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Dorchester Center, MA 02124
Physical Address
304 North Cardinal St.
Dorchester Center, MA 02124

Discover Boston’s coastline with a private 6-hour day trip exploring Cape Ann, Salem, and North Shore towns, led by an expert guide and private transport.

This private day trip from Boston offers a personalized journey along Massachusetts’ scenic North Shore, visiting iconic spots like Cape Ann, Salem, and charming towns such as Gloucester, Manchester-by-the-Sea, and Rockport. Priced at $615 per person, the tour lasts approximately 6 hours and includes hotel pickup and drop-off, making it an easy, hassle-free way to see some of New England’s most picturesque coastal towns.
Known for its stunning rocky coastlines and colonial architecture, this tour is perfect for travelers who want a flexible, in-depth experience with plenty of time to explore. The private guide leads your exclusive group, ensuring a tailored experience with photo opportunities, local insights, and visits to charming main streets. Keep in mind, the price does not include food, drinks, or attraction tickets, but the flexible itinerary and personal attention make it well worth the investment.

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The tour begins at 12 Farnsworth Street in Boston, where a private vehicle awaits your group. From here, the guide takes you along Massachusetts’ North Shore, renowned for its breathtaking coastline and quaint towns. The drive itself offers many opportunities for photos of rocky cliffs, lighthouses, and ocean views, setting the tone for a day of scenic beauty.
This private transportation ensures a comfortable, flexible pace, with the ease of hotel pickup and drop-off. The guide’s local knowledge makes the journey informative and engaging, highlighting the area’s history and natural features as you go.
The first major stop is Cape Ann, where your group explores several of its charming towns. The highlight here is the stunning views of the rocky coastline, perfect for photos. You’ll visit Gloucester, famous for its fishing industry and historic harbor, and Rockport, a town known for its art galleries, seafood, and Bearskin Neck.
Each town offers free time to wander main streets, browse shops, and enjoy the coastal scenery. The guide recommends a local restaurant for lunch, giving you a chance to sample regional cuisine while soaking in the sights. Expect about 3 hours at this stage, with no entrance fees involved.
Next, the tour proceeds to Salem, a town with a storied past and picturesque harbor. Visitors have about 3 hours to explore, with the opportunity to stroll its colonial architecture and quaint streets. Salem’s history is deeply linked to the 1690s Witch Trials, which adds a fascinating layer to its charming streets and buildings.
While no attraction tickets are included, the guide helps you appreciate Salem’s historic landmarks and coastal beauty. The town’s quaint atmosphere offers plenty of spots for photos and independent exploration, making it ideal for history buffs and fans of scenic coastal towns alike.

This private tour emphasizes flexibility, allowing your group to tailor the experience based on your interests. The guide is available to answer questions, recommend spots, or adjust timing at each location. This personalized approach offers a level of comfort and attention not found with larger group tours.
The English-speaking guide is professional, friendly, and intuitive, ensuring that your day flows smoothly. With plenty of time at each stop, you can explore at your own pace, take photos, or enjoy lunch at your leisure.
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The tour is praised for its stunning coastal scenery, with glimpses of lighthouses, rocky shores, and charming harbor towns. The beautiful scenery of Gloucester’s coast and gardens stands out as a highlight, as noted in reviews.
Photographers will appreciate the ample time to capture the picturesque towns and natural vistas. The guide’s local insights help you identify the best spots for photos and share interesting facts about the area’s geography and history.

Both reviews highlight Tim, the guide, as an excellent and intuitive storyteller. His enthusiasm and deep knowledge turn the tour into a memorable experience. He adapts to your interests, making sure the experience feels personal and engaging.
The guide’s familiarity with the area and friendly demeanor are often cited as major strengths, helping visitors feel comfortable and well-informed throughout the day.
The tour starts at 12 Farnsworth Street in Boston and concludes with drop-off at your hotel or central Boston. The confirmation arrives immediately upon booking, and most travelers can participate, with most operating in good weather conditions.
Given the average booking window of 37 days in advance, it’s advisable to reserve early to secure your preferred date. Since this is a private tour, only your group participates, adding to its exclusive feel.
This tour appeals most to visitors seeking a personalized introduction to Massachusetts’ North Shore. It’s ideal for those who want to see several towns in one day without the hassle of planning, and who appreciate having flexible time for exploration. The $615 price point reflects the private nature and personalized service, making it well-suited for couples, families, or small groups.
The tour is best suited for most travelers, as the itinerary involves moderate walking and scenic drives. Keep in mind that food and attraction tickets are not included, so plan accordingly for meals or additional sightseeing.
This tour captures the best of Massachusetts’ North Shore, combining scenic vistas, historic towns, and local culture. The combination of beautiful scenery, personalized guiding, and convenient logistics makes it a compelling choice for those wanting an intimate look at the region.
While the tour focuses on the towns and landscapes, the flexible schedule and expert guidance ensure a pleasant and enriching outing. It’s a great way to experience Massachusetts’ coastal beauty without the crowds or rigid group itineraries.
In summary, this 6-hour private trip offers a relaxed, customizable way to explore Massachusetts’ North Shore. The stunning scenery, charming towns, and personalized service distinguish it from larger group tours. The expert guidance enhances the experience, making it ideal for those who value comfort and flexibility.
While the price might be a consideration for some, the private nature and in-depth exploration justify the cost. Travelers who enjoy photography, history, and scenic drives will find this tour especially rewarding. It’s an excellent way to see Cape Ann’s rocky coastlines and Salem’s historic streets in one memorable day.
“The scenery of the coasts and gardens. Gloucester is beautiful. Tim our guide was excellent. He was very intuitive as to our tastes. Salem wa…”
How early should I book this private tour?
Most bookings are made around 37 days prior, so early reservation is recommended to secure your preferred date.
What is included in the tour price?
The private transportation, hotel pickup and drop-off, and an English-speaking guide are included. Food, drinks, and attraction tickets are not.
Is this tour suitable for all ages?
Most travelers can participate, and the moderate walking makes it accessible for many. Check weather conditions for comfort and safety.
Can I customize the itinerary?
As a private tour, the guide can offer recommendations and adjust timing based on your interests, providing a tailored experience.
What are the main highlights of this tour?
Expect stunning seaside views, visits to Gloucester, Rockport, Salem, and Manchester-by-the-Sea, plus ample photo opportunities and local insights.
What should I bring?
Bring comfortable shoes, a camera, and any snacks or drinks you prefer, since food and drinks aren’t included in the tour price.
How does the weather affect the tour?
The experience requires good weather; if canceled due to poor conditions, you’ll be offered an alternative date or a full refund.
Where does the tour end?
The tour concludes with drop-off at your hotel or in central Boston, with the guide providing assistance for your onward journey.