Verified Review icon check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag pet-dog svg-multiunit Default Owner Icon heart-filled
Book Online or call HomeAway Booking Assistance 888-829-7076
Book Online or call HomeAway Booking Assistance 888-829-7076

37 ft. Boat Downtown Key West Marina Stay/Sail Charter Sailboat & Go Sailing

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


About the property

Obsession 37 ft. Sailboat 2 cabins 2 bathrooms, living room and galley

Tax Season Blues? Our special "Tax Rebate Charter Special" is around $100 off per night minimum stay only two nights. We have to get away too sometimes. And that's to a local beach! But you can stay two nights with a 2 hour sunset sail worth $345. Book now this will close out soon dates: April 14-24th, 2017. So get your inquiries in this week. Get out of that pile of papers now!

Our Charter Boats are In a MARINA ON LAND with 24 hour security; and you choose when you want to have a SAILING CRUISE and can upgrade and add any more sailing you wish! Avoid being stuck on a dead boat on anchor in middle of the ocean, with out amenities our company has - AC, working bathrooms or "heads" as we call them, propane stove, small appliances- Electricity, Coffee Pots, Utensils, Plates, Pots and Pans, Working Propane Stoves for Cooking! Working Toilets and Running Water plus Owners/Guests Personal Marina Based Hot Showers! Laundrymat! Toilets! Access just steps away to Restaurants and a Beautiful POOL if you buy food and beverage. PLUS you get an actual boat cruise/sailing time.

Who wants to be on a boat in the harbor without these amenities and have to wait to get a water taxi? You cannot use the private showers on land unless you are at our marinas and have a personally assigned key worth $50 if lost or stolen. CHOOSE WHAT KIND OF ACCOMMODATIONS YOU REALLY EXPECT.

Want a tropical economical adventure vacation? All of our boats have sailing included. Now featuring charters with minimum 2 night availabilities.

Tropical temperatures with mild day temperatures 75-82 degrees, nights are 55-65 degrees and it's warm and wonderful sunshine with green leaves and tropical waters and colors. Lots to see and do on the island or sailing with us. Get personal attention and escape the ordinary big schooner experience. Take the helm, pull up a sail or just let our first mate wait on you and your whims. Relax on the bow of your own sailboat.

April is gorgeous here. Bird spring migrations happen too. Ibis 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 345 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 sailing value (if not sure please ask) appreciated by hard working crew. 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 here direct through Home away or VRBO.

This is our economy boat, large enough for a family two adults with 2 small children, or another couple; and if you have other guests in town up to six people (including you and your partner/spouse) are allowed to go sailing.

(Maximum preferred is 2 adults and 2 children but there are also two couches for maximum of six passengers for staying aboard )

NOTE: this is the boat any medium to small animals allowed with a $125 pet clean up fee non refundable.PLEASE advise if you wish to bring an animal.

Fun for everyone in the center of downtown Key West. Add to your sailing with our many sailing options after you book with Home away. 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. We can accommodate you this 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. Charter and stay and sail 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.

Mild Spring and Summer 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.

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 Home away family since 2009. See some of our reviews at our main Home away listing under Wild Thing sailboat. Feel free to check Trip Advisor.

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

More Details

Albert Tropea
Member since: 2008
Speaks: english
Response time:
Within a few hours
Response rate:
Calendar last updated:
April 21, 2017

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 Key West

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.


Historic Seaport Boat Accommodation and Amenities

Property Type:
  • boat
  • Guests provide their own meals
Floor Area:
  • 500 sq. ft.
House Rules:
  • Max. occupancy: 4
  • non smoking only ...
  • pets considered
  • Minimum Age Limit for Renters ...
  • children welcome ...
Location Type:
  • Beachfront ...
  • Downtown ...
  • 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 , boat showers and toilets/heads on boat
    Bathroom 2 - toilet , shower
  • 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 , V birth double
    Bedroom 2 - 2 double , 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 Renters Welcome
  • limited accessibility
Pool / Spa:
  • Communal Pool ...
  • arboretum
  • bay/sound
  • botanical garden
  • churches
  • cinemas
  • coin laundry
  • festivals
  • library
  • marina
  • museums
  • playground
  • recreation center
  • reefs
  • restaurants
  • synagogues
  • waterfalls
  • winery tours
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • eco tourism
  • luaus
  • paddle boating
  • scenic drives
  • sight seeing
  • walking
Local Services & Businesses:
  • ATM/bank
  • fitness center
  • groceries
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • basketball court
  • cycling
  • deepsea fishing
  • fishing
  • fly fishing
  • golf
  • hiking
  • jet skiing
  • paragliding
  • pier fishing
  • sailing
  • scuba diving or snorkeling
  • skiing
  • snorkeling
  • sound/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.

Learn more about this vacation rental at the owner's website:


4/5 -
(2 traveler reviews)

37 ft. Boat Downtown Key West Marina Stay/Sail Charter Sailboat & Go Sailing
average rating of 4.0 based on 2 reviews

Perfect location

  • 4 of 5

Its a perfect location for a slightly different kind of trip to Key West. No golf cart/scooter/or even bike rental needed here. You can just walk everywhere. Many thanks to Capt. Albert for the hospitality.

  • Submitted: Nov 2, 2016
  • Stayed: Oct 2016
  • Source: VRBO, from HomeAway
Did you find this review helpful?
1 0

Key West snorkeling Reef trip

  • 4 of 5

Location was great close to restaurants shops and the downtown area sailing to The Reef was the highlight Of our trip

  • Submitted: Jul 22, 2016
  • Stayed: Jul 2016
  • Source: HomeAway
Owner's Response: Thanks a lot for being our favorite return Obsession customer! Glad always when you choose us while in Key West. Capt. Albert
Did you find this review helpful?
1 0


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

Historic Seaport Boat Rental Rates

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly Event
Tax Rebate Charter Special
Apr 14 2017 - May 24 2017
2 night minimum stay
My Standard Rate
2 night minimum stay

Additional information about rental rates

children under 17 $0
4th additional adult $45
3rd additional adult $45
Pet Fee $125

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

  • Canceled bookings will not receive a refund
Enter dates for accurate pricing
Send Email Send Email

Partner Offers

You might like these similar properties