Trip Review with Teen

Question

Tonight is our last night in Key West and I figured I would do a quick trip review with a focus on vacationing here with a 15 year old boy. This was an impromptu Spring Break with just me and my son this time and anything that was planned I did within 48 hours of arriving. We built in A LOT of relaxation time which was hard for my go-go-go personality. But it was perfect. Hotel review is at the end.

FRI - landed in KW at 8:20pm.

Late dinner delivery by Stinkin' Crawfish. We really liked it and I'm sure in the restaurant would have been even better.

SAT

Jet Ski Tour with Fury Water Adventures. This was SO worth it! Our guide was fantastic - funny, informative, checked in on all of us at each stop, gauged how fast we wanted to be going, etc. The waters were VERY choppy and the waves 75% of the time were intense. This is not for the faint of heart and we had one person in our group that had never driven a jet ski before -- she did great, but if that had been my first time, I'd be scarred for life. You really get to see some great highlights of Key West from the water along with learning things that I definitely did not know about. We were out on the water for 90 minutes.

Dinner at Two Friends Patio - I had been here many years ago and it was still great! We lucked out with no wait on a Saturday night at prime time.

Mallory Square for sunset. My son loved this area and it was very active with the performers on this night! Ducked in and out of all the vendors and shops.

Walked around Duval Street and stopped in a bunch of shops. This was around 7pm-8pm and the activity was just picking up in the area. It was fun to linger outside some of the bars where the live music was already going. My son is very into music so this was super enjoyable for him.

Ghosts & Gravestones Doomed Trolley Tour - We did the 8:30pm tour and the trolley was full. This is not a scary/spooky tour. It's filled with KW history, some myths that have research behind them to turn them into (mostly) factual info, and a great tour of KW at night. We were really happy to get to see more of KW this way. Is it a little corny? Sure. Did we both enjoy it? Sure did! I wouldn't waste precious daytime hours doing this tour, but a great way to wind down the evening.

After the tour, we weren't ready to go back to the hotel yet so we walked around Duval Street again and then ended up at a Gelato/pizza place where the gelato was incredibly good. I believe it was called Duetto's (on Green St).

SUN (Easter)

We attended mass at the Basilica of St Mary Star of the Sea and we were warmly welcomed and thanked for being there. A great experience for Easter.

Brunch at Bagatelle. I am so glad I had decided on this place for Brunch. It was fantastic. The service was very slow in the beginning. I think we sat for over 20 minutes without waters or being acknowledged, but we weren't in a hurry and were just patient. The server we ended up having was wonderful (and busy!). Food was well prepared, incredibly fresh and a great menu.

Walked around some of the shops, purchased some bracelets and made our way to Key Lime Pie Company for some pie cups that we ate at their counter. Delicious of course! This place is not much to look at inside, but the focus are the pies so fine by me!

Pool day the rest of the day. My son loved the pool bar with non-alcoholic frozen drinks! Probably a highlight of the day for him. LOL

MON

Picked up a rental car at the KW Airport early this morning after breakfast at the hotel. (Alamo was excellent at the KW rental counter).

Drove to Key Largo with a stop in Marathon to just bum around a little, check out some of the fishing areas.

Made our way to Key Largo for our next big adventure of the trip -- Dolphin Plus Marine Mammal Responder. I found this place through a travel blog I loosely follow and the blogger had done a quick write up on a drive from Key Largo to Key West and what not to miss. This place was mentioned and being a huge dolphin lover, I knew I had to check it out. I booked the Connect to Protect Swim for both me and my son. This was going to put us directly in the dolphin's lagoon habitat with time with the dolphins. I had to make sure this wasn't going to be a "Show" or something the dolphins were being mistreated with. It was definitely not that and all proceeds go directly to continue to fund the facility, the research and a new rehab center they are in the process of building. I could go on and on, but I encourage you to check it out! We spent quality time with the dolphins and it was clear they are not forced to do anything they don't want to be doing. They are on their own time for sure! We greatly enjoyed the experience -- my son's smiles were everything!

On our drive back to KW, we stopped at Shrimp Shack in Islamorada, featured on Diners, Dives and Drive-In's. We always try to find one of these places when on vacation and this one did not disappoint! Worth the stop!!

We had planned to stop at Boondocks in Summerland Key for mini golf, but at this point, we were exhausted and decided to head back to KW.

TUE

Slept in today and after all the dolphin excitement yesterday (and still sore from that jet ski adventure!) it was much needed.

Brunch at Blue Heaven. We figured we would have an hour wait, but that was fine. We were looking forward to just chilling out in their waiting "garden", but to our surprise they called us for our table in 20 min! My son loves egg benedict and declared this was one of his favorites he's ever had. It WAS good. Such a great experience here with live music, outdoor dining that is beyond unique, amazing service and exceptional food. So happy we made the effort to go!

Attempted to get to the Southernmost Point buoy, more so for the photo op than anything else, but the lines were of course crazy long. We had driven past it on the Ghost tour at night, but we snapped a daytime picture and called it good. ha ha.

Went to Higgs Beach for a short time - this was a stop on the Ghost tour as well (you don't get off the trolley) and I wanted to see it up close. We hadn't brought our beach gear with us, but it's a great spot if you wanted to set up for a half or full day.

This was another pool day so that we could relax on our last day. So glad we did! Ordered more fun frozen drinks from the pool bar. Spent hours at the pool today.

Brady's Pub for dinner. It's a VERY local spot, but we were craving a good burger and this came up as the place to go -- it also bears the name of my son so we took it as a sign. :) It was great food -- with all the local flair. Worth a stop, even though the entire place turned their heads to stare when we walked in. Ha ha! You know it's good then!

Quick stop at Smather's Beach tonight to grab some pictures and watch the sun almost set. Another great beach with volleyball nets already set up and great parking.

Ended up back in Old Town and grabbed key lime pie to go from Key Lime Bakery. We had so much key lime pie this trip, I'm not sure which was best, but my son declared this one to be. The experience inside the bakery is lacking for sure. Rude, no greeting, no thank you, no nothing. Grabbed our slices out of the case, placed them in front of us and spun the credit card machine around. Then disappeared to the back. So odd. But the pie sure is good! :)

We fly out tomorrow, but we will be back for a longer trip next time!

Doubletree by Hilton Grand Resort (I'm a Hilton Diamond member and KW has a good selection of Hilton branded hotels to select from now)

I'm not even sure how to grade this place. Nothing is bad, but it's certainly not worth the price tag. Then again, not sure what would be with hotel prices where they currently are.

Pros: Great pool area, plenty of lounge chairs, adirondack chairs, small tables. Also has stocked pool towels, restrooms and that pool bar we loved so much. They also have poolside servers who were fantastic. On Saturday, they also had live music at the pool which we loved. My son really enjoyed that -- steel drums/singer.

I know a lot of people will only stay in/around Old Town, but I had no desire to be that close to the activity. We needed a mixture of adventure and serious relaxation for this trip so I wanted to be a little outside of the action with the ability to get to/from easily. Doubletree provides a shuttle to Old Town that runs on the hour and is very punctual. They have numerous shuttles and will run a second one as soon as they see they have several people waiting at the hotel. We were on the tail end of Spring Break so I'm sure the weeks before us were busier. But this was so convenient and allowed us to not have a rental every day. The shuttle also is on demand for the airport, which is a great benefit.

There is endless bottled water available at the entrance, which is such a great guest amenity. I do hope though that they will install bottle filling stations soon and eliminate the bottled water. That would be great!

We got a pool view/balcony double queen. There is plenty of space in the room.

Parking is free (aka: included in the resort fee)

Very easy to walk around, though you're not going to walk to actual destinations. Smather's Beach is a little less than 2 miles away. But if you like morning or evening walks, it's great to be able to walk around the very wide sidewalk along the water. We did this often and watched fisherman and just paused to take it all in. Lots of boating activity while we've been here so that's always a nice backdrop as well.

Cons: Breakfast is basically a Hampton Inn breakfast and costs $18.95++ per person. They do have an ala carte menu as well, but the buffet makes the most sense. I'm a Hilton Diamond member so I do receive the daily F&B credit, but this breakfast is pretty disappointing for a Doubletree with "Resort" in it's name.

While our room has plenty of space, beware that the balconies with the double queen rooms are VERY narrow. Fine for two people to be out there, but you are facing each other in chairs slammed up against each side of the wall because that's all there is room for. The rooms with a King bed have much larger balconies, very spacious. Something to consider if you are a family of 4 and need a double queen -- you won't be out on the balcony together. :)

The lighting is terrible. I don't even know what else to say. Just terrible.

The hotel needs a renovation/upgrades. I heard people say they would be starting renovations this Summer and I hope that is true. The furniture in the rooms is dated, worn, missing pieces, etc. The TV is one of the smallest sizes I have seen in a hotel in well over a decade. I can't imagine that this even passes a Hilton QA at this point. No microwave in the room, just a mini fridge (thankful for that!). They are only commanding these rates due to the demand in the area. Without a renovation there is no way this place can keep up with its competitors during the slower times of year.

We had a great mini-vacation! My son gives this two thumbs up and doesn't want to leave.

Answer

Key West is an excellent destination for a vacation with a teen, offering a mix of adventure, relaxation, and unique cultural experiences. Based on this trip review, it’s clear that the combination of outdoor activities, historic sites, and casual dining made the trip enjoyable for both parent and child.

The itinerary highlights a good balance between active excursions and downtime:

Jet Ski Tour with Fury Water Adventures – 90 minutes of high-energy water adventure, suitable for teens who enjoy speed and thrills. The tour also provided educational insights about Key West.
Ghosts & Gravestones Doomed Trolley Tour – a fun evening activity with history and light entertainment, not too scary, and great for winding down.
Dolphin Plus Marine Mammal Responder – an immersive, hands-on experience with dolphins, which provides education and engagement, ideal for animal lovers.
Mini golf at Boondocks (optional) – a relaxed activity that can be fun if energy allows.

Relaxation and pool time were key parts of the trip, showing the importance of downtime for both parent and teen:

Pool days at the hotel with a pool bar offering non-alcoholic drinks were highlights for the teen.
Beach visits, including Higgs Beach and Smather’s Beach, offered opportunities for casual outdoor enjoyment and photo opportunities without pressure.

Dining experiences were varied and highlighted local flavor:

Late dinner from Stinkin’ Crawfish, casual and convenient after travel.
Dinners at Two Friends Patio and Brady’s Pub, offering local cuisine and relaxed atmospheres.
Brunches at Bagatelle and Blue Heaven, with memorable dishes like egg benedict and fresh ingredients.
Key Lime Pie stops at Key Lime Pie Company and Key Lime Bakery, emphasizing the local specialty.

Key West’s walkable areas and evening strolls allowed for exploration of local culture, music, and shops:

Mallory Square for sunset and street performances, engaging for teens.
Duval Street for shops, live music, and casual walking, combining sightseeing and entertainment.
Old Town exploration via shuttle from the hotel provided flexibility without needing a car every day.

The hotel experience at Doubletree by Hilton Grand Resort had both pros and cons:

Pros: Spacious rooms, pool area with bar and live music, convenient shuttle service to Old Town, free parking, and amenities like bottled water and on-demand airport shuttle.
Cons: Breakfast quality underwhelming, narrow balconies for double queen rooms, outdated furnishings, small TVs, limited in-room amenities (no microwave), and general need for renovation.

Overall, the trip was very successful for a parent and teen duo. Key West provided a balanced mix of adventure, relaxation, and local flavor. Teen-focused highlights like jet skiing, dolphins, and music ensured engagement, while pool time and quiet beach walks offered necessary downtime. Dining options were diverse and added to the experience, and the hotel, while needing updates, offered a convenient base outside the busy Old Town area. This itinerary is a solid template for a short Key West trip with a teenager.

Trip Review with Teen

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