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37 ft. Boat Downtown Key West Book Now Holidays, Fantasy Fest 3 Night Min.

Bedrooms 2
Space 500 sq ft
Property type boat
Minimum Stay 2 - 3 nights


About the property

Obsession 37 ft. Sailboat 2 cabins 2 bathrooms, salon and galley

Vacation Sailing Time Charter on your own private sailing vessel for a specific period of time with a customized sailing itinerary!

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. The additional per person charge is $45/per person per night. This boat is best for either one or two couples or a couple with small family of 2 or 3 young children.

Openings for Fantasy Fest and Holidays. We are booked all summer with the Boy Scouts Sea camp! Please join us this Fall or Winter. 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 another two hours for 250 dollars more to schedule a 4-hour sail to the reefs with snorkeling gear included. This is one of the many options you may add later at a discount rate.

Upgrade to as many nights or more sailing at a special low rate, as you like. 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, beachcombing, 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, music, a pool and a beach close by.

(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).


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 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. Cooler temperatures in summer than you would expect.

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, no need to fuss over your hair. Ladies find the relaxed styles clip up or tie back hair, or let hair dry natural. Flip flops or sandals are normal in any place you wish to dine or shop.

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! 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.

Look us up on GOOGLE MAPS behind Waterfront Brewery, The Historic Seaport, Key West, FL 33040. Stock Island is 3 miles away.

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 and see the sea. Capt. Albert - owner since 1995

More Details

Albert Tropea
Member since: 2008
Speaks english
Response time
Within a few hours
Response rate
Calendar last updated:
18 July, 2018

About Albert Tropea

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

Why Albert Tropea chose Historic Seaport

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.

What makes this boat unique

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.


Accommodation and facilities for this holiday boat rental in Historic Seaport, Florida

Property Type:
  • boat
  • Guests provide their own meals
Floor Area:
  • 500 sq ft
House Rules:
  • Check-in: 1:00 PM / Check-out: 11:00 AM
  • Max. occupancy: 4
  • Minimum Age Limit for Renters ...
  • pets considered
  • children welcome ...
  • non smoking only ...
Location Type:
  • Beachfront ...
  • City Centre ...
  • Monument View ...
  • Ocean View ...
  • Oceanfront ...
  • Resort ...
  • Village ...
  • Water View ...
  • Waterfront
  • Adventure
  • Away From It All
  • Budget
  • Family
  • Historic
  • Romantic
  • Sports & Activities
  • Tourist Attractions
  • Air Conditioning ...
  • Clothes Dryer ...
  • Garage ...
  • Heating ...
  • Internet ...
  • Linens Provided ...
  • Parking ...
  • Towels Provided ...
  • Washing Machine ...
  • Coffee Maker
  • Dishes & Utensils ...
  • Kitchen ...
  • Oven ...
  • Pantry Items ...
  • Refrigerator ...
  • Stove ...
  • Dining ...
  • Dining Area
  • seating for 4 people
  • 2 Bathrooms
  • Bathroom 1 - toilet , shower enclosure , boat showers and toilets/heads on boat
    Bathroom 2 - toilet , shower enclosure
  • Basic boat style shower ask to make sure you understand the way that the sink converts to a hand held shower. Toilet paper, towels, wash cloths provided and the bathrooms have some soaps and shampoo, gel and lotions. This is a very basic sailboat that is used for guests to easily learn to sail as it is a very spartan but surprisingly comfortable vessel for it's size - 37 feet by 13 feet wide.
  • 2 Bedrooms, Sleeps 4
  • Bedroom 1 - 2 double bed , V birth double
    Bedroom 2 - 2 double bed , Snug double nine feet long. Slants back end of boat.
  • Each has enough room for two people, but is a basic sailboat. If you wish to have more room or have additional travelers or guests, you may wish to consider a larger vessel for longer stays. Also for your safety and other's comfort no smoking on the boats. While under sail, must be at the back of the boat if you must smoke. Beds will be made linens included.
  • Stereo ...
  • Bicycles ...
  • Boat ...
  • Golf ...
  • Kayak / Canoe ...
  • Lawn / Garden ...
  • Water Sports Gear ...
  • 4 bicycles
  • long term rentals available
  • limited accessibility
Pool / Spa:
  • Communal Pool ...
  • arboretum
  • bay
  • botanical garden
  • churches
  • cinemas
  • laundrette - not serviced
  • festivals
  • library
  • marina
  • museums
  • playground
  • recreation centre
  • reefs
  • restaurants
  • synagogues
  • waterfalls
  • winery tours
Leisure Activities:
  • antique hunting
  • beachcombing
  • bird watching
  • eco tourism
  • luaus
  • paddle boating
  • scenic drives
  • sight seeing
  • walking
Local Services & Businesses:
  • ATM/bank
  • fitness centre
  • groceries
  • laundrette - serviced
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • basketball court
  • cycling
  • deepsea fishing
  • fishing
  • fly fishing
  • golf
  • hiking
  • jet skiing
  • paragliding
  • pier fishing
  • sailing
  • diving
  • ski
  • snorkelling
  • bay fishing
  • swimming
  • tennis
Old town Key West private homes are around your location. Private sailing charters and adventure tours. Lots of boats, parasailing, all kinds of water sports easy to find and museums walking distance as is Duval Street. Many more advantage to being just where the action is and still have peace and quiet at night as there is a noise ordinance 11 pm.


Excellent! 4.6/5 -
(8 traveller reviews)

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37 ft. Boat Downtown Key West Book Now Holidays, Fantasy Fest 3 Night Min.
average rating of 4.625 based on 8 reviews
Columbia, South Carolina

Amazing stay!

  • 5 of 5

Our stay was amazing! Location of the harbor was only 5 minute walk to Duval Street and Mallory Square; never used our car! Captain Albert and Jeff were terrific hosts, and the boating excursion was icing on the cake. Will definitely stay here again.

David and April

  • Review Submitted: 08/05/2018
  • Date of Stay: May 2018
  • Source: VRBO, from HomeAway
Owner's Response: We highly recommend these guests. They will an access to wherever they stay or vacation. Capt Albert
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  • 5 of 5

Had a great time!!more than expected,treated like family❤️Will be back!!!Thank you All

Skip & Belle Keiser

  • Review Submitted: 14/04/2018
  • Date of Stay: April 2018
  • Source: VRBO, from HomeAway
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Tight Quarters but AMAZING Location & Experience!

  • 4 of 5

We originally booked for 2 nights. Asked for an additional night b/c we enjoyed it so much. The boat is what it says it is. It's older but clean enough and all we needed it for was a place to sleep and use as a hub. We had our 19 and 15 yr. old kids with us. Couldn't ask for a better location for access to bars, restaurants, shopping, fishing etc. Can walk to basically any service you might need. The sunset sail was ABSOLUTELY worth the $$. The crew members were super professional yet so friendly. Totally recommend!!!

  • Review Submitted: 03/04/2018
  • Date of Stay: March 2018
  • Source: VRBO, from HomeAway
Owner's Response: Great family fun to be around they enjoyed the experience and showed it with their smiles They wanted to save some money and choose our smallest boat but all worked out happily
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Very Welcoming and Great Location

  • 5 of 5

We had a group of five plus our friend's little french bulldog. Albert our host was very friendly and welcoming and made sure to stop by and make sure we were happy with our overall stay. It was my birthday weekend and we wanted to go sailing with a snorkel tour. Even though we knew there was a storm in the distance the captain still tried to take us out for a little sail, which we were able to see dolphins and the beautiful turquoise waters. Albert made sure to give us a voucher to come back and make up for the rain since we didn't get to snorkel. Thank you so much for the great time we will for sure be back once the weather will cooperate a little more with us. We live in Fort Lauderdale so not too far of a drive to come back. Thanks again see you soon.

  • Review Submitted: 19/03/2018
  • Date of Stay: March 2018
  • Source: HomeAway
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Location, location, location

  • 5 of 5

Thiis is not luxury living, but if you are adventurous and flexible, you won’t find a better location in this price range. Located right in the middle of Key West Harbor (officially known as Key West Bight), your neighbors are million dollar yachts, sunset cruise schooners, Schooner Wharf Bar, The Raw Bar, Turtle Kralls, Pepe’s, and the Coffee Plantation. Just four blocks from Duval, far enough to be away from all the noise and crowds. Caveat: you must step across water (18” wide or so) from the dock and over an 8” high railing to get onto the boat, and there are 5 steps straight down from the cockpit to get into the cabin/settee and seperate master berth. There’s a private rear berth with toilet too. Toilets are tiny, and flush with a hand pump, easy to use. If you want lux, you can book a room at the Marker hotel/resort instead, just up the harbor walk from this boat for $500+/night, located right behind Schooner Wharf (so not actually water front). My party opted for less $, with a location right IN the water.

  • Review Submitted: 09/03/2018
  • Date of Stay: March 2018
  • Source: VRBO, from HomeAway
Owner's Response: We were delighted that Bill enjoyed being an adventurer with us and had real fun it seemed to like the staff and we hope he comes back again soon! We want anyone who likes to enjoy being close to downtown and to take a cruise out on the water to charter with us because our rates are all inclusive of the charter trip. Thank you for sharing! Capt. Albert with Ronda
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Nice an cozy for those that like the water....

  • 5 of 5

It was amazing. Sleeping on a boat was on my bucket list an captain Albert made that happen. Me an my buddy can't wait to get back there...

  • Review Submitted: 01/06/2017
  • Date of Stay: May 2017
  • Source: HomeAway
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Nearest Airport
2 Miles
Key West Airport
Nearest Barpub
25 Metres
Schooner Wharf Bar
Nearest Ferry
100 Metres
Ft Meyers-Key West Ferry
Nearest Golf
1.5 Miles
Key West Golf Club Stock Island
Nearest Train
50 Metres
Conch Train a tourist touring train
Nearest Motorway
0.5 Miles
US 1
Nearest Restaurant
25 Metres
Turtle Kraals
Nearest Beach
1.5 Miles
Fort Zachary Taylor
Car: not necessary

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.


Rates & Availability

Rental Rates for this holiday boat in Historic Seaport, Florida

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly Event
Off Season Charter
5 Sep 2018 - 15 Oct 2018
2 night minimum stay
Fantasy Festival
24 Oct 2018 - 29 Oct 2018
3 night minimum stay
My Standard Rate
2 night minimum stay
Notes: Rates are based on 2 guests; add AU$61 per night, per additional guest

Additional information about rental rates

Pet Fee AU$168.96
toddler with parents AU$0
laundry and cleaning AU$121.65

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 Obsession is our economy boat perfect for short getaway charter with savings for young family with two small children. Normally two adults enjoy Obsession, but there are 2 cabins and 2 bathrooms and a large salon. Further we have a no refund policy. In the case of an emergency, foul weather, any reason you cannot complete or use your charter a voucher will be issued to you for the amount of time of type of charter

Owner's Cancellation Policy

  • No refunds for cancellations made after payment is made
Contact Owner

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