Each boat is owned, operated and insured independently. Encore Sailing Charters acts only as a reservation agent and is not responsible for any incident on the boat or lawsuit.

Sailing Cruises and Corporate Retreats
Experience the Joy of Sailing!

Sailing Cruises and Charters on Florida’s Gulf of Mexico Coast
Experience the thrill and beauty of sailing without a crowd (no more than six guests). Our sailing cruises and sailing charters gives you the opportunity to handle the helm, raise the main, trim the jibes or just relax on the sailboat. Encore Sailing Charters offers competitive prices in the Tampa Bay/Clearwater area. Our sailing cruises include a United States Coast Guard licensed captain, fuel and soft drinks along with an unforgettable experience.

Enjoy Florida’s West Coast and take a sailing cruise of your choice. We are flexible on making arrangements to meet your needs. If there is inclement weather, we simply change the cruising date. We want you to have a pleasant and fun sailing experience. Get away from the hectic world and find a little piece of paradise!



  Sunset Cruises – Departs from Dunedin Municipal marina two hours before sunset, sailing through Clearwater’s Intercoastal passage. Duration of cruise approximately four hours.
  Moon Light Cruises - Departs from Dunedin Municipal marina at dusk and sails along the Gulf of Mexico. Enjoy the colorful lights of the city’s skyline.
  Sailing Lessons – Private or group sailing classes taught by a U.S. Coast Guard licensed Captain with extensive sailing experience.
  Dolphin Lookouts – While sailing look for playful dolphins swimming in the ocean along side the sailboat.
  Overnight Cruises – Sail to a secluded cove and spend an evening under the stars.
  Custom Cruises – Arrange a cruise according to your requirements.
  Gift Certificates – Purchase a gift certificate for that special someone.
  Special Occasions – Birthdays, Anniversaries, Job Promotions, Engagements, Vow Renewals, Weddings etc. For the memory of a lifetime, plan your proposal and wedding ceremony aboard our luxury yacht.
  Yacht Delivery – Professional, safe and worry free delivery of your yacht to any destination in the free world.

with Captain Jerzy Milrad
- 200 Ton U.S. Coast Guard Licensed
- Sailing Endorsement
- Unlimited Radar Endorsement

Luxury Yacht Cruises
Ideal for Corporate Retreats & Business Meetings

Looking for a unique place to hold your business meetings?
We offer plenty of space around a large table in the main cabin of our 54-foot, luxury yacht. You can have your meetings in exotic islands on the anchor or while cruising the Gulf of Mexico and Intercoastal. During the trip you can get to know each other and at the same time enjoy the beautiful scenery, sunsets or lights of the coastline. We can provide catered food and any other special requests.

Treat Yourself to a
First Class Sailing

If you’re looking for excitement and an entertaining time, you’ve just found the right place.
Take a cruise on a beautiful luxury yacht with a central cockpit and spacious deck where you can enjoy sailing with all the amenities and comforts of home. The yacht has four guest cabins with private bathroom and showers, traditional salon, satellite television and satellite communications and much more! Captain, Jerzy Milrad is ready to take you on a personal adventure as far as you wish or just spin around Tampa Bay, the Gulf of Mexico or explore the Florida Keys. With Encore Sailing Charters, the choice is yours.

Encore Sailing Charters offers luxury cruises on the
Irwin 54 Foot Yacht and the Catalina 42 Foot sailboat.

Irwin 54 Foot Yacht
Sunset Cruises $695 3 hours +
Half Day Sailing $695 4 hours +
Full Day Sailing $895 8 hours
Overnight $1500 24 hours
Weekend $2500 Friday to Sunday
Full Week $4500 7 Full Days

Catalina 42 Foot

Sunset Cruises


3 hours +

Half Day Sailing $400 4 hours +
Full Day Sailing $600 8 hours
Overnight $1300 24 hours
Weekend $1900 Friday to Sunday
Full Week $4000 7 Full Days

Note: Special Requests are also accepted.


Oatmeal, eggs, toast, cold cereal, orange juice, coffee.

Sandwiches (hotdogs, hamburgers), salads (potato, bean, macaroni).
Steak, spaghetti and meatballs, beverages.

Note: Special Arrangements can be made to meet your needs. Enjoy a romantic dinner on deck, wake up to breakfast in your private cabin or celebrate a special occasion with that special someone.
6 Guests Maximum

CALL: 727-642-2828

email: encoresailing@yahoo.com

Sailing Cruises from New Port Richey Location

In addition to our Dunedin location, Encore Sailing Charters offers sailing cruises leaving from New Port Richey, Florida which is a 15 minute drive North on U.S. 19.

Directions: From U.S. 19 go to the Floramar Ter intersection turn left and then take an immediate right onto the service road running alongside U.S. 19. Park in front of the dock.

New Port Richey marina prices:

  Hours Hunter 30” Jeanneau 34”
Sunset Cruises 3 hours $300 $ 300
Half Day Sailing 4 hours $300 $ 300
Full Day Sailing 8 hours $500 $ 500
2-Day/1-Night 36 hours   $1050
Dinghy(with Outboard), kayak & snorkeling equipment is available.
6 Guests Maximum      

Check out our weddings. For pricing call 917-494-9003 or email us.

Boating Information

CALL: 727-642-2828
email: encoresailing@yahoo.com


Captain Jerzy thanks for a great sail. We all had an awesome time. We’ll keep in touch.

Dayton, OH

We just wanted to thank you for a great afternoon of sailing. We enjoyed the cruise with you very much. You’re a great Captain!

Chris, Kim & Cameron
Abilene, TX

Thanks for making the perfect day come true!

Hudson, FL

We had a nice relaxing time and appreciated your concern for making the trip as pleasurable as possible.

Denver, CO

Captain Jerzy thank you for being our perfect captain on Sunday. It turned out to be a most perfect day with the most perfect group of people and the most perfect captain. We loved our sail! Two of the individuals have never sailed prior to Sunday and are now hooked!!! Don (the birthday boy) and I will be calling you again for future sails. Thanks again!!!

Deena & Don
Port Richey, FL