The Best Places for Sightseeing in Florida

Yes, it’s beaches and sunshine. Yes, it’s theme parks and palm trees. But it’s also Art Deco neighborhoods that feel like film sets, quiet island roads lined with sea grapes, historic coastal towns, and wildlife-rich waters where dolphins and manatees appear like they belong in the itinerary.

If you’re planning a trip built around exploring – not just relaxing – Florida is one of the most rewarding states in the country to travel through. The best sightseeing days here might include a sunrise walk on sugar-white sand, a museum afternoon under tropical skies, and a sunset boat ride where the only soundtrack is the water.

This Wander guide covers the best places for sightseeing in the Sunshine State, from iconic coastal cities to island escapes and scenic shoreline drives. And, we explore luxury Florida vacation rentals – highlighting the perfect bases for you to return to after long, sunny days of sightseeing.

1. Miami (Best for Culture, Architecture, and Iconic Florida Energy)

Miami is Florida’s most cinematic city. The skyline rises from Biscayne Bay, pastel Art Deco buildings glow under the sun, and entire neighborhoods feel like curated worlds – from Little Havana’s Cuban cafés to Wynwood’s open-air galleries.

For sightseeing, Miami delivers variety. You can do a full day of exploring without ever repeating the same atmosphere twice.

Best sightseeing experiences in Miami

• Walk Ocean Drive for Art Deco architecture and that classic Miami Beach vibe

• Explore Wynwood Walls, where street art turns entire blocks into an outdoor museum

• Visit Little Havana for cafés, cigar shops, and Domino Park

• Spend an afternoon at Pérez Art Museum Miami (PAMM)

• Take a sunset cruise across Biscayne Bay for skyline views

Travel tips for Miami sightseeing

• Start early – Miami heat builds fast, even outside summer

• Plan one “culture day” and one “beach day” for balance

• For the best skyline photos, visit Biscayne Bay at golden hour

Where to stay in Miami

Wander Miami Waterfront – 10 guests, 5 bedrooms
This five-bedroom retreat offers a calmer, more private side of Miami. With space for ten guests, it’s an ideal home base for families or groups who want to sightsee all day and return to a peaceful waterfront setting at night. A pool, hot tub, and serene outdoor space make it easy to unwind between city adventures.

2. Orlando & Kissimmee (Best for Family Sightseeing and Iconic Attractions)

The Orlando and Kissimmee area is a sightseeing destination on its own scale. It’s not just theme parks – it’s immersive entertainment, world-famous attractions, and the kind of experiences that feel like they were designed to impress every age group at once.

October through spring is especially ideal for sightseeing here, with more comfortable temperatures and a packed calendar of events.

Best sightseeing experiences in Orlando & Kissimmee

• Spend a day at Walt Disney World for iconic rides, shows, and fireworks

• Visit Universal Orlando Resort, especially for Harry Potter fans

• Explore ICON Park for panoramic city views

• Take a boat ride through Winter Park, one of the prettiest neighborhoods nearby

• Visit Gatorland for a classic Florida wildlife experience

Travel tips for Orlando sightseeing

• Build in rest days – sightseeing here can be surprisingly exhausting

• Arrive early to major parks for shorter lines and cooler weather

• Stay in a large home if traveling with family groups – it makes the trip feel smoother

Where to stay in Kissimmee

Wander Orlando Sanctuary – 28 guests, 12 bedrooms
This twelve-bedroom estate sleeps up to twenty-eight guests, making it ideal for large families or multi-family trips. With room to spread out and recharge, it turns a theme park vacation into a luxury retreat. It’s the kind of stay where sightseeing days end with pool time and relaxed evenings at home instead of another crowded restaurant.

Where to stay in Orlando

Wander Orlando Tideview – 6 guests, 4 bedrooms
Designed for smaller groups or families who want privacy and comfort, this four-bedroom retreat sleeps six guests and provides an easy base for exploring Orlando’s attractions. It’s ideal for travelers who want sightseeing by day and quiet evenings away from the crowds.

3. Destin (Best for Coastal Scenery and Emerald Water Views)

Destin is the Emerald Coast at its most dramatic – bright white sand, water that looks unreal, and a harbor that feels lively without becoming chaotic. It’s a destination where sightseeing doesn’t mean museums and monuments. Here, the sights are natural: the coastline, the sunsets, the boats, the color of the Gulf.

If you want Florida sightseeing that feels open-air and effortlessly beautiful, Destin belongs at the top of your list.

Best sightseeing experiences in Destin

• Walk the Destin Harbor Boardwalk for boat views and waterfront energy

• Visit Henderson Beach State Park for dunes and quiet coastal trails

• Take a dolphin cruise or sunset sail on the Gulf

• Explore Crab Island (by boat) for shallow-water scenery

• Drive Scenic Highway 98 for Gulf views

Travel tips for Destin sightseeing

• Book boat excursions early – they sell out fast in peak seasons

• Plan beach sightseeing early morning for softer light and fewer crowds

• Destin is best experienced outdoors, so pack accordingly

Where to stay in Destin

Wander Destin Harborfront – 18 guests, 7 bedrooms
This seven-bedroom luxury retreat sleeps up to eighteen guests and feels made for Destin’s harbor lifestyle. With expansive gathering spaces and a waterfront setting, it’s ideal for large groups who want to explore the coast, take boat days, and return to a private home that feels like a resort.

4. Inlet Beach (Best for Scenic 30A Drives and Coastal Town Sightseeing)

Inlet Beach is one of the most visually stunning corners of Florida. It sits near Scenic Highway 30A, where architecture feels intentional, beach towns feel curated, and the coastline is lined with dune lakes, boardwalks, and pastel storefronts.

This is Florida sightseeing with a softer, more refined aesthetic – the kind of place where even a simple bike ride feels like an experience.

Best sightseeing experiences in Inlet Beach & 30A

• Bike along Scenic Highway 30A through beach towns and coastal trails

• Visit Rosemary Beach for boutique streets and architecture

• Explore Alys Beach for striking whitewashed design and hidden courtyards

• Stop at Camp Helen State Park for trails and dune lake views

• Spend time near coastal dune lakes, a rare natural feature

Travel tips for 30A sightseeing

• Renting bikes is one of the best ways to explore

• Sunrise and sunset offer the most beautiful light for coastal scenery

• Restaurants fill up quickly on weekends – plan ahead

Where to stay in Inlet Beach

Wander Inlet Beach Timber – 6 guests, 2 bedrooms
This two-bedroom retreat sleeps six guests and offers a refined, peaceful base near Florida’s most scenic coastline. It’s perfect for couples or small families who want to spend their days exploring 30A’s beach towns, dune lakes, and coastal parks – then return to a calm, luxury space that feels tucked away.

5. Sarasota (Best for Museums, Waterfront Views, and Refined Coastal Culture)

Sarasota is where Florida feels elegant. The city blends Gulf Coast scenery with cultural depth – art museums, gardens, and waterfront views that make sightseeing feel layered rather than one-note.

It’s a great destination if you want a trip that balances beach time with architecture, history, and a slower pace.

Best sightseeing experiences in Sarasota

• Visit The Ringling Museum, a landmark cultural attraction

• Explore the Ringling gardens and waterfront views

• Walk the Sarasota bayfront for sunset scenery

• Take a day trip to nearby barrier islands

• Enjoy local galleries and arts districts

Travel tips for Sarasota sightseeing

• Pair museum visits with beach afternoons for a balanced itinerary

• Sarasota is ideal in fall through spring when temperatures are milder

• Plan a day trip to Siesta Key for iconic sand and sunsets

Where to stay in Sarasota

Wander Sarasota Luxury – 18 guests, 8 bedrooms
This eight-bedroom estate sleeps up to eighteen guests and offers a high-end base for a Sarasota sightseeing trip. Spacious interiors and resort-style amenities make it perfect for groups who want to explore by day and unwind in style by night. It’s an ideal choice for family gatherings or milestone trips with a refined Gulf Coast feel.

6. Siesta Key (Best for Beach Sightseeing and Sunset Scenery)

Siesta Key is famous for its sand – powdery, bright, and almost unreal in the afternoon sun. But beyond the beach itself, sightseeing here is about atmosphere: warm Gulf evenings, calm water, and sunsets that feel like a daily event.

This is Florida sightseeing at its simplest and most beautiful.

Best sightseeing experiences in Siesta Key

• Spend time at Siesta Beach, one of the most iconic in the U.S.

• Walk to Crescent Beach for a quieter shoreline

• Explore Siesta Key Village for shopping and casual dining

• Take a kayak tour through mangroves and bay waters

• Plan a sunset beach picnic

Travel tips for Siesta Key sightseeing

• Arrive early for the best beach conditions and parking

• Sunset is the must-do sightseeing moment here

• Gulf waters stay warm long into fall

Where to stay in Siesta Key

Wander Siesta Key Haze – 11 guests, 5 bedrooms
This five-bedroom luxury home sleeps up to eleven guests and offers a beautiful base for Gulf Coast sightseeing. With generous space and elevated design, it’s ideal for groups who want beach days, sunset walks, and the kind of Florida evenings that don’t need much planning – just time outside.

7. Marco Island (Best for Wildlife Sightseeing and Gulf Coast Nature)

Marco Island feels calm, polished, and close to nature. Sightseeing here is less about busy attractions and more about the environment: mangroves, lagoons, wildlife cruises, and wide Gulf sunsets.

It’s one of the best Florida destinations for travelers who want natural sightseeing that still feels luxurious.

Best sightseeing experiences in Marco Island

• Take a boat tour through the Ten Thousand Islands

• Look for dolphins, manatees, and coastal birds

• Visit Tigertail Beach for long shoreline walks and shelling

• Enjoy sunset views along the Gulf

• Book a fishing charter for classic coastal Florida scenery

Travel tips for Marco Island sightseeing

• Morning wildlife tours often offer the best sightings

• Pack binoculars if you enjoy nature watching

• Marco Island is ideal for slow-paced sightseeing with plenty of downtime

Where to stay in Marco Island

Wander Marco Vista – 10 guests, 5 bedrooms
This five-bedroom retreat sleeps up to ten guests and is a perfect base for Marco’s waterfront sightseeing. It’s designed for travelers who want relaxed luxury: space for families, outdoor living, and easy access to boating, beach time, and sunset-focused days.

8. Sanibel (Best for Shelling, Wildlife, and Scenic Island Sightseeing)

Sanibel feels like Florida’s quieter side – where sightseeing is built around nature rather than nightlife. The beaches are famous for shelling, the biking paths are scenic and peaceful, and wildlife preserves give the island a slow, restorative atmosphere.

It’s a destination where the sights are subtle, but unforgettable.

Best sightseeing experiences in Sanibel

• Go shelling early in the morning along the shoreline

• Visit J.N. “Ding” Darling National Wildlife Refuge

• Bike the island’s trails for nature views

• Explore the lighthouse area and coastal paths

• Take a boat tour for dolphin sightings

Travel tips for Sanibel sightseeing

• Shelling is best at low tide

• Sanibel is best enjoyed slowly – plan fewer activities per day

• Bring bikes or rent them for the full island experience

Where to stay in Sanibel

Wander Sanibel Views – 6 guests, 3 bedrooms
This three-bedroom beachfront retreat sleeps six guests and offers direct access to the island’s natural beauty. Designed with luxury finishes and a refined atmosphere, it’s ideal for travelers who want quiet mornings, scenic biking afternoons, and Gulf sunsets right outside their door.

9. Captiva (Best for Scenic Island Views and Golden Hour Sunsets)

Captiva is where Florida feels most cinematic. The island is lush and quiet, the beaches are wide, and the sunsets are legendary. Sightseeing here is simple: walk the shoreline, watch the sky change color, and enjoy the kind of calm that feels rare.

Captiva is perfect for travelers who want their Florida trip to feel private and immersive.

Best sightseeing experiences in Captiva

• Watch sunset from the beach (Captiva is famous for it)

• Take a boat tour around nearby islands

• Explore coastal wildlife and shelling beaches

• Enjoy long beach walks with minimal crowds

• Visit nearby island restaurants for waterfront dining

Travel tips for Captiva sightseeing

• Plan your day around sunset – it’s the main event

• Stock up on supplies early; island options are limited

• Captiva is ideal for couples or families seeking a slower pace

Where to stay in Captiva

Wander Captiva Bayfront – 8 guests, 4 bedrooms
This four-bedroom bayfront home sleeps eight guests and offers an elevated island base with beautiful water views. It’s ideal for families or small groups who want to explore Sanibel and Captiva, enjoy beach days, and spend evenings watching the sky shift over the water.

10. Mexico Beach (Best for Quiet Coastal Sightseeing on the Forgotten Coast)

Mexico Beach is part of Florida’s “Forgotten Coast” – a stretch of shoreline that feels undeveloped, calm, and refreshingly real. Sightseeing here is about wide beaches, soft sunsets, and coastal drives where you can go miles without seeing crowds.

It’s a perfect destination if your idea of sightseeing is scenic, slow, and natural.

Best sightseeing experiences in Mexico Beach

• Walk uncrowded beaches and watch the sun rise over the Gulf

• Visit nearby state parks for coastal trails

• Take a day trip to Cape San Blas for dunes and nature views

• Enjoy fresh seafood in small local restaurants

• Explore scenic coastal drives with stops along the water

Travel tips for Mexico Beach sightseeing

• Plan for quiet travel – nightlife is minimal

• Pack supplies if you want to cook at home

• This area is best for travelers who want calm over activity

Where to stay in Mexico Beach

Wander Mexico Beach Serenity – 12 guests, 5 bedrooms
This five-bedroom coastal retreat sleeps twelve guests and offers the kind of space that makes a slow Gulf Coast trip feel effortless. It’s ideal for families or groups looking for privacy, scenic beach days, and the relaxed atmosphere that defines the Forgotten Coast.

11. Jacksonville & Flagler Beach (Best for Atlantic Coast Sightseeing and Scenic Drives)

Florida’s Atlantic coast has a different feel than the Gulf – a little wilder, a little breezier, and perfect for scenic driving. Flagler Beach offers relaxed beach-town sightseeing with easy access to Northeast Florida highlights like St. Augustine and coastal parks.

It’s a great option if you want to see a quieter, more natural side of Florida.

Best sightseeing experiences near Flagler Beach

• Drive the scenic A1A for Atlantic views

• Explore Flagler Beach’s pier and shoreline walks

• Visit nearby St. Augustine, the oldest city in the U.S.

• Stop at coastal parks and lookout points

• Spend time in beach cafés and local shops

Travel tips for Flagler Beach sightseeing

• Plan a day trip to St. Augustine for historic sightseeing

• Atlantic beaches can be breezier – pack light layers

• Sunrise is especially beautiful on this side of Florida

Where to stay near Flagler Beach

Wander Flagler Beach Modern – 8 guests, 4 bedrooms
This four-bedroom retreat sleeps eight guests and offers a stylish, comfortable base for Atlantic Coast sightseeing. It’s perfect for families or small groups who want to explore Flagler Beach, drive the coastline, and experience Florida’s historic northeast without the crowds of bigger resort towns.

What Makes Florida So Good for Sightseeing?

Florida’s best sightseeing isn’t always about landmarks – it’s about variety. Few states offer this much contrast in one trip:

• City skylines and Art Deco neighborhoods

• Wildlife-rich mangroves and island coastlines

• Theme park spectacle and quiet beach-town calm

• Emerald Gulf water and rugged Atlantic shores

You can build a trip that feels fast-paced and iconic, or slow and restorative – often without changing your flight plan.

Make Your Florida Sightseeing Trip Feel Effortless with Wander

Florida rewards travelers who slow down enough to see it properly.

Whether you’re exploring Miami’s culture, chasing sunsets in Captiva, driving 30A’s scenic coastline, or planning a family theme park trip through Orlando, the right home base changes everything. Wander’s luxury vacation rentals across Florida make sightseeing feel smoother – giving you space, privacy, and resort-level comfort between every adventure.

From waterfront retreats to island escapes and family-sized estates, these homes aren’t just places to stay. They’re part of the journey.