Key West Travel Guide – Part 2

Things to know about Key West, Accommodations, Travel Logistics & Cost


Things to Know:

  • Cash – Remember to get cash out before going on any tourist type activity. There was definitely a big tipping culture, and there will be a tipping portion of the program when the event concludes. It’s so rare that I carry cash nowadays, and the use of it is starting to grind my gears. I would much prefer electronic transactions. Opportunity Alert for Tourism Providers: Start advertising Venmo friendliness. This would be sure to increase tip yield from Millennials who scarce carry cash.
  • Huge Party City – I knew Key West was somewhat a party destination but I didn’t know how big of a party destination it was. Bars open at 7:00 AM and close at 4:00 AM. There were tons of people around. Most of the action is on or clustered around Duval Street. The crowd was a little older, it wasn’t underage seeming kids/21 year olds at the bars. There were a couple of Drag Queen bars, one in particular seemed to be lit 24 hours a day. It can be pretty loud if you are staying near Duval street, so something to consider when selecting where to stay.
  • Open Container Rule – You can walk through Key West with beverages, but they have to be contained in plastic cups.
  • Chickens – There were chickens roaming around all over the place. I heard varying stories as to why this was the case, but basically there are so many at this point they can’t be controlled.
  • Proximity to Cuba – Key West is a mere 90 miles from Cuba.
  • Walkability – Once you are on Key West, it’s very walkable. A lot of people used bikes to get around also, which is another great option.



Orchid Key Inn – We stayed here the whole time and loved it here. Great location, and had a community feel vs. a typical hotel.  It was a one floor inn which sometimes freaks me out as the door is right to outside, but it was good to be able to pop right in and out of the room. The room we were in was updated w/ stylish decor. We spent a ton of time at the pool, and there was a little bar on site. They made delightful bloody mary’s that had house made jalapeño infused vodka. The staff couldn’t be nicer, we even ran into a staff member while out on one of the boat cruises.

We didn’t even realize they had breakfast every morning included which was pretty  fresh. They also had happy hour with hour d’ourves and drink discounts. They also gave you a number of drink coupons when you arrived. When we booked the Orchid Key Inn we were just looking for a crash pad that had a pool, so our expectations were exceeded.They offered a return discount, and I’m sure we will be back!

Factors in Determining A Key West Hotel (aside from Cost):

  • Pool – The pool was so essential to the trip, definitely check out the pool/hot tub situation before booking a Key West Hotel. With the weather as hot as it is sometimes a good pool is so important to be dipping into between activities and meals.
  • Bar/Food – The onsite bar situation was also clutch especially with the coupons so we didn’t have to leave as much and could enjoy drinks by the pool. Definitely scope out the breakfast situation as well. As mentioned the continental breakfast here was great, and definitely saved us some $$ from going to eat offsite. Normally I write off continental breakfasts as they are typically not good.
  • Location – Key West is pretty walkable overall, so as long as it is somewhat near Duval Street it will be fine. The location of Orchid Key Inn is great because you are off a side street but can pop onto Duval or over to the beach easily. Being near one of the beaches wasn’t as important as I thought it was going to be since we spent less time there than I thought we would. The only thing some other places had over Orchid Key was that some of them had private beaches. It’s completely fine not to be at a hotel with a private beach, but would definitely be nice.

Travel Logistics

We flew from Boston to Miami and then drove to Key West from Miami. The other option was to fly to Miami and take a connecting flight to Key West. The cost of flying into Key West was a lot higher, and didn’t save us any time, so we opted for the longer drive. I’m not one for long car rides but the ride was actually nice, you can see the ocean most of the time after you hit the keys about an hour in. It took around 3.5 hours. We didn’t hit any traffic.

We stopped at this fruit stand called Roberts Here? in Homestead Florida and had these fruity milkshakes that were super thick and delicous. We got a gaubanaa milkshake and a key lime one.

We used the rental car exactly 0 times after we arrived in Key West, only used it again to drive back. There is hardly anywhere in Key West you can’t walk or bike to, and parking was scarce so it never made sense to use the car.

Trip Cost

Cost Breakdown:

  • Round Trip Flights for 2, 5 nights in hotel & Rental Car = $2600
  • Food & Drinks, Activities and Miscellaneous Costs for 2  = Roughly $1400
    • Activities = Roughly $500:
      • Lloyd’s Bike Tour: $35 X 2 = $70
      • Sunset Cruise: $100ish X 2 = $200
      • Kayak and Snorkel Day Tour: $120ish X 2 = $240
  • Total: Approximately $4000 for two people 6 Days 5 Nights

Where we could have saved:

  • We booked somewhat last minute – about 2 weeks in advance so I’m sure we could have done better w/flight and hotel if we could have booked further in advance and had a wider range of available dates.
  • There were some rock bottom priced Spirit Airlines flights into Fort Lauderdale. If you don’t mind adding 1.5 hours to the driving commute, could have saved some more there.
  • We could have mapped out our happy hours slash drinks better. We just kind of meandered without any strategy.
  • Obviously the activities we did cost money, but I wouldn’t have cut any of these out

Where we did okay:

  • Meals- We actually didn’t spend as much here as I would have expected as a proportion of our total spending. We didn’t end up doing alot of sit down meals. Eating breakfast at the hotel helped here.

Overall this was an expensive trip for staying within the country.  Now that we know the deal, and have a place to stay with a return discount I’m sure we could do better next time around.



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