5 Sightseeing Tours in Gloucester That You Shouldn't Miss

August 22, 2021 Tambra Mccollister

With its sandy North Shore beaches, rocky outcrops, green parks, hemlock woods and wild estuaries full of shorebirds, it is no wonder that Gloucester has attracted such a rich and diverse artists' community. Fitz Hugh Lane, Winslow Homer and John Sloan are just some of the artists who have taken inspiration from Gloucester's beautiful surrounds. Still boasting dozens of galleries and boutiques, as well as museums, theaters and an artists' colony, the city's art scene clearly continues to thrive.
Restaurants in Gloucester

1. Ultimate Boston Self-Guided Combo Tour

Boston Common, 139 Tremont St, Boston, MA 02111, USA Boston City Day Trips
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5.0 based on 1 reviews

Explore Boston, Cambridge, Cape Ann, and more! This package covers Boston's iconic Freedom Trail (Old North Church, Faneuil Hall, & more), Harvard University, the Harborwalk, and a scenic waterfront drive around nearby Cape Ann. This is the ultimate "must-do" package for a trip to Boston and New England. This self-guided tour allows you to explore Boston’s historic wonders with maximum flexibility and value. Purchase one tour per car. Everyone can listen at the same time! Within 30 mins we'll send you a unique password and an app. Download the app onto your phone, enter the password, and download tours. Head over to the first stop. Launch the app and simply follow the instructions from there! Stick to our recommended route and speed limit for the best experience. No expiration — the tour is available from the minute you book until forever! This tour does not include entrance to attractions along the route. Check pandemic rules and opening hours before your visit.

Inclusions: Freedom Trail Tour (Languages: English, Spanish, Chinese), Harborwalk and Tea Party Tour, Scenic Cape Ann Tour, Harvard Yard Tour, Cape Cod and Provincetown Tour, GPS Map, Audios and Text, Online Support

Exclusions: Admission to Paid Attractions

Reviewed By Trek697070

Loved that the tourguide started the topic before we arrived at the destination and was occasionally comical. Didnt love that the map feature didnt let us know when we detoured. Would like to see "places to park" especially if you have an oversized vehicle.

27 Rogers St, Gloucester, MA 01930, USA 7 Seas Whale Watch
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4.9 based on 1,230 reviews

Guaranteed Sightings!  7 Seas Whale Watch is located in the heart of historic downtown Gloucester, MA and in one of the busiest parts of Gloucester harbor. As soon as you board the Privateer you will be surrounded by the sights and sounds of Gloucester’s working waterfront. You may see fishing boats unloading fish, lobster men baiting and setting their traps, and perhaps even some of our indigenous wildlife such as Harbor seals, Gray seals, and various species of birds. The tour begins with a harbor tour of Gloucester Harbor starting with Cape Pond Ice (which most of you have seen on Wicked Tuna and ends at the Dog Bar Breakwater.  A typical trip is anywhere from 3-4 hours but may be extended if the whales move further out for feed.  The Privateer IV was built for 300 passengers but we only book to 150 to ensure the comfort and safety of our passengers and is equipped with restrooms, and on-board food Galley and bar.

Inclusions: A 3 and a half hour to 4 hour excursion.

Exclusions: Alcoholic drinks (available to purchase), Food and drinks (available for purchase)

Reviewed By 535lienn

This is my first time going for the whale watch and it turned out to be so perfect in terms of the weather, the service provided by the staff, and most important - the whales. I have taken so many pictures of these magnificent creatures! Staff are very friendly and supportive.

3. Whale Watching Tour in Gloucester

415 Main St, Gloucester, MA 01930, USA Cape Ann Whale Watch
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4.8 based on 2,431 reviews

You are guaranteed whale sightings on this whale watching tour out to Stellwagen Bank, a national marine preserve about 12 miles off the coast of Gloucester deemed one of the "Top 5 Whale Watching Destinations in the World" by the World Wildlife Fund due to the wide variety of whale species whom migrate to the coast of Gloucester, Massachusetts every year to feed on the abundant natural resources. This is one of the best whale watching in New England as it's an awe-inspiring experience which every human being should have the opportunity to appreciate.

Inclusions: Naturalist onboard, Professional guide, Full galley

Exclusions: Food and drinks, Gratuities, Hotel pickup and drop-off

Reviewed By MikeF8272020

The crew was fantastic and very helpful! The Captain was amazing at getting us directly to the whales and they didn’t disappoint.

4. Scenic Cape Ann Self-Driving Audio Tour in Gloucester and Rockport

Gloucester Visitor Center at Stage Fort Park, 24 Hough Ave, Gloucester, MA 01930, USA Boston City Day Trips
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3.8 based on 13 reviews

Discover Cape Ann with a self-guided audio tour along the scenic waterfront! Enjoy the vistas, beaches, and natural beauty of this quintessential New England coastline at your own pace. Visit the famous Fisherman's Memorial, beautiful Beauport, and the scenic Harborwalk, all while diving into the stories of Massachusetts of days past with this self-guided driving tour. Recommended: purchase one tour per car. Everyone can listen at the same time! Within 30 min, we'll send you two things: a unique password and an app. Download the app onto your phone, enter the password, and download the tour. When you arrive, go to the Gloucester Visitor Center, launch the app, and follow the instructions! Stick to our recommended route and speed limit for the best experience. This is not a ticket to attractions along the route. Check COVID rules and opening hours before your visit. No expiration — the tour is available from the minute you book until forever!

Inclusions: GPS Map, Audios and Text, Online Support

Exclusions: Admission to Paid Attractions

Reviewed By R7356OOpaulah

This was an awesome way explore Cape Cod. We loved that we could tour the Cape at our own pace. I’m excited to plan our next self guided tour in the near future.

5. Private tour to northern Massachusetts coast from Boston - Hotel pick up

Boston, MA, USA Tour Travel & More Boston

Enjoy this private full day tour with your own private driver and official tour guide and explore the vibrant coast of northern Massachusets. Get ready to explore the most beautiful beaches and the nicest spots in this wonderful area. We will pick you up from your hotel or place of choice (hotel or apartment) in Boston and take you on this private tour, with your own chauffeur and guide to the northern coast of Boston. During your full day private tour you will visit Gloucester and Rockport. You will explore its beautiful rocky coast and sandy beaches. You will of course have free time for lunch along the tour. SAVE COVID-19 SAFE - As this is a private tour we take care of maintaining social distance

Inclusions: Hotel/apartment pick-up and drop off in Boston, Local Taxes, Official Tour Guide for 8 hours, Private Tour, Private luxury vehicle with driver for a maximum of 8 hours, SAVE COVID-19 SAFE

Exclusions: Entrances Fees, Food and Drinks, Gratuities

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