Romance & Adventure: A 5-Day Relaxing Key West Getaway

Before you go: A little pre-work

Before you pack your bags and head to paradise, there are two key reservations you should make to ensure your trip is smooth and stress-free:

Dinner at Latitudes: This will be a highlight of Day 4, offering incredible waterfront dining on Sunset Key. It's one of the most romantic and unforgettable dinner spots in Key West, and reservations book up weeks in advance.

Sunset Sail with Sebago Watersports: This will be on Day 3, and it’s a must-do for an unforgettable sunset experience on the water. Sebago offers a variety of sail options, whether you want live music and cocktails, a champagne sunset cruise, or a more private, upscale experience. Pick the one that matches your vibe and lock it in early!

Don’t worry — if either of these is booked, I’ll have back-up recommendations in the itinerary!

Day One: The journey begins — Miami to Key West

Welcome to the start of your Key West adventure! First things first — fly into Miami International Airport, preferably in the early morning (because trust me, you’ll want the whole day to soak up the drive). Once you land, skip the long rental car lines and grab a ride from Sixt — they’re the easiest and fastest to work with. If you check in, virtually, all you have to do is grab your keys from the attendant and hit the road. No waiting, no hassle — just pure vacation mode.

Now, you might be wondering — why fly into Miami instead of Key West? Simple: it’s way cheaper, and the drive through the Florida Keys is one of the best parts of this trip. Picture turquoise waters, endless sky and the legendary Seven Mile Bridge stretching out ahead of you — it’s the ultimate road trip with built-in ocean views.

First Stop: Key Largo — Lunch with a side of laid-back vibes

By now, you’re probably starving, and lucky for you, Key Largo has some solid food spots. If you’re feeling super casual, swing by Shipwrecks Bar and Grill — this place is as Keysey as it gets. Grab a cheesesteak or a hot dog. Kick back on the patio and enjoy the company of their local porch cats, who will absolutely try to charm you into sharing your food.

Want something a little less dive-bar and a little more diner-style? Mangrove Mike’s Café is another great option. It’s still not a five-star, white-tablecloth kind of place, but it’s a notch above Shipwrecks in terms of atmosphere while keeping that Keys charm.

After lunch, hop back in the car and keep heading south — the real magic of the Keys is still ahead!

Next stop: Rain Barrel Village — A little shopping in paradise

As you continue your scenic drive down the Keys, make a pit stop at Rain Barrel Village in Islamorada. Trust me, this place is worth the stop! It’s not just another roadside shopping spot — it literally feels like you’re wandering through a rainforest filled with the cutest little shops. The whole place has that artsy, laid-back, tropical vibe that makes the Keys so special.

You’ll find local artwork, handmade jewelry, souvenirs and all kinds of one-of-a-kind treasures — perfect if you’re looking for a unique gift (or just want to treat yourself). Plus, the shop owners are some of the friendliest people around. Whether you’re just browsing or buying, you’ll feel welcome.

Oh, and don’t forget to snap a pic of "Big Betsy," the giant lobster statue out front — it’s basically a rite of passage.

Once you’ve had your fill of shopping (or at least made peace with how much space you have in your suitcase), it’s time to hit the road again. Next stop: even more adventure!

Keep an eye out for Fred the Tree

As you cruise across the iconic Seven Mile Bridge, be on the lookout for Fred the Tree. This is a scrappy little Australian pine growing right in the middle of the old bridge. Against all odds (and without soil!), Fred has been thriving for over 30 years, surviving hurricanes, blistering sun and the salty sea air. Around the holidays, a mysterious group known as "Fred’s Elves" decorates him with twinkling lights, adding a little extra magic to the drive.

Spotting Fred is like another little Keys initiation — give him a wave as you pass by!

Welcome to Key West — Time to check in!

Congratulations, you made it! Now that you’ve arrived in Key West, it’s time to check into your hotel or Airbnb and settle in. Drop your bags, freshen up and get ready for the island vibes to officially take over. The rest of the trip is all about relaxing, exploring and soaking up everything this magical place has to offer.

Next up? The perfect first-night dinner spot to kick off your stay!

First night dinner: Mangia Mangia Pasta Café

After a long day of traveling and taking in the sights, it's time to slow down and enjoy a romantic, cozy dinner at Mangia Mangia Pasta Café. This underrated gem is the perfect place to unwind, with its quiet atmosphere, authentic handmade pasta and a fantastic wine selection.

Everything here is fresh, homemade and bursting with flavor — you can literally taste the love in every bite. Whether you go for a classic like Lobster Fra Diavolo or a comforting bowl of Carbonara, you really can’t go wrong. Pair it with a glass of Italian wine (or let them pair it for you), and you've got the perfect first-night meal to ease into vacation mode.

After dinner, take a leisurely stroll through the quiet streets of Key West. Stop for a nightcap at a local bar — or just head back to your hotel and rest up for a fun-filled day tomorrow!

Getting around Key West

Parking in Key West is limited, so here are your best options for getting around:

• Electric Sidewalk Scooters: The easiest and most fun way to explore! Download the app, pay per ride and go — they're stationed all over the island.

• Road Scooters: Available through rental companies if you want something a little faster.

• Walking: If you’re staying close to the action, strolling around is a great option.

• Driving: Doable, but be prepared to spend 10–15 minutes finding parking.

Breakfast at Blue Heaven

Start your day with breakfast at Blue Heaven. The food is always fresh, and the laid-back tropical atmosphere is the perfect way to ease into your morning. They often have live music, and if you're in the mood for a little morning indulgence, their Bloody Mary bar is excellent.

Relaxing at Dante’s Pool Bar

After breakfast, head over to Dante’s Pool Bar. This is a great spot to relax and cool off. It's a swim-up pool bar where you can grab a drink, play pool, beer pong or just lounge in the water. I always recommend keeping your swimsuit under your clothes in Key West so you’re always ready to jump in.

Games at The Retro Room

Once you’ve had some time to unwind, make your way to The Retro Room. This arcade and game bar is a great way to escape the midday heat. They have everything from old-school arcade games to board games, so whether you’re into pinball or a game of cards, it’s a fun stop before heading out for some shopping.

Shopping and dinner on Duval Street

Next, take a walk down Duval Street, where you’ll find an eclectic mix of boutiques, souvenir shops and quirky island finds. If you need a little snack along the way, stop at Kermit’s Key Lime Shoppe for a frozen key lime pie on a stick. It’s one of those things you have to try at least once while in Key West.

For dinner, grab a table or a seat at the bar at Sloppy Joe’s Bar. This iconic spot has been around since 1933 and offers more than just its famous sloppy joes. The menu has plenty of options, and there’s live music every night.

Sunset at Mallory Square

End the night at Mallory Square for the Sunset Celebration. This is my personal favorite tradition of Key West, where locals and tourists gather to watch the sun sink into the horizon. There are street performers, musicians and a festive atmosphere that makes it a memorable way to close out your second day in paradise.

Rise & shine: Breakfast at Breakfast Club, Too

Start your day with a relaxed and satisfying breakfast at Breakfast Club, Too. This spot is known for its stuffed French toast, and over-the-top Bloody Marys. Whether you’re in the mood for something sweet or savory, you’ll find this a great way to fuel up for the day ahead. Head back to your room after breakfast to prep for the rest of the day!

Beach day prep: Sun, sand & survival kit

Before heading back out, take a few minutes to get beach-ready. The Key West sun is no joke, so pack sunscreen and reapply throughout the day. Staying hydrated is just as important, so bring plenty of water and something with electrolytes like Gatorade. Bug spray is also a good idea since the flies & gnats can be a little much at certain times of the year. Now you’re ready to take on the day!

Toes in the sand: Smathers Beach fun

With soft sand and crystal-clear water, Smathers Beach is a perfect spot to spend the morning. Whether you want to lounge under the palm trees, go for a swim or rent some water sports equipment, this beach has it all. There’s plenty of parking, so feel free to drive if you’d rather not walk, scoot or bike.

Lunch with a view: Salute! On The Beach

Just a short drive up the road, Salute! On The Beach is a great place to enjoy fresh seafood and Italian-inspired dishes with a laid-back, oceanfront atmosphere. Grab a cocktail, take in the view and enjoy a slow, easy lunch. Again, there’s plenty of parking here for your convenience. After lunch, take a walk along Higgs Beach and out onto Higgs Pier. It’s a peaceful area with beautiful ocean views and a nice place to pause and enjoy the moment before heading back to freshen up.

Refresh & recharge: Late-afternoon break

Head back to your hotel or Airbnb for a little downtime before the evening. Shower, cool off and get ready for a relaxed but unforgettable night ahead. If you plan to get photos on the Sunset Sail, don’t forget to throw on a cute, island-vibe outfit!

Sunset bites: Dinner at A&B Lobster House

For a great meal before your sail, A&B Lobster House is a solid choice. Located right on the water near the marina, it has a warm, old-school feel with a menu full of fresh seafood and perfectly cooked steaks. If you’re in the mood for something a little fancy but still laid-back, this is the spot. The outdoor seating overlooks the harbor, making it a great place to relax before setting off on the water.

Set sail & soak it in: Sunset cruise

Cap off the day with a sunset sail across Key West’s beautiful waters. Many options include complimentary drinks, live music or a quiet, romantic setting, so there’s something for every vibe. No matter what you choose, watching the sun dip below the horizon from the deck of a boat is one of the best ways to experience Key West.

Start the day right: Sunrise at Emma Carrero Cates Pier

Kick off the morning with a peaceful sunrise at Emma Carrero Cates Pier. It’s a quiet spot with a great view, and watching the sky light up over the water is a perfect way to ease into the day. While in Key West, it’s a must to experience their beautiful sunrises at least once.

Breakfast & a cocktail: Southernmost Sandy’s Cafe

After the sunrise, take a short walk over to Southernmost Sandy’s Cafe for a Cuban-style breakfast and a frozen cocktail. Whether you grab a breakfast sandwich or some conch fritters, it’s an easygoing and delicious way to fuel up for the day ahead. Since you’re in the area, stop by the Southernmost Point for the classic Key West photo. It’s a fun little touristy moment to check off the list.

Gear up: Snorkel stop at Divers Direct

Next, swing by Divers Direct to pick up some snorkel gear. A full-face snorkel that covers your nose is a solid choice. This makes it easier to breathe while you explore underwater and prevents any allergic reactions to anything in the water.

Secret snorkeling spot: An off-the-radar adventure

This hidden snorkeling spot is one of my favorite finds. The water is crystal clear, and the marine life is incredible. Just keep in mind that this is completely at your own risk — there are no lifeguards, and it’s rare to see other people around. If that feels a little too adventurous, you can always opt for a guided snorkeling trip instead.

Lunch break: Two Friends Patio Restaurant

After a morning in the water, head back to town and grab lunch at Two Friends Patio Restaurant. It’s a relaxed spot with fresh seafood, sandwiches and refreshing cocktails — perfect for a laid-back afternoon.

Cheap drinks & a local bar dog: The Dive Bar

For a no-frills drink and a fun atmosphere, stop by The Dive Bar. The drinks are cheap, the vibe is casual and if you’re lucky, you might even get to toss a ball for the resident bar dog.

Meet some ocean friends: Key West Aquarium

Take a break from the heat and check out the Key West Aquarium. They focus on marine life conservation and often have rescued animals they’re rehabilitating, so there’s always something interesting to see.

Dinner with a view: Latitudes

Head back to your room to freshen up before dinner at Latitudes. You’ll take a quick ferry ride over to Sunset Key for an unforgettable meal with an oceanfront view. Whether you go for fresh seafood or a perfectly cooked steak, this is one of the best dining experiences in Key West. After dinner, you can enjoy their private beach on the island while you wait for the ferry back!

One last meal: Brunch at Boondocks Grille & Draft House

If you have a later flight, take a scenic drive up to Boondocks Grille & Draft House for one final island meal. They open at 11 am and serve up a great brunch with a laid-back, tropical vibe. It’s a nice way to soak in the last bit of the Keys before heading home.

Time to head back: Airport & goodbyes

After brunch, make your way back to the airport, return your rental car and get checked in. As you take off, start planning your next trip — because once you’ve been to Key West, you’ll definitely want to come back.