Set sail from Punta Gorda / Port Charlotte on an unforgettable mile-building adventure to two of Florida’s most iconic destinations: the Dry Tortugas and Key West. Gain valuable offshore sailing experience, including overnight passages, with the option to earn your ASA 106 Advanced Coastal Cruising certification.
After an overnight passage, arrive at historic Fort Jefferson in Dry Tortugas National Park, home to one of the largest brick structures in the United States. Explore the impressive fortress and snorkel through crystal-clear waters along the fort’s moat walls and nearby coral reefs.
Continue to Key West, where you can discover Ernest Hemingway’s favorite haunts, tour his historic home and museum, or explore the Key West Shipwreck Museum. Soak up the island’s lively atmosphere, enjoy waterfront dining, and sip a classic Rum Runner at one of the local bars.
After two memorable nights in the Conch Republic, set sail for the return passage to Punta Gorda / Port Charlotte, completing an exciting journey filled with offshore sailing, exploration, and adventure.
This learn-to-sail vacation with Whitecaps Sailing School offers the following optional certification:
¤ ASA 106 | ADVANCED COASTAL CRUISING
* ASA 106 is available for an additional $350 per person. ASA 105 certification is a prerequisite.
Depart from the sailing base in Punta Gorda / Port Charlotte and sail approximately 20 nautical miles to Pelican Bay, near Boca Grande Pass. This introductory sail allows you to become familiar with the boats and their sailing characteristics before the longer passages ahead. Enjoy lunch and dinner onboard before spending the night at anchor.
Depart Charlotte Harbor and begin an offshore passage toward the Dry Tortugas. Cover approximately 131 nautical miles over 21 hours, sailing throughout the day and night while rotating watch duties. Gain valuable experience in offshore navigation, overnight sailing, and watchkeeping as you make your way toward Fort Jefferson.
Arrive at Fort Jefferson in Dry Tortugas National Park and enjoy a well-deserved rest after your overnight passage. Explore the historic fortress, one of the largest brick structures in the United States, and snorkel along the fort’s moat wall and nearby coral reefs. Enjoy all meals onboard and spend the night at anchor.
Depart Fort Jefferson and sail approximately 40 nautical miles toward the Marquesas Keys, a passage of about seven hours. Continue developing your coastal cruising and navigation skills while enjoying the waters of the Florida Keys. Anchor for the evening and enjoy all meals onboard.
Set sail for Key West, covering approximately 22 nautical miles in about four and a half hours. Arrive in the famous Conch Republic and dock for the evening. Head ashore to enjoy dinner at a local restaurant and experience Key West’s lively nightlife.
Spend the day exploring Key West’s historic attractions, including the Ernest Hemingway Home and Museum and the Key West Shipwreck Museum. Discover the island’s colorful streets, waterfront restaurants, and famous local bars. Enjoy another evening in Key West before spending the night onboard.
Depart Key West early in the morning for the return passage to Punta Gorda / Port Charlotte. Sail approximately 152 nautical miles over 25 hours, rotating watch duties throughout the day and night. Put your offshore sailing, navigation, and watchkeeping skills into practice while enjoying meals onboard.
Arrive back at the sailing base in Punta Gorda / Port Charlotte in the early morning, completing your eight-day sailing adventure. Disembark and say farewell to your instructor and fellow sailors after a memorable journey through the Dry Tortugas and Key West.
Please Note. This itinerary is meant to serve as an example, however, it is important to note that the actual itinerary is subject to change due to weather conditions or circumstances beyond our control.
We have reserved fully equipped and comfortable 37′ and 32′ monohulls for this trip. Max. 3 participants and instructor per boat.
Recently completed my 101/103/104 combo with Whitecaps. Very friendly team, responsive and knowledgeable. The boat used for training was in great shape and of perfect size for learning.
My partner and I had an amazing experience at Whitecaps Sailing in Port Charlotte, Florida, where we completed our ASA 101/103/104 course with Captain Lee. The course was incredibly informative, and we truly appreciated Captain Lee’s deep expertise and the personalized 1:1 instruction he provided. By the end, we felt confident and well-equipped to embark on our own charters in the future. Jean and Mila at Whitecaps were also fantastic. They were highly responsive to our questions before the course and went above and beyond to ensure the boat was prepared and a dock was arranged despite challenges from two hurricanes. We can’t recommend Whitecaps highly enough for anyone looking to learn or advance their sailing skills!
