Top Cleveland Seasonal & Special Occasions

Cruise Cleveland’s waterfront aboard a tropical tiki-themed party boat and enjoy scenic views of the Cuyahoga River, Inner Harbor, and downtown skyline. Bring your favorite beverages, relax with friends, and take in iconic waterfront landmarks from a unique perspective on the water. This fun and social cruise is perfect for celebrations, sightseeing, or simply enjoying Cleveland’s vibrant waterfront. - Cruise the Cuyahoga River and Cleveland Inner Harbor. - Relax aboard a tiki-themed party boat with music and a lively atmosphere. - Enjoy views of Cleveland’s skyline, Rock & Roll Hall of Fame, and Browns Stadium (weather permitting). - BYOB experience with ice, coolers, and an onboard restroom provided.

Discover the secrets of our unique bourbon and rye whiskey production during this exclusive behind-the-scenes tour. Gain insight into the innovative techniques that distinguish our spirits from the rest, while enjoying a guided tasting session that highlights the rich flavors and craftsmanship in every sip. This tour not only offers a chance to see the distillation process up close but also allows you to taste the difference firsthand, making it perfect for whiskey enthusiasts and curious beginners alike. - Go behind the scenes to learn about bourbon and rye production - Enjoy a guided tasting experience featuring our finest spirits - Discover the innovations that set our distillery apart - Perfect for both whiskey enthusiasts and newcomers to the world of spirits

See a spookier side of Cleveland—and discover sights and stories you would never encounter on your own—on this evening walking tour. Explore the city's dark corners in the company of a guide, and learn all about its (allegedly) haunted history, from historic battles to the casualties of organized crime. Visit landmarks like the Arcade, Soldiers and Sailors Monument, Connor Palace, and more, all in one night out.

If a standard history tour does not appeal, combine history with delicious food on this guided tour. Explore Cleveland's Little Italy neighborhood and learn about the Italian culture that has held firm here for generations. Visit some of the area's best restaurants, some long-standing, some newer, and sample such typical dishes as pasta, pizza, and meatballs.

Whether you’re a local or a tourist, get to know Cleveland better on a food-focused tour of its coolest neighborhoods. With a small group of like-minded travelers and your foodie guide, start the tour at the West Side Market. Continue to a Mexican restaurant, a brewery, an ice-cream shop, a butcher, and more. Come hungry and enjoy tasty samples at each stop.

Cleveland has wine bars. What it needed was a better way to connect them. Uncorked in The Land is a 3.5-hour night out connecting 3 amazing wine bars with premium open-air golf cart rides between every stop. You’ll spend 45 to 55 minutes at each stop, giving you enough time to sip, snack, and enjoy each place. Between stops, the music stays on while the cart cruises your group through Gordon Square, Ohio City, and Tremont. The experience includes a complimentary snack at Wyne Tasting & Cocktail Bar, one complimentary wine tasting at both Market Avenue & La Cave Du Vin. Additional wine, cocktails, food, and beverages are available for purchase directly from each venue. This is built for girls nights, birthdays, friends nights out, double dates, visitors, and groups who want something more memorable than dinner followed by a group-chat debate about where to go next. No Napa needed. This is Cleveland wine done right.

Holly Jolly Hunt is a scavenger hunt that is played using an app on your smartphone, that brings your entire family and friends together for holiday cheer. During the adventure you’ll be seeking out all the traditional, and even the non-traditional holiday items we all see this time of year around the city. You’ll get points for each item you find. The goal is to capture as many items as you can in order to score as many points as possible and get 1st place on the leaderboard. Along the way you’ll be asked to perform silly holiday themed tasks meant to bring laughter and smiles to everyone involved. Come play with us. Young or old, this is a scavenger hunt for everyone that enjoys this time of year. We promise you will create holiday memories that you will not forget! Holly Jolly Hunt can be played in any city!

⭐ Top-Rated Vacation Photoshoots 2025 We’re not just photographers, we’re storytellers capturing your holiday exactly as it feels. With over six years of experience photographing travellers around the world, our small team specialises in authentic, natural photography that truly reflects your trip. In Cleveland, we combine creativity with local knowledge to show you hidden gems, secret angles, and the best light. You’ll not only get beautiful, professional photos but also insider tips to make the most of your time here. We’re proud to be recognised among the top-rated photography tours of 2025, trusted by travellers worldwide for our relaxed style and stunning results.

Pints on the Patio is Cleveland’s sunny-season brewery experience, built for birthdays, friend groups, bachelor and bachelorette weekends, visitors, locals, and anyone who believes beer tastes better outside. The experience begins and ends at BrewDog Cleveland Outpost, where free parking makes it easy to leave the car behind and let us handle the rest. Over 3.5 hours, ride between 3 of the best patios in premium golf carts with comfortable seating, Bluetooth soundbars, LED lighting, and music between stops. No parking shuffle. No long walks. No rideshare roulette. You’ll visit BrewDog for riverfront views, $5 beers, and 50% off appetizers; Saucy Brew Works for $4 beers and 50% off select appetizers and pizzas; and Collision Bend for waterfront patio views, discounted beers, and select offers. Food and drinks are purchased directly from each brewery. We provide the ride and discounts It’s patios, pints, music, and premium golf cart rides wrapped into one very Cleveland summer day.