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!

Every gift purchased includes:

  • FREE GIFT PACK
  • FREE EXCHANGES
  • NO EXPIRATION DATES

Instant e-Gift

How It Works Video

Latest Review

Blue Crab Chesapeake Bay Charters

5 stars

We spent 2 wonderful hours in the company of Captain Mark and his First Mate on their beautiful boat they were delightful hosts. The weather was perfect and we were under sail all the way - what a lovely, relaxing experience it was! We would definitely recommend Blue Crab to all our friends and family. 

- Post - Rock Hall  10/5/2013

Buy a Gift Certificate

Secured by GeoTrust Accepted Credit Cards Click to verify

Sailing Experiences Experience Gifts    

Sunset Sail on the American Rover

Enjoy a Two Hour Schooner Sailing Trip on the Elizabeth River

4 stars

Sit back, relax and enjoy a two-hour Sunset Cruise aboard the Tall Ship American Rover on the Elizab

Metro: Norfolk

participantsparticipants Price for 2 Participants:

$50.00View Activity

Sail San Francisco Bay

Learn Sailing on the San Francisco Bay with a Two Hour Lesson

5 stars

Considering getting into the sport of sailing? This Two-Hour San Francisco Bay Introductory Sailing

Metro: San Francisco

participants Price for 1 Participant:

$60.00View Activity


Salem Sound Schooner Sailing

Enjoy a Schooner Sail For Two Aboard Historic Salem Sound

5 stars

Step aboard the beautiful Schooner Fame, a full-scale replica of Chebacco fishing schooner, for a on

Metro: Boston

participantsparticipants Price for 2 Participants:

$60.00View 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. Departi

Metro: Norfolk

participantsparticipants Price for 2 Participants:

$70.00View Activity


Chicago Skyline Tall Ship Sail For Two

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

4 stars

Relax and enjoy one of the most exciting sailing experiences in Chicago, a Sailing Adventure in the

Metro: Chicago

participantsparticipants Price for 2 Participants:

$72.00View Activity

Pirate Cruise In Clearwater For Two

Sail In A Pirate Ship With Captain Memo

5 stars

Ahoy, Mateys! On this unique tour you and your guest will join Captain Memo and his band of pirates

Metro: Tampa

participantsparticipants Price for 2 Participants:

$74.00View Activity


Newport Schooner Sailing

Enjoy a Newport Harbor Sail on the Schooner Adirondack II

5 stars

This is the perfect way to see the sights of Rhode Island’s beautiful coastline with a guest.

Metro: Providence

participantsparticipants Price for 2 Participants:

$78.00View Activity

Schooner Sailing Portland Maine

Enjoy a Two Hour Windjammer Sail in Maine For Two

5 stars

Step aboard the extraordinary and have the experience of a lifetime aboard Schooner Bagheera or Wend

Metro: Portland

participantsparticipants Price for 2 Participants:

$78.00View 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 s

Metro: Corpus Christi

participantsparticipants Price for 2 Participants:

$78.00View 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

Metro: Multiple

participantsparticipants Price for 2 Participants:

$80.00View Activity


Boston Harbor Schooner Sailing

Enjoy a Two Hour Sightseeing Boston Sail Aboard an 80' Schooner

Step aboard the beautiful Schooner Adirondack III; 80-foot wooden replica of a classic turn of the c

Metro: Boston

participantsparticipants Price for 2 Participants:

$84.00View Activity

San Diego Schooner Whale Watching

Enjoy a Four Hour San Diego Schooner Sail & Whale Watching Tour

5 stars

Experience the magnificence of whale migration season as you relax and enjoy the luxurious Schooner

Metro: San Diego

participants Price for 1 Participant:

$85.00View Activity


Sunset Schooner Sail in San Diego

Enjoy a Two and Half Hour San Diego Sunset Schooner Sail

5 stars

Enjoy a beautiful Summer Sunset Sailing excursion on San Diego’s beautiful Big Bay and ocean's

Metro: San Diego

participants Price for 1 Participant:

$85.00View Activity

Rockport Harbor Schooner Sailing For Two

Sail on a Schooner in Rockport Harbor Maine For Two

5 stars

Step aboard the Schooner Heron for a Two and Half Hour Afternoon Sail and narrated tour of Robinson

Metro: Bangor

participantsparticipants Price for 2 Participants:

$90.00View Activity


PAGE (ITEMS 1 - 14 of 53) : 1 2 3 4 VIEW ALL