Planning a getaway to Naples, Florida? Three nights is just enough time to get a taste of what makes this little slice of Southwest Florida so special. Think mornings by the Gulf, afternoons exploring town, sunset dinners, and plenty of time to slow down by the pool.

When you stay with Navigate Naples, you have more than just a place to stay. Our dedicated team is here to help you experience Naples like a local, from our favorite restaurants and beaches to activities, excursions, and in-home experiences.

Not sure where to begin? Here’s how we’d spend three perfect days in Naples.

Day 1: Beach Day + Night Out

There’s only one way to start a Naples vacation: head straight to the Gulf.

Spend your first morning at Vanderbilt Beach , one of our go-to beach spots in North Naples. Pack your swimsuit, cover-up, flip-flops, sunscreen, hat, sunglasses, and a good book, then settle in for a relaxing morning by the water.

Another beautiful option nearby is Delnor-Wiggins Pass State Park, known for its natural shoreline and clear Gulf waters.

Before packing all of your beach gear from home, check the amenities at your Navigate Naples vacation rental. All of our homes include beach towels, chairs, an umbrella, cooler, and beach toys! 

Once you’ve had enough sun, head back to your vacation rental, cool off, and get ready for dinner.

For your first evening, make a reservation at The Turtle Club. It’s one of our favorite recommendations for watching the sunset while enjoying dinner near the water, and reservations are definitely recommended.

Another favorite is BALEEN, where you can dine along the beach. For an extra-relaxed evening, check out the firepits on the sand, which are first come, first served and offer food and drinks.

After dinner, head back to your Navigate Naples vacation rental for a quiet night before another full day of exploring.

What to pack for Day 1: Swimsuit, cover-up, flip-flops, sunscreen, hat, sunglasses, book, tote bag, dinner outfit, sandals, and a lightweight layer.

Day 2: Coffee + Shopping + A Night at Mercato

Start day two with coffee at one of our local favorites.

If you’re staying in North Naples, stop by Narrative Coffee Roasters at Mercato for your morning coffee before heading out for the day. Acopio Coffee is another great option nearby.

Then it’s time for a little shopping.

Spend the afternoon at Waterside Shops, where you’ll find an open-air setting filled with designer stores, boutiques, restaurants, and plenty of palm trees. Wear a comfortable daytime outfit and walking shoes, and don’t forget your sunglasses and some water.

If you have extra time, you can also explore The Village Shops on Venetian Bay, Fifth Avenue South, or Third Street South for even more shopping and dining.

Head back to your vacation rental in the late afternoon to relax and get ready for a night at Mercato.

Start with dinner at Bar Tulia Mercato for Italian-inspired dishes and cocktails, or keep things casual at The Hampton Social or Rocco’s Tacos & Tequila Bar.

Not ready for the night to end? Mercato has plenty of options within walking distance. Stop by Beeline for cocktails or head to Blue Martini Lounge for a livelier night out.

For something a little different, Estia is another Navigate Naples favorite for dinner and cocktails, especially if you’re looking to keep the night going. On weekends, they have a DJ beginning later in the evening.

What to pack for Day 2: Comfortable daytime outfit, walking shoes, sunglasses, reusable water bottle, a nice dinner outfit, sandals or heels for women, and a lightweight sweater.

Day 3: Explore Naples + Pool Day

For your final day, enjoy a slower morning.

Grab coffee and breakfast, then choose your own adventure for the morning. Rent bikes and explore the area, get out on the water, or simply take one last walk along the beach.

If you want to explore Naples on two wheels, Big Momma’s Bicycles is one of the options included in our local guide. If getting out on the water sounds more your speed, our Navigate Naples team can also help point you toward boating and other local excursions.

Then head back to your vacation rental and spend the afternoon doing absolutely nothing but enjoying the sunshine.

Most of our Navigate Naples homes feature private pools and outdoor living spaces, so some of the best vacation days happen without ever leaving your vacation rental.

Put on your swimsuit, grab a book, bring your favorite snacks and drinks outside, and enjoy one last afternoon in the Florida sunshine.

And if you don’t feel like getting ready to go out again that evening, make it a night in.

Navigate Naples can help arrange in-home experiences that make staying in feel just as special as going out. Depending on what you’re looking for, that could mean a private chef, bartender, charcuterie board, or another personalized experience right at your vacation rental.

If you do want one last dinner out, consider Gumbo Limbo at The Ritz-Carlton, a casual tiki-style restaurant right by the beach, or head to The Bay House for your final Naples dinner.

What to pack for Day 3: Casual clothes, comfortable shoes, swimsuit, cover-up, hat, sunscreen, book, and your favorite poolside outfit.

What You Can Leave at Home

One of the best parts about staying with Navigate Naples? You may be able to pack a little lighter.

All of our vacation rentals are fully stocked so you can settle right in and enjoy. Here’s a list of some of the essentials you’ll find waiting for you:

Beach towels
Bath towels
Washcloths
Basic toiletries
Kitchen gear
Beach umbrellas
Beach chairs
Beach toys

Less time packing means more time getting excited for your Naples getaway.

Make Your 3 Days in Naples Your Own

The best Naples itineraries leave room to slow down.

Maybe your morning at Vanderbilt Beach turns into an entire beach day. Maybe you skip shopping and spend the afternoon by your private pool. Or maybe you decide you want to get out on the water and see Naples from a completely different perspective.

That’s the beauty of vacationing here.

When you stay with Navigate Naples, our local recommendations and concierge services can help you make the most of your time, whether you’re looking for the perfect dinner spot, a day on the water, an in-home experience, or simply the best place to watch the sunset.

Three days may go quickly, but with a little beach time, great food, shopping, exploring, and plenty of time by the pool, you’ll get a pretty good taste of the Naples lifestyle.

Ready to spend three days in paradise?

Find your perfect Naples vacation rental with Navigate Naples and start planning your stay.

Where to Stay: 9320 Vanderbilt

Looking for the perfect home base for your Naples getaway? 9320 Vanderbilt Drive is conveniently located near Vanderbilt Beach and Mercato, putting you close to many of the stops on this itinerary.

The five-bedroom home features a private pool and spa, outdoor entertaining spaces, two kitchens, and plenty of room for families and groups. It’s also stocked with beach chairs, towels, toys, an umbrella, coolers, and pool floats, making it even easier to pack light.

Come stay awhile with Navigate Naples.