Florida Keys

We travel to the Florida Keys every year for my husband’s birthday the first week of April. It’s a quick 3 hour flight from Boston and just what we need after a long, cold winter. We’ve stayed up and down the Keys, and are buying a time share in Key West this year. It’s kinda like our second home down there lol. So here’s all our favs, from resorts to activities to restaurants, to help you plan your next trip!

Hotels & Resorts

  • Ocean Key Resort & Spa, Key West – top rated luxury hotel right on Duval Street. Has a large pool area with private cabanas and lots of kids’ programs, as well as a restaurant on site and direct access to the famous Sunset Pier.
  • Southernmost Beach Resort, Key West – The largest, and best IMO, resort on the Island. Spread across six acres and two city blocks of prime Key West real estate, the resort offers guests great luxury accommodations in a tranquil setting. One of the only hotels to have beach access, the property also includes three pools, lush gardens, fantastic water views, and hammocks to rest in while you enjoy them. Also has restaurant, gym, & spa onsite.
  • Hyatt Centric Key West Resort & Spa – Beautiful waterfront resort; we’re looking at time shares here. Private beach with a floating dock area and a large swimming pool with a waterfall. There’s also 2 restaurants, a full-service spa, and gym. Resort staff can also facilitate a variety of water sports, from sailing and fishing excursions to kayak and sea-doo adventures.
  • Tranquility Bay Beach House Resort, Marathon – Sits on a 1,000 foot stretch of private beach and spreads across 12 acres right on the water. It was absolutely gorgeous. Made up of a number of luxe Victorian-style homes done up with tropical decor and divided into two and three bedroom suites. It is a great choice for families or anyone looking to save some money by cooking for themselves, as each suite has a full kitchen. You walk out your back door onto your deck and then step off right into sand.
  • Amara Cay Resort, Islamorada – Similar to Tranquility Bay, this place looks like a freakin’ screen saver. It sits on a stunning stretch of private beach with thatched huts and sun loungers plus hammocks. Onsite activities include scuba diving, kayaking and stand up paddleboarding. The pet-friendly property also has a swimming pool, hot tub, gym, and Italian restaurant known for its porterhouse steak.
  • Playa Largo Resort & Spa, Key Largo – Luxury resort with private beach and beautiful pool area with a poolside bar. It’s also another screen saver worthy view! Just an hour’s drive from Miami, the Resort has hammocks and sun loungers strewn along its sandy shore, and kayaks and paddleboards are available for guests to use. Amenities include a restaurant, kids’ club, swimming pool, spa, and gym. There is also a private marina on-site, with multiple charters.

Things To Do

  • Deep Sea Fishing – we did a private charter with High Class Hooker Charters and it was so much fun! Highly recommend them as the have a prime dock slip on Sunset Pier. Also, restaurants in the keys will cook your catch for dinner if you bring it in. It’s a thing down there. The Florida Keys is a nationally protect coral reef park and some of the best fishing in the world.
  • Scuba Diving in John Pennenkamp Coral Reef State Park – This is an activity I will never partake in due to my own phobia lol, but if you’re into diving you have to do it in the keys. Established in 1963, the park was the first undersea park in the United States. John Pennekamp Coral Reef State Park, and the adjacent Florida Keys National Marine Sanctuary, cover approximately 178 nautical square miles of coral reefs, seagrass beds and mangrove swamps. The park extends 3 miles into the Atlantic Ocean and is approximately 25 miles in length. These areas were established to protect and preserve a portion of the only living coral reef in the continental United States. Also home to the infamous sunken statue Christ of the Deep.
  • Fan Boat Tour of the Everglades – It’s a little bit of a drive (2 hours from Marathon) but so totally worth it. Everglades National Park is one of the most protected areas in the United States and is home to the North American Alligator population. We did our tour with Everglades Safari Park; the only gators they have in captivity are rescues or descendants of rescues and it is against the law to release captive alligators back into the wild in Florida. They have a factual alligator show and the don’t make the alligators do any tricks or anything, they just toss food into their mouths and pet their chins, which they seem to like lol. I swear the gator was wagging his tail! But definitely humane and respectful throughout the entire park.
  • Sunset Festival in Mallory Square – The Key West Sunset Celebration invites everyone to partake in watching the glowing pink and red sun sink into the Gulf of Mexico horizon. The nightly festival hosts visitors from all over the world who come to take part in the magicians, jugglers, clowns, psychics, local musicians, artists, and food vendors that combine for an incredible cultural experience.
  • Duval Street – The world famous Duval Street runs through the heart of Key West, beginning at the Atlantic Ocean, and ending at the Gulf of Mexico. The south end of the street is home to the Southernmost Point buoy and is a mix of early Key West Victorian mansions and bungalows dotting the neighborhood. Art galleries, boutiques, and inns line the sidewalks. This end of Duval is more residential and less filled with tourists. The north end of the street is Mallory Square & the Sunset Festival. Duval Street is often bumpin’ with a carnival like atmosphere that lasts until dawn and beyond. In fact, the ritual has a name known to tourists and residents as the “Duval Crawl.” The street is lined with over 300 bars, including several famous stops – Sloppy Joe’s, the original Margaritaville, Fogarty’s, The Flying Monkey’s Bar, Willy T’s, The Bull & Whistle, and Rick’s Cafe.
  • Dry Tortugas National Park – Dry Tortugas National Park is in the Gulf of Mexico, west of Key West. It comprises 7 islands and protected coral reefs. The park is noted for abundant sea life, tropical bird breeding grounds, colorful coral reefs, and legends of shipwrecks and sunken treasures. You can also dive the Windjammer Wreck, a famous sunken shipwreck from 1875. The islands are only accessable by boat or sea plane. There’s a ferry out of key west of you can book a charter through several local companies.

Restaurants Outside of Key West

  • Sundowners – Key Largo
  • Snook’s Bayside & Grand Tiki Bar – Key Largo
  • Marker 88 – Islamorada
  • Castaway Waterfront Restaurant & Sushi Bar – Marathon
  • Sunset Grill & Raw Bar – Marathon
  • Hog Heaven Bar & Grill – Islamorada (don’t let the name fool you! This place has bomb BBQ and awesome cocktails on a gorgeous waterfront inlet with live music.)
  • Hidden Pig – amazing outdoor garden breakfast spot in Marathon

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