Imagine combining the best of Florida’s local cuisine with stunning lakeside scenery in one memorable experience. That’s precisely what the Winter Haven Food Tour & Tipsy Sunset Cruise offers. Priced at $165 per person and lasting about three hours, this tour takes you through the heart of Winter Haven, blending delicious bites with breathtaking views.
Our guide, whose name I wish I remembered (they’re friendly and informative), led us through a carefully curated route. We loved the variety—starting with a coffee and muffin stop at the site of the original Publix supermarket, which offers a hint of local history right alongside your morning caffeine. Then, at The Treasured Olive, we experienced the delightful flavors of infused olive oils and creamy gelato, making it clear why this shop is a crowd favorite. Later, sampling spring rolls and dumplings at Thai Haven provided a perfect contrast—satisfying, flavorful, and authentic Asian cuisine. The tour wraps up at a charming bakery, where we indulged in cakes and cookies.
A highlight that sets this tour apart is the combined experience—not just eating but also relaxing on a scenic sunset cruise, sipping cocktails and taking in lakeside vistas. We especially appreciated this touch of relaxation after an active walk through town. One minor consideration: the cost doesn’t include alcoholic drinks, so plan to bring your own or purchase drinks during the cruise. This experience is best suited for those who enjoy good food, a bit of walking, and relaxing scenery—perfect for couples, friends, or anyone wanting a taste of true Florida charm.
Key Points

- Authentic Local Cuisine: Multiple stops featuring regional and Asian flavors.
- Scenic Sunset Cruise: A relaxing way to enjoy Winter Haven’s lakes and waterways.
- Informative Guide: Knowledgeable, friendly guides enhance the experience.
- Flexible Booking: Cancel up to 24 hours in advance for a full refund.
- Value for Price: Combines food and scenic views for a solid 3-hour outing.
- Accessible & Family-Friendly: Wheelchair accessible and suitable for a variety of travelers.
An In-Depth Look at the Winter Haven Food Tour & Tipsy Sunset Experience

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Starting Off with a Local Flavor
From the moment we met outside the parking garage on 3rd Street NW, we felt this tour would be a relaxed yet engaging adventure. Our guide quickly set a friendly tone, explaining that we’d explore Winter Haven’s culinary gems and learn about the city’s history along the way. The first stop is simple but meaningful: coffee and muffins at the original site of a Publix supermarket. This early glimpse into the town’s retail roots makes this stop more than just a caffeine kick; it’s about appreciating the area’s development.
Tasting the Olive Oils and Gelato at The Treasured Olive
Next, we crossed over to The Treasured Olive, a shop that invites you to sample infused olive oils and artisanal gelato. We loved the way the owner explained the different oil infusions—think garlic, basil, and lemon—highlighting how they can elevate everyday dishes. The gelato was smooth and bursting with flavor, a perfect palate cleanser before the next culinary chapter.
Asian Flavors at Thai Haven
Walking into Thai Haven, the scent of spices and fresh ingredients instantly put us in a good mood. We sampled spring rolls and dumplings, both of which were fresh, flavorful, and crafted with care. The authenticity was noticeable, and the portion sizes were generous, leaving us satisfied but eager for the next stop. Several reviews mentioned how the Asian cuisine provided a satisfying contrast to the earlier stops—something you’ll appreciate if you enjoy diverse flavors.
More Great Tours NearbySweet Endings at a Local Bakery
Our final tasting was at a cozy bakery, where we sampled cakes and cookies. The desserts were rich without being overly sweet, and the variety offered a satisfying conclusion to the food portion of the tour. Several guests appreciated how the bakery’s treats made for a perfect snack to enjoy during the next part of the experience.
Scenic Sunset Cruise: The Perfect Finish
After walking and tasting for about two hours, we boarded the Tipsy Sunset Cruise—a boat that takes you across Winter Haven’s lakes and waterways. We loved the stunning views of the sunset reflecting off the water, combined with the gentle sway of the boat. Though alcoholic drinks aren’t included, you can bring your own or purchase cocktails on board, making for a relaxed, social atmosphere. The cruise offers a different perspective on the town, exposing you to the natural beauty that defines Winter Haven. Several reviews highlighted how peaceful and scenic the cruise was, especially as the sun dipped below the horizon.
Practical Details and Tips
This tour usually runs in the afternoon, making it a perfect way to spend a leisurely early evening. The group size is manageable, allowing for personal interaction with your guide and a more intimate experience. The walk involves some moderate walking, so comfortable shoes and weather-appropriate clothing are recommended. Since the tour is wheelchair accessible, it’s adaptable for most guests.
The price of $165 covers all food tastings, your guide, and the cruise, but keep in mind that alcoholic drinks are extra. When considering value, it’s an all-in-one outing that combines culinary delights with scenic relaxation, which many guests found to be a worthwhile investment.
Why This Tour Works Well for Travelers

This experience is ideal for food lovers who want to explore regional flavors without a lot of fuss. It’s also perfect for those who enjoy scenic views and relaxing boat rides—great for couples or groups of friends looking for a memorable outing. If you appreciate authentic local eats and a laid-back vibe, you’ll find this tour hits the right notes. Families with older children might enjoy it too, especially if they’re interested in both food and nature.
The Sum Up

The Winter Haven Food Tour & Tipsy Sunset Cruise offers a well-rounded taste of what makes this Florida town special. You’ll walk away with a deeper appreciation for local and Asian cuisine, plus a stunning view of the lakes that define Winter Haven’s landscape. The combination of delicious bites, informative storytelling, and scenic tranquility makes this a compelling choice for travelers seeking both culinary and visual delight.
While the price might seem steep for some, consider that it includes a variety of tastings, a guided experience, and a scenic boat ride—all in one package. If you’re looking for a relaxed yet engaging way to enjoy Florida’s culinary and natural beauty, this tour is a solid pick.
This experience is particularly suited for those who value authentic local food, love scenic views, and enjoy learning about a town’s character through its flavors and landscapes. It’s a balanced, enjoyable outing that leaves you feeling satiated—both in belly and in soul.
FAQ
What is the duration of the tour?
The tour lasts approximately three hours, typically scheduled in the afternoon, making it a perfect early evening activity.
What is included in the price?
The fee covers your tour guide, food tastings at multiple stops, coffee and/or tea, and the scenic sunset cruise.
Are alcoholic drinks included?
No, alcoholic beverages are not included. You are welcome to bring your own or purchase cocktails during the cruise.
Where do I meet the tour?
You should meet outside the Parking Garage at 3rd Street NW and Ave A NW. The guide will be waiting there to start your adventure.
Is the tour wheelchair accessible?
Yes. The tour provider states that it is wheelchair accessible, making it accommodating for most guests.
Can I cancel if my plans change?
Absolutely. You can cancel up to 24 hours in advance for a full refund, offering flexibility in planning.
What should I wear?
Dress comfortably for walking and the weather, as the tour involves some outdoor strolling. Good walking shoes are recommended.
Does the tour include enough food?
Yes, each stop offers generous tastings, including regional bites, Asian dishes, and desserts, making it a satisfying experience.
Is this tour suitable for children?
While primarily geared towards adults, older children who enjoy food and scenic boat rides will likely enjoy the experience.
In sum, if you’re after a relaxed, flavorful, and scenic afternoon in Winter Haven, this tour delivers on all fronts. It combines the delicious and authentic with the visual and tranquil, giving you a well-rounded taste of what makes this town worth exploring.
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