Orlando Like a Local Off the Beaten Path Private Tour

Discover Local Orlando on a Private Off-the-Beaten-Path Tour

If you’ve ever visited Orlando, you’re probably thinking about its world-famous theme parks, but this private tour offers a refreshing alternative—authentic, local experiences that reveal the city’s hidden treasures. Priced at just $96 per person for roughly six hours, this tour is ideal for travelers who want a personalized, relaxed look at Orlando beyond its touristy reputation. Guided by Brittany, you’ll enjoy private hotel pickup, which means no need to worry about navigating busy streets or figuring out public transit.

Two aspects we especially love about this experience are the visit to historic downtown Orlando with handcrafted cocktails, and the scenic boat tour through Winter Park’s canals. These moments provide genuine local flavor and a sense of place that big theme parks simply can’t offer.

A potential consideration is that this tour involves some walking and outdoor time—so it’s best suited for those comfortable with moderate activity levels. Also, unlike large group tours, you should be prepared to purchase your own food and drinks at various stops, which adds a bit of flexibility but also some planning.

This experience suits travelers looking for something authentic and intimate, especially those eager to explore Orlando’s hidden corners, local cuisine, and scenic waterways. If you want a break from Disney and Universal, but still crave a well-organized, engaging day of discovery, this private tour delivers.

Key Points

• Personalized Experience: A private tour led by Brittany ensures a flexible, tailored exploration of Orlando’s lesser-known spots.
• Cultural & Scenic Highlights: From historic downtown to scenic boat rides, the tour offers a well-rounded glimpse of the city’s charm.
• Local Flavors: Enjoy handcrafted cocktails, tapas, wines, oysters, and craft beers—perfect for food and drink lovers.
• Convenient Transport: Includes private pickup, a scenic train ride, and boat tour, making logistics smooth and enjoyable.
• Flexible & Private: Only your group participates, offering intimacy and the chance to customize your experience.
• Cost & Value: At $96, the tour packs in multiple activities and sights, making it a good value for those seeking authentic Orlando.

A Deep Dive into the Orlando Like a Local Tour

Starting Off: Hassle-Free Hotel Pickup & Downtown Orlando

Your day begins at Westgate Lakes Resort & Spa with a private pickup—a real perk that sets a relaxed tone. Brittany, your guide, greets you with a friendly welcome, promising a day of local discovery. The first stop is Downtown Orlando, a vibrant area often overlooked by visitors fixated on the theme parks.

Here, you’ll unwind at The Wellborn, a charming spot tucked away with beautiful garden surroundings. It’s a perfect setting for handcrafted cocktails and tapas, giving you a taste of Orlando’s quieter, sophisticated side. As one reviewer noted, “We loved the way the garden oasis felt like a secret retreat in the city.” This spot highlights the city’s ability to surprise with hidden gems that offer both ambiance and quality drinks.

Next, a leisurely stroll through Lake Eola Park showcases Orlando’s iconic scenery. You’ll see the lively swan boats, the city skyline, and lush green spaces—great for photos or simply soaking in the local vibe. Many travelers appreciate the chance to escape the crowds and enjoy some peaceful outdoor time.

Exploring Orlando’s Hidden Corners: Orange Avenue & Corona Cigar Co.

Your journey continues along Orange Avenue, famous for its lively nightlife and boutique shops. The highlight here is Corona Cigar Co., home to one of the world’s largest humidors. Whether you’re a cigar enthusiast or just curious, stepping inside offers a taste of Orlando’s luxury side. One reviewer remarked, “It’s like stepping into a cigar-lover’s paradise—impressive selection and knowledgeable staff.”

Scenic Ride to Winter Park: SunRail & Charming Park Avenue

A scenic train ride aboard SunRail takes you to Winter Park, a picturesque area known for its beautiful architecture and boutique shopping. The train ride itself is a highlight—it’s a local way to see the city and relax en route. Many find it a delightful change from driving or group bus tours.

Once in Winter Park, you’ll explore Park Avenue—a walkable street lined with wine bars, oyster shacks, and craft breweries. The tasting experience here is considered a real treat; sampling wines, oysters, and craft beers while browsing boutique shops offers a true taste of local leisure. Travelers have mentioned enjoying the delicious food and the lively atmosphere that makes Winter Park special.

The Grand Finale: Scenic Boat Tour on the Winter Park Chain of Lakes

The day winds down with what many rate as the most memorable part: a romantic boat tour cruising through the Winter Park Chain of Lakes. Gliding past historic estates, lush landscapes, and canals, you’ll see why this area is called the “Venice of Florida”. Several reviews mention the stunning views and peaceful atmosphere as highlights. As one guest put it, “It’s like a different world—so lush and elegant, with plenty of photo opportunities.”

This final stretch encapsulates the tour’s focus on authentic scenery and laid-back luxury, a perfect way to end your day.

What Travelers Can Expect

Transportation: The tour includes private hotel pickup, a scenic train ride, and a boat cruise—all designed for easy, relaxed travel without the hassle of parking or navigating unfamiliar streets.

Duration & Pacing: At approximately six hours, the tour balances sightseeing, tasting, and relaxation. You’ll have ample time at each stop without feeling rushed.

Food & Drink: While the tour features several excellent stops for local culinary experiences, guests are responsible for purchasing their own alcoholic beverages and snacks. This allows flexibility but requires some planning if specific dietary preferences are involved.

Group Size & Intimacy: As a private tour, only your group participates, allowing for personalized interaction and the chance to customize or linger at preferred spots.

Weather & Flexibility: The tour is weather-dependent—a clear day ensures smooth sailing, especially for the boat tour. Brittany offers options for rescheduling or refunds if weather conditions aren’t cooperating.

Authenticity & Value: Why This Tour Works

What makes this experience stand out is its focus on local flavor and scenic beauty. You get a personalized guide who offers insights into Orlando’s hidden stories and neighborhoods—something large, cookie-cutter tours can’t match. The inclusion of scenic boat rides and a train journey adds a leisurely, scenic dimension that elevates the experience from just sightseeing to truly enjoying the city’s laid-back, elegant side.

Though priced modestly, the tour packs in diverse activities—from cultural stops to scenic cruising—making it a cost-effective way to see more of Orlando without feeling like you’re rushing through.

Who Should Consider This Tour?

This tour is perfect for couples, small groups, or solo travelers who want an intimate, educational, and scenic experience. It’s especially suited for those interested in local culture, scenic waterways, and authentic city neighborhoods rather than the crowds and lines of theme parks. If you’re looking to savor Orlando’s hidden charms and enjoy a personalized day, this tour fits the bill.

Frequently Asked Questions

What is included in the tour?
The experience covers private transportation, a scenic train ride, and a boat tour on the Winter Park Chain of Lakes. You’ll visit downtown Orlando, Winter Park, and enjoy tastings at various local spots.

Are snacks or drinks included?
No, guests are responsible for purchasing their own alcoholic beverages, food, and snacks at the stops.

How long is the tour?
The tour lasts approximately six hours, from 10:00 am pickup to returning to the meeting point.

Is this a group or private experience?
It’s a private tour, meaning only your group participates, providing a more personalized experience.

What should I wear?
Comfortable casual clothing suitable for walking and outdoor activities. Bring sunscreen and a hat for sun protection, especially during outdoor stops and boat rides.

Can I customize the itinerary?
While the itinerary is planned, the private nature allows for some flexibility—discussing your interests with Brittany could enhance your experience.

Final Thoughts

This Orlando like a Local tour offers a rich, authentic look at a city often overshadowed by its famous theme parks. It’s ideal for those who value personalized attention, scenic views, and local flavors. The combination of cultural stops, excellent food and drink, and picturesque scenery makes this a memorable way to see Orlando from a different perspective.

It’s especially suitable for travelers seeking a relaxed, intimate, and scenic day that captures the essence of Orlando’s hidden gems rather than the crowded tourist spots. Whether you’re a history buff, a foodie, or just someone eager to uncover Orlando’s quieter side, this tour delivers a genuine, enjoyable experience.

Note: To ensure a seamless experience, check the weather forecast and plan to purchase your preferred snacks and drinks during stops. With its blend of beautiful scenery, local flavors, and personalized service, this tour is a wonderful choice for those wanting to experience Orlando like a true insider.