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  • Private

Cape Cod & Provincetown Day Tour

Quick Details

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

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:

Your tour starts with either a 90-minute ferry ride (seasonal from mid-May to mid-October) or a 2-3–hour car ride along the South Shore from Boston. By ferry, you’ll leave Boston Harbor with a lovely view of the Boston skyline from the bay. If you choose the drive, you’ll meander through small towns like quaint Sandwich and Chatham and beautiful natural spaces like the National Seashore. (Quick tip: During high season, we recommend the ferry to avoid heavy traffic!) On the way, you’ll get the chance to know your guide – and vice versa – and hear about the colorful history of Provincetown, widely regarded as Cape Cod’s most popular destination, as well as some of 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. 


To begin, we’d always recommend starting with the highlights of the area, like 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 structures in the US – and see some of the most sweeping views of the Cape! The next stops should 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. Along the way, we’d recommend grabbing a snack at a local favorite like Provincetown Portuguese Bakery while doing some people-watching of Ptown’s colorful characters. We’ve got lots of recommendations for fantastic lunch spots (somewhere for “lobstah” maybe?)!


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 tour. If you would like to relax a bit more, feel free to spend your time sunbathing along Race Point or Herring Cove beaches. We can help you end your day in true Ptown style with a Portuguese-style clambake and seashore view from a restaurant! Whatever you choose your day to include, we’re positive you’ll be taken by Ptown’s charm and local flavor!