You’ve worked hard for years and the time has finally come to retire. Those first few months (and sometimes years!) can be a glorious time of freedom, giving you the opportunity to take that trip you’ve always dreamed of. And what better place than Cape Ann for your “Retirementmoon” (a mashup of retirement + honeymoon)? With something for everyone, no matter the season, we’re sure you’ll love your stay.

Lighthouses and Beaches
No trip to Cape Ann would be complete without at least one trip to the beach. All of our beaches (and lighthouses!) are worth a visit, but these are the ones at the top of our list:
- Half Moon Beach is a quieter beach with stunning views, located in Stage Fort Park, allowing you to enjoy a picnic before heading to the rocky shores.
- If soft sand, calm water, and lighthouse views are more your speed, you won’t want to miss Wingaersheek Beach.
- While many of the lighthouses in Cape Ann are only accessible by boat, Eastern Point Lighthouse does allow visitors to drive close to the lighthouse.
- Looking to see as many lighthouses as possible? Then the Cape Ann Harbor Tour Lighthouse Cruise is just what you’re looking for. Over the course of 2.5 hours you’ll see six lighthouses and learn all about the history of the area.

Museums and Tours for Every Interest
It would take us ages to list all of the adventures you can go on just by visiting our local museums or heading out with an experienced tour guide, but here are a few of our favorites.
- Travel back in time and visit The Hammond Castle Museum, a true European castle built by John Hammond. With a calendar chock-full of events you could easily spend the day in this medieval wonder.
- Join profession photographer Kirk R. Williamson of Cape Ann Photo Tours as he takes you to some of the best spots in the area to capture the beauty of Cape Ann. There’s no need to be a pro, Kirk loves to work with photographers of all levels.
- Cape Ann Foodie Tours are known as “the most delicious way to discover Cape Ann”, and we couldn’t agree more. The Taste of Gloucester Tour will make sure you hit every local gem where you’ll taste some of the best food we have to offer while learning more about Gloucester.
- Dive into the history of Essex shipbuilding with a day at the Essex Historical Society and Shipbuilding Museum!

Arts, Culture, and Entertainment
There’s always something happening in Cape Ann, and not just in summer!
- Head to the Rocky Neck Art Colony to see the works of our local artists. With exhibits happening in three locations you could easily spend a day visiting each of them while also visiting their artist neighbors.
- The Orchestra on the Hill always has something exciting planned, and often blends music with performance art.
- We love getting in a show at the North Shore Music Theatre, and are sure you’ll enjoy it as well!

Winter Birding
Birding is fantastic year-round on Cape Ann, but winter is the best season. You don’t have to take our word for it, the Bird Watcher’s Digest agrees! Not only will you see a wide variety of winter birds during your stay, but you’re also likely to catch sight of some uncommon birds, including the King Eider as well as Harlequin Ducks.

Where to stay
The perfect location is close enough to everything you want to do, while still feeling like a getaway from the normal hustle and bustle of life. We have vacation rentals for every budget and every season, each one the perfect place to enjoy your retirement honeymoon. Whether you’re looking for a luxury waterfront vacation rental or a beach bungalow tucked away on the beach, we can make your retirement honeymoon everything you dream of. Give us a call today at +1 (978) 290-4331, or book directly online. Either way, we can’t wait to see you!
Looking for things to do by season? Look no further!