Plan a Girlfriend Getaway to the Florida Keys

Day 1: Make your first road trip stop in Key Largo for boating, scuba diving, and lots of seafood. Plan a diving or snorkeling trip for you and your friends, and have fun with the fishes. Snorkel John Pennekamp Coral Reef State Park with a private snorkeling charter to explore under the sea. Check out Keys Diver Daily Snorkel Tours for a reef tour or summer sunset tour.

Eat your fill of fresh seafood at Ballyhoo's Historic Seafood Grille, an eatery housed in a 1930s conch house; the Key Largo Conch House Restaurant, where you can get breakfast, lunch, or dinner; Snappers Oceanfront Restaurant & Bar, where you can enjoy ocean views; and Skippers Dockside, where you can enjoy seaside eats.

Stay at Kona Kai Resort, Gallery, and Botanic Gardens in Key Largo, and you’ll be resting your head in a tropical paradise. In addition to a top-notch resort, it’s an ethnobotanic teaching garden and one of the only frost-free tropical botanic gardens in the U.S.

Day 2: Rent kayaks with your friends and paddle out to the picturesque mangroves in Key Largo or Islamorada. Florida Bay Outfitters has all you need to launch your paddling excursion. Explore the ocean and its navigable shallow waters for a fun day trip. Also check out Indian Key Historic State Park and Lignumvitae Key Botanical State Park for swimming and hiking. Both are accessible by boat—contact Robbie's Marina at (305-664-9814) for a rental. Drive to Long Key State Park, southwest of Islamorada, for swimming, hiking, bird watching, kayaking, and picnicking.

After all the snorkeling, hiking, and swimming, stop into local favorite Mangrove Mike’s Cafe or the Beach Cafe at Morada Bay for sustenance. Go ahead and book an upscale dinner at Chef Michael’s and Pierre’s Lounge & Restaurant at Morada Bay, a fun treat that you and the girls can look forward to. Dress up for dinner, and prepare to be pampered.

Book beachfront at Amara Cay Resort or find classic oceanfront cottages at Pines & Palms Resort, both in Islamorada. With blue skies and emerald waters all around, you’ll be feeling like a local in no time. Check to see if your accommodation offers bikes and kayaks (Pines & Palms does!). Depending on where you book, you may be able to skip extra rental fees for activities during your trip. Try the Creekside Inn for a great budget-friendly option.

Day 3: Marathon’s calling. We’ve already outlined what to do, see, and eat in Marathon, but this spot is just so charming, we’ll recommend it again. Bask on the sands at Sombrero Beach and explore the coastline.

Settle in for eats at The Island Fish Co., Tiki Bar and Restaurant, or the Keys Fisheries Market & Marina. No matter where you stop to place your order in Marathon, you’ll be pleased. You should also grab a bite to eat at the Butterfly Café at Tranquility Bay Beachfront Hotel & Resort (This is also where we recommend you book your Marathon stay. Read on, and you’ll see why.)

Book your rooms Tranquility Bay Beachfront Hotel & Resort in Marathon for the ultimate Keys stay. It’s unforgettable. Spend a few hours here, and you’ll want to move into this 12-acre property. Spend the night, and you’ll declare that you’re never leaving.

Day 4: 15 miles southwest of Marathon is Big Pine Key. Grab your snorkeling gear and head to Bahia Honda State Park, just west of Big Pine Key, for a day trip and plenty of time spent in the ocean. Book a daytime tour with Big Pine Kayak Adventures to get out on the water and explore this picturesque locale too.

Check into Deer Run Bed & Breakfast with your girls. It’s not hard to relax in these surroundings. With waving palm trees overhead and a pink sunset in the distance, you’ll be wishing for this road trip to go on and on. Deer Run even serves a vegan breakfast, so no worries for those with dietary requirements.

Day 5: Enjoy all that Key West Has to offer. Go see the southernmost point in continental U.S., take a few pictures, and stroll along the beach. Meander charming neighborhoods, cafes, and shops. Browse your way through the shops of Mallory Square and Duval Street, and then rent a few bikes to pedal leisurely through town. (Eaton Bikes has cruisers for you.)

Don’t skip a meal in Key West. Have brunch at Blue Heaven, and don’t wait too long to indulge in a slice of Key lime pie. It’s a requirement. Blond Giraffe has portable ones (that are dipped in chocolate and served on a stick), or you can get classic iterations at Key West Key Lime Pie Co. and the incredibly Instagrammable Kermit’s Key West Key Lime Shoppe. Have dinner at Nine One Five Restaurant and Bar on Duval, and thank us later.

Stay at The Southernmost House in Key West, a gorgeous, historic bed and breakfast that is also a member of the Southern Living Hotel Collection. Enjoy the oceanfront pool and dreamy architecture. If you can pull yourself away from the pool, stop by the Ernest Hemingway Home and Museum, Key West Butterfly and Nature Conservatory, and Dry Tortugas National Park.