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Xperience Days

  • Salem Sound Sailing
    Salem, MA
  • Boston Schooner Sailing
    Boston, MA
  • Boston Sunset Sail
    Boston, MA
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Sailing Experiences in Massachusetts

Take to the seas with one of these exciting Sailing Experiences in Massachusetts. Whether you are searching for a gift for the aspiring sailor or a fun family friendly gift, these New England Sailing Experiences are sure to excite!

Schooner Sailing Trips offer the chance to sit back and relax and enjoy the beautiful coastal views and marine life. From Romanic Sunset Sails and relaxing Sightseeing Day Sails to exciting Sailing Lessons, there is something that will please everyone. Great for both locals and visitors, these Massachusetts Sailing Experience Gifts make wonderful Birthday Gifts, unique Anniversary Gifts, fun Father’s Day Gifts and more!

“Great time. Crew were informative, friendly and knowledgeable. Wonderful way to spend a couple of hours. My husband and I would do [the Salem Sound Schooner Sailing] again. Thanks to our children for a great Christmas gift.” -Sandy

Captain Mike was nice and mellow and his boat was very nice. The time sped by as we relaxed and watched all the other boats on the water.


PA

On my Bucket List was to sail on a tall ship. Friends gave me the gift of the Clipper City Sail. It was an exciting experience! The crew was great and the sail was a nice trip around the harbor in spite of the smog from Canada hazing up the views. My only complaint is that there were MANY more people on the ship than there were places to sit. I noticed several elderly people struggling to stand and children hanging on to their parents. I, myself, was fine, but wouldn’t have minded an extra handrail. All in all, I had a lovely afternoon!


Fleetwood, PA

It was a beautiful experience, the ride was relaxing, beautiful scenery, Captain Marci and Mrs. Suzanne, excellent people.


Baltimore

What a relaxing sail on the Chesapeake from Rock Hall, MD! Captain Mark was very knowledgeable about the area! What a perfect summer day!


Landenberg, PA

Key West Sunset Sailing and Open Bar Key West, FL

Key West Sunset Sailing and Cocktail Experience ›

Savor A Key West Sunset Aboard A Historic Schooner With An Open Bar And Stunning Views

Price for 1 Participant $109
(0 ratings)
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Key West Tall Ship Sailing Adventure Key West, FL

Key West Traditional Tall Ship Sailing Adventure ›

Sail a Majestic Schooner in Key West and Experience 19th Century Adventure on the Open Water

Price for 1 Participant $99
(0 ratings)
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Key West Tall Ship Sailing Adventure Key West, FL

Key West Tall Ship Sailing Adventure ›

Sail the Majestic Schooner in Key West and Experience a Historic Tall Ship Adventure

Price for 1 Participant $54
(0 ratings)
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San Diego Sailing Yacht Bay Tour San Diego, CA

San Diego Bay Scenic Sailing Adventure ›

Sail Through San Diego Bay on a Scenic Yacht Tour and Discover Iconic Landmarks and Wildlife

Price for 1 Participant $95
(0 ratings)
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Chesapeake Bay Sailing Trip Rock Hall, MD

Chesapeake Bay Sailing ›

Enjoy a Relaxing Scenic Sailboat Ride on the Chesapeake Bay

Price for 2 Participants $120
(89 ratings)
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Schooner Sailing Portland Maine Portland, ME

Sailing Maine ›

Experience the Beauty of the Maine Coast on a Two Hour Windjammer Sail for Two

Price for 2 Participants $140
(5 ratings)
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San Diego Schooner Whale Watching San Diego, CA

San Diego Whale Watching ›

Enjoy a Half Day Schooner Sailing Whale Watching Adventure

Price for 1 Participant $105
(8 ratings)
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Marina Del Rey Sailing Charter Marina del Rey, CA

Marina Del Rey Sailing ›

Enjoy a Private Two Hour Skippered Charter Sail For You and Your Friends in Marina Del Rey

Price for 2 Participants $560
(8 ratings)
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15 Christmas Gift Ideas for Dads Who Have Everything

15 Christmas Gift Ideas for Dads Who Have Everything

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  • Nov 2023
  • Gift Ideas , New York Sights
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  • Flying Experience Gifts , Lifestyle Activity Gifts
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  • Food and Wine Experiences , Skydive Experience Gifts
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Latest Reviews

  • I recently attended a cooking class with Karen Lee, and it was a fantastic experience from start to finish. Karen took the time to connect with me beforehand, asking about my preferences and thoughtfully customizing the menu. The quality of the ingredients was top-notch, and I picked up so many valuable cooking tips. Everything we made turned out absolutely delicious! The next day, Karen sent beautiful photos of our dishes, adding a special touch to the whole experience. I highly recommend her classes to anyone looking for a fun and memorable cooking experience.

    - New Jersey
    Verified Xperience Days Participant
  • I bought a flying lesson for my 17 year old grandson who is very interested in flying. He had a great time with Andrew, his instructor. He couldn’t quit smiling and talking about it all day!

    - Crystal MN
    Verified Xperience Days Participant