December Holiday Specials! Time Charter on your own private sailing vessel with a customized sailing itinerary! Located in the City of Key West Downtown celebrating with beautiful lights, easy to walk everywhere during holidays. Ask about special parking for stays of 3 or more days (please check with us). Get a package that includes a favorite past time, sailing included with all time charters. Reduced until for more Savings now!
Sunset sailing for two nights charter stay
Get 4 hour snorkeling 3-5 or more nights.
IMPORTANT: Our Boat is at a marina attached to walkway to land based facilities too. Regular Bathrooms, Laundry, regular toilets and all facilities on boat works too - air conditioning, running water with boat bathrooms, galley to cook and enjoy coffee, and electricity - YOU ARE NOT ON ANCHOR. We take a crew and take you on your charter sail. Our boat is licensed by State of Florida, Insured, USCG approved operating fully registered sailing vessel.
Nearby swimming nearby restaurant with a pool, small pocket park beach; or make a day trip to a state park beach by taxi or bicycle.
Right Now book in November minimum of two nights at a big discount and receive a sunset 2 hour sail! Hurry this offer could be sold out without notice.
This is our economy boat, great for a couple only or a family with small children due to space. Snug cabins are a money saver for those who are adventurous vacationers who like to go hiking, swimming, snorkeling, sailing. This boat design has more stepping up and down, smaller and is more challenging for those with mobility issues and we can guide you to one of our bigger boats or nearby hotels. Small dogs allowed with your family at an additional cleaning fee.
NOTE: rates based on the first two people. Please let us know if others will join you as we will set up linens and towels for two people usually a couple, but let our office know are you two individuals. Small additional fee per person. Keep in Mind: This boat is best for either one or two couples or a couple with small family of 2 or 3 young children who are economy minded and are adventurous travelers who like to go camping, glamping, recreational vehicle vacations.
Openings for Fall - Winter Holidays. November is a migration month for many birds and birding trips. Sea Turtle, Dolphins and Reef Fish are visible.
Obsession now includes a full fishing license for the entire boat. Also enjoy peace of mind with smoke detectors and carbon monoxide detectors and mounted fire extinguishers throughout your vessel.
Your Time Charter is on your schedule. Your captain will take direction from you for your family or friends.
Start with this popular Basic Time Charter, 2 nights with a sunset 2-hour sail. Holidays and Fantasy Fest 3 night minimum.
Customize your charter to add more sailing.
Design a Sailing Time Charter that suits your personal requirements. Depending on the length of time you choose, add more nights or more sailing at a discount. Plan to upgrade to a half day 4-hour sail or a full day 8-hour sail for time to go snorkeling the reefs, learning sailing techniques, fishing, beach combing, exploring or bird watching near uninhabited islands. Go sailing with a USCG licensed captain and knowledgeable helpful first mate.
Our Docks are in The Historic Seaport, in downtown Key West. Sailing departure is up to your family, corporate team or friends.
If you have a family that wants something fun and explores outdoors, this is it. If your corporate group wants to schedule a sailing team building exercise, Time Charters can match your needs. Meals are on your own unless arranged with your crew in advance for your Time Charters.
Check for special inclusive details.
Charter Boat has electricity, running water, 2 bathrooms with holding tanks, air conditioning at the dock, propane stove, coffee pot, electricity, 6’3” headroom and everything you will need for your chartering experience. Owners/Guests Personal Marina Based Showers, Laundry mat and Toilets. Restaurants, also nearby find music, a pool and a even a small pocket style beach close by. Beautiful State Park Fort Zachary Taylor is perfect to take a taxi or bicycle and spend the entire day as a fully functioning all day away with showers, bathroom/changing rooms, all day picnic areas, all day small food vendor. Rent umbrellas or a lounge chair.
(Maximum preferred is, 2 couples or 2 adults with 2 children couches make for a maximum of six passengers; talk to us about your number of guests).
PLEASE ADVISE US HOW MANY PASSENGERS WE DO SET UP LINENS AND TOWELS ACCORDING TO NUMBER OF PEOPLE. NOTE: ONLY $45 PER PERSON MORE PER PERSON PER NIGHT FOR CHARTER OVER TWO PEOPLE WITH TOWELS AND LINENS. RATES ARE BASED ON DOUBLE OCCUPANCY - (TWO PEOPLE). Tell us if you are a couple or two individual traveling on vacation.
NOTE: on this boat any medium to small animals are allowed with a $125 pet clean up fee non refundable. PLEASE advise if you wish to bring an animal. Other future guests could be allergic -we love animals too!
Cabins offer a double bed aft and double v-birth forward plus two salon couches. Obsession is an amateur or sailor’s choice 6’3” headroom two separate cabins, with a very large living room (salon). A private Time Charter with you and your family or friends only. Sailors love this boat because of its weight, stability and ability to sail fast.
If Key West is calling your name with mild subtropical temperatures average most every day, a Time Charter with this sailing adventure and fun could be what you want. Charter Obsession and sail aboard a sailboat like a local!
Obsession is an economical for a small family on a budget or a couple getaway.
This is a working sailboat with diesel engine and sail ready.
Enjoy a sailing Time Charter for your next visit to Key West. Live the life of an old town sailor aboard Obsession 37 foot O’Day.
There is a constant breeze from the Gulf Stream to the Gulf of Mexico. Mild winters make this a sailor's dream setting.
Key West is an island, 130 miles “at sea”.
Located in famous Key West Historic Seaport two blocks from downtown.
Sub tropical environment, laid back living like a local, it’s flip flops, or walking shoes, bring two sets of swim wear or shorts and t-shirts, tropical long cotton dresses, basic casual wear everywhere.
This Sailboat is set up for both local Time Charters and long-distance Time 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.
Romantic getaway charters, or family Time Charters are available. Bring your bucket list buddies, friends or the office. Let’s go sailing! Got a group - we have three boats side by side.
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 and what the CITY is known for. All about a ten-minute stroll away to the downtown nightly Sunset Festival on Mallory Square, all the museums, and all the festivals. A beautiful State Park on the ocean is near by. Air Conditioning, water and electricity in port. Direct Current batteries are for charters off docks. Please let us know if any medical issues requiring more power. Swimming pools nearby when you make a food and beverage purchase as their guests.
Our Company is licensed by the City of Key West as a Time Charter operation. Also, being properly insured including for snorkeling means that this is a trusted professional Company for Time Charters since 1995.
Weddings, Anniversaries, mile marker Birthdays, Honeymoons, Key West Adventures overnight at anchor or extended sailing are just a few choices you may upgrade to as a customized Time Charter. We do all types of sailboat Time Charters. Ask for specific rates for what you wish to add to your Basic Charter. Tell us what your special occasion is and what you wish to do.
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. Connections for your cell phones and laptops welcome. 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 Time Charter with us 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.
See GOOGLE MAPS behind Waterfront Brewery, The Historic Seaport, 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 as far away as ten miles from Key West the actual town and island. 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.
Often imitated seldom duplicated located on the island 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 see the sea. Capt. Albert - owner since 1995