Planning a trip to Nantucket? You’ve probably come across many options for exploring this charming island, but if you’re all about flexibility and a personal pace, a self-guided tour might just fit the bill. The Discover Nantucket Self-Guided Biking or Driving Tour offered by Drives and Detours promises a flexible way to soak in the island’s highlights, from historic landmarks to stunning beaches. We’ve looked into what it offers, and in this review, I’ll share what you can genuinely expect — the good, the not-so-good, and who this experience might suit best.
What we really like about this tour is how it balances sightseeing with a sense of independence. With insider tips and detailed routes provided via a mobile app, you can explore at your own pace, which is a big plus if you dislike rigid schedules. Plus, focusing on iconic landmarks and scenic spots makes this a great choice for those wanting a broad overview without the hassle of group tours or guided bus trips. That said, a potential drawback is the reliance on your own device and some technical hiccups, as a few users reported connectivity issues. So, if you’re tech-adverse or need a seamless experience, this might be worth considering.
This tour is well-suited for independent travelers, couples, or small groups who enjoy the freedom to explore without a set timetable. It’s ideal if you’re comfortable with using a smartphone and prefer a customizable itinerary. However, it might not be the best fit if you want a guided experience with a personal guide explaining each point of interest in detail.
Key Points

- Flexible exploration: Choose biking or driving and set your own pace.
- Includes insider tips: The app provides helpful insights on what to see and do.
- Iconic landmarks: Visit notable spots like the Atheneum, Hadwen House, and Straight Wharf.
- Good for tech-savvy travelers: Requires a smartphone, earbuds, and a charged device.
- Pricing reflects value: At $13 per person, it’s quite affordable for a comprehensive island tour.
- Variable reviews: Some users loved the route and insights, while others faced technical issues.
What You Can Expect from the Tour

This self-guided experience offers a well-rounded glimpse of Nantucket’s personality, blending history, architecture, and natural beauty. Starting from the corner of Broad and South Beach Street — a spot right near some of the island’s iconic scenery — you’ll download an app that guides you through a 3-hour journey. You can choose to bike or drive, depending on your preferences and physical condition.
The tour covers from Madaket to Sconset, offering a full sweep of the island’s highlights. Along the way, you’ll learn about Nantucket’s past and see some of its most meticulously preserved 18th-century homes. If history is your thing, you’ll appreciate the stops at the Oldest House and the museum honoring America’s first female astronomer. The route also passes by the oldest operational windmill in the country, a sight that captures Nantucket’s historic ingenuity.
Appreciate having local insight? Here are other guided experiences in Nantucket we've examined
The Landmarks and Points of Interest
One of the highlighted attractions is the Atheneum, a historic library with a distinctive façade and a window into the island’s literary and cultural roots. The Hadwen House offers a glimpse of classic Nantucket architecture, and Straight Wharf provides picturesque views of the harbor. These stops, suggested by the app, give a feel for what makes Nantucket so special.
The journey also includes some scenic natural spots — beaches and vistas that let you appreciate Nantucket’s coastal charm. The seaside town of Sconset, with its charming cottages, is a popular stop, especially as it once housed one of the first trans-Atlantic wireless stations, adding a layer of historical intrigue.
The Experience & How It Works

Once you arrive at the starting point, your journey begins as soon as your phone detects your location. The app provides a route map, points of interest, and insider tips. For the best experience, you’ll want a smartphone with a good battery life, earbuds or a speaker, and some snacks and water for breaks.
The duration is around 3 hours, which makes this suitable for a relaxed afternoon. You can take your time exploring, stopping for photos, or grabbing lunch. Since it’s a private group experience, you won’t be stuck with strangers, and you control your schedule.
Technical Aspects & Connectivity
Some reviews have noted connectivity issues, with one traveler mentioning it never connected to CarPlay in the car. Others found the app slow to download but still enjoyed the overall experience once set up. To minimize frustrations, make sure your device is fully charged and ready, and consider using earbuds for better audio clarity.
The flexibility of unlimited access means you can revisit parts of the route or extend your exploration if you wish. The tour also offers full refund options if you cancel 24 hours in advance, adding peace of mind to your planning.
More Great Tours NearbyIs It Worth the Price?

At $13 per person, this tour is quite affordable, especially considering you get unlimited access and the ability to explore at your own pace. Compared to guided tours that often cost much more and follow strict schedules, this is a budget-friendly option that offers a lot of control. If you’re someone who likes to customize your sightseeing experience, the value is there.
However, keep in mind that entrance fees to museums or attractions are not included, so if you plan to visit specific sites, you’ll need extra cash or tickets. Also, transportation (bike rentals or car) is up to you, which could add to your overall cost if needed.
Enjoy cycling? We've looked into these other two-wheeled adventures in Nantucket
Who Is This Tour Best For?

This experience caters well to independent travelers who prefer self-directed exploration. It’s especially good for those comfortable with smartphone navigation, seeking cost-effective ways to cover a lot of ground, and who enjoy scenic drives or cycling. It’s also suitable if you want to avoid large group tours or guided bus rides and instead carve out your own adventure.
If you’re traveling with a partner or a small group and enjoy the flexibility of choosing your schedule, this is a good fit. However, if you’re looking for in-depth guided commentary, a more structured tour might suit you better.
Final Thoughts

The Discover Nantucket Self-Guided Biking or Driving Tour offers a flexible, affordable way to see the island’s highlights without the constraints of a scheduled guide. With the convenience of a mobile app providing insider tips and routes, you’re free to customize your day and focus on what interests you most.
The experience shines when the technology works smoothly, and you’re comfortable navigating with a smartphone. It’s especially worthwhile for those who enjoy scenic drives, historical landmarks, and exploring at their own pace. If technical issues or the lack of guided narration are deal breakers, you might want to consider other options.
Overall, if you’re an independent traveler craving control and flexibility without breaking the bank, this tour provides a good introduction to Nantucket’s charm.
Discover Nantucket Self-Guided Biking or Driving Tour
FAQ

How long does the tour take?
The tour lasts around 3 hours, but you can take longer if you wish, thanks to unlimited access.
Do I need to bring my own transportation?
Yes, you need to have your own bike or car rental. The tour itself doesn’t include transportation.
Is the tour suitable for families?
This experience is best suited for individuals comfortable with smartphones and self-guided navigation. It wasn’t specifically designed for children, but families with older kids who enjoy tech and exploring might find it engaging.
What do I need to participate?
A charged smartphone, earbuds or a Bluetooth speaker, and snacks or water are recommended. The app is available once you meet at the starting point.
Are there any extra costs?
Yes, entrance fees to attractions are not included, and transportation or bike rentals are up to you.
Can I cancel if my plans change?
Yes, you can cancel up to 24 hours in advance for a full refund.
Is there a guided narration?
No, it’s self-guided, but the app offers insider tips and interesting facts.
What should I do if I encounter technical difficulties?
You might find some connectivity issues, so ensure your device is well-prepared before starting. It’s always good to have a backup plan like offline maps or additional guidebooks.
There you have it — a practical, honest look at a flexible way to see Nantucket on your own terms. Whether you’re a history buff, a scenic lover, or just someone who appreciates independence, this tour gives you the tools to craft your perfect day on the island.
You can check availability for your dates here:More Cycling Tours in Nantucket
More Tours in Nantucket
More Tour Reviews in Nantucket
More Nantucket experiences we've covered
- Beyond the Cobblestones Self Guided Audio Tour of Nantucket
- Nantucket: Guided Scenic Island Driving Tour
- Nutty Nantucket Scavenger Hunt
- Nantucket Coast to Coast Self-Guided Biking or Driving Tour
- Nantucket: Downtown Walking Tour
- Nantucket: Guided Bike Tour
- Private Nantucket Beach Fishing Activity with a Guide
- Beyond the Cobblestones Self Guided Walking Tour of Nantucket
- Historical Tour of Nantucket
