Explore the Florida Keys by Slingshot
Discover the beauty of the Florida Keys with five self-guided Slingshot adventures departing from Keys Vacation Supply Rentals in Marathon. Cruise across iconic bridges, explore tropical islands, discover local favorites, and enjoy unforgettable waterfront sunsets.
Every route starts and ends at our Marathon location, near Mile Marker 48, with options for an 8-hour adventure or a 24-hour rental. Every stop on your route is loaded into the Slingshot's GPS, so just press GO for turn-by-turn directions.
Keys Day Date
8-hour rental · $324.45 · Approximately 50 miles round trip
Enjoy a relaxed day exploring the Lower Keys! Cross the iconic Seven Mile Bridge, spend time swimming and relaxing at Bahia Honda State Park, and stop for local favorites on Big Pine Key.
Included: One portable cooler and two beach towels.
Departure: 10:00 AM
Return: By 6:00 PM
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Your Keys Day Date Itinerary
10:00 AM — Pick up your Slingshot
Keys Vacation Supply Rentals, 2225 Overseas Highway, Marathon (near MM 48). Your portable cooler and two beach towels will be ready for you.10:15 AM — Seven Mile Bridge
Enjoy one of the Florida Keys' most iconic drives. Please do not stop on the bridge for photos.10:45 AM — Bahia Honda State Park
36850 Overseas Highway, Big Pine Key (MM 37). Swim, relax with your beach towels, and explore the Old Bahia Honda Bridge trail. Park admission is additional.12:30 PM — Explore Big Pine Key
Enjoy the scenery and keep an eye out for Key deer. Please observe posted speed limits and never feed the wildlife.1:00 PM — Lunch at No Name Pub
30813 Watson Boulevard, Big Pine Key (MM 30.2). Stop for pizza or burgers at this famous local spot, known for its ceiling covered in dollar bills. Food is at your own expense.Afternoon — Enjoy the Lower Keys
Take your time exploring the area and enjoying the scenery before heading back toward Marathon.By 6:00 PM — Return your Slingshot
Return the vehicle, cooler, and towels to Keys Vacation Supply Rentals.Photo tip: Capture the turquoise water and historic bridge at Bahia Honda, and take your Slingshot photos only from safe, designated parking areas.
Please note: Food, park admission, fuel, and other personal expenses are not included in the rental price.
Island Bites & Sunsets
24-hour rental · $427.45 · Approximately 70 miles round trip
Head east to Islamorada for coffee, waterfront dining, island stops, sunset entertainment, and dessert before returning the next morning.
Included: Cooler and two beach towels.
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Island Bites & Sunsets — 24-Hour Itinerary
Explore Islamorada's coffee shops, waterfront restaurants, beautiful beaches, and unforgettable sunsets. Enjoy the freedom of keeping your Slingshot overnight and returning it the next morning.
Day 1 — 10:00 AM: Pick Up Your Slingshot
Keys Vacation Supply Rentals, 2225 Overseas Highway, Marathon (near MM 48). Your portable cooler and two beach towels are included.10:45 AM — Coffee at Midway Cafe & Coffee Bar
80499 Overseas Highway, Islamorada (MM 80.5). Start the day with coffee and a fresh pastry. Food and drinks are at your own expense.11:45 AM — Robbie's of Islamorada
77522 Overseas Highway (MM 77.5). Watch the giant tarpon and, if you wish, feed them. Admission and fish buckets cost extra.12:30 PM — Lunch at the Hungry Tarpon
Enjoy waterfront dining beside Robbie's tarpon docks. Lunch is at your own expense.2:00 PM — Anne's Beach
Relax by the shallow turquoise flats and take a walk along the boardwalk.4:00 PM — Appetizers at Lazy Days Restaurant
79867 Overseas Highway, Islamorada (MM 79.8). Enjoy oceanfront seafood and appetizers with a view. Food is at your own expense.6:00 PM — Sunset Supper at The Lorelei
Islamorada, bayside near MM 82. Enjoy waterfront dining, sunset views, and live entertainment. Dinner is at your own expense.8:15 PM — Scenic Drive Back Toward Marathon
Head west along US 1 through Layton and Long Key.8:45 PM — Dessert at Sweet Savannah's
8919 Overseas Highway, Marathon. Treat yourself to homemade ice cream or chocolate-covered Key lime pie.Day 2 — By 10:00 AM: Return Your Slingshot
Return the Slingshot, cooler, and towels to Keys Vacation Supply Rentals. If time allows, consider an optional sunrise drive over the Seven Mile Bridge before returning.Rental Price: $427.45 for 24 hours
Includes the Slingshot rental, one portable cooler, and two beach towels. Food, drinks, activities, fuel, and other personal expenses are additional.
Alternative Sunset Stop: Morada Bay Beach Cafe in Islamorada is another option for waterfront dining and sunset entertainment. Check current opening hours before departure.
Key West Famous Must-Sees
24-hour rental · $427.45 · Approximately 100 miles round trip
Visit Key West's famous landmarks, historic homes, lighthouse, Southernmost Point, and Mallory Square.
Included: Cooler and two beach towels.
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Key West Famous Must-Sees — 24-Hour Itinerary
Experience the best of Key West in one unforgettable day. Visit famous landmarks, explore historic attractions, enjoy local food, and finish with the iconic Mallory Square sunset.
9:00 AM — Pick Up Your Slingshot
Keys Vacation Supply Rentals, 2225 Overseas Highway, Marathon (near MM 48). Your portable cooler and two beach towels are included.10:15 AM — Mile Marker 0
409 Whitehead Street at Fleming Street, Key West. Snap a photo at the famous beginning or end of US Highway 1. Free to visit.10:30 AM — Truman Little White House
111 Front Street. Explore the historic winter White House associated with President Harry S. Truman. Admission is additional; confirm current hours before visiting.12:00 PM — Lunch at Sloppy Joe's
Duval Street. Enjoy lunch at one of Key West's best-known historic bars and restaurants. Food is at your own expense.1:15 PM — Ernest Hemingway Home & Museum
907 Whitehead Street. Explore Hemingway's former home, writing studio, gardens, and famous six-toed cats. Admission is additional.2:30 PM — Key West Lighthouse & Keeper's Quarters
938 Whitehead Street. Climb the lighthouse steps for panoramic views of the island. Admission is additional; check current hours before your visit.3:15 PM — Southernmost Point Buoy
1400 Whitehead Street at South Street. Take a photo at the famous landmark marking 90 miles to Cuba. Free to visit; lines can be long.Optional Stop — Key West Butterfly & Nature Conservatory
1316 Duval Street. Walk through a tropical butterfly habitat if time allows. Admission is additional.Optional Stop — Fort Zachary Taylor Historic State Park
601 Howard England Way. Explore the historic fort or relax at the beach. Park admission and parking rules apply.Sunset — Mallory Square
Enjoy street performers, waterfront views, and Key West's famous sunset celebration. Free to visit.Next Morning — Return Your Slingshot
Return the vehicle, cooler, and towels to Keys Vacation Supply Rentals by 9:00 AM, within your 24-hour rental period.Rental Price: $427.45 for 24 hours
Includes the Slingshot rental, one portable cooler, and two beach towels. Museum tickets, food, fuel, parking, and other personal expenses are additional.
Travel Tip: Park once in Old Town and explore the nearby attractions on foot. Never stop on the Seven Mile Bridge or along the highway for photos. Allow extra time for traffic, parking, and walking between attractions.
Sunset & Supper Overnight
24-hour rental · $427.45 · Approximately 80 miles round trip
Enjoy an afternoon drive, scenic photo stops, waterfront dining, and a beautiful Florida Keys sunset.
Included: Cooler and two beach towels.
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Sunset & Supper Overnight — Full Itinerary
2:00 PM — Pick Up Your Slingshot
Keys Vacation Supply Rentals, Marathon. Your portable cooler and two beach towels are included.2:30 PM — Drive the Long Key Bridge
Enjoy scenic views of the Florida Keys and the historic Long Key Viaduct. Please do not stop on the bridge for photos.3:00 PM — Anne's Beach
Enjoy the turquoise shallow flats, take a walk along the boardwalk, and capture some beautiful photos.4:00 PM — Betsy the Giant Lobster
Visit Rain Barrel Village in Islamorada and take a photo with the famous giant lobster.5:15 PM — Sunset Supper at Morada Bay Beach Cafe
Enjoy waterfront dining, tables on the sand, and beautiful sunset views across Florida Bay. Food and drinks are at your own expense.8:00 PM — Ride Back to Marathon Under the Stars
Enjoy the scenic drive west along US 1. Drive carefully and watch for wildlife after dark.Next Morning, 8:00 AM — Curry Hammock State Park
Start your morning with a peaceful beach walk and coffee. Park admission is additional.10:00 AM — Return Your Slingshot
Return the Slingshot, cooler, and towels to Keys Vacation Supply Rentals in Marathon.Rental Price: $427.45 for 24 hours
Includes the Slingshot rental, one portable cooler, and two beach towels. Food, fuel, park admission, parking, and other personal expenses are additional.
Photo Safety: Never stop on a bridge or highway shoulder to take photos. Use designated parking areas.
Middle Keys Beauty Loop
8-hour route listed at $324.45 · Approximately 40 miles
Discover Marathon, Key Colony Beach, Curry Hammock, and Duck Key, with waterfront views and local food stops.
Included: Cooler and two beach towels.
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Middle Keys Beauty Loop — Full Itinerary
Explore the beautiful Middle Keys with waterfront neighborhoods, tropical nature trails, local food stops, and scenic island drives. This route showcases the beauty of Marathon and the surrounding islands.
10:00 AM — Pick Up Your Slingshot
Keys Vacation Supply Rentals, 2225 Overseas Highway, Marathon (near MM 48). Your portable cooler and two beach towels are included.10:15 AM — Crane Point Hammock & Adderley House
5550 Overseas Highway, Marathon. Explore tropical hammock trails and discover the historic 1904 Adderley House. Check opening hours and admission before visiting.11:30 AM — Sweet Savannah's Bake Shop & Ice Cream Cafe
8919 Overseas Highway, Marathon. Take a snack break for homemade ice cream or chocolate-covered Key lime pie. Treats are at your own expense.12:00 PM — Explore Key Colony Beach
Take the scenic loop via Sadowski Causeway and enjoy the waterfront homes along East and West Ocean Drive. Continue to Sunset Park for beautiful views where Vaca Cut meets the Atlantic.1:00 PM — Lunch at Sparky's Landing
Sadowski Causeway, Key Colony Beach. Enjoy a waterfront meal beside the charter fishing boats. Food and drinks are at your own expense.2:15 PM — Curry Hammock State Park
Near MM 56, Marathon. Relax on the oceanside beach, spread out your towels, and enjoy the coastal scenery. Park admission is additional.3:15 PM — Duck Key & Hawks Cay Resort
Near MM 61. Explore the scenic roads and bridges connecting Duck Key's small islands, with views of turquoise canals. Please park safely before taking photos. Resort facilities may require a dining or spa reservation.Optional Scenic Drive — Long Key Bridge
Enjoy the beautiful water views along this iconic stretch of the Overseas Highway. Never stop on the bridge or highway shoulder for photos.By 6:00 PM — Return Your Slingshot
Return the Slingshot, cooler, and towels to Keys Vacation Supply Rentals in Marathon.Rental Price: $324.45 for 8 hours
Includes the Slingshot rental, one portable cooler, and two beach towels. Food, fuel, admission fees, parking, and other personal expenses are additional.
Photo Safety: Use designated parking areas and never stop on bridges or highway shoulders for photos. Drivers should remain focused on the road while passengers take pictures.