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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

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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St. Augustine Nights of Lights Boat Tour St. Augustine, FL

St. Augustine Nights of Lights Celebration Cruise ›

Experience The Nights Of Lights Celebration Aboard Fury's Catamaran In St Augustine

Price for 1 Participant $69
(0 ratings)
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Lake Erie Two Hour Sunset Sail Erie, PA

Lake Erie Sunset Sail ›

Watch the Sun Go Down On Lake Erie on this Scenic Two-Hour Sailing Trip

Price for 1 Participant $180
(0 ratings)
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Rappahannock River Sunset Sail Weems, VA

Sunset River Cruise VA ›

Enjoy a Private Sunset Cruise on Rappahannock River in Weems

Price for 2 Participants $250
(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)
View Activity ›

15 Christmas Gift Ideas for Dads Who Have Everything

15 Christmas Gift Ideas for Dads Who Have Everything

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  • 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

  • Our experience was nothing short of extraordinary! Abby proved to be an exceptional host, radiating warmth and professionalism. She was thoroughly prepared upon our arrival and spent the evening skillfully guiding us through the cooking process while sharing stories from her culinary and restaurant journey.

    The event was both entertaining and educational, packed with fun moments and valuable takeaways. Abby elevated our understanding of food and hospitality, offering countless insights into cooking techniques and the art of entertaining.

    I couldn’t recommend this experience more highly! It was the perfect birthday gift for my husband, a true food and entertaining enthusiast. He was absolutely thrilled, making it an unforgettable evening with friends. Simply perfect!

    - Abigail's Kitchen
    Verified Xperience Days Participant
  • The flight was enjoyable and informative.

    - Concord
    Verified Xperience Days Participant