines, jellies, and sauces crafted from local produce, giving you a taste of the region’s culinary ingenuity. The tasting concludes with a souvenir etched glass. The winery staff shares insights about how these products are made and how you can incorporate them into your own cooking.
This tour is ideal for those who enjoy learning about regional foods and sampling unique products, especially as a fun way to support local artisans. Reviewers praise the hometown hospitality, noting that it’s a “fantastic gift” and a “fun, educational experience”. The affordable price point makes it accessible for most travelers, and the tasting is quick but memorable.
Bottom Line: Perfect for foodies wanting to experience authentic local flavors without breaking the bank.
3. Chatham Bites and Sights Walking Guided Food Tasting Tour
Number 3 is a 3-hour walking tour through Chatham, featuring multiple tasting stops at local eateries. Led by a local expert, the tour showcases seasonal bites from beloved spots and hidden gems. It offers a relaxed pace with stories about local legends, tradition, and the people behind the food. The tour includes lunch-sized tastings, a dessert, and one alcoholic drink, with additional drink options available.
Guests rave about the quality of the food and the knowledge of the guide, Mike, who is praised for being personable and flexible. This tour is great for first-timers or those wanting to enjoy Chatham’s culinary scene in a social, informal setting. The price of $98 is reasonable considering the multiple stops and experience.
Bottom Line: If you’re into food and local stories, this walking tour hits the spot.
4. Kayak The Creek Nature Tour
Number 4 features a 5-star rated kayak tour in the Scorton Creek area, operated by RideAway Adventures. It’s a 2-hour trip through Cape Cod’s most scenic tidal flats, part of the Great Marsh eco-system. The tour is suitable for all levels, with top-of-the-line equipment and a small-group environment. Expect to see bird activity, wildlife, and enjoy the varied water—salt, brackish, and fresh—creating a rich natural experience.
The guides are known for their local knowledge and friendly approach. Reviewers mention beautiful scenery and the birdlife as highlights, though some suggest an earlier start to avoid low tides. Price-wise, at $80 per person, it offers great value for an intimate outdoor adventure.
Bottom Line: For a peaceful paddle immersed in nature, this tour is hard to beat.
5. The Martinis & Mingle Tour
Number 5 is a 2-hour Provincetown tour blending history, cocktails, and local flavor. Starting at The Harbor Lounge with a Cape Cod Blueberry Vodka Lemonade Martini, you’ll explore Commercial Street’s iconic spots, including Lobster Pot and Old Colony Tap. The tour features stories of Ptown’s bohemian past and LGBTQ+ culture, making it a lively and engaging experience.
Tour guides like Cathy earn rave reviews for their knowledge and humor. The $78 price includes multiple tastings and a chance to soak in the atmosphere of Provincetown’s colorful streets. It’s perfect for history lovers with a palate for craft cocktails.
Bottom Line: A fun, social way to enjoy Provincetown’s art, history, and nightlife in a relaxed setting.
6. Cape Cod & Provincetown Self-Guided Driving & Walking Audio Tour
Number 6 offers flexibility for independent explorers. For $24.99, you get an app with GPS, audio, and text guides covering Cape Cod’s highlights, from lighthouses to beaches. The tour begins at the Cape Cod Visitor Center and includes optional detours like Scargo Tower. It’s perfect for self-paced discovery and return trips over a year.
Reviewers love the value and customization, noting that it takes you off the beaten path and enhances your experience with local stories. The 2-3 hour tour is a practical way to see Cape Cod’s essential sights without being tied to a schedule.
Bottom Line: Best suited for self-sufficient travelers wanting a flexible, informative tour.
7. Cape Cod Explorer Tour
Number 7, the Cape Cod Explorer, is a 2-hour kayak tour operated by RideAway Adventures. Covering Popponesset Bay, River, and Mashpee River, this trip offers birdwatching, wildlife viewing, and access to the Popponesset Spit. It’s great for all levels thanks to top-notch equipment and small groups.
Guests comment on the spectacular scenery and the knowledgeable guides. At $80 per person, it’s an excellent choice for water lovers wanting to explore Cape Cod’s natural habitats. The conservation focus makes it appealing for those interested in environmental education.
Bottom Line: This kayak tour is a wonderful way to connect with Cape Cod’s coastal environment.
8. National Seashore Tour with Guided Hike
Number 8 combines driving and walking to showcase Cape Cod’s seashore highlights. For $75, you visit Pilgrim Landing, Beech Forest, and Cape Cod National Seashore with a knowledgeable guide. The guided hike through Beech Forest offers a chance to see migrating birds, ponds, and flora.
Guests praise the friendly guides and “beautiful scenery,” and the easy walk makes this suitable for most fitness levels. The small-group format allows for plenty of questions and interaction. It’s ideal for travelers who want a combination of scenic views and cultural insights.
Bottom Line: A balanced mix of nature and history in a comfortable, engaging tour.
9. Mayflower Trolley Tour!
Number 9 is a 50-minute trolley ride through Provincetown’s historic streets. For $46, it offers a rundown of the town’s art scene, maritime history, and famous landmarks like the Pilgrim Monument. The guided narration covers fascinating stories from the 1620 landing to today’s vibrant culture.
Since it operates May through October, it’s a seasonal favorite. Reviewers appreciate the informative guide and easy pace, making it suitable even for those with limited mobility. The trolley format provides a relaxed, convenient way to see Provincetown.
Bottom Line: Perfect for history buffs or those wanting a quick, rundown.
10. Local Legends and Lobster Roll Tour
Number 10 is a 2-hour culinary and cultural tour centered on Anthony Bourdain’s favorites. Starting with lobster rolls and Portuguese malasadas, this tour passes by legendary spots like the Lobster Pot and Spiritus Pizza. Tour guide stories highlight seaside lore and local legends.
With a price of $92, it offers a casual yet immersive way to learn about Provincetown’s food scene and its bohemian roots. Reviewers mention how informative and lively the stories are, making it an entertaining experience.
Bottom Line: Ideal for food lovers wanting an inside look at Ptown’s culture and culinary history.
11. Provincetown Self-Guided Walking Audio Tour
Number 11 is a self-paced walking tour for $14.99. It covers the Pilgrim Monument, adams Pharmacy, and historic landmarks, with an app providing GPS-guided narration. It’s perfect for those who prefer exploring independently without the pressure of a group.
Reviewers appreciate the flexibility and detailed explanations, especially for short visits. It’s a cost-effective way to bring history and culture alive at your own pace.
Bottom Line: Great for independent travelers who want a personalized experience.
12. Private and Fully Customizable Cape Cod Dream Boating Adventure
Number 12 offers a luxury private boat charter lasting from 4 to over 8 hours, tailored to your interests. Led by CAP’n JP, the trip visits Pleasant Bay, Cape Cod National Seashore, and the Chatham Fish Pier. You choose your stops, making it the most customizable tour on our list.
Priced at $399 per group (up to 6), it’s a premium experience suited for families, couples, or groups celebrating special occasions**. Many reviews mention the value of personalized attention and authentic boating experiences. It’s perfect for those who want a day on the water on their terms.
Bottom Line: For ultimate flexibility and privacy, this boating adventure is hard to beat.
How to Choose the Best Tour for You
Selecting the right tour depends on your interests, budget, and fitness level. If you want to capture stunning night photos, the Private Guided Night Photography Tours (more info) is an unmatched personal experience. For foodies, the Chatham Bites and Sights Tour (more info) or the Lobster Roll & Legends Tour (more info) will satisfy your appetite for local flavors.
Outdoor lovers might prefer kayaking with options like the Cape Cod Explorer Tour (more info) or the Kayak The Creek Nature Tour (more info). For those who want flexibility, the Self-Guided Driving Tour (more info) allows you to explore at your own pace.
Booking early is recommended for popular dates, especially for private or customizable experiences. Consider your time, interest in outdoor activities or culture, and budget to find the perfect match.
Final Thoughts
Cape Cod offers a wide array of tours that suit many tastes—from personalized night photography lessons to relaxing boat trips and tasty food walks. If you’re into nature and outdoor adventures, the Kayak The Creek Nature Tour or Self-Guided Driving Tour are excellent choices. For history and culture enthusiasts, the Provincetown Trolley or Walking Audio Tour provide engaging insights.
Two standout options are the Private Guided Night Photography—great for serious photographers—and the Customizable Boating Adventure—perfect for those seeking a luxurious, tailored experience. Either way, booking early ensures you won’t miss out on these memorable Cape Cod experiences.