Calypso Sailing | Top Boat Rental in Key Largo, FL Skip to content

Calypso Sailing

99701 Overseas Hwy, Key Largo, FL 33037

About

In Key Largo, Florida, Calypso Sailing provides sailing charters and luxury sailing vacations aboard Leopard catamarans, monohulls and an 80-foot schooner. Bareboat and captained options are available, with half-day, full-day and overnight catamaran charters. Monohull trips include snorkeling and sunset outings, while group charters can be customized for day or extended voyages. The African Queen also runs canal and dinner cruises from Marina Del Mar.

The operation sails the Florida Keys, Bahamas and beyond, with departure locations at Marina Del Mar in Key Largo plus Key West and Stock Island marinas. Groups of six to 38 can book day, sunset or overnight sailing trips, helping tailor a day on the water to their plans. Options range from a small-group sail to extended cruising, with a choice of bareboat or captained service. Contact Calypso Sailing to plan a charter.

Features

  • Bareboat and captained charters
  • Half day to overnight trips
  • Customized group voyages
  • Snorkel and sunset trips
  • Canal and dinner cruises

Amenities

  • Rentals
  • Fleet & Boat Types
  • Waterfront & Access

Why book with us

  • Choose bareboat or captained sailing options
  • Plan trips from half day through overnight
  • Customize a group day or extended voyage
  • Sail the Florida Keys, Bahamas and beyond
  • Book trips for groups of six to 38

Frequently Asked Questions

What's included with a rental at Calypso Sailing?

Rentals from Calypso Sailing include life jackets, safety equipment, comfortable seating and dockside assistance. Amenities vary by boat and by season, so confirm what comes with the boat you book.

How old do you have to be to rent a boat in Florida?

Florida law requires you to be at least 18 to rent a livery vessel other than a human-powered vessel. Florida sets no general minimum age to operate a boat, but a personal watercraft operator must be at least 14.

Under section 327.395, anyone born on or after January 1, 1988, operating a vessel powered by 10 horsepower or more must carry the required boating safety credentials. An exemption applies when accompanied by a credentialed or exempt person age 18 or older who is attendant to the operation and responsible for safe operation and violations. The rental operator sets its own booking minimum subject to state law, so confirm it when booking.

Source: Florida Fish and Wildlife Conservation Commission (myfwc.com)

Do you need a boating license in Florida?

Florida does not issue a boating license, but operators born on or after January 1, 1988, must carry photo ID and a Florida Fish and Wildlife Conservation Commission boating education card when running a vessel with a motor of 10 horsepower or more. This includes personal watercraft. There is no general minimum age for boats; personal watercraft operators must be at least 14, and no one under 18 may rent any vessel other than a human powered one. Exemptions include Coast Guard licensed masters, private lake or pond operators, operators accompanied aboard by someone 18 or older who holds the card or is exempt and is responsible for the vessel, and nonresidents with proof of a NASBLA-approved out of state course. Any non exempt operator may instead pass an FWC approved temporary certificate exam and carry that certificate with photo ID for 90 days.

Source: Florida Fish and Wildlife Conservation Commission (myfwc.com)

Where can you go boating from Key Largo, Florida?

From Key Largo, you can choose sheltered bayside water or the more exposed ocean side. Card Sound and Blackwater Sound are shallow, generally smooth Intracoastal waters. Blackwater Sound connects through the marked Marvin D. Adams Waterway to Largo Sound, an enclosed, shallow area between Key Largo and El Radabob Key. From Largo Sound, a marked channel through South Sound Creek reaches Hawk Channel, the less sheltered Atlantic-side option.

Public put-ins include the John Pennekamp Coral Reef State Park marina at Largo Sound and Mike Forster Memorial Park on the bayside of Key Largo.

Source: NOAA Office of Coast Survey (nauticalcharts.noaa.gov)

What are the most popular boating destinations near Key Largo, Florida?

From Key Largo, boaters can visit North Nest Key in Florida Bay for its dock, picnic area and island setting; Key Largo Dry Rocks to snorkel near the Christ of the Deep statue; Grecian Rocks for shallow reef terrain and a seagrass bed; and Molasses Reef, a heavily visited scuba site known for clear water, fish populations and a spur-and-groove reef formation. Together, these stops offer a practical mix of island picnicking, snorkeling and diving for a day on the water.

Source: Everglades National Park (nps.gov)

Location

99701 Overseas Hwy, Key Largo, FL 33037

Disclaimer

This listing was created using artificial intelligence and publicly available data. The information presented may be inaccurate, outdated, incomplete, or incorrect. Slipstream does not verify, endorse, or guarantee the accuracy of any listing content, including but not limited to contact information, pricing, services offered, hours of operation, or business status.

All content is provided “as is” and without warranties of any kind, express or implied. Slipstream expressly disclaims all liability for any loss, damage, or reliance arising from the use of this information. Users are solely responsible for independently verifying all details directly with the business.

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