Road trip Tampa to Key West best things to see, do, eat, places to stay, best pit stops along the way. Romantic weekend or fun trip with friends. Favorite must see places for your adventure.
Having made this trip dozens of times we’ve included our favorite hacks, local haunts, must see spots, must eat and drink favorites. From iconic, old Florida classics to modern first class resorts to everything in between.
Travel the Florida Keys like a native with this guide to everything you need to make this weekend special.
Road Trip Tampa to Key West- First Pit Stop Ft. Myers
Ft. Myers is a great weekend getaway from Tampa in its own right. It is also the perfect overnight spot if you are headed to Key West and want to get a head start by leaving after work instead of making the drive in a single day. About three hours from Tampa, depending on starting point and traffic, Ft. Myers is the perfect pitstop for fuel, coffee and a bathroom break.
Key West Express
A fun twist to the classic road trip. Make it a hybrid excursion. Drive to Ft. Myers and cruise the three hour Key West Express ferry from Ft. Myers to Key West. There are three levels to the ferry, be sure to get their early to ensure your best seat and find a place to park. There is food, tv’s, sundeck and a bar onboard. There’s air conditioning. It’s a three hour trip to Key West.
The ferry departs Ft. Myers by 8am, sharp, they stop boarding at 7:30am, don’t be late and be sure to get there early enough to find a place to park. There is onsite parking but the lot fills up fast. You don’t want to be scrambling at the last minute.
The ferry docks at the Key West Wharf. You can rent scooters or golf carts at the Wharf or walk down a few blocks for cheaper rental prices. The ferry departs at 5pm. You don’t have to return the same day, so book a hotel in the Key West for a night or two for a great weekend getaway.
Drive down the night before and grab a room to ensure a hassle free departure. Then enjoy a romantic walk on the beach, watch the sunset and enjoy a cocktail at one of the many beachside bars.
Los Dos Cristianos
Coffee shop with breakfast sandwiches, one mile off of 1-75. Freshly roasted and ground coffee beans make for the start of a great cup of coffee. For those that prefer a hot cup of tea or a boba tea, there are plenty of options including matcha. Breakfast sandwiches and a variety of pastries are also available.
Los Dos Cristianos is convenient, has a clean bathroom and relatively quick service. The staff is friendly, parking is easy and serves a solid cup of coffee or traditional matcha latte. The building is attached to a gas station so if you are traveling with others someone can get the coffee while someone else pumps the gas.
Mantanzas Inn Bayside Resort and Marina
Charming Inn and a convenient location, close to everything. Mantanzas Inn is located on the river and one block from the beach, bars, shops and restaurants. Clean. On site restaurant and rooftop bar. Music. Great views. Delightful staff. Pool and hot tub are clean and well maintained. No frill rooms with mini fridge. Nonsmoking rooms. AC works fine. Decent water pressure in showers. Comfortable beds with quality sheets and bedding.
Road Trip Tampa to Key West- Second Pit Stop Naples
Big Cypress National Preserve
Take Tamiami Trail for the scenic drive to the Florida Keys through the Everglades and Big Cypress National Preserve. Be sure to fuel up before you get on this part of the Tamiami Trail as there are no gas stations on Alligator Alley. There are several rest stops with nature viewing areas and plenty of airboat tour locations.
Our favorite place to stop is the boardwalk at the Oasis Visitor Center on the East entrance. We love to play “I Spy a Gator” and see who can see on e first. Please don’t feed them, it makes them aggressive towards humans, and its against the law.
Oakes Farms Seed to Table Market
Grocery store and food court. Oakes Farms indoor farmers market style experience is less than a mile off 1-75. Grab lunch and coffee or tea. Pick up snacks for the roadtrip. If you are spending the night in Naples there is music and beer or cocktails available.
Road Trip Tampa to Key West- Third Pit Stop Homestead/Florida City
Gateway to the Florida Keys. If you are driving after work it’s a perfect place to spend the night, get up early for sunrise and breathtaking morning views for your trip to the Keys. It’s also safer than trying to drive down to the Keys in the dark. Even though they’ve put up more fences, Key Deer still frequently try to cross the road leading to bad roadtrip memories.
Last Chance Saloon
Family owned. Classic dive bar. Outside courtyard with music. Pool tables, video games and shuffleboard. Full bar. When you visit the Last Chance Saloon, be sure to look for the Hidden Gems Florida sticker on the white refrigerator. Say hi to owner, Linda if you go, tell her we sent you and she will give you a coveted Last Chance Saloon sticker.
Road Trip Tampa to Key West- You’re Here- Key Largo, Florida
Baker’s Cay Resort
Part of the Hilton family, Baker’s Cay is an upscale resort and a destination all its own. Splurge on upgrading your room to a water view for a perfect romantic getaway. Complimentary kayak and paddle boards. Small sandy beach. Three pools. Pool bar. On-site restaurant. Delicious breakfast.
This place holds an extra special memory as this is where I first learned how to paddle board. The boards are right there waiting for you, no reservation needed, just grab one and go.
Caribbean Club
Iconic dive bar. Featured in the classic Key Largo film featuring Humphrey Bogart and Lauren Bacall. The Caribbean Club is the oldest bar in the Upper Keys. Great place to grab a beer, listen to local music and watch a Key Largo sunset.
Florida Bay Outfitters
Great selection of bathing suits and SPF clothing. Reasonable prices. Florida Bay Outfitters has kayak, paddle board and Hobie sailing kayak rentals. Staff is friendly, helpful and knowledgeable.
If you prefer a guided tour, they offer a three hour mangrove kayak tour.
Lots of paddling gear and other gadgets for your next paddle on the Hillsborough River when you get home.
Exploring the Florida Keys- Islamorada, Florida
Islamorada is known for its tiki bars, famous sand bar, fishing, warm, shallow, pristine waters and abundance of marine life. We like it for its great food, relaxing atmosphere and abundance of locally owned historic inn’s, bars, and restaurants. It’s got history, unique shopping and great places to get out on the water.
Aquaholics Paddles
Reasonable prices on kayak and paddle board rentals. In addition to rentals, Aquaholic Adventures offers tours and lessons, including a night tour which is on our to-do list for our next visit.
Florida Keys Brewing Company
Perfect place for lunch and a flight of microbrewed beers. Food truck onsite. Florida Keys Brewing has a some fun tropical logo merchandise including SPF shirts, buffs, tumblers and other fun souvenirs. Listen to local music in the shady courtyard while you grab a bite and a brew.
Our brew picks are the Bale Beach Pale Ale and Smuggler’s Moon Oatmeal Stout.
Our food picks are anything from the Jalisco Taco Truck– have tried them all, you can’t go wrong.
Sid & Roxies Green Turtle Inn and Restaurant
More like an Islamorada institution. The first Rustic Inn was built in 1935 and was a local watering hole during Prohibition. Rich in history and staying power the Green Turtle Inn has endured several Florida hurricanes and multiple proprietors. A favorite of both locals and celebrities this is a true class and one of our favorite hidden gems.
Our picks: Blackened Grouper, Key Lime Pie Martini
Sunset Inn
Iconic old Florida motel. The Sunset Inn has been completely renovated but maintains its nostalgic era charm. Clean. No frills room equipped with a full size refrigerator. Pool area is immaculate. Some rooms have entrances to both the street and the courtyard for easy access to the pool. Oversized chess game and paddle ball.
Breakfast and lunch available next door at Mangrove Mike’s Cafe. Be sure to go hungry, portion sizes are huge.
Unique gifts and island inspired jewelry at the Lobster Trap Art Gift Shop and Gallery. The photography is breathtaking and framed using old lobster traps for truly interesting art items.
Exploring the Florida Keys- Marathon, Florida
Keys Fisheries Restaurant, Market and Marina
If you are looking for fresh caught fish or seafood and a magnificent Florida Keys sunset, look no further. The Keys Fisheries Restaurant offers a full menu and full bar downstairs. Picnic style seating overlooking the water.
Upstairs, the Sunset Saloon has a full bar and raw bar with spectacular views. Get there early, the upstairs gets crowded right before sunset.
The market sells fresh caught fish and seafood to go as well as soups, sauces and dips.
Exploring the Florida Keys- Key West, Florida
So many independent bars, restaurants and cafes. One trip is never enough. Here are just a few of our off the beaten path favorites.
Dog Beach
Located next to Louie’s Backyard. Louie’s has both an upscale oceanfront restaurant and more casual wine bar and cafe. Fun place to let the dogs run and play in the beach while you enjoy a cocktail and snack from the bar. Dog Beach is the only pet friendly beach in Key West where you can let your dog splash in the water and sand, unleashed.
Island Dogs Bar
Just off Duval Street, Island Dogs Bar is a perfect spot to grab a cold one after your trolley tour. Known for the come as you are vibe, live music, cold beer and the perfectly crafted Key Lime Pie Martini.
First Flight Island Restaurant and Brewery
Microbrewery located in the historic Pan Am Headquarters building. Romantic garden courtyard shaded by mature banyan trees, tropical foliage and exotic orchids. Delicious eats. Fun Pan Am memorabilia in the retail area. Popular spot to view special event parades.
Our food picks: Ahi Tuna Poke
Our drink picks: Captain Maverick IPA, Old Havana Red Amber Ale
Road Trip Tampa to Key West- Final Thoughts
We hope you found something new for you next roadtrip from Tampa to the Florida Keys. Send us your favorites and be sure to tag #hiddengemsflorida so we can share in your adventure. Be sure to follow us on social for more iconic, vintage, classic and fun Florida hidden gems.
