Key West, Florida

• More about your oliver guide: Sabrina Eliasoph
• Trip type: Family, Beach
• Activity level: easy
• Ideal length of trip: 4 nights is perfect

to & from

Easiest to fly directly in Key West (EYW); but many people start their trip in Miami and drive the four hours down the Keys. I heard there can be a lot of traffic on the many bridges down so we chose to fly directly into Key West.

Where to Stay

Parrot Key Resort– This resort is in center of island, so only drawbacks are that you are an Uber ride (10 minutes) or 1/2 hour bike ride away from downtown. We actually enjoyed being removed from the hustle bustle of downtown. This resort has the most terrific set up of rooms for family with 3 kids; one main master bedroom/ bath, a living room w/ couch that our son slept on; and an upstairs room with twin beds and its own bathroom, for our daughters and balconies on both sides of the suite. There are 4 pools– they are small, not huge, but the grounds are lovely and very lush and landscaped with lots of tropical greenery. The resort runs shuttles to Smathers Beach and also to downtown a few times a day. The concierge help was fantastic; they helped us book our tours and itineraries and are very friendly. The hotel has a small beachfront w/ hammocks and lounge chairs. Looks out on to a Bay, not open water, but it’s pretty enough and you can catch a great sunset, with cocktail in hand. The restaurant at the main pool has a great bar–not the best food, but perfect for breakfast or lite lunch or a snack.

Sunset Key Cottages– We actually initially tried booking this but it was sold out. It is definitely very upscale and probably more luxurious than Parrot Key, but also pricey.

Where to Eat and Drink

We ate at some really good restaurants, that were also fun for the kids. We did one date night at a perfect place that I would say would not be great for kids. I would caution that downtown Key West, from one end of Truman and Duval gets pretty honkey town-ish. Almost like a mini New Orleans Bourbon Street. We walked this strip on a Saturday night and there are lots of young college bars and live music places, but probably not the kind of place you’d want to be out at night with kids.

Our favorite restaurants included:

Little Pearl– This restaurant is delicious and is price fixe 4 course menu but you can choose amongst a few options each course. It is small, intimate and has a real culinary vibe. Perfect date night. We loved it. Hard to get a reservation so book in advance.

Latitudes– This is the restaurant at Sunset Cottages. I would recommend lunch there so you can enjoy the view. It is upscale and delicious and because you are on an island, off main Key West, it feels special. Would recommend lunch instead of dinner, so you can enjoy the view. Reservations are a must.

Blue Heaven -This is iconic Key West restaurant, with a fun large outdoor, open backyard space and live music. Famous restaurant and is always busy. The food is solid and the scene is fun, upbeat and perfect for families. Sand in between all the tables and the service was good too. Open for lunch as well.

Louie’s Backyard

What to Do

We loved mixing our days with at least one activity– be it exercise or cultural– and then spending rest of day relaxing at the beach. You can do so much from biking, to kayaking, to paddle boarding, to snorkeling, to jet skiing, to kite surfing, to swimming, to fishing, to museums, to shopping, etc. Key West definitely has a good mix for kids of all ages and family outings.

• Fort Zachary Taylor State Park- this is a state park that sits right off on the western most part of Key West. It has probably the prettiest of beaches. We had our uber driver drop us at the main gate to walk in (you have to pay for entrance as it
• Smathers Beach- this beach was the beach we frequented the most as it was easy access from our hotel and it is very much a laid back, wide open beach, with lots of pretty sand and calm turquoise water. It is just an easy beach. 
• Lazy Dog Keywest- this is where you can go and organize a tour through the mangroves either on paddle board or on kayaks. Really fun to experience the mangroves this way and our guide gave us lots of interesting marine biology information. Fun fish and sea life to see but also just great exercise. The tour we took was 2 hours which was perfect.
• Sunset Key- it is fun to go over to the resort at Sunset Key, as they take you over on a boat and you do feel like you're on a private island, away from the main town.
• Ernest Hemingway House- whether you're a bookworm or not, this is a very interesting cultural place to visit. Hemingway lived in Key West for many years, in the 30's, when it was really still just being developed. You can tour his beautiful home and see how life in the Keys influenced his writing and his stories. He also built the first swimming pool in all of the Florida keys and the engineering behind it is really impressive. Definitely a landmark not to miss if you are in the Keys.
• Snorkeling, Biking, Jet skiing, Kite Surfing, Parasailing, etc-- these are all activities offered on the island and can be arranged through your hotel
• Southernmost Point- go get your picture at the official Southernmost point in the continental USA

inside scoop

Key West has a REALLY touristy area on Duvall Street. While it’s fun to walk and see it at least 1x in your visit, stay away from the main drag.On the other side of Duval and Truman it becomes much more upscale, with lovely shopping boutiques and upscale restaurants. It almost looks like New Orleans on the beach in certain neighborhoods and it’s fun to just walk around the streets.

• There is a lot of naval history there with the proximity to Cuba. You can feel it and there are bases that you can tour and learn more about just how close we came to warfare during Bay of Pigs.
• Make sure to have dinner reservations in advance of your trip. It's a small island and most of the really good places get booked up quickly. We made all of our reservations about 3 weeks before the trip and while we got in everywhere, times were already limited.

skip it

Duval Street is a tourist trap. Maybe go 1x to see it but do not eat downtown and I think one visit is enough. There is some real “cheeseburger in paradise” action — skip it.

What to Pack

Most of Key West is casual. Bathing suits, flip-flops, water shoes for some of the rocky beaches. A light jacket for winter months at night. Some of the restaurants were slightly more dressy but overall, this is a very low key Key! Lots of sunscreen!

• Make sure to have towels from your hotel when you go to the beaches.