Call Now! (239) 200-9899

Fort Myers Beach | Sanibel | Captiva | Cape Coral | Bonita Beach | Estero | Naples

Plan Your Catamaran Sailing Cruise in 3 Easy Steps:

1. Select Among Our Private Sailing Cruises, Sightseeing Tours, or A Sunset Cruise

  • image

    Private Sailing Cruises

    Reserve the Old Glory for a private sailing cruise to Sanibel Island, Estero Island, San Carlos Bay or into the Gulf of Mexico. Read More
  • image

    Sightseeing Tours

    Join us aboard the Old Glory catamaran for a sightseeing sailing tour of Fort Myers Beach, Pine Island Sound or Sanibel Island. Read More
  • image

    Sunset Cruises

    Book an unforgettable private sunset cruise aboard our 35-foot sailing catamaran! Departing daily at 5:30. 3 Hours. Bring up to 6. Read More
  • 1

Private Cruises vs. Sightseeing Tours: What's the Difference? 

Our private cruises offer maximum flexibility, allowing you to customize virtually every aspect of your catamaran sailing cruise, including: Departure time, cruise duration, itinerary, activities and more.

Your party of up to six (6) total passengers will have the boat all to yourselves (aside from the Captain and 1st Mate, of course, who will be  operating the vessel and letting you relax while underway). The private sailing cruise itineraries listed here are among our most popular, but they are only suggestions — we're happy to let you decide where we go and what we see and do within the duration of your cruise.

Keep in mind that if you wish to book a private cruise online and don't see a convenient departure time or duration that works best for you, just give us a call or send an email and we'll be happy to make arrangements (subject to availability).     



Old_Glory_Sailing_Catamaran_Check_Weather_Forecast_SAIL_SWFL_Cruises2. Check the weather & wind/sea conditions forecast for the day you plan to sail. 

Be sure to keep an eye on the weather as it gets closer to your reserved date. is a great source of accurate forecast data

And be sure to check wind and sea conditions! On days when the wind is too strong or the water is too rough, we will not go out. 

Windfinder is a great app for checking wind strength and direction; it also gives you the waves heights and tons of other great, useful info. 




10-20 knots of wind is our "sweet spot" for sailing...anything less can still provide a very relaxing sail, we just won't be moving very fast. More than 20-25 knots of wind speed means we'll have to either reduce sail (reef) or not sail at all and run the boat's twin diesel engines instead. 

In the event of high winds (above 25 knots sustained wind speed) or dangerous, foul weather (squalls, thunderstorms) we will have to reschedule your cruise for another time. If you can't make it out with us another day and you've paid in advance, refunds are provided. 

Learn more about our weather policies by reading our blog post, "'Weather' We Sail or Not" here.


3. Check Our Availability Calendar and Book Your Cruise Online!

If you have any trouble booking your private sailing cruise or sightseeing tour using our online booking system, contacting us is easy: This email address is being protected from spambots. You need JavaScript enabled to view it., give us a call or fill out the form here.

We are happy to help answer any questions you might have. Please note: a non-refundable deposit/partial payment of $120 will be required to reserve your catamaran sailing cruise if you book over the phone or email. This deposit covers your first hour. The balance of your fare will be due in cash the day of cruise or paid with credit/debit card by making prior arrangement with us. 


What to Bring Aboard with You

Please wear sandals, white-sole sneakers, or boat shoes. No black-sole shoes, high heels or cowboy boots, please!

  • Sunscreen, sunglasses, hats

  • A cooler for your beverages, snacks, lunch, etc.
    (We provide ice & bottled water only; unless you'd like to arrange for us to pick up lunch for your party ahead of time, for an extra fee).

    Please note: Consumption of alcoholic beverages for passengers over 21 years of age during your cruise is permitted; public intoxication, drunk & disorderly conduct aboard the vessel, is not! We reserve the right to terminate your cruise early for violating this policy and no refund will be given.

  • Jacket or sweater (you likely won't need one from April through October).

  • Towels, mask, snorkel (if you plan on going swimming).

  • Cell phone

  • Sea-sickness medication (if you're prone to sea sickness, take it before we cast off).

  • Don't forget your camera


What to Leave Ashore

We want everyone who joins us to have a fun, relaxing and safe time. Please act reponsibly at all times both for your own safety as well as the safety of everyone else aboard. Please do not carry onto the vessel anything dangerous or illegal, including:

  • Weapons

  • Illegal drugs

  • Explosives, fireworks, candles, flammable liquids

  • Stress, anxiety & bad attitudes