My stay at Margaritaville Beach House Key West & my transportation via Key West Express were comped for this post however all opinions are my own.

Looking for an easy getaway that feels worlds away from Naples? Then you need to check out how easy it is to take the Key West Express to Key West, complete with a stay at Margaritaville Beach House Key West.

While Southwest Florida has no shortage of beautiful beaches and waterfront restaurants, sometimes it’s fun to trade the Paradise Coast for something completely different. That’s exactly what we did on a recent quick getaway to Key West.

This itinerary is perfect for Naples locals looking for a staycation, snowbirds wanting a new adventure, or visitors hoping to add something special to their Southwest Florida vacation.

The best part? You don’t need a full week off work to make it happen.

This post explore two different quick getaways from SWFL to Key West: a 2 night/ 3 day itinerary and a 3 night/ 4 day itinerary. Of course you can easily adjust this to make more of your time in Key West. Nothing is stopping you from spending more time in The Conch Republic!

Table of Contents

2 Night Naples to Key West Itinerary

3 Night Naples to Key West Itinerary

FAQ about Naples to Key West

Two Night Naples to Key West Itinerary – 48 Hours in Key West

Day 1: Ferry to Key West, Explore Old Town, Check into Margaritaville Beach House Key West

Wake up early and head to the Key West Express terminal.

My biggest piece of advice is to arrive early enough to secure a table inside the ferry. Trust me—you’ll appreciate the air conditioning and comfortable seating during the crossing.

The ride across the Gulf takes approximately three and a half to four hours depending on weather conditions.

Bring a book, a deck of cards, snacks, and cash for the onboard bar. Internet service can be limited, so this is a great opportunity to disconnect and enjoy the journey.

Be sure to spend some time on the upper deck during departure and arrival. We’ve spotted dolphins, manatees, and all kinds of marine life while entering and leaving the harbor.

Once you arrive at the Key West Bight Historic Seaport, skip all the transportation offers and opt for the free shuttle to Margaritaville Beach House Key West.

Want more information about traveling via the Key West Express? Check out my review here.

Enjoy Lunch at Waterfront Brewery Key West

Located just steps away from Key West Bight Historic Seaport, Waterfront Brewery not only has great food, it is the pick up location for the complementary shuttle to Margaritaville Beach House Key West.

The shuttle leaves Waterfront Brewery every hour on the half hour, and leaves the hotel every hour on the hour. That gives you just enough time to walk from the Key West Express to Waterfront Brewery and enjoy a welcome to Key West lunch.

While the food, drinks, and location are great, the arcade games at Waterfront Brewery really add to the experience. If you are traveling with kids, this is a great way to entertain them.

Check Into Margaritaville Beach House Key West

Once you’ve enjoyed lunch, head to Margaritaville Beach House Key West.

Located just steps from Smathers Beach, the resort offers spacious rooms, a beautiful pool area, beach access, and a complimentary shuttle into Old Town Key West.

One of my favorite touches was the welcome drinks. Adults receive frozen margaritas while kids are treated to frozen strawberry daiquiris. It was the perfect way to kick off our island getaway.

After checking in and settling into your room, spend some time exploring the property or relaxing by the pool.

Early Dinner

Choose one of the many local restaurants in Old Town before heading back to your resort for the evening. Or opt for a dinner at Tin Cup Chalice Bar & Chill at Margaritaville Beach House Key West. They have a great selection of appetizers and main dishes.

Sunset Cruise

Head back to Old Town Key West to get on a sunset cruise with Sebago Watersports.

I personally suggest going on the Captain’s Choice sunset cruise. It comes with tapas, shrimp, wines, champagne, and soft drinks. This one is great for adults and kids.

Day 2: A Full Day in Key West

Today is all about enjoying everything that makes Key West special.

Start your morning with breakfast at Tin Cup Chalice Bar & Chill at Margaritaville Beach House. We enjoyed breakfast there during our stay and found the food delicious and reasonably priced.

After breakfast, head to Smathers Beach.

Because the resort is located just steps from the island’s largest beach, it’s easy to spend a few hours swimming, shelling, or simply relaxing in the sunshine before heading into Old Town.

Morning Activities in Key West

There are so many fun things to do in Key West! On this particular day I suggest getting a Lyft to drive you from Margaritaville Beach House Key West to the Southernmost Point Buoy.

You’ll get a picture of the Southernmost Point Buoy before the crowds line up and then you can walk down Whitehead or Duval Street for a day of exploration.

Start with a visit to the Key West Butterfly and Nature Conservatory. Even if you decide not to visit, you should stop into the gift shop to see some of their unique gifts.

From there head to the Ernest Hemingway Home and Museum. This one is definitely worth the price of admission. Dare I say a must-do on any Key West trip?

Pro tip: make sure to read the signs along the way at the Hemingway Home. You’ll learn so much not only about Hemingway but Key West.

Next up stop by Moondog Bakery & Cafe. This is one of two Michelin recognized restaurants in Key West and it is definitely worth a visit. You can go ahead and grab lunch here or just sit down for a snack and a drink. Anything goes in Key West!

After fueling up you’ll be ready for some more walking. Get back on Duval and explore the shops or head over to Truman Park and visit the Truman Little White House- the only Presidential Museum in Florida- on your way.

Lunch

If you’re still hungry after Moondog, grab lunch in Old Town Key West. You really can’t go wrong with any spot.

Afternoon- cool down with a water activity

This is a great time for one of Key West’s signature experiences:

• Snorkeling excursion
• Kayak tour
• Beach day
• Pool day
• Rent a fishing pole

Personally, I think one of the best things about Key West is that you don’t need a packed itinerary. The island practically encourages you to slow down. This is a great time to relax by the pool at the Margaritaville Beach House Key West or walk over to Smathers Beach to try to find your own conch shell!

Evening in Key West, Dinner & Sunset at Mallory Square

Get back on the shuttle and head to Mallory Square for the famous Sunset Celebration.

Street performers, musicians, artists, and incredible waterfront views create one of the most memorable experiences on the island.

Whether you choose a waterfront seafood restaurant or a casual island café, take your time and savor your last evening.

If you have kids with you, I highly suggest hitting up a restaurant with live music before sunset. This is a great way to experience live music with your kids before the bars get crazy at night!

Traveling without kids? This is a good time to experience a bar on Duval Street. All of them are fun, but I highly suggest Sloppy Joe’s and Hog’s Breath Cafe. Both are iconic staples on Duval Street.

Day 3: Continue to Explore Key West & Return to Southwest Florida

Pack your bags and let Margaritaville Beach House Key West hold onto them until you are ready to leave. Boarding for the Key West Express doesn’t start until 5 so you have plenty of time to enjoy one last day on the island.

Pro tip: Don’t want to go back to the hotel for your luggage? You can store your luggage with Paradise Porters at Key West Bight Historic Seaport. You have the option to drop it off or have them pick up from your hotel.

Breakfast at a Key West Michelin recognized Blue Heaven

It’s one thing to eat at one Michelin recognized restaurant during a vacation. Visit two and now you are venturing into real foodie territory! I definitely suggest you swing by Blue Heaven for your final breakfast in Key West. Everything is delicious but I particularly love the eggs benedict made with lime hollandaise sauce.

Last Chance to Finish Everything on Your Tourist List

This is the time to walk around Old Town Key West and do some more of these touristy things. Here are some of the best ones we have done and would do again.

• Key West Aquarium
• Shipwreck Museum
• Books & Books Key West– owned by Judy Blume!
• Key Lime Pie Tasting
• Art Gallery Crawl
• Key West Light House
• Fort Zachary Taylor State Park

4:30- Grab a Cuban Sandwich

Trust me on this one- stop by Cuban Coffee Queen on your way to the Key West Express and get a couple Cuban sandwiches and coffees to go for you to enjoy on the Key West Express.

Head to the seaport and get ready to board the Key West Express.

BONUS- Make It a 3-Night Getaway: Add a Night at The Luminary Hotel & Co.

If you have an extra day to spare, I highly recommend extending your trip with a night at The Luminary Hotel & Co. in downtown Fort Myers.

Located along the Caloosahatchee River, The Luminary offers a completely different experience from both Naples and Key West. While Key West is colorful, quirky, and laid-back, downtown Fort Myers blends historic charm with a growing food and arts scene.

You can either visit on your way into Key West or on the way back. Either way here are some tips.

Start your afternoon by checking into the hotel and exploring the River District.

The walkable downtown area is filled with local restaurants, coffee shops, boutiques, murals, galleries, and historic buildings. It’s the perfect place to spend a leisurely afternoon before heading to Key West or winding down after your island adventure.

One of my favorite things about staying at The Luminary is its location. You can easily park the car and spend the rest of the evening on foot.

Afternoon

Spend time exploring downtown Fort Myers:

• Browse local boutiques
• Walk along the riverfront
• Visit the Fort Myers Mural Society murals
• Stop into local art galleries
• Grab coffee from a downtown café

Dinner

Downtown Fort Myers has become one of Southwest Florida’s best dining destinations. While you have plenty of places to choose from, I recommend eating at Silver King Coastal Kitchen located in The Luminary.

Rooftop Drinks

Before calling it a night, head upstairs to Beacon Social Drinkery, the hotel’s rooftop bar.

The views over the Caloosahatchee River are spectacular, especially at sunset.

It’s the perfect place to toast the beginning—or end—of your Key West getaway.

Frequently Asked Questions About Traveling from Naples to Key West

How far is Key West from Naples, Florida?

Key West is approximately 271 miles from Naples. Depending on traffic and your method of transportation, the trip typically takes between 5 and 6 hours.

Is it quicker to drive or take the Key West Express?

The Key West Express is usually slightly faster.

The drive from Naples to Key West typically takes about 4.5 to 5.5 hours, depending on traffic along the Overseas Highway.

The Key West Express ferry from Fort Myers Beach takes approximately 3.5 to 4 hours, but you’ll also need to factor in the drive from Naples to Fort Myers Beach, check-in time, and boarding.

That said, many travelers find the ferry less stressful because they can relax, read, enjoy a drink, or watch for dolphins instead of focusing on traffic.

What is the fastest way to get from Naples to Key West?

Flying is generally the fastest option.

While there are not always direct flights available, flying can significantly reduce travel time compared to driving or taking the ferry.

However, flights are usually the most expensive option.

Is the Key West Express worth it?

In my opinion, yes.

The ferry transforms transportation into part of the vacation experience. Instead of spending hours behind the wheel, you can relax, enjoy the views, read a book, play cards, or grab a drink from the onboard bar.

For many Southwest Florida residents, it’s one of the easiest and most enjoyable ways to visit Key West. See my full review of the Key West Express here.

Can you do a day trip from Naples to Key West?

Technically, yes.

However, I wouldn’t recommend it.

By the time you account for travel time, you’ll spend much of your day getting there and back. Key West is best enjoyed with at least one overnight stay so you can experience the sunset, nightlife, beaches, and unique atmosphere of the island.

How many days do you need in Key West?

I recommend spending at least two nights in Key West.

This gives you enough time to explore Duval Street, visit popular attractions, enjoy the beaches, watch the sunset at Mallory Square, and experience the laid-back island lifestyle.

Three nights is even better if your schedule allows.

Is driving the Overseas Highway worth it?

Absolutely.

The Overseas Highway is considered one of the most scenic drives in the United States. The route takes travelers across dozens of bridges while offering spectacular ocean views throughout the Florida Keys.

If you’ve never driven it before, it’s worth experiencing at least once.

Is Key West family-friendly?

Yes.

While Key West is known for its nightlife, there are plenty of family-friendly activities including Smathers Beach, the Key West Aquarium, the Butterfly Conservatory, the Ernest Hemingway Home, Truman Waterfront Park, fishing, snorkeling, and sunset cruises.

We visited with our three boys and found plenty to keep everyone entertained.

What is the best time of year to visit Key West?

Winter and spring are the most popular times to visit because of the comfortable temperatures and lower humidity.

However, these months also bring larger crowds and higher hotel prices.

Summer can be hot, but it’s often easier to find deals on accommodations and attractions. We have visited during rainy season and I can confidently say that a rainy day in Key West is still a great day in Key West.

Should I stay overnight in Fort Myers before taking the Key West Express?

If you have the flexibility, it can make the trip more relaxing.

Staying in Fort Myers or Fort Myers Beach the night before allows you to avoid an early morning drive from Naples and arrive at the ferry terminal with plenty of time to board and secure good seats.

What is the best area to stay in Key West?

It depends on your travel style.

If you prefer beach access, a resort atmosphere, and a quieter setting, staying near Smathers Beach is a great option. We enjoyed our stay at Margaritaville Beach House Key West because it offered easy beach access while still providing a complimentary shuttle into downtown.

If you want to be within walking distance of Duval Street and nightlife, consider staying in Old Town.

Is Key West worth visiting from Naples?

Without question.

One of the things I love most about Key West is how different it feels from Naples. The colorful architecture, historic streets, live music, sunsets, and laid-back atmosphere create a completely different Florida experience.

Whether you’re a local looking for a staycation or a visitor exploring Southwest Florida, Key West is well worth adding to your itinerary.

Why This Itinerary Works So Well

What I love most about this itinerary is that it feels much bigger than a three-night getaway.

In just a few days, you’ll experience:

• A relaxing waterfront resort
• A scenic ferry ride across the Gulf
• Historic Old Town Key West
• Duval Street
• Smathers Beach
• Key West sunsets
• Island dining and nightlife

Most importantly, you’ll discover a side of Florida that feels completely different from Naples.

If you’re looking for a long weekend getaway that’s easy to plan but unforgettable to experience, this Naples-to-Key West itinerary is hard to beat.