“Take the Drama out of your Dreams” with Jeff & Jean

Specializing in Yacht Sales and Training to assure your successful Cruising. See our latest Listings at our Brokerage Web Site: TCSYachtSales.com

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The Five Step Plan to Your Cruising Dream

Focused on Couples, our Five Step Plan to Your Dream offers a path that can take you from “wondering if we can do this” to having a successful and rewarding cruising experience on your own boat, minimizing the drama and maximizing the dream along the way. As Two Can Sail, we can help both of you on each of the Five Steps, meeting the needs of novice and experienced sailors alike.

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Couples Cruising with
Two Can Sail

Our Sample the Life Style and Try A Cat catamaran sailings allow you to learn while enjoying sailing between islands plus time to; dinghy about, swim, snorkel, walk on a secluded beach, or just lie on the deck at night star gazing far away from the city lights.

When you are ready to purchase your own boat, our Boat Shopping, Buyer’s Broker and Surveying skills will assist you in finding the boat that best matches your interests and budget.

Please visit the pages below to learn more about Two Can Sail’s new Book: “Two Can Sail: The 5 Step Plan to Buy a Boat to Go Cruising” as well as a variety of sailing and cruising education opportunities, Seminars, Buyers Broker program, Surveying, and Couples Sail Training offerings

Thank you for visiting Two Can Sail!
Jeff & Jean

Our Upcoming Events

  ONA” 2021 Privilege 510 Owners Version for Sale by TCS now!

D.C. Boat Show   May 3-5, 2024

Annapolis Boat Show
October 10 – 14, 2024

Two Can Sail Yacht Sales & Service, Inc.

Catamaran Cruising Seminar, Annapolis
October 11, 2024

Two Can Sail Yacht Sales & Service, Inc.

Examples of Two Can Sail Fleet

Calypso Sailing School: Mark & Sharon, Leopard 48 “Calypso”.     www.calypsosailing.life


Gone Again Sailing School: Jim & Bonnie, Lagoon 42 “Gone Again”.      www.goneagainsailing.com


Two Can Sail Yacht Sales & Service, Inc.

Viking 70 MY “Dream Wave II” Raymond & Dahlene, Bahamas

2021 Amel 50  “Fregata”, Dan & Sandy, Florida to New York

Our Book is Here!

Now available as an EBook as well! Buy it here on-line or get your signed copy at one of the upcoming Boat Shows!

Two Can Sail Yacht Sales & Service, Inc.

Learn More About Us

Two Can Sail Yacht Sales & Service, Inc.


Interview with Jeff and Jean

Two Can Sail Yacht Sales & Service, Inc.

Jeff & Jean’s cruising boat, Skye 51 Ketch



Two Can Sail Yacht Sales & Service, Inc.