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Cape Cod & Provincetown Private Driving Day Tour

Quick Details

8-Hour Private Driving Tour
9-Hour Private Driving Tour

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A private tour with WeVenture Boston is always a completely custom itinerary, created just for you and your group! A private city tour of Boston can be from 8 hours – 9 hours, depending on the destination. Pick-up and drop-off locations are the group’s choice. While many visitors to Boston have specific sites they would like to see, many are happy to let our team create a custom itinerary that fits their interests, budget, mobility, and timeline. Typically, tours spend most of their time in and around central Boston, but we welcome any ideas for your dream tour.

No two groups are alike and we will plan a trip tailored to your group’s interests, budget, and needs. Below are some sample itineraries to use as inspiration for your perfect tour:

Full-Day Tour:

Enjoy a private ride from Boston along the South Shore all the way to beautiful Cape Cod. 

After a two- to three-hour relaxing ride while you get to know your local tour guide, you’ll cross over the Sagamore Bridge, the gateway to Cape Cod! Once in the area, you’ll have the chance to meander through small towns like quaint Sandwich and Chatham and beautiful natural spaces like the National Seashore.

Farther along, we’ll arrive in Provincetown at the very tip of Cape Cod, widely regarded as the area’s most popular destination. Here, you can learn about the town’s storied history as the first arrival point of the Pilgrims, an infamous fishing town, an artist colony, and haven for alternative lifestyles. 

Among other highlights of the area, you can opt for a tour stop at the Pilgrim Monument & Museum, built to commemorate the first landing of the Mayflower Pilgrims in the US in 1620. One of our favorite things to do here is to climb to the top of the monument – currently the tallest granite structure in the U.S. – and see some of the most sweeping views of the Cape! 

Our next tour activity will be a walk down the never-boring Commercial Street, the heart of Ptown’s universe. The three-mile stretch spans the town and provides access to Ptown’s notable landmarks, local art galleries, unusual souvenir shops, cabaret entertainment, and interesting architecture. 

At any point during your private Cape Cod tour, we can stop for snacks or a full meal at one of many incredible and eclectic restaurants in Ptown. Your tour guide will have plenty of recommendations!

Ptown also offers several one-of-a-kind experiences. You might board private transportation for a tour of the Ptown sand dunes, explore Ptown’s various nature trails by bicycle, or jump on a private schooner for a whale-watching tour. If you would like to relax a bit more, feel free to spend your time sunbathing along Race Point or Herring Cove beaches. 

For the ride back, we can build in time to stop at some very unique shops in the various towns along the Cape. If you’re a foodie, we always recommend a trip to The Atlantic Spice Company in Truro: this shop has over 350 products that include spices, herbs, teas, extracts, salts, essential oils and much more!

If artwork is more your style, a stop at Sydenstricker Glass in Brewster will give you a unique one-of-a-kind gift from Cape Cod. Want to have some of the best raw oysters around?  The town of Wellfleet has many great oyster bars with the freshest seafood pulled right from the local waters.