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7 Things To Do In Gloucester, MA For A Relaxing Vacation

Things To Do In Gloucester MA

Are you experiencing burnout? How about a quick relaxing gateway to Gloucester, Massachusetts?

From Idyllic beaches to delicious food, historical landmarks, and quaint streets, you will have enough activities to unwind and recharge.

So, pack a travel bag, grab your SPF 60 sunscreen, and explore these seven things to do in Gloucester, MA.

1) Get Your Vitamin Sea At Gloucester’s Beaches

Calling all beach bums and sun lovers to discover the coastal paradise at Gloucester!

Soak up the sun, step on powdery sand, and take in the beauty of the ocean at any of these destinations.

  • Good Harbor Beach – Sink your toes in the sand and let the waves roll in as you admire the crystal-clear waters of Good Harbor Beach

  • Wingaersheek Beach – Grab your sunscreen and explore the stunning vistas of Ipswich Bay at Wingaersheek Beach.

2) Raise The Sails On New England Coastline

You spend the better part of your life on land. How about you explore the beautiful coastline of Gloucester, Massachusetts, for a change?

Learn how to sail a boat, watch seagulls flying overhead and dolphins swimming in the distance in an immersive Atlantic voyage.

As much as structured public boat tours are great, book private charters, which offer a more personalized experience. You can sail in the afternoon, during a sunset, or even overnight.

Hang out with your friends on a 4-hour coastal sailing voyage before starting the real party.

If you are a couple, you can marvel at the different hues the sun sets in downtown Gloucester and Eastern Point by booking a 3-hour sunset sailing cruise.

3) Get Your Culture Fix At The Museum

Explore the true history of Gloucester, Massachusetts by checking out its top museums. Gloucester is not shy from artifacts and important relics.

You can take in the history, culture, and art of the city by visiting any of the museums below:

Hammond Castle Museum

Explore Medieval Times at Gloucester’s Hammond Castle to witness panoramic views of the Atlantic Ocean. Home to the father of radio control”, John Hays Hammond Jr., the castle has exquisite interior and exterior features.

Cape Ann Museum

If you are a ship fanatic, you already know Fitz Henry Lane. Cape Ann Museum stores some of his best works of mid 19th century. There are also other famous works by painter Winslow Homer who lived on Ten Pound Island in the 1880s. Many of the artists also display their art in Rocky Neck.

Maritime Gloucester

The city has established itself in the fishing industry. Inspiring discovery, this museum will take you into deep waters while still on land. Take your family and friends to explore the wonders of marine life.

Beauport, The Sleeper-McCann House

With lush gardens, perennial flowers, and endless coastal grass, the Beauport house is nothing short of a fairy tale. Sink in Gloucester’s gothic, early colonial, and medieval architecture by going to Gloucester’s Eastern Point.

4) Go For Picnic

Do you want to feel like a first settler? Bring your food and treats for a picnic at Stage Fort Park. Don’t forget to get your fish treats from Gloucester fishermen. They have the most affordable and fresh seafood if you don’t want the pain of cooking during your vacation.

Stage Fort Park is home to Half Moon Beach and Cressy’s Beach. So your friends can enjoy a game of basketball, baseball, or tennis. If all these games don’t cut it, you can play volleyball on the sand.

You can also indulge in outdoor concerts, festivals, and farmers’ markets at the premises.

Don’t worry if you’re traveling with your pet to Gloucester. Go to Ravenswood Park with your dog to play in small waterfalls and streams without a leash.

5) Take Pictures At A National Historic Landmark

How do you say you were in Gloucester, Massachusetts, without saying it? A picture is worth a thousand words, and there is no better place than Gloucester Harbor.

Your friends can get many Instragrammable moments at these top national historic landmarks:

  • Gloucester Fisherman’s Memorial Monument

  • Ten Pound Island Lighthouse

6) Go For Whale Watching In Downtown Gloucester, MA

Can you prove you sailed deep waters if you don’t go whale watching?

Whale watching is iconic in downtown Gloucester with plenty of the majestic creatures swimming so close to boats and yachts.

Get a salty breeze in your hair as you spot massive tails of whales peeping through the waters. You will surely enjoy the magnificent humpback breaching the surface and leaving a thunderous splash. Hopefully, you don’t mind a little salt in your hair.

7) Romance At The Lighthouse

Light up your night at Gloucester Harbor’s lighthouses. Rising against the city’s shoreline backdrop, the lighthouses beckon every nautical wanderer to come and explore.

Make sure you climb to the top of these towers to soak in breathtaking views of Cape Ann and the Atlantic Ocean beyond:

  • Eastern Point Lighthouse

  • Annisquam Lighthouse

Sail Your Problems Away

The worst part about traveling is that it always comes to an end. But you can make your vacation last forever by adding one final relaxing itinerary. Book a luxury yacht charter ride with Artemis Sailing Charters as one of the last exciting things to do in Gloucester, MA.

Feel the wind in your hair and the peacefulness of the ocean waves one last time before leaving Gloucester’s endearing coastline.

4 hours
Group Size
1 to 6

4 Hour Coastal Sailing Voyages. Sailing from 11-3 each day

We welcome you aboard ARTEMIS for a 4 hour voyage departing from and returning to beautiful Gloucester harbor. If you’ve ever heard the term” we’ll go where the wind takes us” well then you’ll begin to understand that our direction of sail or itinerary is based on the direction from which the wind is blowing. Whether it’s sailing down the coast to Marblehead or Salem, heading offshore to get away from land and search for marine life or working our way up to the magnificent twin Lighthouses of Thatchers Island, you will have much to see. Maybe you’ll want to learn a little about sailing a take a turn at the wheel! It seems that we’re often hungry at sea and you’ll love our yummy and healthy sandwich wraps served on deck. We will provide still and carbonated water but feel free to bring some beverage of your choice to stock in the ice chest.

6 Reviews verify
3 hours
Group Size
1 to 6

3 hour Sunset Sailing Cruise. Sailing from 4-7 each day.

Watching the reds, oranges, and yellows of the sky as the sun sets over Gloucester Harbor is a spectacular sight.
Do you know what elevates the amazing sight of a sunset even more?
A sunset cruise!
Sunset cruises offer a fun and satisfying experience of being on a boat during the intriguing and dramatic sunset hours.
But what exactly are sunset cruises? Read on to find out all you need to know about taking a cruise at sunset and if it’s right for you!
Why Take a Sunset Cruise?
Taking a cruise at sunset is the perfect way to see the take in the bold colors, see the view of the shore from the water and make some fantastic memories. Here are some reasons you should definitely take a sunset cruise.
Positive Vibes
Sunset cruises are all about positive energy—laughter, smiles, relaxation, and entertainment. It’s nearly impossible to experience a sunset cruise and leave feeling anything less than completely satisfied. You might feel a little sad, but it’s only when the cruise is over lol!
Great Vacation Experience
Taking a cruise at sunset is one of the great opportunities of being on vacation. It’s a great way to see the nearby coastline from the water and learn more about the place you are visiting.
For an extra special outing, book a cruise at sunset on the day you arrive or the day you depart—the memories will certainly be extraordinary!
Celebrate Events
What better way is there to celebrate a special event or occasion that to plan a cruise at sunset? Being on the water, taking in the scenery, and watching the sky’s vibrant colors is a great way to emphasize the festive feel of the day!
For Inspiration
A boat cruise, especially a sunset cruise, is a great moment to reflect on life. It makes you feel positive, grateful and inspired, and open to all the other wonderful experiences life has to offer.
What Occasions Can You Celebrate on Sunset Cruises?
There is no limit to the reasons to take a sunset cruise. Here are some of the occasions, events, and special days you can celebrate with a sunset cruise.
Date Night
Of all the romantic date ideas, taking your beloved on an enchanting sunset cruise will win every time! To be on the water is a great way to spend an evening date, and pair that with the ultimate romantic sunset, and it’s guaranteed to be a date you’ll remember forever. Want to pop the question—consider a sunset cruise.
Trying to find an experience that will add some pizazz to a loved one’s birthday celebration? Look no further than a sunset cruise. The magical orange and red-tinged sky is the perfect backdrop for a magical and unforgettable birthday.
What better way to celebrate your retirement than to book a cruise that will take you off into the sunset! It’s a great way to say goodbye to one phase of your life and onto the next.
Work Celebrations
Maybe you got a big promotion, saying goodbye to a colleague, or need to do something fun to celebrate the completion of a big, successful project. When nothing short of extraordinary will do, a sunset cruise just might be the answer!
Romantic Evening for Two
Having a drink and delicious appetizers on a cruise while watching the sun set below the horizon is nothing short of magical. It’s the perfect place for a combination of great food, good company, and one of nature’s greatest shows.
Nature Exploration
Our waters are full of vibrant marine life and the dusk hours can be the perfect time to see them in action. Watch the egrets returning to their nests on Ten Pound Island and see the fish taking their last jumps before the sun fully sets.

6 Reviews verify
3 hours
Group Size
1 to 6

Restorative Retreat on the Water June 23, 2023. 11am-2pm

This unique 3 hr retreat combines guided restorative yoga with some relaxing sailing aboard Artemis. Lunch is included.