Florida

What can we say, Key West tropical, with a Caribbean flavor where everyone drives on the right side of the street (mostly), speaks English (mostly) and where you can use US dollars for food and drink (all the time), especially margaritas. Can Jimmy Buffett be far away?



  Pilot House is a beautifully decorated Victorian mansion that won a prestigious award a few years ago for its restoration, called the "Excellence Award for Preservation." The hotel is NOT a nudist resort but you can use the pool and hot tub au naturel.

Guest rooms are furnished with a careful blend of antiques and decorated with tropical furnishings for the discriminating tastes of experienced travelers. The resort offers unique lodging accommodations with 14 guests rooms to choose from, all with private bath, color cable T.V., phone, air conditioning and paddle fans.

The property consists of 2 buildings: The Victorian Mansion which offers 8 guest rooms and the pool side Cabana building which offers 6 guest rooms....best for easy access au naturel to the pool.

Another option you have is the Pier House Hotel, right in downtown Key West. With its own little stretch of private beach, the property bills itself as "topless" friendly so it's worthy of applause for sure. Location, location, location: The hotel's address is # 1 Duval Street, at the foot of the one of the most fun streets in the USA or anywhere for that matter. Disneyworld can't come close, especially during the annual FantasyFest in October. Pier House has 142 hotel rooms and suites with four unique bars and three restaurants. The hotel's PR says: " Indulge yourself with a treatment from the island's only full service spa."

Guest house B&Bs are located throughout the city and offer a great option for private, party oriented, clothing-optional groups of like-minded adults. Typical room count is from 6 -12, good for 10-25 people or so.

Marreros is a 12-room Guest House with a clothing optional swimming pool but it's not a nudist resort. Merreros is perfectly located a half block from Duval Street, the heart of Key West.

A recent guest reports: "We stayed at Marrero's three nights a few weeks ago and already have reservation for a week in June 2008. The mansion 1/2 block from Duval Street, the owner (John) is a great guy and treated us very well. The clothing optional pool was nice and most everyone there was nude. The room we were in (#26) was impressive with 11 foot ceilings and old trim and woodwork. We would recommend this place to anyone."

Chelsea House also provides a clothing optional sun deck above its 2nd floor but you must wear a swim suit to use the pool.

The Atlantic Shores Hotel location has been replaced by a condominium project....a wave of the future as Key West has been found by the real estate developers. Go now before it turns into Miami Beach.

  Pilot House is located in the heart of the Key West Historical district on Simonton, walking distance to most attractions.

Private guest houses and B&B homes for up to 6-12 couples are also scattered throughout the town, great for groups.

Depending upon traffic conditions, weather, time of day and day of the week, a drive from Miami should take you 3-5 hours by car down U.S. Highway 1. You can sail there or fly into Key West International Airport, serviced by all major air carriers from other major Florida gateways including Miami, Ft. Lauderdale, Tampa and Orlando.

Fun ways of getting around town include renting bicycles, mopeds, three- and four-wheeler buggies, open air cousins of golf carts. Since Key West is only about 4-5 miles long and 1-2 miles wide at spots, you can see the whole place easily using any of the transportation choices above.

Another unique way to see everything is to walk... since most places of interest are convenient to Old Town anyway. A mile or two walk is not only good for you, you get to see and discover everything up close and personal.

Shop Discount Airfares
All Major Carriers - 24/7 Reservations & Booking


  Pilot House offers 14 rooms as a guest house only....no meals. The main mansion includes guest rooms with kitchens or kitchenettes.

The guest houses and B&Bs offer accommodations and some provide daily breakfast only. Most include a private swimming pool, usually out back, for sun and fun plus a hot tub.

  The Pilot House has no food service. Restaurants, bistros and a grocery store are nearby. The main house includes rooms with kitchens....however, most women don't mix "vacation and kitchen" in the same sentence!

Guest houses and B&Bs include accommodations and some offer daily breakfast only. Most have a private swimming pool usually out back, for sun and fun plus a hot tub.

Great restaurants, bistros, bars, fast food joints and downright dives are spotted all over Key West with the greatest concentration in and around Duval Street, N. Roosevelt Blvd and along Greene and Front Streets in Old Town. Numerous dockside bars and restaurants dot the harbor in the historic seaport section of Old Town adjacent to Caroline Street.

The largest restaurant and bar complex dockside in Key West is the Conch Republic on Caroline with dining tables and its great bar facing the seaport. Plenty of drinks, beer, wines and fun to choose from. In addition, try the great boiled spicy deep-sea shrimp there...you won't find more tender and juicy fresh shrimp anywhere else. Catch of the day and other house specialty dishes complete the menu. A big plus, happy hour is 4-7 PM, so you can mellow out over 3 hours if you like. There's usually live music at the bar to groove by, troll or just enjoy the one you're with.

Other top restaurants in town include Bagatelle, Cafe Med, Cafe Sole, La Trattoria & Virgilio's, Mangoes, Nine One Five, Rooftop Cafe, Square One and The Catch Cafe & Wine Bar. The most fun is to simply pub crawl and pick a restaurant wherever you decide to stop. You really can't go too far wrong as the dining scene is competitive. The further you drift from the tourist areas, however, the more reasonable the prices. For a little breakfast hole in the wall, stop in at Pepe's across the street from Conch Republic. Pepe's is also good for a meal anytime of day or night.

Other favorites include Blue Heaven and Louie's Backyard, a great place for dining and enjoying your significant other

Bar wise, there seems to be one on every other block on the main streets. The one that packs the most per square foot is the 3 story building where The Bull, The Whistle and the Enchanted Garden are located.....at the corner of Duval and Caroline. The Enchanted Garden on the roof boasts a clothing-optional bar for drinks and a view.....most times, you'll find more curious on lookers than folks dropping their drawers.

There's Naked Lunch off of Duval for a different way to grab a bite to eat. For you fast food franchise aficionados, there's Denny's, IHOP and other plastic renditions of Americana spotted all over Key West. Tourism magazines are available for free most places so gab one when you arrive and plot your course from there.

One note. The list above can and will change as bars and restaurants change hands, names and locations often, so plan to explore Key West with an open mind.

Needless to say, you won't go hungry or thirsty on the island.

  Pilot House rates run from low $100s/room/night for two up to $350/room/night for full suites.

Guest house B&Bs have similar rates.

For clothing-optional choices, you'll find Pilot House and Marrero's Mansion arguably the only two that offer swimming pools where you can enjoy the water nude. Pilot House also has a private hot tub on the grounds, too. The Red Rooster Inn (B&B) also claims its roof is clothing-optional. Numerous guest house and B&Bs can be rented outright for small groups from 6-12 or more couples where you can turn your housing choice into a clothing-optional experience around the pool. At least 100 B&B and guest houses are scattered around Old Town and Key West so you've got lots to choose from if you want to rent an entire building for a weekend or longer party.

The former Deja Vu is no longer clothing optional and does not exist. The hotel complex has been re-leased and is now called the Truman House, a conventional motel that welcomes everyone. Also the Atlantic Shores is no more.

  Adults only for the most part at the resorts mentioned. But throughout the town and beach all ages are seen there.

  Key West is where the Caribbean, New Orleans and Bahamas seem to meet in one place, where the natives are friendly and the fun non-stop.

Plan to walk everywhere you can. The most fun is in front of you and not necessarily in your car.

The entire world it seems has discovered Key West, so you may be shoulde-to-shoulder with tourists down Duval Street once you venture out, especially during the weekends or when the cruise ships dock.

Diner Shores Restaurant faces South Street and is open for breakfast, lunch and dinner with happy hour from 3 PM to 9 PM. Live entertainment is provided about twice a week. Atlantic Shores and the Diner Shores are both on the sunrise side of Key West, next to Duval, the main street for Key West where you can walk 12 blocks to the other end to the heart of the town of Key West, with lots of shopping, dining, discos, clubs and boutiques for just about anything and everything.

The comments below come from a client who is a resident of Key West.

Key West is not as open minded as many people think it is. True, Fantasy Fest is once a year but even that is being cracked down upon....but the PARTY still continues.

Most guest houses have a private swimming pool and hot tub in the back of the property. Bedrooms can run from 3-4 up to 12-15 or so, perfect for a small group.

The food in Key West runs from seafood to steaks mostly. One could eat out at an elegant restaurant or a small, family run place. Recommend El Siboney for good Cuban food, not a fancy place but family owned and operated.....and GREAT food.

For seafood, almost anyplace here is good.

Now, for night life.....there is not a lot of open minded places down here. One that stands out is the Garden of Eden (GE) down town above the Bull Bar on Duvall, the main street in Key West. GE is the only clothing-optional bar down town or in the Keys for that matter. During the day, it's a mix of people. During the holidays and on weekends, it's a great place to meet old friends and make new ones.

That's a taste of Key West. One really needs to come and enjoy the town for a few days at least. You have just about everything one is looking for in a tropical destination and you can make a party just about anywhere so why not in Key West.


One store we personally enjoy is Fast Buck Freddies, about 4-5 blocks from the foot of Duvall, next door to Jimmy Buffett's Margaritaville Cafe. (Guys--Here's a tip: Ask for the Fart Machine at Fast Buck Freddies in back room if you're really sophisticated--it costs less than $20 including batteries. You will surprise your friends and anger your wife---hey, it's a guy thing).

A good saloon in town: Hog's Breath. (better than no breath at all!)

  Expect to see lots of spots that look like Disneyworld....mass tourism arrived in Key West big time years ago, so don't expect lots of cute little bars or restaurants that quaintly reflect the Key West of years gone by.....there're not there. When you see Ripley's Believe It or Not and the big cruise ships move in, you know the Key West of Ernest Hemingway's day is long gone.

Do expect lots of choices about where to spend your money, though.

Other than the 2-3 guest houses, resorts plus a bar or two that permit clothing-optional sunbathing, you can always put your swim suit on and enjoy Higgs Beach, Rest Beach or Smathers Beach, on the south/south east side of the island,near the airport. Smathers use to tolerate a bit of nude sunbathing on the north/east end but due to the local "do gooders," you won't find any public beaches where you can legally drop your drawers.

Numerous tourist choices will boggle your mind including walking tours, sailing, diving, snorkeling, shopping, seeing the butterfly conservatory, touring museums, gardens, historic homes & mansions, art galleries, light houses, Hemingway's guest house and Mel Fisher's Maritime Museum. For the adventurous, you can kayak, go sailboarding, kite boarding, flying in a seaplane or biplane, visit and sail with the dolphins or party on the big catamarans for a day of snorkeling, reefing and sunning. You can even Yoga by the Sea if you're into soothing your soul. Pick up any tourism magazine for free at most restaurants or shops and plan your days and nights accordingly. Ride the Conch Train from downtown with open air coaches pulled by a tractor whose driver will entertain you with a running narrative of local Key West tales.

If you just like to wing it, start at the intersection of Duval and Greene Street, the main line where it mostly happens, and go walking from there. Parallel streets and intersecting streets off of Duval offer lots of nooks and crannies to explore. Don't venture down some dark alley in the middle of the night, though. Stay in the lighted areas and be aware of your surroundings.

Of course, just about every month in Key West is an excuse to have some kind of festival and fun, the most famous of which is the Fantasy Festival, over 25 years since it started. Fantasy Fest occurs about the last 10 days of October, starting generally the week just prior to Halloween. Events include costume competitions, street fairs, masquerade balls and the grand parade finale. The local Caribbean community kicks off the weekend before with the Goombay Festival, celebrating Caribbean and African culture. Located in Key West's Bahama Village neighborhood, the Caribbean celebration includes a festival of music, dance, art and craft and food.

You can even win $1,000 at Hogs Breath's Saloon's home made bikini contest or enter you and your dog in Fantasy Fest's Pet Masquerade, where pets and owners both compete in a look-alike contests. Hey, it's not Mardi Gras in New Orleans, but it does seem to be more user friendly and smaller than the million-member mob that invades Louisiana's Bayou City each winter.

Bars and nightclubs include A & B Lobster House, Aqua, Berlin's, Bourbon Street Pub, Half Shell Raw Bar, Hard Rock Cage, Hog's Breath Cafe and Bar, Kelly's Caribbean Bar & Grill, La Te Da for gay acts, Louie's Backyard, Mangoes, PT's Late Night, Schooner Wharf Bar, Sloppy Joe's Bar and Turtle Kraals Bar. Note: These may change names, change locations or change owners without notice so use the list as a general guide.

Funkiness reins supreme at lots of clothes, boutique, art and head shops in Key West, with lots of selections for main line tourists as well as gays, lesbians and folks of all persuasions.....from key lime products to voodoo and incense shops, you'll surely find a good reason there to spend your money.

 
Tourists everywhere, every fast food franchise is there.
     
Bars and restaurants everywhere--not necessarily bad, but usually expensive.
     
Some of the Key West guest houses and older, Victorian homes are simply outstanding to see.
     
Key West is just one of a kind. It's a mix of Miami, the Caribbean, and just about everywhere else. the locals are an adventursome and fun-loving lot. You have to go... at least once.
     
  Parking is hard to come by. Take lots of quarters to feed the meters if you drive a car in Key West, especially over the weekends or during holidays and special events.


  Key West is a year-round destination and is frost-free during the "winter." Great weather most of the time, but avoid the hot summer during hurricane season. Fantasy Week, usually before Halloween, IF YOU CAN FIND A PLACE TO STAY! Runs New Orleans' Mardi Gras a close second.

  We wish they would limit the tourist quota.

Lower restaurant prices.

A four-lane highway from Miami to Key West.

Wish more guest houses were nude friendly, but rent a whole place and bring your own party. Money talks, especially when you offer to take over a complete B&B for a few days.

Wish parking your car was more convenient on the weekends.

  View the Photo Album
We have a limited photo album of Key West resorts... so we can use many more. Why not send in yours? You can contribute to this section - all you have to do is go to our Contribute Trip Report / Photographs page.

  View Trip Reports
We have a few, but we need more trip reports from from folks who have recently visited Key West. You can contribute to this section - all you have to do is go to our Contribute Trip Report / Photographs page.

   
  You can arrive any day of the week so call CASTAWAYS TRAVEL for your vacation. You can stay as long as you like.

Now that you know, GO! Contact CASTAWAYS TRAVEL via our quotes / reservations page or 800-470-2020 during the business day to book your trip. Thank you for visiting our website. We appreciate your kind consideration.

Castaways Travel
Providing Clothing-Optional Vacations and Cruises Worldwide