Florida Keys Sailing AdventuresOne-Week & Two-Week Cruises

This is your chance to sail with us in the Florida Keys. Our weeks-long sailing adventures are a great opportunity for you to enjoy all the keys have to offer.

Join us aboard S/V Sea Dancer, our Classic 41 ft ketch rigged (Two Mast) sailing yacht. She was made for the islands with her full but shallow keel and wide roomy interior. Equipped and designed with distance sailing in mind, she has the latest in electronics and safety equipment. Her large and open deck has plenty of room to spread out.

Sea Dancer has comfortable overnight accommodations for up to 4 guests.

There are two separate cabins along with two bathrooms on board. The Aft owners suite has a large bed with plenty of storage, along with an en-suite bathroom and shower. The forward stateroom has split bunk style births and privacy doors, where our crew typically sleeps. Her main saloon has a large dining table that converts into a bed that can comfortably accommodate two. However, our guests can decide which cabin works best for them and the crew. She has a wide and accommodating main saloon with stove/oven, microwave, toaster, separate freezer and fridge.

Catch fresh fish and lobster (in season) Fishing/Lobster licenses are included, and grill out on the aft deck. Swim or snorkel some of the best waters that Florida has to offer. Enjoy the use of onboard water toys such as stand up paddle boards.

Choose Your Leg

1. Week 1: Punta Gorda to Key West
2. Week 2: Key West to Islamorada
3. Weeks 1 & 2: Both legs - the sailing trip of a lifetime!

Spring 2022, Florida Keys Adventure Sailing Punta Gorda FL to Islamorada FL

We offer two different legs on this route. You may choose between Week One, our Punta Gorda to Key West Gulf Crossing sailing leg. Or Week Two, our Key West to Islamorada Florida Keys-hopping sailing leg. Or sign up to do the entire trip for a sailing trip of a lifetime.

Florida Keys Adventure Sailing Week One Punta Gorda FL to Key West FL

Week one is our Punta Gorda to Key West leg, set up to have both a mix of Island hopping along with the adventure of off shore sailing. This leg is for the more adventuress sailor that is looking to enjoy the experience of off shore and distance sailing. You can expect to get more hands on sailing experience along with night time long distance legs. We will depart from our home dock in Punta Gorda FL and head south through Charlotte Harbor to the islands of the west coast. Some options would be to stop at Cayo Costa beach, Captiva and Sanibel islands. We have the option to also sail in the intercostal towards Ft. Myers and Ft Myers Beach. We will pass the Cape Romano Shoals before heading to open seas. Stops can include Ft. Myers Beach, Naples, Marco Island and places in between. Try your luck at offshore fishing. (Fishing/Lobster licenses is included.)

Once we approach the Keys, we will enter the Key West Northwest channel or Garrison Bight channel before ending up at Down Town Key West municipal wharf marinas. Here you will spend your last night on the boat, at the dock. Enjoy your last night exploring the city before departing the next morning. (Transportation back to Punta Gorda/ Ft. Myers via the Key West Express or Key West airport can be arranged).

Florida Keys Adventure Sailing Week Two Key West FL to Islamorada FL

Your Sailing adventure will begin at the Historic Town of Key West. You will spend your first night at the dock, giving you a chance to explore the city before departing the next morning. We will leave the dock and head towards Islamorada FL. We will do a mix of gulf and ocean sailing while stopping at some of the best reefs to snorkel and swim at. We will drop anchor at some remote locations where we will spend the night under the stars (weather permitting of course). Try your luck at fishing to catch dinner. (in season) while enjoying the local wildlife. (Fishing/Lobster licenses is included.) As we work our way towards Islamorada, we will make stops at Marathon and sail under the 7 mile bridge. Additional stops and local bars and restaurants maybe arranged. You sailing adventure will conclude at a local marina where you will then depart. (Transportation back to Key West or to an Airport can be arranged.)

Fall 2022, Florida Keys Adventure Sailing Islamorada FL to Punta Gorda FL

We have two different routes for you to choose from. Pick between our Florida keys sailing week, departing from Islamorada FL and heading to Key West. Or our Gulf Crossing sailing, that departs Key West and arrives at Punta Gorda FL.

Florida Keys Adventure Sailing Week One Islamorada FL to Key West FL

Week one of our Florida Keys Sailing Adventure. You will depart Islamorada in the afternoon and head west to explore the many islands of the Florida keys. Some highlights will include snorkeling/swimming at some of the best reefs the keys have to offer. We will drop anchor at some remote locations where we will spend the night under the stars (weather permitting of course). Try your luck at Fishing and lobster hunting while enjoying the local wildlife. (Fishing/Lobster licenses is included.) At the end of the week we will dock at Key West. Here you will spend your last night on the boat, at the dock. Enjoy your last night exploring the city before departing the next morning. (Transportation back to Islamorada or Key West airport can be arranged).

Florida Keys Adventure Sailing Week Two Key West FL to Punta Gorda FL

Week two of our Florida Keys Sailing Adventure will begin at the dock at Key West. Enjoy the day in Key West before you board Sea Dancer and head to sea. We will spend the first night in Key West so you can relax and take in the Famous Mallory Square sunset. The next morning we will depart from Key West and stop at a local reef for snorkeling/swimming, before departing the keys and heading north across the Gulf of Mexico. This leg of our adventure will take us past the Cape Romano Shoals, past the famous dome houses of Marco Island, and north all the way up to Charlotte Harbor. Depending on weather and time constraints, we may make stop overs at Marco Island Yacht Club, Naples Sailing Yacht club, Ft Myers Beach, Sanibel Island, and the Captiva Islands. This is some of the best island hopping north of the keys. There will be plenty of time for offshore fishing and stargazing, including the option to sail throughout the night. We can arrange to drop you off at Ft Myers area if you prefer or you can sail the remaining way back to our private dock in Punta Gorda. Transportation back can be arranged in advance.

Additional Information for all our Sailing Adventures

All of our sailing adventures includes a USCG Captain that will safely guide you along your sailing adventure. You are however welcome to help sail the yacht as much or little as you like. Provisioning options for meals and drinks are available. We can order and have all provisions already onboard. Meals can be pre-planned for you. (best option if you don't want to plan out meals.) Or if you prefer, you may pre-order your week worth of provisions and we can have them delivered to the yacht before departure. (Best option if you have dietary needs or special request.) Guest are responsible for their own meals while onshore. Please keep the captain and crew in mind when you order your provision, as you will be responsible for supplying crew meals also. A selection of water toys such as Stand Up Paddle boards, fishing gear, etc is provided onboard. Please bring your own mask, snorkel and fins. An inflatable tender with outboard may also be provided. The boat is outfitted with basic amenities such as bath/beach towels and cooking supplies. Any special request will need to be made in advance. While we will do our best to give you a great sailing experience, please keep in mind this isn't a cruise ship and such, our amenities are limited. Itinerary and stop overs are subject to weather and time restrictions. We will do our best to meet your requests.