Cape Anne Area Guide


Nothing says “Summer” like a day at the beach, so pack your sunscreen and come explore Cape Ann’s miles of beautiful coastline! Most of the beaches listed are

a short walk, bike ride or drive from our rental properties.

* Due to the impact of Covid19,  please check

for state and local area updates available on prior to your stay for up to date restrictions and guidelines.


Cape Anne Area Guide


Cape Ann offers a wide variety

of cuisines from fine dining to BYOB to takeout.

Our seacoast neighborhoods

have them all!


Here are a few suggestions of area favorites. In summer high season, it is always best to reserve ahead. 

Reach out to our Concierge for any dining needs including reservations during your stay or

for other creative dining experiences including Private Chefs and Catering for a romantic dinner or family gathering onsite.


Cape Anne Area Guide

Hidden Treasures

...Local Favorites

Cape Ann is filled with hidden treasures that give insight into our rich history and heritage.

Let us guide you to the road less taken!  Click for more information.


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paper house 2
paper house 2

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Cape Anne Area Guide

Fun Activities

1. Adventures

Whether you’re planning a fun filled family vacation, a romantic getaway or a relaxing time away, Cape Ann offers a full range of outdoor activities and adventures by Sea and by Land.  Ask our Cape Ann Concierge for a list of charter, cruise,private rental referrals as well as bike rentals, walking trails, recreational activities like golfing or  touring and exploring suggestions to explore Cape Ann by land.  From art colonies to whale watching, Cape Ann has it all.

2. Whale Watching

Cape Ann is known as the “whale watching capital of the world.” These beautiful sea animals can be seen flipping their tales thru the the waves as close as 15 miles off our protected coast line. From ages 9 to 90, whale watching is a must on visitors “to do list.”

3. Fishing

Cape Ann’s waters are known globally for its “bounties of the sea” and Gloucester is the oldest sea port in the nation and remains one of the busiest fishing ports on the East Coast. From cod to haddock to stripers to lobster to shell fish, you will enjoy the freshest seafood either caught by you or a local fisherman. Cape Ann offers  numerous private rental and charters so take advantage of the ocean’s gifts and “catch your dinner” fresh from the sea.

Fishing in the Ocean

4. Sailing and Boating

From the majestic schooners to the romantic boat cruises to sail  and motor charters Cape Ann offers it all. Catch the cooling breezes as you set sail for a day on the sea or relax on one of the many lunch, brunch and dinner cruises both on the ocean and on the river. For a night to remember, book a charter for a clambake or barbecue on the sandbar and watch the sun set.

Ship's Wheel

5. Kayaking, Stand up Paddleboarding, Canoing or Snorkeling

Bring your own gear or rent what you need for a day of fun and exercise the “Cape Ann way” - on the water! Paddle board or kayak along the salt marshes, tidal creeks and wild life on the Essex River.  For a special treat after your outdoor adventure, have some fried clams. Essex is the home of the fried clam - created over 100 years ago by “Chubby Woodman”.

6. Biking, Walking, Hiking

Cape Ann prides itself on the acres of parks and protected environments that house our beloved wildlife. There are numerous bike and walking paths thru out our parks that are  quiet havens for picnics and peaceful solitude. Or take advantage of our magnificent coastal scenery and know that there is truly a “heaven on earth! “

Kayak Fun
Bike Trail

7. Galleries, Antiques, Shopping and more

The arts play a strong role in Cape Ann’s history. Rocky Neck in Gloucester is one of America’s oldest, continuously working art colonies, Rockport is one of our country’s oldest art colonies and is home to over 30 galleries as well as the famed Shalin Liu Performing Arts Center,  and both Essex  and Manchester by the Sea  are havens for antique lovers  and interior designers and decorators and  a mecca for artisan jewelry, folk art and more.  Cape Ann is home to many quaint and unusual shops with one of a kind artisan creations. Take home a piece of Cape Ann and enjoy it all year long as a memory of your stay.

Antique Shop

8. Recreation

Book a Tee time, take a yoga class,  bring the family bowling, jog the coastline, hike the parks, or go horseback riding. Cape Ann is the home for fun fitness!