Cape Ann is located on the North Shore about 45 minutes from Boston. Cape Ann consists of Gloucester, Essex, Manchester-by-the-sea, Rockport and the easternmost part of Beverly. This local vacation getaway is best known for its beautiful scenery, art galleries galore, soul-satisfying seafood and river cruises. Known as one of the best whale watching capital of the world, this is a wonderful destination for where you get to experience everything the ocean has to offer with a special emphasis on the wildlife.

WHERE TO STAY: Beach & King Street Inn in Rockport. This is an intimate private beach home that feels like home.

WHERE TO EAT: Down River Ice Cream in Essex. This is the kind of ice cream that is decadent enough to have for dinner.

WHAT TO DO: Cape Ann Whale Watch in Gloucester. You will see so many whales and have so much fun on this whale watch that you will absolutely forget about the crisp breeze nipping at your skin. But still, bring a sweatshirt!

HOW TO GET THERE: You can get to Cape Ann by water or land.

Insider Tip: Bring a sweater on whale watching trips.


Read the Massachusetts vacation guide for Nantucket Island, Martha’s Vineyard, Cape Cod and The Berkshires.Let’s be friends: Follow me on Instagram, Twitter, Pinterest and like me on Facebook.


Picture source 1, 2, 3.