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Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

42 ft Sailboat DOWNTOWN Key West Private Vacation Charters

Bedrooms 2
Space 600 sq. ft.
Property type boat
Minimum Stay 2 nights


About the property

Key West Sailboat Moon Dance 42 ft. Irwin Sailboat 2 cabins 2 bathrooms

We are OPEN for your sailing vacation plans for 2018!

Book your last minute winter break limited availability in December plenty of great dates in January - WARM UP WITH US HURRY! bring a sand shovel instead of snow shovel!

Welcome aboard your dream vacation. If you love unique vacations, choose a sailing charter vacation! If you enjoyed "glamping" or camping, traveling in an RV, staying in a cottage and nature, get the best of both worlds in Key West on your own sailboat charter.


Your 2 nights charter free 2 hour sunset sail!

Charter 3-5 or more nights 4 hour free reef snorkeling trip!

Cleaning and laundry fee $100 is not refundable. Towels and linens will be set up.

$45/per night per bed each extra person after two people, all ages.

There are no taxes on charters.

Toddlers or under five years old, sleeping with mom or dad no charge.

Gratuities appreciated usually plan cash for 20% of value of sailing trip.

When you book here and Homeaway will collect processing and commission fees.

IMPORTANT: you must disclose to our crew in advance non swimmers or recent surgeries so that we may plan for your safety. We cannot be otherwise responsible. REMEMBER - You will be in a boat on the water.

Please give us an emergency contact from back home on land.

United States Coast Guard Licensed for up to six people total.


Charter sailing with your crew will include snack trays or sandwiches.

Book a charter and ask about your fun options for 2018.

Dive the reefs or go exploring dolphin playground maybe diving a wreck. We have fishing and snorkeling gear to choose your activity. Take the helm, pull up a sail or Your Captain will safely take you where you wish to go and see at sea what you want or Relax on the bow of your own sailboat.

Custom Optional Discounted Charters to Choose from after you have your standard rate package:

Ask about custom add on's after you book here.

Fruit Tray for your Sunset with water and sodas included.

Sandwiches or cheese/crackers/fruit tray with water and sodas included plus you choose snorkeling or fishing gear also included.

You can use the private showers on land when you are at our marina as our guests and have a personally assigned key worth $50 if lost or stolen.

Key West is tropical year around, mild day time temperatures! Reefs and sailing on your own charter boat make memories for a lifetime. Swimming and Snorkeling or Fishing are available year round. Much to see and do in downtown Key West just steps from your boat off the docks.

It's the best of both worlds in Key West. Downtown location and a water sports attraction.

This is our big and roomy boat just kick back and relax. Special custom packages you may upgrade after you book with Home away, that you can add later to include day trips & excursions at sea. For the most fun you can have on a boat! Established in Key West Historic Seaport since 1995.

Larger interior than you would expect, 42 ft. Irwin sailboats are roomy and perfect for those with a family and the V birth is specially designed by former owner to be comfortable for someone over 6 foot 3 inches tall. 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.

Walk to downtown five minutes away. Moon Dance has a large deck to relax by day or night on your own boat; we do not sleep in the opposite side of the boat unless you go off shore and choose to take a fully provisioned 24 hour excursion with crew included.

Moon Dance has large v birth HUGE bed shaped almost like a heart, king size bed in the master cabin and private bath. MOON DANCE CAN TAKE TWO COUPLES and two small children or two singles on couches in living room/ salon.

MAXIMUM six people licensed only for six for all charters.

Set your date and book now then add sailing once you are booked. We take Master Card, VISA or Discover.



Live the life of an old town sailor aboard Moon Dance. All charter meals on your own at any of the restaurants unless you want upgraded overnight charter at anchor with crew and provisions. If you want to cook on board, the first mate can show you how to cook with propane powered oven and range top. Coffee pots provided.

Look up Key West Waterfront Brewery; the pier going behind that building is where E Docks are. Located in famous Historic Seaport two blocks from downtown Key West. Upgrade and go out into nature and stay on anchor overnight! Book now and upgrade according to your plans and the weather.

We are members of Home Away since 2003.

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, you are in the American Caribbean.

Highly rated on Trip Advisor. Tell us if you are celebrating a special occasion. Moon Dance beautifully laid out with an oversized v-birth almost a heart shape king sized bed and private bathroom.

Celebrate Weddings, Honeymoon or Birthdays with your sailing charter.

This Sailboat set up for local charters and off shore or long distance charters, with fully operating kitchenette and boat style bathrooms. WIFI while in port, and Access To Marina Bathrooms & Large Showers and Laundry.

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. 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 legal live aboard charter operation and we are properly insured including for snorkeling, and are your professional team for charters.

(Plan a cash (or credit card) for your captain and mate as 20% gratuity based on the Posted Private Sailing Charter values of sailing - however, it's up to you to tip as you wish).

Connections for your cell phones and laptops welcome. Ask your first mate how to use FREE marina wi fi in port. 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 and have 12 volt power off shore.

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 up Historic Seaport Marina on GOOGLE MAPS 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.

Proud to be a part of dream sailing vacations since 1995 at the same location! Book your couples getaway weekend, your couples' getaway, a small family vacation or plan a dream wedding now for "the most fun you can have on a boat!" See our YOU TUBE channels for more fun.

See you soon!

Capt. Albert with Ronda

More Details


Historic Seaport Boat Accommodation and Amenities

Property Type:
  • boat
  • Guests provide their own meals
Floor Area:
  • 600 sq. ft.
House Rules:
  • Check-in: Flexible
  • /
  • Check-out: 11:00 AM
  • Max. occupancy: 4
  • Max. adults: 2
  • Min. age of primary renter: 21
  • Children welcome
  • Parties/events not allowed
  • Pets considered
  • Non smoking only
  • Noise Ordinance 11 pm please no smoking on the boat - docks only. Advance notice cleaning fee small pets $125.00 Please call ahead day before.
  • Cleaning fee non refundable: $75.00
Location Type:
  • Beachfront ...
  • Downtown ...
  • Monument View ...
  • Ocean View ...
  • Oceanfront ...
  • Resort ...
  • Village ...
  • Water View ...
  • Waterfront ...
  • Adventure
  • Away From It All
  • Family
  • Historic
  • Romantic
  • Sports & Activities
  • Tourist Attractions
  • Air Conditioning ...
  • Clothes Dryer ...
  • Fitness Room / Equipment ...
  • Garage ...
  • Heating ...
  • Internet ...
  • Linens Provided ...
  • Living Room ...
  • Parking ...
  • Towels Provided ...
  • Washing Machine ...
  • Coffee Maker
  • Dishes & Utensils ...
  • Kitchen ...
  • Oven ...
  • Pantry Items ...
  • Refrigerator ...
  • Stove ...
  • Dining ...
  • Dining Area
  • seating for 6 people
  • 1 Bathroom
  • Bathroom 1 - toilet , shower , these are sailboat bathrooms and you may use marina showers
    Bathroom 2 - shower
  • larger bathroom / or called heads and showers than normally associated with boats this size
  • 2 Bedrooms, Sleeps 4
  • Master Bedroom - 2 king , huge oversized v birth almost heart shaped large king
    Season Not Available - 1 double , 1 twin/ single , The guest cabin has a double and single bed -Not Available
  • V birth is large and considered the master cabin.. There are two beds in Aft Stateroom great for kids or two couples
  • Long-term Renters Welcome
  • arboretum
  • bay/sound
  • botanical garden
  • churches
  • cinemas
  • coin laundry
  • festivals
  • library
  • live theater
  • marina
  • museums
  • playground
  • recreation center
  • reefs
  • restaurants
  • synagogues
  • waterfalls
  • winery tours
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • eco tourism
  • paddle boating
  • photography
  • scenic drives
  • sight seeing
  • walking
Local Services & Businesses:
  • ATM/bank
  • fitness center
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • basketball court
  • cycling
  • deepsea fishing
  • fishing
  • fly fishing
  • golf
  • hiking
  • jet skiing
  • paragliding
  • pier fishing
  • roller blading
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • sound/bay fishing
  • swimming
  • tennis
  • water skiing
  • water tubing
  • wind-surfing
Old town private homes are around the area. Charters are private and can be customized. Shops, restaurants and entertainment walking distance. Yachts or sailboats this size are easy for you to take the helm or pull sails with your family. Small shops and eclectic gift shops and local color and flavor of the old Key West are existing side by side. Two blocks from the activities including festivals and nightly sunset celebration at the Mallory Square with museums all short walk. Your charter must include a sailing trip. You may upgrade and add sailing after you book online or call and book with us in person. You pretend to be the owner and tell us what you wish to do with your charter time.


4.5/5 -
(4 traveler reviews)

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42 ft Sailboat DOWNTOWN Key West Private Vacation Charters
average rating of 4.5 based on 4 reviews
Boulder, Co

Ladies Weekend

  • 5 of 5

We had a wonderful time aboard Moondance! We stayed a full week, three day of which were at sea at the beginning of Feb '17.

It wasn't ritzy or flashy but it was cozy and so close to everything in Key West! You really can't beat the location. If you are able bodied, which you may need to be to navigate the steps, hallways and small quarters, you can walk to almost anywhere. We only had to take a cab from the Key West airport to the dock. We walked everything else: to FZT Beach, restaurants, bars, grocery stores, etc. And our neighbors at the dock were great; if you need any tips or advice, they are great resources.

We set out for a 3 day sailing adventure and it was a wonderful experience. Our captain (Tom) and our other crew member (Mark) were so great and we felt very safe and comfortable, even being 3 single gals. We spent time on deserted islands, exploring mangrove forests, snorkeling and just relaxing, reading and chatting. We helped sail the boat too, learning a bit about sailing. We even helped catch a fish! Wahoo is delicious and Mark and Tom prepared it wonderfully for our afternoon snack and dinner!

Tips and Tricks: There are showers on the boat but while in dock, it's so much better to go use the dock showers made available to you during your stay. Again, nothing ritzy but wonderful after a day at the beach to get clean and ready for a night out in Key West.

Also, if you plan on cooking, choose very simple meals as the kitchen is quite small and running multiple burners on the gas stove can be a challenge. Also, the fridge is small so don't buy too many groceries that need to stay cool.

Lastly, don't forget the rum! 8^)

We had a great time and hope to return again soon. Thank you Albert, Mark and Tom!

  • Submitted: Apr 10, 2017
  • Stayed: February 2017
  • Source: VRBO, from HomeAway
Owner's Response: Hi Haley! we appreciate your honest and thorough review as people do need to know something about how the locals' lifestyle living can be in Key West. Do come back and stay with us again as we want more input and help from people who stay aboard to always improve our guests' experience. Come back in August to see the reefs again or in November when the temperatures are mild and migration of many birds come to Key West (not just tourists~) thanks gain, Capt. Albert 305-304-4911
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1 0

What a memorable and relaxing stay!

  • 4 of 5

What a unique way to visit Key West. The sailboat was docked in a location within walking distance to most of the sights and plenty of options for food. It was quiet and peaceful. The rooms, being in a sailboat, where a little small but comfy. We did have a little difficulty when first arriving because we came in so late and had to find things like the light switches. The showers were at the marina - not overcrowded but the a/c was too low and it was difficult to change afterwards with all the humidity. Best part was the price included a sunset sail and we were able to sail the boat ourselves. Terrific value. Captain Al was quite interesting, and all his crew mates were wonderful.

  • Submitted: Jul 9, 2016
  • Stayed: June 2016
  • Source: HomeAway
Owner's Response: We remember this charter well two of the guests were from my original home area. Very fit and fun. Their arrival was very late much later than scheduled, it happens especially on a week end. They arrived about mid night I was standing by on the phone to check them in and answer their questions.
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0 0

Great crew, special time, small boat!

  • 4 of 5

Loved the privacy and having our own chef who also happened to be the first mate. We were very well taken care of. Everything we needed was available. The crew also gave us enough alone time and was never too chatty or invasive. The one thing we didn't like was how small the boat was for us. My husband is 6' tall and he hit his head too many times. It was also impossible for him to fit in the head. Not that we expected him to fit comfortably, but he literally couldn't even sit in it or extend his arms for a tiny bit. It was impossible. Other than that, it was an awesome time in Wild Thing!

  • Submitted: Apr 7, 2016
  • Stayed: April 2015
  • Source: HomeAway
Owner's Response: Very nice review, we try to be attentive to our guests. All 3 of our boats have the normal 6'3" headroom for sailboats that size. It does take a little getting used too but 6' is not an unusual size of a person on our boats. We had a charter last week, in fact, the gentleman was 6'5" and he navigated the inside of the Wildthing very well. His size 15 shoes restated his size. All in all we are very happy they had a good time and our crew presented themselves in a considerate manner. Capt Albert
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0 0

Great, unique experience!

  • 5 of 5

The boat wasn't Miami chic brand new or anything, but was well cared for, very clean, and the service was very polite and responsive. The A/C cut out in the middle of the night and they came over right away to fix it.

We were surprised how quiet it was at night, especially with Schooners Warf Bar just a couple hundred yards away. It was great to just lay on top of the boat and watch the stars at night or relax on it during the day. Walking the docks to check out all the boats was pretty cool.

I really enjoyed living the lifestyle of a sailboat bum for a few days. I highly recommend this over a hotel room if you don't mind using the shared, yet private showers at the end of the dock. If traveling with a friend, having 2 suites, each with private baths, a living room/galley, a "patio" up top, and a lounge "bed" up top at the front of the boat offers a lot more than 2 queen beds in a hotel room. We felt extremely safe and private from the neighboring boats and dock traffic except for the occasional friendly smile or wave hello.

The location was great with a 5 minute walk to Duval St and a quick bike ride anywhere else. There's plenty of restaurants and a convenience store right by the dock.

The sail was a great bonus. The crew were incredible hosts and bartenders we shared some great stories with.

Will definitely do this again!

  • Submitted: Apr 9, 2015
  • Stayed: January 2015
  • Source: HomeAway
Owner's Response: Hi there Robert! It's almost that time of year again and we hope you will be back! Weather should be cooperative in the fall so make your plans and call us again soon. Thanks for the very kind words. We work hard since 1995 to be able to provide you that comfort and fun time so close to everything. Thanks again, Capt. Albert
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4 0


Albert Tropea
Member since: 2008
Speaks: english
Response time:
Within a few days
Response rate:
Calendar last updated:
February 20, 2018

About Albert Tropea

Captain and owner, Albert Tropea, Jr. sailed the Greek Islands, East and West Coast, the Bahamas and Mexico as well as taken trips to Cuba several times being the lead captain for Proctor Gamble specifically The Gamble Family, Helen Curtis and has over 50,000 sailing miles. Each of the staff, mate, cleaning crew, licensed captains are individually trained and evaluated for their ability to maintain charters in open waters for a perfect safety record. This boat was purchased in 2011.

Albert Tropea purchased this boat in 1995

What makes this boat unique

All three of this company's boats are located minutes from everything you came to Key West to see. The location in the historic seaport is safe with 24 hr security and you can adapt your charter to anything you want to do even after you arrive. See our legacy listing with our reviews ID # 229193. Moon Dance is the latest addition to our fleet to meet the demands of a wider larger vessel where children may enjoy lots of room and parents more privacy.


Nearest Airport
2 Miles
Key West Airport
Nearest Barpub
25 Metres
Schooner Wharf Bar
Nearest Ferry
180 Metres
Fort Meyers-Key West Ferry Boat
Nearest Golf
1.5 Miles
Key West Golf Club
Nearest Train
100 Metres
Conch Train Tourist sight-seeing
Nearest Motorway
0.05 Miles
US 1
Nearest Restaurant
25 Metres
Turtle Kraals
Nearest Beach
1.5 Miles
Fort Zachary Taylor State Park
Car: not necessary

LOCATION LOCATION LOCATION! 3 blocks from Duval downtown City of Key West on the Island of Key West! Not 3 miles away where many charters invite you. Everything you ever heard about the laid back living is true. It is an easy to walk, no car needed once you take a taxi to your Historic Marina next to Schooner Wharf Bar and Restaurant, be up close to what you came to Key West the island to see. One of 3 sailboats charter 1, 2 or 3 boats for parties, friend or family getaways. the other boats are 44' Wildthing # 229193 and 37' Obsession # 3936222

Downtown Key West Historic District location and famous Duval Street is about 2 blocks away. All the Museums, Art Galleries, Famous Bars and Restaurants, Nightly Mallory Square Arts Sunset Festival is a short stroll to the Downtown Key West Area. NO CAR NEEDED. Rent a bicycle for easy as you go all around the two by four mile island. Hemingway's Home, The Butterfly Museum and Emporium, Mel Fisher Museum, Customs Historic Museum, The Wreckers' Museum and the Aquarium are only 10 minutes stroll not a long taxi ride from another island. Why not choose us first!

Moon Dance is a 42 ft. large restored Irwin mono hull with fully replaced motor, AC, wiring other features in 2003 and 2014 renovated re-varnished appointments. Large cabins and large bathrooms for families and especially favorite boat for tall guests. Ted Irwin's finest design on this solid fiberglass 1975 ocean queen with a Teak and lush interior.

The location of our boats allow you many choices! We can take you to the reefs, to the dolphin playgrounds, or to dive a wreck. We go further than the patch reefs other charters go to from the next island over.

Perfect for families and two couples especially designed for adults who are tall with longer and larger beds in the private two cabins. Bathrooms/heads are over-sized. One of the cabins has an extra twin bunkie if a small child needs to stay with you. Plus we have lush salon couches for additional children or two singles.

$475/night starting Stay/Sail Charter package. Includes basic 4 hr sailing to the reef with snorkel gear. Book online your basic stay, just call us to upgrade or add more sailing time (call or decide when you get here) Two larger boats best for two couples or families with up to six persons. Smaller economy boat one couple 2 children.

Add additional sailing during your stay. A la carte menu must call direct to get special package: Ask about any discounts as a current customer you normally receive unpublished specials)...

$600 for another 4-5 hour half day.

$900 for a full 7-8 hr day.

or choose $1400.00 for 24 hr at sea Key West Sailing Adventure

1100 for additional nights at sea (meals included on 24 hr sail)

Call for personal pricing and custom or last minute unpublished sailing packages.

Three night minimum preferred and last minute packages subject to availability.

See website for a la carte pricing and other ideas.

Part of the Homeaway family since 2009.

See our parent listing (Wild Thing ID # 229193) for reviews and more details! Also check that calendar for dates! same rates as Moon Dance!

Wedding, honeymoons, special anniversaries, birthdays.

Celebrate the historic sailing living on the sea life of the #Florida Keys #key west style!

If our calendar is not showing this boat available for your preferred dates, see also (Obsession #393622- our 37 ft. O'Day the economical sailor's choice).

More information and pictures soon, call Captain Albert today 305-304-4911

9 am - 9 pm EST

Often imitated seldom duplicated, we are the ONLY legal charter company approved by USCG with licensed captains to take you on your adventures for staying on boat overnight and doing off dock adventures on anchor, located on the real island of Key West proper approved and licensed by the CITY of KEY WEST. Check our location on GOOGLE MAPS 201 William Street, Key West, FL 33040. Caution - always know before you go, where is your boat located. Annexed Stock Island has approval to use "Key West" in their address (no post office on Stock Island). Buyers should always check and know what is around their destination for your safety. Design your day your way, stay/sail aboard sailboats where you can Live Like a Local Play Like a Millionaire!


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

3rd person extra bed $45
5th person extra bed $45
6th person extra bed $45
Pet Fee $125
Cleaning & Laundry Fee $100
4th person extra bed $45

Downtown Key West Marina, you will be able to stay at docks with air conditioning, running water, electricity and free wi fi. We are well known in Trip Advisor history and our reviews on our original site Wild Thing #ID 229193 as we have been a part of the Homeaway family since February 2003. We respect your privacy and do not stay on board only come to boats for charters. Also will include free linen and towel changes if you need at any time and usually check your boat and offer to replace linens, pump out the holding tank, put water in the tanks and always have people trained to help with any nautical questions or issues anytime. We are usually available 9 am - 9 pm and have access to immediate help as needed with a licensed captain and other technicians, so let us do the work you can relax in good nautical and USCG approved vessels. In case of bad weather, emergencies no refunds will be issued only a voucher for the remaining portion of your charter or in its entirety. The voucher will remain available for you at your convenience upon availability. Further you may sell your voucher. Stay in the historic seaport, old town Key West lifestyle, in the actual Key West City. You must pay City Parking available at lot near boats, or covered lot nearby or off street parking. Check with your crew if you are not sure. Call the day before arrival to insure location is understood and to check weather and last minute details.

Owner's Cancellation Policy

  • Canceled bookings will not receive a refund

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