HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
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
Book Online or call HomeAway Booking Assistance +44-800-085-3815
Book Online or call HomeAway Booking Assistance +44-800-085-3815

37 ft. Charter Sailboat & Sailing Downtown Key West

People4
Bedrooms 2
Bathrooms2
Property type boat
Minimum Stay 3 nights

Overview


Details
Property
boat
People
4
Bedrooms
2
Bathrooms
2
Minimum Stay
3 nights

Description

Photos and Description of this 2 bedroom holiday boat in Historic Seaport - Key West Sailing Adventure

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

Thaw out with us this December and January 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. Sailing is included on every charter. 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.

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 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 Offer may be withdrawn at any time, so hurry and book now!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 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. 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. 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.

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.

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
Suitability:
  • Long-term Renters Welcome
  • Minimum Age Limit for Renters
  • children welcome
  • limited accessibility
  • non smoking only
  • pets considered

Owner
Albert Tropea
Member since: 2008
Speaks English
Response time:
Within 12 hours
Response rate:
100%
Calendar last updated:
6 December, 2016

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.

Reviews

2 holidaymaker reviews

37 ft. Charter Sailboat & Sailing Downtown Key West
average rating of 4.0 based on 2 reviews
4

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.

  • Review Submitted: Nov 2, 2016
  • Date of Stay: Oct 2016
  • Source: VRBO, from HomeAway
Did you find this review helpful?
1 0
4

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

  • Review Submitted: Jul 22, 2016
  • Date of Stay: 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

Location

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.

Photos

Prices & Availability

Prices for this holiday boat in Historic Seaport, Key West

Rental Basis:
per property
Owner accepts payment in:
USD
Convert Currency
Rental Period Minimum Price Additional Nights Weekend Night Weekly Monthly Event Price
 
My Standard Rate
3 night minimum stay
£965
for 3 nights
From
£298
£1,879
 

Additional pricing information

children under 17 £0
Pet Fee £99
3rd additional adult £36
4th additional adult £36

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.

Owner's Cancellation Policy

  • 0% refund for cancellations more than 0 days before check-in date.
Enter dates for accurate pricing
Enquire Now Enquire Now
Available arrival
Available
Unavailable

Facilities

Accommodation and facilities for this holiday boat in Historic Seaport in Lower Florida Keys

Property Type:
  • boat
Meals:
  • Self-catering
Floor Area:
  • 500 sq. ft.
Location Type:
  • Beachfront ...
  • city centre ...
  • Monument View ...
  • Ocean View ...
  • Oceanfront ...
  • resort ...
  • village ...
  • Water View ...
  • Waterfront
Theme:
  • Adventure
  • Away From It All
  • Budget
  • Family
  • Historic
  • Romantic
  • Sports & Activities
  • Tourist Attractions
General:
  • Air Conditioning ...
  • Clothes Dryer ...
  • Garage ...
  • Heating ...
  • Internet ...
  • Linens Provided ...
  • Parking ...
  • Towels Provided ...
  • Washing Machine ...
Kitchen:
  • Coffee Maker
  • Dishes & Utensils ...
  • Kitchen ...
  • Oven ...
  • Pantry Items ...
  • Refrigerator ...
  • Hob ...
Dining:
  • Dining ...
  • Dining Area
  • seating for 4 people
Bathrooms:
  • 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.
Bedrooms:
  • 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.
Entertainment:
  • Stereo ...
Outside:
  • Bicycles ...
  • Boat ...
  • Golf ...
  • Kayak / Canoe ...
  • Garden ...
  • Water Sports Gear ...
  • 4 bicycles
Suitability:
  • Long-term Renters Welcome
  • Minimum Age Limit for Renters ...
  • children welcome ...
  • limited accessibility
  • non smoking only ...
  • pets considered
Pool / Spa:
  • Communal Pool ...
Attractions:
  • 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
Notes:
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.

Partner Offers

 
Portable wifi hotspot