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Discover Winter Haven’s flavors with a foodie tour ending with a stunning sunset cruise, offering delicious tastings, scenic views, and local stories.
If you’re considering a way to savor the best of Winter Haven, Florida, this Food Tour & Tipsy Sunset Cruise offers a lively blend of local flavors and beautiful scenery. Designed for those who love good eats and relaxing views, this experience promises three hours filled with delightful bites and stunning lakeside vistas. Whether you’re a foodie eager to taste regional specialties or someone looking for a laid-back way to enjoy Florida’s waterways, this tour aims to satisfy both cravings.
What we particularly like about this tour is its combination of tasting local cuisine—from coffee and muffins to gelato and Asian dishes—and the relaxing sunset cruise that caps off the afternoon. Plus, the fact that it’s accessible and flexible with options like free cancellation makes it a practical choice. That said, keep in mind that alcoholic drinks are not included, so if you’re hoping for included cocktails on the cruise, you’ll need to budget extra. This tour suits curious travelers who appreciate authentic tastes and scenic relaxation, especially those wanting a full taste of Winter Haven’s local personality.

This tour, offered by Winter Haven Food Tours LLC, combines two distinct but complementary activities: a food crawl through some of Winter Haven’s favorite local spots and a sunset cruise across Central Florida’s lakes. Priced at $165, it offers an approachable window into the culinary and natural beauty of the region, all within a manageable three-hour window.
Starting Point & Timing
The meeting point is outside the Parking Garage at 3rd Street NW and Ave A NW. The tour typically runs in the afternoon, making it an ideal way to extend your day or prepare for dinner with a little pre-meal excitement. The group size is generally manageable, and the tour features a live English-speaking guide who adds local insights and humor along the way.
What’s Included & What’s Not
The tour includes the guide, coffee and/or tea, food tastings at various stops, and a lunch experience. However, alcoholic drinks are not included—so if you’re looking to sip cocktails during the cruise, you’ll want to bring some cash for drinks on board or purchase them beforehand.
Accessibility & Flexibility
Designed to be wheelchair accessible, the tour is also flexible with free cancellation up to 24 hours in advance, offering peace of mind for planning. You can reserve now and pay later, which is especially helpful if your plans are still fluid.
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Our journey begins with a warm welcome—literally—with coffee and muffins, a simple yet effective way to energize before the tastings begin. This stop also offers a peek into the local scene, perhaps seeing the original site of the Publix supermarket, giving a nod to Winter Haven’s place in Florida retail history.
Next, your taste buds will be introduced to infused olive oils and artisanal gelato at The Treasured Olive. This specialty shop is a highlight, especially for those who appreciate flavored oils and unique sweets. It’s a chance to learn how regional ingredients or local craftsmanship elevate everyday staples.
More Great Tours NearbyTraveling further, the group hits Thai Haven, where spring rolls and dumplings provide a satisfying taste of Asian flavors. The reviews mention that this stop is a favorite because of the authenticity and freshness of the dishes, giving a more global dimension to the local culinary scene. Expect to enjoy dishes that balance spices and textures, a good contrast to the earlier stops.
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The tour wraps up with a visit to a bakery, where cakes and cookies serve as a perfect sweet note. It’s a friendly, convivial ending that leaves everyone with a smile and a full stomach.

After the food adventure, the party moves to the lake for the Tipsy Sunset Cruise. While the tour itself doesn’t include alcohol, the cruise’s relaxing atmosphere and lakeside views make it a prime spot for enjoying a drink—be it a purchased cocktail or a bring-your-own. The cruise typically lasts for a while, offering ample time to unwind and admire Florida’s cathedral of water and sky.
Guests have praised the stunning sunset views and the peaceful lakes, which provide a stark contrast to the lively foodie stops. It’s a chance to reflect on the flavors and sights, making for a well-rounded day.

From the reviews and descriptions, it’s clear that the tour’s pace is leisurely and friendly. The walking part involves going into shops and restaurants, so comfortable shoes are a must. The group size is manageable enough for personalized attention but large enough to create a lively atmosphere. The guide’s local insights add color, making the experience more than just a food tasting—it’s a cultural glimpse into Winter Haven’s community life.
Some reviewers mentioned that the food stops are well-chosen, with enough variety to keep everyone interested. The scenic views on the cruise are often highlighted as a standout feature—who doesn’t love watching a Florida sunset over tranquil lakes?
At $165, you’re paying for a thoughtfully curated experience that combines local flavors, charming scenery, and relaxation. It’s a good value considering the diversity of tastings and the scenic cruise included. For travelers who enjoy gourmet bites, cultural stories, and lakeside sunsets, this tour delivers on all fronts.
It’s especially suited for those who want to see Winter Haven beyond the theme parks and experience its authentic side. If you’re traveling with friends or family, the mix of social eating and tranquil scenery makes for a memorable outing.
However, if your main goal is a purely culinary adventure or a party atmosphere, you might find the cruise component a bit mellow. Conversely, if you prefer a more intense food tour with more stops, this might feel slightly condensed.
This Food & Sunset Cruise in Winter Haven offers a balanced blend of culinary discovery and natural beauty. It’s perfect for food lovers wanting a taste of local cuisine and for anyone who appreciates scenic lakeside views in Florida. The relaxed pace makes it suitable for all ages and mobility levels, and the flexibility with cancellation and payment options adds to its appeal.
Travelers looking for a casual, authentic experience that showcases Winter Haven’s community, flavors, and scenery will find this tour well worth the price. It’s a gentle but engaging way to spend an afternoon, leaving you with both full belly and peaceful mind.
What’s the meeting point for the tour?
The group meets outside the Parking Garage at 3rd Street NW and Ave A NW, a convenient and recognizable spot in Winter Haven.
How long does the tour last?
The entire experience takes about three hours, usually in the afternoon, making it easy to fit into a day of sightseeing.
Are food and drinks included?
Yes, the tour includes food tastings like coffee, olive oils, gelato, and Asian dishes, along with a lunch. Alcoholic drinks are not included, so plan to purchase drinks separately if desired.
Is the cruise suitable for everyone?
Yes, the cruise is wheelchair accessible, and the relaxed lakeside setting is suitable for most visitors. It’s a peaceful way to unwind after the food stops.
Can I cancel if my plans change?
Yes, you can cancel up to 24 hours before the tour for a full refund. The booking also allows you to reserve now and pay later.
What should I wear?
Dress comfortably for walking around and exploring shops and restaurants. Florida weather can vary, so layering and comfortable shoes are recommended.
Is this tour family-friendly?
While suitable for most, families with young children should consider their comfort with walking and the cruise’s pace. It’s generally a relaxed outing for all ages.
In essence, the Winter Haven Food Tour & Tipsy Sunset Cruise delivers a hearty slice of local life, blending flavor, scenery, and a touch of leisure. It’s an engaging way to experience what makes Winter Haven special beyond its famous attractions—perfect for those who enjoy savoring the moment, one bite and one sunset at a time.
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