Top Clearwater Holidays

Take your booze cruise to the next level and hop on a floating tiki bar on Clearwater Beach. Gently float on the Gulf of Mexico while enjoying your favorite cocktail and admiring the natural landscape of Florida’s coast. Bring your choice of beverages and snacks on board and play your favorite tunes with the provided Bluetooth speaker for a relaxing day on the water.

Clearwater has some of the best voted beaches in the United States and this exciting tiki tour is a great way to experience the Gulf waters. Hop aboard the only U.S. Coast Guard certified tiki boat in Clearwater Beach for a fun day under the sun. Perfect for celebrations, this cruise can hold over a dozen people for a party. An open bar with beers and cocktails is included.

Take a tour of one of Florida's handful of wineries on this excursion in Clearwater. Follow your guide through a tour of the winery whilst you learn about wine production methods. Then, enjoy a tasting of three onsite-produced wines. Nibble charcuterie as you go to keep your palette neutral so you are able to pick up on the unique flavor profiles.

Spice up any Florida vacation with a cruise on Tampa Bay. Beginning in Clearwater, enjoy a beautiful sunset (depending upon the time of year) and listen to live music on board the elegant 'StarLite Majesty' yacht. Choose from one of the open-air observation decks or the climate-controlled dining cabin inside. For dinner (at own expense), choose from several delicious gourmet meal entrees along with salad, dessert, and coffee or tea. Then dance the night away or take a romantic stroll along the deck.

Watch as day turns into night off the coast of Florida on this sunset cruise from Clearwater. Enjoy the scenery and peaceful calm of a late-afternoon cruise on board a vessel with plenty of space to stretch out and soak up the breathtaking view. Watch a beautiful Florida sunset as the sun glows and gently settles into the Gulf of Mexico. Toast the new evening with a glass of Champagne.

Step off the dock and into the nightlife vibe of Downtown Indian Rocks Beach—only on the water. This 2-hour private evening cruise is the perfect extension of the local bar and restaurant scene, offering a relaxed, social atmosphere as you glide through the calm Intracoastal Waterway. Bring your favorite drinks, cue up the music, and let Captain Chris, a U.S. Coast Guard veteran with over 40 years on these waters, handle the helm. You’ll pass island lights and waterfront restaurants, spot dolphins at dusk, and soak up that unmistakable coastal energy that makes IRB a local favorite. No set schedule, no crowds—just good company and easy-going Florida vibes. Highlights • 2-hour private evening cruise from IRB • Bring your own drinks & playlist • Dolphin-spotting at dusk • See waterfront bars & restaurants • Hosted by a local USCG-licensed captain End the night the local way—“Boat Like a Local” and make your evening unforgettable on Indian Rocks Beach's coastal waterways.

Clearwater is known for its beaches and sunsets, but there’s a different tale to this Gulf Coast city when the stars come out. Join this spine-tingling small-group walking tour through Clearwater’s Safety Harbor, covering documented true crime, local legends, and paranormal activity at historic landmarks—no costumes or theatrics. Includes entry to the Safety Harbor Resort and Spa lobby, and guests participate in hunting for ghosts using paranormal equipment.

You will hear firsthand accounts of murders and other serious crimes that have occurred over time, all within and around the Tampa Bay area. Your tour guide has over three decades solving crimes and making arrests in the Tampa Bay area. This is not like other tours because you will hear inside details of the information that was not disclosed to the public and press. Get ready to put your detective skills to use. Your guide will take you to hidden gems that only locals know about. You will laugh and cry and have an adventure that is so much fun, it’s criminal. Rain or shine, the mystery awaits you. Come step on board and prepare for a day of nonstop intrigue. The Wine and True Crime tour is a perfect way to celebrate a birthday, girls’ night out, Bachelorette Party, Divorce Party or any other celebration!

Relax & Shred – The Ultimate 2-Boat Adventure in Clearwater Beach! Get ready for the perfect blend of chill and thrill on our two-boat private tour for up to 12 guests (6 per boat)! Hop aboard our spacious pontoon party boat to relax, soak up the sun, and cruise the stunning waters of Clearwater Beach. At the same time, our high-performance AXIS wake boat brings the action—offering wake surfing, wakeboarding, and tubing for adrenaline lovers. The best part? You can switch between both boats throughout the tour, so everyone gets to enjoy the full experience. We'll also anchor at a local island beach for some laid-back beach time—swimming, shelling, or just lounging like a local. It’s the ultimate Clearwater watersports and pontoon combo tour for families, friends, and thrill seekers alike!

This boat is entirely yours for the ultimate party experience! Explore the vibrant heart of Clearwater in style with our Island Hop and Dolphin Watch. Hop aboard our spacious boat (up to 20) as we set sail through the beautiful bay. This adventure is perfect for famlilies, birthdays, bachelorettes, bachelors, corporate outings, and people just looking to have a fun day on the water. But the excitement doesn’t stop there! Anchor at a shallow island in the middle of the bay, where you can walk onto this awesome tiny sand beach and take a refreshing dip in the waters. At the sandbar, we can turn up the music to keep the atmosphere going. No pedaling is necessary since we haven an engine, it is motorized only. With the freedom to BYOB (Bring Your Own Beverage) you can sip on your favorite drinks while you soak in the sun and enjoy the company of your own private Island Party. Book your tour today and get ready for a day of pure fun and excitement.

What makes this half-day adventure truly special is the freedom to turn a boat ride into your own private day on the water. With four full hours, there’s no rush—just plenty of time to bounce between hidden islands, hang out at sandbars, swim in crystal-clear shallows, or kick back with your crew and enjoy the ride. Instead of a quick pass-through, you can actually live each stop—linger a little longer, explore a little more, and let the day unfold however you want. Spot dolphins along the way, chase the best views, or drop anchor and relax like you’ve got your own slice of the Gulf. With a local captain guiding the way and total flexibility built in, it feels less like a tour and more like your own floating island day party—laid-back, adventurous, and completely on your terms.