Sailing Experiences

Life On The Ocean Waves

Sit back, set sail, and see the world from a whole new perspective with one of our superb sailing experiences!

It’s difficult to describe the feeling of freedom that you get when out sailing... gliding through the swell with the wind in your face and the sun sparkling on the water's surface is nothing but pure pleasure! We offer sailing experiences all over America that will give you a chance to cruise in a beautiful sailboat getting a taste of the sailor’s life! Whether you want a romantic sunset sailing trip, a city skyline sightseeing tour, or even a schooner sailing and whale watching adventure, you’ll find the perfect sailing experience here on Xperience Days!

So if you’re a landlubber who wants to find your sea legs or you’re looking for an exciting gift for adventurous loved ones, try one of our sailing experiences!

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Latest Review

Sailing Trip

5 stars

We were treated very well by Captain Mike & Suzanne. My husband has to use crutches to walk from a back injury. They were extremely helpful & concerned about his comfort. It was one of the best experiences we've encountered! I recommend a Chesapeake Bay Sailing Trip to anyone! 

- Beth & Allen Haught - Rock Hall, MD  10/10/2014

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Sailing Experiences Experience Gifts    

Private Sailing Charter in Austin

Enjoy a Relaxing Scenic Sail On Lake Travis, Texas

Enjoy a two-hour private Sailing Adventure and tour of beautiful Lake Travis. Located just 30 miles Northwest of Austin, Lake Travis is a Sailor's paradise in the heart of Central Texas.   During this Austin outdoor adventure you will have the opportunity to sit back, relax and enjoy the suns...

Metro: Austin

participantsparticipants Price for 2 Participants:

$300.00View Activity

Chicago Skyline Tall Ship Sail For Two

Sail on a Tall Ship For Two From Chicago's Navy Pier

5 stars

Relax and enjoy one of the most exciting sailing experiences in Chicago, a Sailing Adventure in the Windy City on the 148’ four-mast Tall Ship WINDY. Built of modern materials, but like the old trading schooners and sail training ships, the WINDY has all the character and charm of the great da...

Metro: Chicago

participantsparticipants Price for 2 Participants:

$72.00View Activity


Lake Michigan Sailing Charter

Peacefully Sail on a Two Hour Private Lake Michigan Sail From Racine

5 stars

Enjoy a spectacular two-hour skippered charter afternoon sail or sunset sail on beautiful Lake Michigan. Upon your arrival at Gaslight Pointe Marina, located in Racine, Wisconsin, you and your guests will board the Espiritu, a classic 41’ Newport Sailing Vessel. Enjoy breathtaking sites of th...

Metro: Milwaukee

participantsparticipants Price for 2 Participants:

$190.00View Activity

Sailing Lessons on Lake Michigan

Enjoy a Three Hour Introductory Sailing Lesson from Racine, Wisconsin

Imagine yourself at the Helm of a classic 41’ Newport Sailboat during an exciting three-hour private sailing lesson in Racine, Wisconsin. Learn how to sail as your knowledgeable Captain covers everything about the fundamentals of sailing on Lake Michigan. This Sailing Lesson in Wisconsin is sp...

Metro: Milwaukee

participants Price for 1 Participant:

$200.00View Activity


Gourmet Sailing on Lake Michigan

Enjoy a Private 3 Hour Chartered Lunch or Dinner Sail with this Skippered Charter in Racine, Wisconsin

5 stars

Sit back, relax and enjoy a three-hour private Sailing Charter on Lake Michigan. With unique sites, peaceful sounds and a delicious meal aboard the 41 ft. Newport Sailing vessel Espiritu, this is sure to be a delightful escape and an exciting trip on the Lake. On this three-hour skippered sail you...

Metro: Milwaukee

participantsparticipants Price for 2 Participants:

$295.00View Activity

Sailing Lesson In Corpus Christi

Two Day Introductory Keelboat Sailing Lesson On Corpus Christi Bay

Enjoy an introductory two day sailing course as you learn fundamentals of sailing in Corpus Christ, designed for beginners. On the first day of your sailing course, you will have a 1½ hour classroom session. Afterwards you will hop on the boat , usually a Hunter 34' sloop, to ...

Metro: Corpus Christi

participants Price for 1 Participant:

$315.00View Activity


Private Gourmet Sail In Corpus Christi

Private Gourmet Sail On Corpus Christi Bay For Two

5 stars

Enjoy a romantic evening sail on the beautiful Corpus Christi Bay and indulge in a delicious gourmet dinner for two. You and your guest will begin your evening aboard a classic yacht, taking in the sites as you sail to a wonderful Corpus Christi waterfront restaurant for an exquisite dinner for...

Metro: Corpus Christi

participantsparticipants Price for 2 Participants:

$335.00View Activity

Half Day Skippered Charter In Corpus Christi

Enjoy a Four Hour Private Skippered Charter On the Corpus Christi Bay

You and up to five guests will step aboard the 34’ Hunter ‘Tour De France' and embark on a scenic four-hour skippered sailing adventure on Corpus Christi Bay. On this sailing charter, you will enjoy unique views of the Corpus Christi skyline. During your private sail, you...

Metro: Corpus Christi

participants Price for 6 Participants:

$360.00View Activity


Full Day Skippered Charter In Corpus Christi

Enjoy a Full Day Private Skippered Charter On Corpus Christi Bay

Step on board your own Private Eight-Hour Skippered Charter set to sail around the gorgeous Corpus Christi Bay in Texas. You and up to five guests will step aboard the 34’ Hunter ‘Tour De France' and embark on a scenic eight-hour skippered sailing adventure on Corpus Christi Bay. On thi...

Metro: Corpus Christi

participants Price for 6 Participants:

$540.00View Activity

South Padre Island Snorkeling Sail

Dive In & See What's in the Sea in South Padre with this Snorkeling Trip

Explore the diverse marine life in the Gulf of Mexico during this three-hour Port Isabel Catamaran sailing excursion! The excitement of this experience gift beings when you boarding The Southern Wave Catamaran and meet the friendly Captain and Crew. Once ready, you will set sail, heading out of the...

Metro: Corpus Christi

participantsparticipants Price for 2 Participants:

$78.00View Activity


Stars and Stripes Sailing In Hilton Head

Sail Hilton Head in an America's Cup Vessel with a Guest

Experience a memorable two-hour Sunset Sail on a living piece of yachting history— the streamlined America's Cup racing yacht the Stars and Stripes. Set sail out of Hilton Head Island and enjoy this amazing scenic sail. The Sail America Foundation commissioned four 12 metre yachts to sup...

Metro: Savannah

participantsparticipants Price for 2 Participants:

$100.00View Activity

Jacksonville Introduction to Sailing

Learn to Sail During a Four Hour Sailing Lesson on the St. Johns River

Enjoy the fresh air and beauty of St. John’s River during a four-hour sailing lesson in Jacksonville, Florida. Taught by a seasoned Sailor and Certified Instructor, you and your guest will get a taste of what it’s like to sail during this half-day Introductory Sailing Course. The fun of...

Metro: Jacksonville

participantsparticipants Price for 2 Participants:

$232.00View Activity


Charleston Tall Ship Sailing Tour

Enjoy a Two Hour Sailing Tour of Charleston Aboard the Schooner Pride

5 stars

Discover the beauty of Charleston Harbor as you and a guest enjoy a two-hour sightseeing sail aboard a classic 84’ Tall Ship Schooner.  The fun of this experience gift begins at the Charleston's Aquarium Wharf when you board the Schooner Pride and meet the friendly Captain and Crew. Once...

Metro: Charleston

participantsparticipants Price for 2 Participants:

$92.00View Activity

Clearwater Beach Pirate Cruise

Sail with Captain Memo On this Pirate Cruise from Clearwater Beach

5 stars

Ahoy, Mateys! On this unique tour you and your guest will join Captain Memo and his band of pirates on a cruise along the shoreline of Clearwater Beach! The two of you will board the authentically designed, Pirate’s Ransom Pirate Ship. As you board the ship, you will be greeted by some very f...

Metro: Tampa

participantsparticipants Price for 2 Participants:

$74.00View Activity


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