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    

Sailing in Baltimore Harbor

Enjoy a Three Hour Sail Around Baltimore's Inner Harbor

5 stars

Sit back, relax and enjoy time on the water with a beautiful three hour sail in the Harbor, one of America's oldest seaports. board a Sonar 23, a wonderful little, day sailor that comfortably holds up to 4 passengers. Starting with Baltimore’s famous Inner Harbor, you will sail past Fort...

Metro: Baltimore

participantsparticipants Price for 2 Participants:

$330.00View Activity

Baltimore Harbor Sailing Charter

Enjoy a Full Day Sail of Baltimore's Inner Harbor

5 stars

Sit back, relax and enjoy time on the water with a beautiful full day sail in the Harbor, one of America's oldest seaports. You will then be greeted by your experienced Captain who will provide you with an enjoyable and personalized experience aboard a Beneteau 343 or 331, a great cruising vessel th...

Metro: Baltimore

participantsparticipants Price for 2 Participants:

$1,045.00View Activity


Chesapeake Bay Sailing Trip

Enjoy a Relaxing Scenic Sailboat Ride on the Chesapeake Bay

5 stars

Enjoy the beauty of the Chesapeake Bay during an hour and a half sightseeing sailing trip aboard the Crab Royale, an Irwin 40 MKII. This five-star rated experience gift is one of the best things to do on Maryland's beautiful Eastern Shore! The fun begins in Rock Hall, MD when you meet with the...

Metro: Multiple

participantsparticipants Price for 2 Participants:

$88.00View Activity

Yorktown Virginia Sailing

Sail Two Hours on The York Town River Sailing Trip For Two

5 stars

Sit back, relax and enjoy a two-hour cruise aboard the Tall Ship Alliance on the York River. Departing from the Riverwalk Landing Pier in Yorktown, this Schooner Sail is the perfect way for you and your guest to enjoy views of historic Virginia. You will board the 105', three-masted gaff-rigged sch...

Metro: Norfolk

participantsparticipants Price for 2 Participants:

$77.00View Activity


Sunset Sail on the American Rover

Enjoy a Two Hour Schooner Sailing Trip on the Elizabeth River

5 stars

Sit back, relax and enjoy a two-hour Sunset Cruise aboard the Tall Ship American Rover on the Elizabeth River. Departing from the Waterside Marketplace in Norfolk, this Schooner Sail is the perfect way for you and your guest to enjoy views of historic Norfolk, Virginia.   The fun of...

Metro: Norfolk

participantsparticipants Price for 2 Participants:

$55.00View Activity

Barnegat Bay NJ Sailing

Sail Three Hours on New Jersey's Barnegat Bay & Toms River

5 stars

Experience the thrill of NJ Sailing with a US Coast Guard Licensed Captain during a public three hour sail aboard the beautiful new Hunter 44 Sailing Yacht, Express Mail. Sit back and enjoy the sights down the shore while basking in the warm summer sunshine. Or, lend a hand and learn the rope...

Metro: Multiple

participantsparticipants Price for 2 Participants:

$198.00View Activity


Manhattan Clipper Ship Sailing

Sail on Manhattan's Beautiful Clipper City Tall Ship For Two

5 stars

Watch the New York City Skyline drift by as you step aboard the beautiful Clipper City Tall Ship, a 158 foot replica of a classic turn of the century Timber-Hauling Topsail Schooner. Departing from Battery Park on the Hudson, this beautiful 1½ hour sightseeing sail in New York Harbor is a gre...

Metro: New York

participantsparticipants Price for 2 Participants:

$99.00View Activity

New York Craft Beer Tasting Sail

Sail & Taste Craft Beer During a Two Hour NYC Tall Ship Sail For Two

5 stars

Discover the mouth-watering world of Craft Beer during this two-hour Manhattan Tall Ship Sailing excursion. Aboard the beautiful Clipper City Tall Ship, a 158 foot Topsail Schooner, you and your guest will discover tasty new brews as you learn about the art of beer. Departing from Battery Park on t...

Metro: New York

participantsparticipants Price for 2 Participants:

$143.00View Activity


Schooner Sailing In New York

Enjoy a Relaxing Two Hour Scenic Sailing Trip in New York Harbor

5 stars

Watch the Manhattan Skyline drift by as you step aboard the beautiful Schooner Adirondack or Adirondack III; 80-foot wooden replicas of a classic turn of the century Pilot Schooner. Departing from Chelsea Piers on the Hudson River, this beautiful two hour sail in New York Harbor will treat ...

Metro: New York

participantsparticipants Price for 2 Participants:

$110.00View Activity

Sunset Schooner Sailing New York

Take in the Views of Sunset in New York Harbor During a Schooner Sail

5 stars

Watch the New York City Skyline drift by as you step aboard the beautiful Schooner Adirondack or Adirondack III; 80-foot wooden replicas of a classic turn of the century Pilot Schooner. Departing from Chelsea Piers on the Hudson River, this relaxing two hour sunset sail in Manhattan is a wonderful...

Metro: New York

participantsparticipants Price for 2 Participants:

$141.00View Activity


Schooner America Sailing New York

Enjoy a Breathtaking Sail in New York Harbor aboard the America 2.0

Step aboard this 105’ Schooner for an exciting two-hour sailing adventure through New York Harbor. This experience gift is an outdoor adventure you and your guest are sure to remember for years to come. The excitement begins at Chelsea Piers on the west side of Manhattan where you will board...

Metro: New York

participantsparticipants Price for 2 Participants:

$128.00View Activity

Schooner America Sunset Sail New York

Enjoy a Scenic Sunset Sail in New York Harbor Aboard the America 2.0

Take in the picturesque views of a Manhattan Sunset aboard the America 2.0, a 105’ Schooner. This breathtaking two-hour sailing adventure through New York Harbor is an adventure gift you and your guest are sure to enjoy. The fun begins at Chelsea Piers in Manhattan where you will step board t...

Metro: New York

participantsparticipants Price for 2 Participants:

$159.00View Activity


Schooner America Brunch Sail New York

Enjoy a Delicious Brunch in New York Harbor Aboard the America 2.0

Enjoy Sunday Brunch out on the water during this two-hour scenic New York Harbor Schooner Sailing adventure. You and your guest are in for a treat as you sail aboard the 105’ Schooner America 2.0. This gourmet gift begins at Chelsea Piers Manhattan where you will board this beautiful new ship...

Metro: New York

participantsparticipants Price for 2 Participants:

$159.00View Activity

Morimoto Sushi and Sake Sunset Sail

Savor a Sushi & Sake Sunset Sailing Cruise Aboard the America 2.0

5 stars

All aboard for an evening of fun during a gourmet sailing adventure in New York Harbor! During this two-hour Sunset Sail you will savor a fresh sushi and sake pairing selected by Iron Chef Morimoto himself! This delightful experience gift begins at Chelsea Piers where you will board the beautiful 1...

Metro: New York

participantsparticipants Price for 2 Participants:

$275.00View Activity


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