Travel Florida Plan a Girlfriend Getaway to the Florida Keys By Caroline Rogers Caroline Rogers Caroline Rogers is the travel and culture editor at Southern Living, where she writes and edits travel stories exploring the American South. She also contributes articles about books, arts, and the outdoors to the brand's digital platforms. She joined the magazine in 2016 and since then has reported on the beaches of the Florida Keys, opera in Houston's Theater District, and waterfalls across West Virginia, among many other spaces and places. Southern Living's editorial guidelines Updated on June 26, 2017 Share Tweet Pin Email Trending Videos Photo: MyLoupe/Getty Images Is there a more perfect road trip? The Florida Keys are a 120-mile stretch of picturesque islands connected by bridges traversing sapphire blue Gulf waters. The Keys are home to the southernmost point in the continental U.S, so set your compass southward, pack your car, grab your girls, and get going. The Florida Keys are the perfect destination for a weekend getaway with your best friends. It's the ultimate beach paradise, with charming small towns, great shopping, plenty of ocean adventures, a Key lime pie or two, and the freshest seafood imaginable to keep you happy all vacation long. Plan a 5-day (or longer!) girls' trip with our recommendations for where to go, what to eat, and where to stay, and you'll be enjoying the South Florida sea breezes in no time. Start in Key Largo, and move southwest on U.S. 1 through Islamorada, Marathon, Big Pine Key, and Key West for a road trip you'll never forget. Follow along for the perfect Keys vacation, which includes everything from snorkeling to seafood dinners to afternoon naps on the dreamy sandy beaches (plus an unexpected event or two). Check out the Keys' calendar of events to help plan your trip, and chart your course through the islands today. 01 of 14 Snorkel in Key Largo Courtesy fla-keys.com 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. 02 of 14 Enjoy Key Largo Seafood Courtesy Snappers Oceanfront Restaurant & Bar 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. 03 of 14 Stay in a Key Largo Botanical Garden David McCleaf 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. 04 of 14 Paddle Out to Islamorada's Mangroves MyLoupe/Getty Images 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. 05 of 14 Have Brunch in Islamorada Courtesy Morada Bay 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. 06 of 14 Stay Seaside in Islamorada Courtesy Amara Cay Resort 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. 07 of 14 Take it Easy in Marathon Courtesy Visit Florida 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. 08 of 14 Marathon Has Eats for Everyone Courtesy The Island Fish Co. 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.) 09 of 14 Find Tranquility in Marathon Robbie Caponetto 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. 10 of 14 Explore Big Pine Key Robbie Caponetto 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. 11 of 14 Book an All-Inclusive Stay on Big Pine Key Courtesy Deer Run Bed & Breakfast 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. 12 of 14 You're on Island Time in Key West Chris M. Rogers 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.) 13 of 14 Key Lime Pie, Anyone? Jeff Greenberg/Getty Images 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. 14 of 14 Book a Southernmost Stay in Key West Courtesy The Southernmost House 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. Was this page helpful? Thanks for your feedback! Tell us why! Other Submit