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7 Amazing Weekend Getaways From Boston After A Busy Week

Weekend Getaways From Boston

Are you looking to switch up your routine? Spice up your weekend getaway from Boston with our fun-certified itinerary. We included nine top weekend getaways from Boston to help you relax and unwind before the weekend ends!

Exploring the picturesque towns, indulging in delicious cuisines, and soaking up the sun are all you need to recharge your batteries. So, pack your bags and hit the road to discover New England’s charm!

1) Go For Bike Riding In Martha’s Vineyard

Start your weekend getaway on a high note by biking in Martha’s Vineyard. Most visitors and locals reach the island by ferry From Woods Hole on Cape Cod. You can also use air transport.

Filled with breathtaking landscapes and sweeping ocean views, the island’s routes are perfect, with little or no traffic. If you are a pedal pro, you’ll enjoy the sandy shoulders and blind curves of Martha’s vineyard.

2) Go For A Relaxing Sailing Voyage In Gloucester

Are you ready to see new horizons? Grab your sailor’s hat and set sail on New England’s coastline.

Gloucester is perfect for crisp ocean air and gentle waves beneath your feet. Begin your world of adventure and wonder by booking a 4-hour coastal sailing voyage on the coastline of New England!

3) Enjoy The White Mountains Hiking Trails

There is no better way to get off a funk than trailing the White Mountains. If you are an adventurous couple, you can romance in the majestic backdrop and pretty waterfalls.

Outdoor enthusiasts know that for adrenaline-fuelled weekend getaways, mountain biking reigns supreme. You will find unique rocky terrain and steep hills that are both challenging and rewarding.

Don’t conclude your trip to New Hampshire just yet. There is still more you can do for a top-notch weekend getaway.

  • Go for a scenic gondola ride

  • Book a ride at Mt Washington Cog railway

  • Kayak at Saco River Tubing

4) Go For A Trolly Tour Or A Food Tour In Newport

Do you want to go back in time? How about hopping on an old-fashioned trolley for a great weekend getaway?

The charming town in Rhode Island offers picturesque ocean vistas, breathtaking architecture, and stunning streets. Bring the past to life with every twist and turn a luxurious trolley in this weekend getaway.

Indulge in Newport’s culinary delights! The city by the sea makes one of the best destinations for weekend trips from Boston for foodies.

Try fine dining at Castle Hill Inn, picnic at Brenton Point State Park, or Instagram your food at the Hammetts Hotel.

5) Enjoy A Meal At Block Island

The top weekend getaways from Boston can’t miss a meal or two. From oceanfront dining to casual picnics, your palate will have a field day at Block Island.

You can pass by The Oar for seafood or drown yourself at the Poor People’s Pub with local craft beers. You can’t have one of the best Boston weekend trips until you exhaust everything the island offers:

  • Ride the Block Island ferry

  • Experience The Mohegan Bluffs

  • Explore The Clayhead Trail

6) Explore The Berkshires In North Adams

The best Boston weekend trips must include visiting North Adams in Western Massachusetts.

Nestled in the middle of the Berkshires, North Adams offers a beautiful blend of outdoor adventure and cultural attractions. Topping the most incredible destinations for anyone seeking a break from the fast-paced city center.

From hiking trails, zip lining, and endless museums, you will have an unforgettable weekend trip.

If you get hungry from all the activities, step into the great restaurants within walking distance of each other. One of the most recommended is Nara Sushi and Village Pizza.

7) Enjoy Pristine Beaches And Instagram Lighthouses In Kennebunkport

Are you a beach bum? Then you have heard of the three beaches in Kennebunkport in Maine.

Mother’s Beach

You can explore the sandy areas of Mother’s Beach, which is the perfect destination for a family trip. It is much easier here to keep an eye on the kids on the seaside playground compared to other beaches.

Middle Beach

If you value solitude and privacy, you will enjoy the serene and secluded Middle Beach. Immerse yourself in nature and embrace the natural beauty of the surroundings on the tranquil sandy beaches.

Gooch’s Beach

Gooch’s Beach is where all the fun happens! Enjoy surfing, whale watching, and endless boat tours. For weekend getaways, always include binge drinking in your itinerary. Quench your thirst and mingle with the locals at Old Vines Wine Bar, just a short walk from the beach.

Explore Instagrammable Lighthouses

Before leaving Maine, don’t miss out on any Instagrammable moment of the lighthouses. You have probably seen Nubble Lighthouse, a famous lighthouse south of Kennebunkport.

You should also check out the following:

  • Goat Island Lighthouse

  • Portland Headlight & Museum

  • Wood Island Lighthouse

  • Boon Island Lighthouse

Plan Your Perfect Weekend Getaway In Gloucester

You already work too hard and live too little! So why not keep your mental health in check by going for the top weekend getaways?

Make it one of your best weekend trips from Boston by booking a luxury charter on the coastline of Gloucester. We at Artemis Sailing Charters help you to sail away your problems before resuming work on Monday!

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.