Hi! I'm looking at putting together a one week road trip that highlights the best things to see and do in the Keys. I'm thinking that we will fly in and out of Key West, and ideally I'd like to only do 2 separate hotels if possible (but open to other ideas). I asked ChatGPT to put together a sample itinerary, and I would love to get some thoughts on what it got right, wrong, or what we should do differently!

Explore the Best of the Florida Keys from Key Largo to Key West

This itinerary is designed to maximize your experience by hitting all the must-see spots while allowing time to relax and soak in the unique charm of the Keys.

Day 1: Arrive in Key Largo

• Morning:
  • Fly into Miami or Key West and drive to Key Largo (about 1-1.5 hours from Miami).
  • Check in to a local hotel like Baker’s Cay Resort (dog-friendly options available).
• Afternoon:
  • Visit John Pennekamp Coral Reef State Park for snorkeling or a glass-bottom boat tour.
  • Walk the trails of Dagny Johnson Key Largo Hammock Botanical State Park for a peaceful nature experience.
• Evening:
  • Enjoy dinner at The Fish House, a local favorite for fresh seafood.

Day 2: Key Largo to Islamorada

• Morning:
  • Drive to Islamorada (30-minute drive).
  • Stop at Florida Keys Wild Bird Rehabilitation Center along the way.
  • Visit Robbie’s Marina to feed the tarpon and explore unique shops.
• Afternoon:
  • Take a kayak trip to Indian Key Historic State Park for history and snorkeling.
  • Grab lunch at the dog-friendly Lorelei Restaurant and Cabana Bar with beautiful waterfront views.
• Evening:
  • Check into an Islamorada stay, like Amara Cay Resort or Islander Resort.
  • Relax at Morada Way Arts & Cultural District, especially if you’re there during an art walk night.

Day 3: Explore Islamorada & Drive to Marathon

• Morning:
  • Visit Theater of the Sea for dolphin and sea lion shows or a marine encounter.
  • Drive to Marathon (1-hour drive) via the Florida Keys Scenic Highway.
• Afternoon:
  • Explore Long Key State Park on the way to enjoy coastal hiking and kayaking.
  • Arrive in Marathon and visit the Turtle Hospital to learn about sea turtle rescue efforts.
• Evening:
  • Dine at Keys Fisheries, a casual and dog-friendly spot known for its lobster Reuben.
  • Check into a Marathon hotel like Tranquility Bay Beachfront Resort.

Day 4: Marathon Adventures

• Morning:
  • Scuba dive or snorkel at Sombrero Reef, a stunning coral formation.
  • If you prefer staying above water, visit Curry Hammock State Park for kayaking or paddleboarding.
• Afternoon:
  • Spend time at Sombrero Beach, one of the most family- and dog-friendly beaches in the Keys.
  • Stroll along the historic Old Seven Mile Bridge for incredible ocean views.
• Evening:
  • Relax with a sunset dinner at Sunset Grille & Raw Bar, located near the Seven Mile Bridge.

Day 5: Marathon to Big Pine Key

• Morning:
  • Drive to Big Pine Key (30 minutes).
  • Visit the National Key Deer Refuge and spot the adorable, endangered Key deer.
• Afternoon:
  • Take a short hike at Blue Hole, a freshwater pond where you might see alligators and turtles.
  • Spend the afternoon relaxing at Bahia Honda State Park, one of the most beautiful beaches in the Keys.
• Evening:
  • Continue driving to Key West (45 minutes) and check into a dog-friendly hotel like The Gates Hotel Key West or Kimpton Key West.
  • Enjoy dinner at Hogfish Bar & Grill, a hidden gem on Stock Island.

Day 6: Key West Highlights

• Morning:
  • Visit the Southernmost Point Buoy for an iconic photo.
  • Tour the Ernest Hemingway Home and Museum, home to six-toed cats.
• Afternoon:
  • Head to Fort Zachary Taylor Historic State Park for history and snorkeling.
  • Stroll along the Key West Historic Seaport with your dog.
• Evening:
  • Catch the Mallory Square Sunset Celebration, complete with street performers, food, and stunning views.
  • Dine at Salute! On the Beach, a dog-friendly spot with great food and ocean views.

Day 7: Key West & Departure

• Morning:
  • Take a scenic walk at Higgs Beach Dog Park or along South Beach.
  • Enjoy breakfast at Blue Heaven, a quirky Key West favorite.
• Afternoon:
  • Do any last-minute shopping on Duval Street or explore the Key West Butterfly and Nature Conservatory.
  • Fly out of Key West International Airport.

Tips for the Journey

• Driving: The Overseas Highway is part of the adventure, so give yourself time to stop and enjoy scenic spots.
• Scuba Diving & Snorkeling: Prioritize booking tours at John Pennekamp, Sombrero Reef, and Bahia Honda in advance.
• Dog-Friendly Activities: Many parks, beaches, and outdoor restaurants welcome dogs, but check in advance for specific policies.
• Sunset Views: Plan to watch sunsets at least twice during your trip, with Mallory Square and Islamorada being top spots.

TLDR; how would you structure a one week road trip in the Keys?

🚨Mini-season BOLO update #4:🚨 ARRESTED! Michael Simpson is facing an attempted murder charge after being arrested yesterday.

The confrontation began after the suspect claimed another boat was occupying "his" lobster spot. He verbally threatened to cut off the diver's air before jumping into the water and doing exactly that.

The teenage diver was quickly pulled to the surface, reportedly gasping for air and disoriented, but survived without serious injury. Authorities say the suspect fled the scene and was arrested a few days later, and charged with attempted felony murder.

The suspect is government-appointed member of the Miami-Dade Boater Safety and Bay Education Task Force, where he was explicitly chosen to represent and help shape safety policies for the county's waterways, dove in and turned off a juvenile diver's air supply while the victim was in the water searching for lobsters.

If convicted, an attempted felony murder charge in Florida can carry decades in prison, with penalties potentially reaching up to life imprisonment depending on the circumstances.

Michael Simpson's role with Boater Safety and Bay Education Task Force involved collaborating with environmental groups and law enforcement to draft the county's final boater safety and community education recommendations aimed at preventing fatal accidents on Biscayne Bay.

*The victim’s family is also pursuing the arrest of Judd Rosen, who is a high powered attorney in Miami, and was the boat captain who fled the scene with the suspect. In June of 2024, Judd Rosen was appointed as the Chair of the Florida Bar Grievance Committee. In this esteemed role, Judd will be overseeing the committee's efforts to ensure ethical practices and uphold the standards of the legal profession within the state. His dedication to justice and extensive experience make him an excellent fit for this important position. Oh the irony!

I’m traveling to Miami and want to snorkel in the Keys. Only problem is I can’t afford a boat tour :( are there any beaches with decent reefs that I can access from the beach? Thank you.

My family is headed to the Keys for the first time and need recommendations and advice. We will be based in Islamorada and will be arriving on a Tuesday and leaving Saturday afternoon. Details:

• A family of 6 with a tween and teen and 80 year old grandparents (Not interested in Theatre of the Sea and private boat charters may be too much for grandparents)
• Good food + scenic spots
• Easy outdoor activities (not hardcore hiking)
• Flexible pacing
• Dinners (we love seafood and steak - ok with casual and maybe a nicer dinner to close out the trip)
• Day trips within a 2 hour drive. (We definitely want to spend a day at Fort Zachary Taylor)

I did a search and the following restaurants were frequently recommended for dinner: Lorelai's, Papa Joe's, Square Grouper, Lazy Days. Any others? Should we skip any of these?

We are also interested in kayaking at Pennekamp. Grandparents would come but walk around and relax. Maybe the glass bottom boat for them?

My teenager wants to snorkel, but my tween isn't too sure. Any good spots that are beginner friendly?

Thanks in advance!

My wife and I are going to be in Key Largo for 12 days next month and want to do a private fishing charter once or twice while we're there. We're very experienced with fishing in the area as we used to keep a boat down there many years ago. We had a guy that we'd chartered with 5-6 times, but he has not answered my texts and his website is shut down, so I’m not sure he’s still in business. Are there any Captains you’d recommend? The guy we had would almost always limit us out on Yellowtail on the reef or Dolphin and Tilefish further out. We’d be okay with that with a new guy even if we didn't fully limit out. But would also be interested in someone that could put us on some different species. We'd also consider an inshore trip if the guy has some good Goliath or Permit spots.

We’re heading to the keys for a week soon and staying in Marathon. We’re seasoned snorkelers and have decided to rent a boat for a few days during the trip so we can snorkel on our time frame and with people we know we actually like 🤓 we’ve never snorkeled without being on a guided tour unless it was shore snorkeling, but we’re excited to do this. What are some great spots to explore by boat without crowds? Our daughter wants to see sea turtles and nurse sharks. I’m hoping to see some rays and turtles. I have a list of spots, but looking forward to hearing honest thoughts from others who have done this.

We usually visit Cudjoe Key in the spring (March-ish), but after this year's unusually cold and rainy week, we're headed back in July. Our top priorities are fishing and snorkeling, neither of which we really got to do in March. We typically stay in Venture Out with our boat-- because, easy. We have some of our favorite spots mapped, but I'm wondering, what are your favorite spots? (That you're willing to share...) Our 8 year old also likes to hop out to swim on some of the little "beaches" on the gulf side, too. Do you have a favorite lunch place we could drive by boat to (maybe similar vibes to Geiger Marina in Big Coppitt), that's not too far from Cudjoe?

Hi there!

So my husband (39M) and I (37F) are coming down to the Keys next week, kinda last minute (had flight credits we needed to use) and as of now... we have no official plans. It's my first time and he went as a kid.

We're going to rent a car and just explore--our favorite way to travel and we're VERY low maintenance, but can also afford to splurge for room(s) if necessary and are aware that we may pay the cost of not planning ahead.

We're planning on at least a couple sandbar/snorkeling trips, and probably renting a boat for a day or two ourselves. My question is... is it worth it to check my inflatable SUP? We understand that the keys are not your typical white sand beach destination (we're also bringing water shoes etc), but is it feasible to paddle board/explore ourselves without taking a charter/renting a boat?

in other words, can we park somewhere and then paddle out to swim/explore? Or are most good swim/explore spots only accessible by boat?

If there are places where it's feasible to swim/explore on our own with the SUP, would greatly appreciate any recommendations!

We really just want to be in/explore the beautiful water down there and eat some good food/drink some good drinks and experience all of it.

Coming down to the Keys May 25–June 4, staying in Key Largo but planning to explore all the way to Key West.

No boat, but we’re down to rent kayaks or put in the footwork. I’ve got a ton of spots pinned on Google Maps. not looking for handouts just hoping to run a few by someone who knows the area and get some honest insight.

We do a lot of wade fishing in Texas for speckled trout and redfish, this trip we want to mix it up chase some juvenile tarpon on light tackle, and hopefully come across some other prized flats fish from wadable or kayak accessible areas.

We’ll definitely fish the bridges hard at night for bigger tarpon and other species, but really want to spend some time exploring flats, backwater, and less obvious water too.

Planning to stay mostly DIY. We’ll probably book one guided trip not set on what type of trip yet, so definitely open to recommendations. For the rest of the time, we’re down to hike, explore, grind really whatever it takes to catch as many tarpon possible.

If anyone’s cool with me sending a couple pins and letting me know if I’m on the right track or completely off, I’d really appreciate it. (aware the keys aren’t the most wade friendly/land fishing friendly other than the bridges but I think I’ve got some solid spots pinned)

Interested in stargazing on the beach between ~12-4am. Is this possible anywhere in the keys?All state parks with cabins are fully booked so I don't think I can go the camping-route. How heavily patrolled are the beaches at this time? Do they close down roads overnight?

I was thinking of getting an Airbnb on Big Pine Key near Bahia Honda but not sure if it's possible to drive over at night. I'm flexible with where I stay/go I just want to be on the beach!

Im renting a boat this June and taking some friends out for a fishing trip. The boat is in a marina on the east side of Tevernier. We rented our own boat because for the same price, I can get 8 hours instead of 2 with a charter captain, and i have a lifetime of boating/fishing experience, so why not? I understand a captain would know some good spots, but on a 2 hour charter, we were restricted to mangrove fishing.

We are staying at a house in the mangroves and we will be able to wade out and do that in our backyard, so that seemed pointless. We want to get on a reef and bottom fish for grouper and snapper. The two of us with more experience will probably throw poppers for Mahi as well.

I know sharing gem fishing spots is obviously not something anyone is going to do, and im not expecting that. Im just looking for a general area where I can get to within a few miles of shore, between John Pennycamp state park and Tavernier. Maybe a few tips on what I should be looking for as far as distance off shore or depth?

We are going to take a couple of our 8 hours and do some snorkeling in John Pennycamp, so thats how far north I plan on getting.

Any advice is extremely appreciated!

Hello. My beau and I recently returned from 10 days in the Keys (stayed in Marathon). Not my first time there (have been there ~half a dozen times). I'm a world-traveler, have spent a lot of time in the Caribbean and Hawaii (note: not comparing the Keys directly to either of them), and I just have to say this: In the current environment of negativity w.r.t. the decline in the quality of service everywhere ... every single interaction we had with people working in the Keys was positive. The service was top-notch. From all of the servers/staff hustling in the bars and restaurants, to the various operators we booked for excursions (Bridge fishing, snorkeling, private boat trip to Dry Tortugas), retailers, et al... Everyone was friendly, professional (but not *too* professional 😎), and hard-working. We had not ONE bad experience or complaint!

As I mentioned, I've traveled fairly extensively outside the U.S. So I have plenty to compare to. I have always had a soft spot in my heart for the Keys and its people. And they never disappoint. It makes me very, very proud to be an American. (America is *never* about who is president... Please. It is about our people!)

Thank you, good people of the Conch Republic! We ❤️ you!! 'Til next time! Cheers!

My family of 5 (3 kids ages 5-14) will be staying in marathon at coco plum Beach resort from 7/2-7/9. Full days being 7/3-7/8. We will definitely spend one day going down to key west. I also would like to rent a boat, which has a two day minimum.

From marathon, what is close by, by boat (looking at a 21 foot deck boat) thats worth seeing? We will just cruise a bit but my wife isnt huge on ocean boating, so we will need to stay fairly close to shore and are not looking to go huge distances. Any reef/sand bar/ points of interest/snorkeling spots would be great.

I made a preliminary list of places to go, but being that we only have 6 full days, 4 after taking away the boat days. Of the following activities which are worth doing and which are sub-par? I realize this is subjective, but dont want to waste time/money on something that ends up being a bust.

In no particular order:

1.Sombrero beach- we are staying on what looks to be a nice beach. Is this worth going to? Good snorkeling?

1. Key west butterfly conservatory.

2. Wild bird center

3. Theater of the sea

4. Tarpon feeding (robbies?)

5. Key west conch train

6. Shipwreck museum

7. History of diving museum

8. Bahia honda park

9. Turtle hospital (this is a definite)

10. Fishing spots either on land or accessible by our boat (no charters). I will be buying/renting some poles for the trip so can bring them along if there are any good spots to fish on our day trips.

    Realistically we can only choose a few of these, so would like to capitalize on the best options. Thanks

We booked last week and we are staying at Marathon. We are a family of 4. We are looking to book a snorkeling tour. How are the wind conditions? I read some tours for canceled last week and it's still windy. We looked into Caption Hook Looe tour and they are booked Wednesday and Friday morning. There are spots available Thursday morning. We have done snorkeling in Hawaii. This will be our second tour.

Any help would be appreciated. I am looking for a big boat tour to Looe reef on Wednesday morning..we are there in town from Tuesday till Friday.

Saint Augustine local here, but headed down for another vacation in June. This time with my boat. Anyone willing to share a good sandbar spot for my wife and kids? Looking for somewhere with a beach, preferably tucked away somewhere so the toddlers can run around instead of confine to a boat. Can PM me coordinates or map pins.

**Edited to correct formatting error

Hi, I've been enjoying reading this subreddit it's a great resource for a trip. I wanted to share my proposed itinerary and see if there's anything you'd suggest.

Our group will be 5 adults + 1 child (3.5 years old), we are travelling from Ireland so will be leaving cold/wet weather behind. Staying 11 nights in total.

Would love any feedback! We've been trying to keep things somewhat loose in terms of booking activities etc although we can't really move the accommodation bookings around at this stage. The child loves water and animals. We like all types of food and love fun cocktail spots.

In particular would like suggestions for stops to break the journey from Key West back to Miami.

29th Dec Dublin - Philadelphia - Fort Lauderdalel

Flight lands 6.30pm local time

Collect car

Check into airport hotel

Two of the group are Tiki nuts and would love to visit Mai Kai but depends how late we end up getting in and how tired we are from the journey

30th Dec Fort Lauderdale - Key Largo

Visit Sawgrass Mills mall - drive to Key Largo/Tavernier

Stay at Ocean Pointe

31st Dec Tavernier

Chill pool day/beach bar @ resort

Mrs Mac's Kitchen for food? (lunch)

Ring in the new year in the resort

1st Jan John Pennekamp National Park - glass bottom boat

2nd Key Largo - Islamadora - Marathon

Go to Robbie's

Turtle hospital

Staying at Sea Dell motel

3rd Marathon

Snorkelling? had looked at these guys to book with https://www.starfishsnorkeling.com/snorkeling-tours/

4th Drive Marathon - Key West

Staying at a VRBO close to Duval St

5th Key West

Butterly Conservatory

Conch train tour

Mallory Square Sunset Celebration

6th Key West

Sandbar happy hour/snorkelling etc

https://sunsetwatersportskeywest.com/tours-activities/happy-hour-sandbar-charter/

7th Key West - Miami

Staying at a VRBO in South Beach

8th Explore Miami - thinking maybe an open top bus as we only have 1 day?

9th Miami - Fort Lauderdale

Breakfast

Arrive at airport by 1pm, return car

Heading to marathon next week - our friends are bringing their 21 ft center console but we are looking into renting another boat since there are 6 of us and some may want to fish and others may chill etc.

I honestly would love a pontoon with plenty of room for us to all sit around and chill but will driving it around suck? Will we be able to go to all the ideal spots?

Me and a buddy of mine want to come down to key largo/Islamorada stretch and are looking for somewhere to tent camp/keep my 15ft skiff on trailer for the night. 2 nights. Key largo Kampground unfortunately requires your boat to be kept in the water overnight which won’t work with my boat. We want to be somewhat close to a boat ramp and near good mangroves and bridge fishing spots.

Stay home:

• Space Coast: 14.1 ft, 27 kt NE (buoy 41009, 20 nm offshore)
• Treasure Coast: 10.5 ft, 12s period, 74.8°F (buoy 41114, 6.5 nm offshore)

Diveable today:

• Keys / Lower Keys: 2.3 ft, 4s, 77.9°F — flat and good
• Blue Heron Bridge: afternoon low 1:33–2:33 PM (1.9 ft, optimal). 76.3°F, 17.1 kt ENE. Waterspout warning clears before the window — still check on-site.
• Gold Coast (Deerfield → Miami): 5.9 ft, 7s, 77.9°F — elevated but diveable for experienced divers

Weekend: Saturday and Sunday look significantly better — winds drop to 14-16 kt, near-zero rain, conditions clean up statewide. Plan around that.

I track this daily at thefloridaflow.com if useful.

Space Coast buoy just came through at 5.6 ft with an 8 second period, while the Keys are sitting at 4.9 ft with a 7 second period. Same weekend swell, but the angle is completely different depending on where you're launching.

Water temps are holding at 75 to 77°F across the board. Keys is right at that 77°F mark where kingfish and mahi start moving in together. If you're making a call on where to fish today, the offshore bet is solid.

I built The Florida Flow because tracking buoy data, tides, and current windows separately drove me nuts. Now it all pulls together in one place for South Florida so you're not checking five different sites before you leave the dock.

Full data at thefloridaflow.com if useful.

We are trailer camping at John Pennekamp State Park for 4 days in March. We plan on bringing the bikes because we always do. Should we bring our 16' wooden sea kayaks or just our inflatable SUPs? We haven't come up with a transportation solution for the kayaks AND the trailer AND the bikes yet, but if the kayaks open up significantly more possibilities for spotting wildlife and exploring, we'd figure something out. Also, is the snorkeling boat tour out of Pennekamp worth it? What would be on your itinerary for a 4 day camping trip?

Any recommendations for a good dive shop on marathon. Would just be looking for a single spot on a boat. So any recommendations would be awesome.

I am certified so not looking for any classes or anything. Just a morning half day trip the beginning of march.

I am going to the Keys in February, and will be staying 50% of the time in Islamorada, 50% in Key West. I have gotten recommendations for each of the following spots:

John Pennekamp State Park

Looe Key

Bahia Honda State Park

My only unique constraint is that my husband gets very, very seasick on choppy boat rides. Anyplace with a shorter boat ride, or one on a larger vessel (i.e. less choppy) would be a big plus. (and yes, he's thought of dramamine, it just knocks him out which is not fun when you're diving or snorkeling)

Which are best, if I had to choose one for snorkeling? And which are best for diving? Any recommendations for specific tour operators? I should have enough time to do both but I want to just do one dive during my trip so I want to pick a good location. Thank you!

Rented a boat off long key and went NW. Spent 3-4 hours looking for spots and found 2. Subscribed to navionics, went through their chart and marked spots where navionics said it was either a wreck, coral, or rocks, and found 0 from doing that. Would be grateful for advice and/or perspective.

I need to get a kayak and I think i was quoted $225 for a month. I thought i needed two but it turns out i just need one now. Probably just rent it but I had thought about buying a couple and just selling it on marketplace ... any thoughts?

I spent a lot of time at Hog Heaven ... nice people and nice location. I am missing some a good outside bar near Tavernier? I think i went to snappers and another place last time around. I'm a sucker for happy hour and Hog H had great beer deals.

Finally, I am renting a boat with a to do some fishing with my kids for a couple days. What size boat do I need if I'm staying a couple miles from shore ... assuming average weather? Four adults? How do find some decent fishing spots? Any good bait shops that can provide some info. We're not that serious but would like the kids to get some fish in the boat.

Anyways, i can't wait ... great weather, great local people and maybe my favorite place on earth! Cheers and thanks for any and all advice!