We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Key West

Free Newsletter

Interested in Key West?

We'll send you updates with the latest deals, reviews and articles for Key West each week.

More Lists
We remove posts that do not follow our Trip Lists guidelines.
We reserve the right to remove any lists for any reason.
Trip List by out_of_VA

Spring Break with teenagers - Key West, FL

Apr 26, 2011  Travelog for myself and family - recommendations for others travelling with teens
4.5 of 5 stars based on 12 votes

What worked and what didn't for a Spring Break trip with middle and high schoolers; reviews of activities, lodging, food and timing that might be of use to others contemplating a trip.

The context:
I was looking for a trip that would be fun for my increasingly independent clan. Oldest son, 17, claims to not like the beach and would prefer if we left him home. Girls, 15 and 13 are sun worshippers and still into the idea of a family vacation. I started looking at all inclusive in the Caribbean and eventually came around to Key West as a more affordable alternative.

I was wrong about affordability. Though the flights weren't too bad and the hotel was free (on points), EVERYTHING else was way more expensive than expected. When planning your trip keep in mind that renting a car/van can be as much as $1,000 a week, meals are expensive for a family of 5, and activities start at about $300, more or less. And EVERYONE expects tips - everywhere you go there is a tip jar - even if you pay, say $500 to go out on a boat operated by the owner, there is a tip jar. People sit out on the street with their dogs asking for tips to take a picture. I was surprised the southernmost point buoy didn't have a jar out. I'm not agains tipping, but it began to feel like a shakedown. (also, expect most activities to have last minute add-ons -Picture CD? $35; T shirt? $30, etc., etc.)

As I fill in the trip list below I'll try to give an opinion of whether it was worth it or not - largely I will say yes, but I'm on the fence about a few decisions we made.

One thing I definitely recommend: before leaving set aside a significant amount of time to browse the destination forums. I was able to fine tune my agenda, come armed with a list of potential restaurants, decide between activities (Dry Tortugas or Dolphins?) and generally gain peace of mind when perusing others' recommendations.

  • Explore locations featured in this Trip List: Key West, Marathon, Grassy Key, Islamorada, Miami Beach
  • Category: Recent trip
  • Traveler type: Culture, Sightseeing, Shopping
  • Appeals to: Families with teenagers, Students, Active/adventure
  • Seasons: Winter, Spring, Summer, Fall
  • 1. Drive from Miami to Key West
    http://floridarambler.com/florida-getaways/florida-keys-roadtrip-mile...

    The Key West forum has a lot of discussion of whether to fly to Key West or to another FL airport and then drive. Because of price and timing it worked out better for us to drive and I am very happy we did. There were no major incidents to shut down the road, the weather was beautiful and the views of the keys spectacular. I've linked here to a mile marker listing to make the drive more interesting. It took us about 4 hours from Miami airport (which was a zoo) to Key West. Oh, and believe everything that is said about speed limits. Pay attention and drive no more than 5 miles over the limit...if you dare.

  • 2. Key West
    Key West, Florida Keys

    Be prepared to be on island time here - service is slow and laid back.
    I was expecting a big gay scene, and though it's certainly gay friendly, and the southern part of the town seems a bit more "gay," there were visitors and residents of all stripes - I guess it's more "live and let live" than "owned" by one group or another. (Why does this matter? Well, when travelling wtih kids, even big kids, it's best to manage their expectations a bit - mine have met and hung out with gay friends and family but an "out" town is just something they needed to hear about once before leaving - there's no way to write this that it's not awkward, but there you have it).
    Although the guidebooks will say this or that establishment is "Old Key West," during Spring Break, or when a cruise ship docks, there is no such thing. Neighborhoods and neighborhood establishments are just as crowded as the tourist attractions and Duval Street restaurants. The only "old Key West" we encountered was on Stock Island. That said, with a little planning, you can do pretty much anything you want to - if an activitiy or a restaurant is an important part of your plans, however, make sure to reserve ahead of time if possible, or be prepared for a long wait.
    Also, true to the island's reputation, there are lots of cats and lots of chickens and roosters wandering around. And lots of dogs. Dogs who must tolerate cats pretty well.

  • 3. Sheraton Suites Key West
    Sheraton Suites Key West, Key West, Florida Keys

    Pros:
    The concierge is terrific. She makes recommendations, reservations, and observations, all with a smile. I really felt she was making recommendations with our best interest in mind, rather than her commission. Big pro.
    The pool and bar area is lovely, and the bartender, though slow, is nice and friendly.
    They have reasonably priced bikes to rent.
    There is a shuttle downtown.
    Rooms are spacious and comfy - for the 5 of us we had two adjoining suites w/kitchenettes (fridge and microwave only) and it was more than enough space. We actually spent more time in the room than we normally do - we had breakfast there and we would come back there between activities, or to get off the beach and out of the sun - really very pleasant.
    There is wifi as well as a business center, but the Internet is painfully slow.
    Cons:
    Location is a pro and a con. We tried to take the hotel shuttle to old town, but the schedule was hard to meet (we didn't know what time we would return but we had to make reservations for the return shuttle before we left). In the end, we drove and parked downtown several times, and it ran us from $5 to $25. There are also bikes, scooters, electric cars, taxis (for 4), maxitaxi vans (charging per person). So it's not difficult, but some may prefer to stay downtown.
    Food: The Sheraton breakfast was about $15.95 and it was a pretty mediocre buffet. I've had a better spread at the Hampton Inn. On the other hand, we didn't overeat. After the first day we went to the grocery store and stocked our kitchenette with breakfast essentials.
    Another con (for me) was the bedding. It's soft and luxurious and....real down. If you have a down allergy be sure to ask for polyester pillows. Once we got that straightened out I slept like a baby.
    No other real cons - it doesn't have the atmosphere of some of the guesthouses downtown, nor is it a full fledged resort, but overall I would recommend it.

  • 4. Conch Republic Seafood
    Conch Republic Seafood, Key West, Florida Keys

    Very nice location on the water in the historic seaport. Food is well prepared. I had the stuffed shrimp - enough to share. There is live music.

  • 5. Smathers Beach
    Smathers Beach, Key West, Florida Keys

    Nice beach 2 miles out of town toward the newer end of the island (subdivisions and strip malls), across from the Sheraton. I understand the sand is trucked in - that's not obvious. The water is calm and shallow and a bit kelpy. Nice place to spend some time and relax.

  • 6. Sunset Water Sports
    Sunset Water Sports, Key West, Florida Keys

    Rented a windsurfer for an hour - that got the kids working together and it got my son out of the room. The windsurfing was a bust in that they only got up for a few seconds each - it was windy and choppy and they were warned ahead of time but they had a lot of fun and it was fun to watch. HOWEVER they were burned to a crisp. Note to self: applly sunscreen and WAIT 15 minutes so it sets in your skin instead of washing right off. The guys running the rental kiosk were brusque but then they took pity on the kids and actually spent some time showing them how to do it. And they got us a good price for parasailing at the other Sunset in Old Town. Their activities seemed to be the most reasonably priced in town. You can also pay one price and play all day. Some examples of prices: Chair - $10; Umbrella - $10 Windsurfer $39 an hour. Make sure to scour the coupon books at the hotel and look for online specials. You will be glad you did.

  • 7. Southernmost Point
    Southernmost Point, Key West, Florida Keys

    Hahaha. A stupid painted buouy at the bottom of Duval street, lines of tourists lining up to take a picture next to it. That's all there is. We walked briskly past it on the way to Ernest Hemmingway's house.

  • 8. Ernest Hemmingway's home
    http://www.hemingwayhome.com/

    Museum dedicated to Hemmingway's time in Key West and renovation of the property. Knowledgable tour guides depicting this slice of Hemmingway's life - one of his most prolific - and some of the characters that inspired his novels and stories (e.g., the Old Man and the Sea). Also the origin of the six-toed cats. Beautiful estate and grounds. Good way to torture teenagers.

  • 9. Duval Street
    Duval Street, Key West, Florida Keys

    Brings to mind Bourbon Street - iconic but is it reflective of the "real" Key West? I enjoyed lower Duval (below Sloppy Joe's) better. Lots of stores and galleries for the kiddos to browse. Disgusting t-shirts and other apparel. Lots of drinking but hard to find a cup of coffee. Basically a tourist trap but worth taking the stroll from southernmost point to the seaport once.

  • 10. Mallory Square
    Mallory Square, Key West, Florida Keys

    This is where "everyone" gathers for the sunset each evening. There are outdoor bars, performance artists, music and.....CROWDS. Oh my goodness. We stayed on the patio outside the Westin a bit further up - still crowded but manageable. The sunset was amazing - made more amazing by the silouettes of the beautiful sailing ships carrying sunset cruise passengers both sober and not.

  • 11. Jimmy McFadden's restaurant and bar
    http://www.mcfaddenskeywest.com/

    Well....this was the first of several amusing restaurant experiences. One of the themes we encountered at several places was scarcity- almost everything we tried to order was not available that day. Strangely, this was the only restaurant along Duval St that was almost empty - not usually a good sign. Once we found the meager pickings availalble from the menu, we had a decent dinner (lobster roll, peel away shrimp, ubiquitous fish sandwich). But the waiter was slightly strange and it took forever to get drinks and to get our check. On another theme, there was something going on in the back - a cop came in and went directly to the kitchen and as staff filed in and out their expressions were grim. We were totally curious but never found out what was up - strangely, however, some version of this happened at a few places we went too. Let's just hypothesize that KW has lots of cops, and other than traffic violations and public intoxication maybe they don't get a lot of other calls. Or maybe they do....

  • 12. White Knuckle Thrill Boat Rides
    White Knuckle Thrill Boat Rides, Key West, Florida Keys

    This was one attraction I am on the fence about in terms of cost. It was fun - not as "thrilling" as promised (I was hoping for something that was kind of like a giant jetski, since kids were not old enough to do that). I thought it was expensive for what we got. On the other hand, the father-son duo was charming and helpful and the dad, who drove the boat, gave an informative overview of some of the trivia about the island and its history. They really wanted us to have a good time and stood around chatting with us when the trip was over. So this is recommended, with some reservations....

  • 13. Key West Golf Club
    Key West Golf Club, Key West, Florida Keys

    My son and husband, who are not golfers, decided to take a lesson and try to play 9 holes. The club was very accomodating and laid back, as is fitting on KW. They had a really good time, and when they came across other players they let them play through and they couldn't have been nicer. If you want to do this, call the club directly (don't go through an agency) and set up a lesson for the late afternoon, then play a late round, when fewer people are on the course.

  • 14. Hogfish Bar & Grill
    Hogfish Bar & Grill, Key West, Florida Keys

    This was one of our better restaurant experiences in that the waitress had a clue what she was doing, but as usual the menu was far from complete. We went there for their specialty - can you guess? - hogfish. Alas, there was only grouper and yellowtail - same as everywhere else on the island. This, however, was Stock Island, with a working marina, locals in the bar (some appeared to live there), working fishing boats, etc. Their card says something about how it's a great restaurant, if you can find it...true enough....even the GPS was challenged in the back roads of Stock Island.

  • 15. Dolphin Research Center
    Dolphin Research Center, Marathon, Florida Keys

    This was a whole day trip for us. The center is a lot smaller than it looks on the website. It takes a little while to get into the flow of it. There are presentations and films all day - the presentations go from how they rehabilitate wild dolphins, to how they train them and how they assess their intelligence. The entry fees are not bad - abuot $20 per person, but they get you with the add on programs - everything from $600/day "be a researcher" to painting with them, meeting them, swimming with them, playing with them. The swim and dorsal pull ($189) looked cool, but not $189 of cool - and it's not very long. My kids did the "dolphin explore" program which seemed good for teens - they "help" the researchers evaluate behavior (e.g., are they left or right dominant? can they remember sequences of objects?). It was really cool and they got to pet the dolphin, play splash with him and"shake hands." It was kind of like the "play with the dolphin" program, ($50, but sold out), but a little deeper.
    We did not, but it would be a very good idea to call ahead and reserve a program. We showed up first thing in the morning and almost every program was already sold out. We were lucky to get what we got - but for 3:15 in the afternoon. So that entailed spending six hours at the place - and it wasn't that big. But between the various programs and watching others swim, and a short fillm on manatees, and going out for lunch, we passed the time quite pleasantly.
    Overall I recommend this facility. There are a number of other dolphin programs out there - they are all expensive, and they seem more "commercial" than this one (which, by the way, was one of the original training areas for "Flipper").
    For more of a Seaquarium type show, someone recommended "Theater of the Sea" in Islamorada to me.

  • 16. The Wreck & Galley Grill
    The Wreck & Galley Grill, Grassy Key, Marathon

    Another funny restaurant experience. Killing time before our dolphin appointment, we went next door for a decent lunch - fish tacos, I believe. All the meals melt together since the majority included fish tacos, fish sandwich or coconut shrimp as options. As usual we were served by a friendly but slow and mildly incompetent waiter. Also, as usual, we didn't get our hopes up that what we wanted would actually be on the menu. And when I ordered coffee, it was HORRIBLE (another recurring theme for us). The waiters response was "oh don't worry - I never charge for coffee - I don't drink the stuff but it always smells terrible and is often sent back." HUH?

  • 17. El Siboney Restaurant
    El Siboney Restaurant, Key West, Florida Keys

    This is an example of a "local" restaurant that tourists rarely visit. Not that week - we waited about an hour for a table and then had some pretty decent cuban food. Service was passable and they had everything on the menu for once.

  • 18. Sunset Water Sports
    Sunset Water Sports, Key West, Florida Keys

    This is the sunset water sports in the Seaport, not on Smathers beach. Kids went parasailing with them. They had a good time, based on the pictures - there was no room for us in the boat. Shop around for this and look for coupons. And, reserve in advance. There were about 8-10 in their group and the trip lasted 45 minutes total. My three went up as a triple ($29 each) and they had a good time. One couple went up and got engaged in the air. That was cute. Of course, on top of the price, there was a strong request for tips.

  • 19. B.O.'S Fish Wagon
    B.O.'S Fish Wagon, Key West, Florida Keys

    One of the highly recommended places from the forum. It's behind the parking lot very close to Sunset Water Sports. Cash only. The fish sandwich (of course) was really excellent (and we tried quite a few of these puppies...). Very casual - you snag a table, place your order, and they bring it out to you. I was confused by the question "fillet or nuts?" They mean do you want your fillet fried whole or cut into nuggets - it took me a while to understand this. I guess I thought it was fried with a nut crust.

  • 20. Fort Zachary Taylor Historic State Park
    Fort Zachary Taylor Historic State Park, Key West, Florida Keys

    Beautiful state park with a very nice, wide beach (possibly sand trucked in here too). There is a small reef where you can snorkel right off the beach. It's deeper than Smathers. There is a pine forested area with tables to sit out of the sun, restrooms, concessions, chair and umbrella rental and parking. There is also a fort to explore and a couple of other small museums. A very pleasant way to spend the afternoon.

  • 21. The Restaurant at La Te Da
    The Restaurant at La Te Da, Key West, Florida Keys

    This was the highest end restaurant we visited. The service was good if a bit snooty The waiter seemed insulted we did not order appetizers - which appeared huge - but he was happier when we ordered a bottle of wine. We also got dessert. So we had a hefty bill, which made him happy. The food itself was delicious. I highly recommend the crispy duck. We had a 6:45 reservation, which was the right amount of time to eat and then get on line for the cabaret upstairs. La Te Da is a lovely inn and the restaurant is next to the pool in a lovely courtyard. The bar scene was hopping too, with a live band and lots of dancing (most of it same sex couples).

  • 22. Randy Roberts LIVE (at La te Da)
    http://web.mac.com/randrob/Site/Randy_Roberts_Live%21.html

    relatively tame drag show/cabaret - R rated but tolerable.

    How did we get here? It was a long journey.... I thought "When in Key West....." but I wasn't sure, so I posted a question on the Key West Forum entitled "Maybe I'm crazy but drag show with kids?" Well THAT elicited a highly spirited debate, some of which got a bit heated. It came down to "You're a terrible mother" vs. "Hooray for you." Eventuallly, based on my concierge's advice, we went. It was fun. My son was uncomfortable. There were a couple of jokes that (I hope!) went over the girls' heads. His Cher costume isn't really complete, so when he turns around you see his derriere - not the end of the world - we all have derrieres. I don't think my kids were scarred for life - the 13 year old was the youngest there (they prefer them 15 and above). There was a 14 year old in the audience too, and they made the mistake of sitting in the front row! The biggest problem was two especially drunk patrons who were very disruptive. When we talked to Randy after the show he was perfectly comfortable with kids in the audience (if they were mature enough to handle it). He said "tonight, as you saw, the kids were not the problem." Do I recommend it for young teens? I would say....it depends.....don't expect kid - appropriate material and don't expect him to tame himself because of who's in the audience - it wouldn't be fair to the other patrons. So make your own decision, or set off a flame war in the forums... your choice!
    From a practical perspective --- the doors open at 8 - the place is small - line up early to get a good seat. Reserve in advance. Expect a 2 drink minimum in addition to the ticket price - and the general request for tips/buy a CD, etc. Expect it to be crowded with little room betwen the tables. Expect drunk people. Have fun.... we had a good time.

  • 23. Islamorada
    Islamorada, Florida Keys

    Lovely Key at the halfway point between Key West and Miami. Stopped here to visit friends, and almost saw a manatee in their backyard canal, but no such luck. The area is known for its fishing.

  • 24. Robbie's
    Robbie's of Islamorada, Islamorada, Florida Keys

    Bar, restaurant and flea market. I heard the food was good, but it was too crowded. People come here (in droves, apparently) to feed the tarpon fish. It was fun to do and to watch. They are big fish with huge mouths and they can jump out of the water to take food (available for a couple of bucks a bucket at the front desk).

  • 25. Lor-e-lei
    Lor-e-lei, Islamorada, Florida Keys

    Lovely restaurant on the water a bit hard to see from the main road. Live music, lovely fish sandwich (or was it fish tacos?) and sweet potato fries for a change. They have, for rent, a pirate sailboat and a motor boat outfitted as a pink cadillac (available for proms and birthday parties).

  • 26. Miami Beach
    Miami Beach, Florida

    I love Miami and South Beach. What a difference 20 or 30 years make. I used to come down to visit my grandmother - all the old hotels, painted white with crumbling facades were winter homes for elderly people. They used to sit out on Ocean drive in metal folding chairs to watch the world (and the grandchildren) go by. We would eat at Wolfies.

    Flash forward to the hopping trendy place now. No oldsters to be found (where did they go?). Wolfies is renovated and reincarnated with a plaque to comemorate what was. The hotels may still be bare bones on the inside, but the outsides and the lobbies are fantastic.

    After Key West, however, I found Miami a bit rough around the edges - lots of drunks and panhandlers, people coming up to you with dubious questions ("Can I borrow your cell phone?" I knew it was a sham, but what did they really want? I didn't lend it out so I never found out.) The tourist traps were even more tourist-y and even more trap-y than in KW. Parking was even harder. But the beach and many of the people on it were lovely. We had warned the kids there might be topless sun bathers, but they didn't encounter any. Overall we wished we had one more day (perhaps an Everglades trip?).

  • 27. Crest Hotel Suites
    Crest Hotel Suites, Miami Beach, Florida
    Show Prices
    Avg price: $349

    Nice old art deco hotel with the most reasonable rates ($115 per room). It was a bit north of ocean avenue - off Lincoln road - three blocks from the beach and 2 blocks from the Lincoln Road pedestrian mall. Smallest bathroom ever. I recommend it for one or two nights.

  • 28. La Cantinetta - Lincoln Road Mall
    http://www.yelp.com/biz/cantinetta-miami-beach

    I'll admit it was somewhat of a tourist trap - see the link above - but we had a very good meal there of home-made pasta and wood fired pizza. It was expensive, but we expected that. Thank goodness we didn't have mixed drinks. I understand they are rip offs. We had a reasonable bottle of wine. We were tired and hungry and this fit the bill - before this restaurant the 2-3 we passed through were hookah bars. Yuck.
    The reason we ended up on the Lincoln Road pedestrian mall is because it was Saturday night and hopping on Ocan drive and most venues were packed. Lincoln Road was packed too, but a little less so. Good to know about this spot between 16th and 17th street just to the west of Collins Avenue.

  • 29. Ocean Drive
    Ocean Drive, Miami Beach, Florida

    You must take a stroll down Ocean Drive. The photo possibilities are endless - gorgeous art deco architecture, antique cars, gorgeous crowd, beautiful views of the beach. It was a real treat and something unique.

  • 30. What we missed....

    For every trip I like to mention what we DIDN'T do so that I can look back and forward at the same time - remembering a good time and hoping to return for more. In that spirit, here's what I would do if I return:
    1. A sunset cruise
    2. A snorkeling trip - believe it or not we never pulled out the snorkel equipment
    3. A kayak tour of the smaller waterways and magrove groves
    4. A walking tour focusing on history and architecture
    5. The day trip to the Dry Tortugas
    In sum: the stuff the kids weren't into!