# Best Massachusetts Mancation Ideas *By James Hills — Updated July 2023* Massachusetts may be difficult to spell, but it is not difficult to find some great options for the ultimate guys weekend or a fantastic mancation. Few states have as rich of a mixture of terrains and opportunities packed into such a small place. For instance, imagine starting in Boston with a pub crawl, followed by a bike tour through gorgeous countryside, kite surfing on the cape and then wrap it all up with a deep see fishing expedition, and a historic reenactment! Just don't forget a classic New England-style clam bake for dinner! ## Deep Sea Fishing Nothing promotes male bonding more than hauling in "the big one" on a deep sea fishing excursion. The [Yankee Deep Sea Fishing Co](https://www.yankeefleet.com/). in Gloucester will take your group to some of the Atlantic's best fishing spots, such as Stellwagen Bank and Jeffrey's Ledge. The nearby Atlantis Motor Inn has an ocean view from every room and a cafe offering hearty breakfasts to get the day off to a good start. If you extend your stay, Gloucester is also home to the New England aquarium; "cool" tours of the Cape Bond Ice Company; and Cape Ann Divers which offers lessons and dives to offshore reefs/shipwrecks. ### Ward Cove Alaska: Authentic Tlingit Culture & Tongass Wilderness Adventures Cruising News and Reviews for west coast cruisers and those considering cruising for the first time. CruiseWestCoast [Read More](https://ads.flowmediamarketing.com/go/mVRHn2kJXpzkAp5Fo5ZudA.621) ### Norwegian Encore Is The World's Best Ship For A Guys Getaway Norwegian Encore cruise ship is our top pick for the ultimate guys weekend getaway at sea. ManTripping [Read More](https://ads.flowmediamarketing.com/go/mVRHn2kJXpzkAp5Fo5ZudA.1482) ### Sri Lanka round tour Sigiriya is the 8th wonder of the world belongs to the 5th Century AD. This is the best place to get an idea about the creativity, water management, landscaping, arts and painting, engineering, city planning of the ancient people of Sri Lanka. Viator (affiliate) [Book on Viator](https://ads.flowmediamarketing.com/go/mVRHn2kJXpzkAp5Fo5ZudA.1814) ### Adriatic Cruising: Why Croatia's Islands Are Perfect for Your Next Mancation Experience Croatia's Adriatic Sea through luxury yacht charters, cruise adventures, and island hopping. Discover Hvar's nightlife, Kornati's wilderness, and Mljet's pristine forests on the ultimate gu ManTripping [Read More](https://ads.flowmediamarketing.com/go/mVRHn2kJXpzkAp5Fo5ZudA.420) Promoted by FlowAds ## Pub Crawls and Craft Breweries A "pub crawl" of Boston's famous Irish pubs is an ideal excuse for a guys weekend or even as part of larger mancations . You can rent your own limo or sign up with one of Boston's many party tour companies. Crawls generally stop at such historic pubs as the Green Dragon, onetime hangout of Paul Revere; Mr. Dooley's, which features live music by Ireland's recording artists; Hennessy's, voted best Boston Irish pub by the AOL city guide; and the Bull & Finch, where "Cheers" was filmed. Most pubs offer Irish American fare or you can opt to partake in a mouth-watering steak at Durgin Park, the Travel Channel's pick as the #1 steakhouse in America. Of course, no visit to Boston would be complete without a trip to the [Samual Adams brewery](https://www.samueladams.com)! ## Biking The Berkshires Massachusetts is covered with bike trails and one of the best jaunts is [New England Cycling](https://bikenewengland.com/berkshire.html)'s six-day tour of the Berkshires in Western Massachusetts. The 30-45 scenic miles traveled each day cover both flat roads and challenging climbs. Three nights' lodging at the Windflower Inn in Great Barrington and two nights ar the Maple Terrace Motel in Williamston are included. The company also offers two-day jaunts from Sheffield to Umpachenee Falls, with a stop at the oldest covered bridge in Massachusetts. Indulging in oyster appetizers, succulent meats, and a 1700s grist mill environment at the Old Mill Restaurant in South Egremont is the perfect end to this trip. ## Historic Reenactments Male history buffs who loved playing with toy soldiers as children will find attending Revolutionary War battle reenactments the ideal mancation. The optimal place to go is [Lexington on Patriot's Day](https://www.battleroad.org/)weekend, a New England holiday commemorating the opening battle of April 19, 1776. Weekend events include historical programs; typical 1776 food; and re-enactments of the battle itself, as well as of events leading up to the war like Paul Revere's ride and the ringing of the Old Belfry bell announcing the coming of the British. It's great fun to enjoy the sights and sounds as spectators; however, if interested in being reenactors, contact the Massachusetts Society of the American Revolution in Mendon at 508/229-1776. September's Pick Amazon (affiliate) ### Kenyon City Grill Portable Stainless Steel Electric Grill Why we picked it: a grill you can actually carry to the campsite, the tailgate or the cabin without borrowing a truck. Stainless, no propane tank to wrestle, and hot enough to cook for four guys rather than reheat for one. [Check The Price](https://ads.flowmediamarketing.com/go/6VhAa5G_CdnLD342daBy7Q.2144) [August's Pick Gorilla Carts Heavy Duty Garden Wheelbarrow, 1200 Lb, Yellow $174.99](https://ads.flowmediamarketing.com/go/6VhAa5G_CdnLD342daBy7Q.2143) [July's Pick Amazon Fire TV Stick HD with Alexa Voice Remote $17.99](https://ads.flowmediamarketing.com/go/6VhAa5G_CdnLD342daBy7Q.2136) [June's Pick Google Chromecast with Google TV 4K HDR Streaming Player, Snow $109.99](https://ads.flowmediamarketing.com/go/6VhAa5G_CdnLD342daBy7Q.2139) Promoted by FlowAds Details Written by: James Hills Last Updated: 22 July 2023 ### 🚢Ready To Book A Vacation? Let us help you plan a cruise, all-inclusive resort, or tour for your next guys trip, family vacation, or romantic getaway. Click here to [**Book Your Next Vacation**](https://www.mantripping.com/vacation-planning.html). #### Which Style Of Amazon Cruise Should You Pick To Explore World's Largest River? Aug 17, 2026 [Which Style Of Amazon Cruise Should You Pick To Explore World's Largest River?](https://www.mantripping.com/travel/amazon-river-cruise-planning-ship-options.html) [Plan Your Next Vacation Today!](https://www.mantripping.com/vacation-planning.html) ### Products & Gift Ideas #### LiberNovo Maxis Chair Review - Finally A Seat That Lets Big Dudes Feel Comfortable At The Desk Sep 10, 2026 [LiberNovo Maxis Chair Review - Finally A Seat That Lets Big Dudes Feel Comfortable At The Desk](https://www.mantripping.com/stuff/libernovo-maxis-big-and-tall-office-chair-review.html) #### FRESKO 4-in-1 Immersion Hand Blender Review Sep 09, 2026 [FRESKO 4-in-1 Immersion Hand Blender Review](https://www.mantripping.com/stuff/fresko-4-in-1-immersion-hand-blender-review.html) #### UGREEN Air Review: Four Slim Chargers And Power Banks I Traveled With This Summer Aug 25, 2026 [UGREEN Air Review: Four Slim Chargers And Power Banks I Traveled With This Summer](https://www.mantripping.com/stuff/ugreen-air-chargers-power-banks-review.html) ### Top Guys Trip Ideas: #### Places Where You Can Go Underground and Explore a Real Mine Feb 27, 2025 [Places Where You Can Go Underground and Explore a Real Mine](https://www.mantripping.com/travel/places-where-you-can-go-underground-and-explore-a-real-mine.html) #### Thoughtful Gestures to Stay Connected With Your Wife During a Guys Getaway Sep 03, 2024 [Thoughtful Gestures to Stay Connected With Your Wife During a Guys Getaway](https://www.mantripping.com/stuff/thoughtful-gestures-to-stay-connected-with-your-wife-during-a-guys-getaway.html) #### Kuwait Travel Guide: What to See and Do On Your Next Guys Trip Jul 09, 2025 [Kuwait Travel Guide: What to See and Do On Your Next Guys Trip](https://www.mantripping.com/travel/kuwait-travel-guide-what-to-see-and-do-on-your-next-guys-trip.html) ### Related Articles #### How to Plan a Destin Guys Trip: Golf, Deep-Sea Fishing, and A Beach-House [How to Plan a Destin Guys Trip: Golf, Deep-Sea Fishing, and A Beach-House](https://www.mantripping.com/travel/destin-guys-trip-planning-guide.html) #### 400 Years of Drinking in One Night: Boston's Most Historic Bars [400 Years of Drinking in One Night: Boston's Most Historic Bars](https://www.mantripping.com/travel/historic-bars-boston-guys-trip.html) #### Psychics, Sacred Vortexes, & Nine Places That Even Skeptics Will Enjoy Visiting on a Guys Trip [Psychics, Sacred Vortexes, & Nine Places That Even Skeptics Will Enjoy Visiting on a Guys Trip](https://www.mantripping.com/travel/metaphysical-guys-trip-destinations.html) #### The Off-Road Trip You Didn't Know You Needed - Craters, Volcanoes, and Dead Sea Cliffs in Israel [The Off-Road Trip You Didn't Know You Needed - Craters, Volcanoes, and Dead Sea Cliffs in Israel](https://www.mantripping.com/travel/offroad-mancation-jeep-tours-israel.html) #### Good Will Hunting to The Departed: A Guys Film Tour of Boston [Good Will Hunting to The Departed: A Guys Film Tour of Boston](https://www.mantripping.com/travel/film-locations-boston-guys-trip.html) - [**](https://www.mantripping.com/search.html) - [**](https://www.mantripping.com/sitemap.html) - [** Polls](https://www.mantripping.com/polls.html) - [Community Login](https://www.mantripping.com/registration/login.html) - [Brand Engagement Newsletter](https://www.mantripping.com/pr-ops-newsletter.html) - [Links](https://www.mantripping.com/links.html) - [Pitch Portal](https://www.mantripping.com/pitch.html) - [Men's Travel Survey](https://www.mantripping.com/the-mantripping-guys-trip-report-spring-2026.html) --- *Source: [Best Massachusetts Mancation Ideas](https://www.mantripping.com/travel/best-massachusetts-mancation-ideas.html)* **Tags:** Mancation , Massachusetts Guys Trip Ideas, Boston Guys Trip Ideas, Travel Ideas