I’m not going to make this post a long, boring recap of our very fun trip to Key West – but I will share with you some of the things I’ve learned on my 5th or 6th trip down to the end of the earth.

I’ve traveled there with my family as a kid, as an adult many times with friends, with my parents, with my husband and with our daughter.  This particular trip was with another couple with whom we’ve been friends for 10 years.  They were celebrating their 10 year anniversary, and Adam and I were celebrating our 5 year.

Do …

• Take the Key West Express from Fort Myers if you want to drink and hang out the whole way there.
• Arrive early to get decent seats.  Four hours is a long ride on bar stools or in 60mph winds and sun.
• Bring your own food, beer and flasks in your carry-ons.  They don’t check anything, and they only take cash.  And the food is horrible.
• Plan some excursions during the day.  Go snorkeling or on a sailing trip.  Head to the Dry Tortugas or to other Keys.  Walking Duval gets old, quickly. Especially when it’s 92 degrees.
• By all means, find someone with a boat or rent one.  And get out on the water. Nothing compares to the peaceful serenity of a personal watercraft and that crystal blue-green water.  Party boats just don’t compare.
• Have a drink at the Green Parrot and at least one meal at Blue Heaven. You will not be disappointed.
• Rent one of those hilarious little electric cars or scooters for an hour (or more, if you can) and tool around the island. Explore the nooks and crannies and imagine living in those tiny shanties. It’s not all about million-dollar boats and $300 hotel rooms.
• Enjoy the true island town during the day, and don’t worry so much about getting out at night. It’s not that great.  Otherwise, have a few day drinks, hit the great bars and restaurants and enjoy the scenery and architecture in the sunlight.

Don’t …

• Take the Key West Express from Fort Myers if you want to enjoy the beautiful drive down the keys or spend any time exploring anything other than Duval Street.
• Think you can just eat something on the boat. If you think the microwavable breakfast sandwiches from Circle K are good, you’re in for a treat.  Otherwise, plan ahead.
• Expect the nightlife of Key West to be different from the nightlife anywhere else in the world.  It’s mostly ridiculously wasted 21-25 year olds, singing along to bar songs at the top of their lungs, spilling out of strip clubs.  Trying to navigate those bars made me realize how much I appreciate a good day drunk and early night in bed.
• Eat at Turtle Kraals. Terrible food, lousy service, pricey menus.  I won’t even link to them, but you’ll be tempted to eat there because of their proximity to the Key West Express and their cold A/C.
• Stay at a condo or hotel without a pool during the middle of summer.  You will not want to walk around all day long – and not having a reason to head back to the hotel will mean you drink way more than you intended.

Of course, there are the obvious to-do’s, like Mallory Square sunset fest – but most of your time in Key West is spent walking around town, taking pictures of chickens in weird places and discussing how awesome it is to walk around with a beer in your hand.  Don’t take those things for granted.