|Minimum Stay||2 - 3 nights|
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Fall and Winter Vacations Available NOW ! Thaw out with us as our winter is like your spring or summer. 75-82 degrees day time temperatures! November is gorgeous here. Bird migrations happen November too. Pelicans already arriving. Double Occupancy 2 adults pricing. Currently children under 18 free - just let us know school age children are coming with you. Plus you receive one of the best Key West Attractions! Receive your own private custom crew sailing trip. While available, two-night three-day stay and sail charter will receive a 2 hour sunset worth 365 dollars. Add more sailing when you get here or upgrade your package. It's the best of both worlds in Key West. Downtown location and a #keywestwatersports attraction. Offer may be withdrawn at any time, so hurry and book now!
Sailing Since 1995 at the same location; just a two block walk to downtown City of Key West where all the fun and excitement begins just steps away from your boat.
Please plan a 15-20% gratuity for your hard working crew. Limited number for the Two nights Stay and Sail - at the docks receive a free 2 hour sunset sail worth $345.00 (gratuities appreciated by your captain and mate) meals on your own at docks. Stay 3 or more nights receive 4 hour sail worth $585 . You may upgrade your sailing portion after booking with Homeaway
This is our economy boat, large enough for a family two adults with 2 small children, and if you have other guests in town up to six people (including you and your partner/spouse) are allowed to go sailing.
Limited Time Offer: Children under 14 no additional charge; just let us know kids are coming aboard after you book (Maximum preferred is 2 adults and 2 children).
NOTE: this is the boat any medium to small animals allowed with a $125 pet clean up fee non refundable.
Fun for everyone in the center of downtown Key West. Add to your sailing with our many sailing options after you book with Homeaway. Please note: Beds are snug double and double v-birth plus one of the two salon couches can pull out for an extra person. Obsession is a true novice and sailor's choice 6'3" headroom two separate cabins. A private charter with you and your family or friends only. If guests are taller than 6 feet please choose either Moon Dance or our Wild Thing sailboat listings. We can accommodate you but this is a smaller spartan spaced sailboat sailors love because of it's weight and ability to sail fast.
If Key West is calling your name with mild subtropical temperatures average 75- 85 degrees most every day , wear flip flops and see flowers blooming all year round near your boat when you walk to downtown five minutes away. Thaw out this winter in Key West and stay aboard a sailboat like a local!
Obsession is a economical and fun option to hotel stay; This is a working sailboat with engine and is more like a recreational vehicle on the water that is perfect for the campers, adventurers and RV crowd. At the docks, air conditioned and Obsession is always ready to go sailing.
Enjoy a sailing charter for your next visit to Key West. Live the life of an old town sailor aboard Obsession
Local favorite restaurants all around your dock; Meals on your own with basic stay and sailing charter Homeaway package.
To add more sailing time or to customize your charter, please call us direct for details after booking basic package here on Homeaway. Perfect one person getaway or couple even a small family on a budget. Due to size of vessel must call ahead for additional passengers over two adults for more adults in order to get approval.
Mild Fall and Winter temperatures. There is a constant breeze from the Gulf Stream to the Gulf of Mexico. Key West is an island "at sea".
Located in famous Historic Seaport two blocks from downtown Key West. Design your sailing charter package, according to your sailing and charter wishes.
Enjoy the ocean breezes while sailing. Sub tropical environment, laid back living like a local, it's flip flops, swim wear or shorts and t-shirts, tropical long cotton dresses, basic casual wear everywhere, no need to fuss over your hair! Ladies, it's best to just pull hair back in bun or pony tail and be relaxed.
Part of the Homeaway family since 2009. See some of our reviews at our main Homeaway listing under Wild Thing sailboat. Feel free to check Trip Advisor. Need a different date? Look at either Moon Dance or Wild Thing sailboats for your private charter.
This Sailboat is set up for local charters and distance charters, with fully operating kitchenette and boat style bathrooms. The land based marina bathroom has a private entrance and is best for long hot showers and morning after coffee to freshen up. Boat showers and toilets for quick visits are easy to operate. Use your hair dryer only at the land based marina due to limits on electric cord to boat.
Do you want more time to see the sea? Why not charter and sail with us on a charter vacation? Romantic getaway charters, family charters available. Bring your bucket list buddies, friends or the office. Let's go sailing! We have USCG licensed captains who know the secret spots and qualified first mates that will swim with your children to make sure that they are having fun while being safe on a USCG Federally documented vessel.
Just a short walk to all the sites and sounds that Key West the island the CITY is known for. All about a ten minute stroll away to the downtown nightly Sunset Festival on Mallory Square, all the museums, all the festivals. Air Conditioning, water and electricity in port. Direct Current batteries on your charters off docks, water and option to bring generator for Air Conditioning at sea, please let us know if any medical issues requiring more power .
We are licensed by the City of Key West as a charter operation and we are properly insured including for snorkeling, and are your professional team for charters.
Freshly painted, varnished and nicely appointed throughout, get two cabins and two bathrooms, full galley and salon. Great for two adults who are not a couple that want their own cabin on their charter. Enjoy a wonderfully comfortable yacht in Old Town Key West.
Weddings, Anniversaries, mile marker Birthdays, Honeymoons, Key West Adventures overnight at anchor. We do all types of sailboat charters.
Always alert us as to any medical concerns of your family. Often our guests tell us we are their bucket list trip. We want to insure your trip is safe, fun and we are properly prepared for any personal needs.
Many people travel with their personal laptops and always ask about equipment that they may use. Connections for your cell phones and laptops welcome. Best wi fi is nearby coffee shops. Use your hair dryers at the land based facility at the head of the docks. If you have any questions- Just ask. Our charter boats leave the docks often and the boats are low-tech for that reason.
Pack light, two bathing suits, two shorts, flip flops, a couple of t-shirts, a pair of exercise long pants, light jacket and walking shoes all that is needed to enjoy a stay in the Key West downtown area and the historic marina where you are close to walking to museums, sunset celebration, all the famous sites are steps away.
Look us up on GOOGLE MAPS Historic Seaport, E Docks, 201 William Street, Key West, FL 33040
Key West - the city and the island is only two by four miles wide. If this is where you want to stay, know that there are several islands that share the same zip code.
Since 1995 our staff is dependable. Know before you go.
Our central location at the end of the chain of the Florida Keys makes it easy to make charter sailing choices into the Gulf Of Mexico or the Atlantic as to the weather and tides or your whim.
Argh me mateys! Be prepared to have fun and adventure!
Often imitated seldom duplicated located on the island and in the City of Key West! Charter the whole boat. One of the best kept secrets in downtown Old Key West in the famous Key West Historic Seaport Marina. Live in the dream and see the sea. Captain Albert
Captain and owner Albert Tropea, Jr has over 50,000 miles and experienced sailing with the very wealthy including the Proctor and Gamble and Helene Curtis groups then modeled his dream to bring basic sailing introduction to the person who wishes to learn about living aboard a boat and chartering at sea adventures.
Albert Tropea purchased this boat in 2007
The Key West Sailing Adventures, Inc. company has been at the same location since 1995 and with Homeaway since 2009. All the main review companies show that he and wife will take your comments to heart and always strive to improve and help make the experience happy and exciting.
Being on board the Obsession saves money and still have a 4 hour sail included. Located right in Old Town Key West, just a few blocks away you have all you came to see within walking distance.
Location was great close to restaurants shops and the downtown area sailing to The Reef was the highlight Of our trip
Historic Marina, historic homes, private homes mostly in the area that are protected and are wonderful to walk around and see. Sailboats abound of every kind and shape fill the Marina facing sunset. We are happy with the opening of the "Waterfront Brewery" a large capacity fun restaurant at the head of our dock. Museums, special attractions and stories, very artistic and eclectic small island community. Walk or bicycle maybe rent a scooter to get around to many things to see on the 2 by 4 mile island of Key West. Make sure that you know we are going to show up on Google Maps as on the actual island and CITY of Key West 201 William Street, Key West, FL 33040 note that Stock Island lower keys is NOT Key West it is partly annexed because it has no post office and uses the same zip code. Be aware of where your property is located. This is our fun economical boat great for two adults, or two adults with two small children or even possibly two couples for a downtown Key West easy access to everything and still quiet enough to be a convenient and fun location. You get the entire boat, we do not share or live on the boat nor do we use one of the cabins for storage. You are in charge! Tell us what you want to do on your 4 hour sail included with your charter. Either take the helm and pull sails with us or be laid back and have a brew or soda and just relax. Since 1995 making Key West memories with return guests Obsession is a reasonable rate for the location, the size and the sailing.
|Rental Period||Minimum Price||Additional Nights||Weekend Night||Weekly||Monthly||Event Price|
Off Season Rates
7 Sep 2016 - 21 Dec 2016
2 night minimum stay
for 2 nights
My Standard Rate
3 night minimum stay
for 3 nights
|children under 18||£0|
Located in the Historic Homes District, featuring a special charm of the old island way. Nearby Key West Museums, sight seeing, special tour trains with art galleries and more. Three boats located side by side in the Historic Seaport make family reunions and special birthdays or weddings possible. Member of Homeaway family since February 2009 please see our listing under Wild Thing listing #229193. Also have Moon Dance listing #3936220 for another choice if Obsession is booked. Obsession is our economy boat perfect for short getaway charter with savings for young family with two small children. Normally two adults enjoy Obsession. Must call ahead for approval and age limit due to size of vessel.