Similar type destinations.
Key West Pros:
Easy to get to direct flight from BOS land and 5 minute cab ride to Duval St. Pro tip Uber if you have 3 or more people in your party. Cab charges $9 per person, Uber was $22 for 4 of us.
Easy to get around/walkable town- Pro Tip Rent a golf cart for lots of fun, never an issue to park it wherever we wanted.
A ton of dining/drinking options.
Friendly Laid Back Attitude.
Clean. They wash down the streets every night.
Key West Cons:
Not great swimming beaches with the few that are there, coral can mess up your feet.
In relation to Playa Del Carmen 2-3 times more expensive for food/drink/accommodations.
Slightly smaller beach weather window (can be cool in February, January)
Playa Del Carmen Pros:
Very inexpensive- $10 buckets of beer on the beach. Great street food all the way up to fine dining options all very reasonably if not cheaply priced. Wider range of dining options with some excellent chefs.
Easy to get around/walkable area around 5th Ave.
Some AirBNB’s that are brand new, enormous and half the cost of Key West Motel accommodations.
Gorgeous white sand beaches/ great beach clubs that serve food and drinks and have great beach chairs for free as long as you order food/ music.
Friendly Laid Back Attitude
Beach weather throughout the year.
Playa Del Carmen Cons:
Harder to get to: Direct flight to Cancun/customs/40 minute cab to Playa Del Carmen is a 6.5 hour deal but not impossible. Pro tip: set up your cab from airport to Playa Del Carmen in advance $($60 vs $100 if you get a cab at airport without having it pre-set up)
Not dirty but not pristine like Key West
Occasional street urchin asking you if you want to buy weed/coke can be unsettling to someone that doesn’t know to just walk past them. None are aggressive.