Update December 21, 2022: Looking to plan a romantic vacation to a Gulf beach destination on Florida's west coast? Let a Florida local help you out! From top hotels to exciting activities, we've got your couples getaway covered. Get ready for a hassle-free Clearwater Beach trip with an itinerary prepared by locals.
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With so many activities and attractions to choose from in Clearwater Beach, planning your itinerary can be overwhelming. Luckily, we've got you covered! Our 5-day trip itinerary is designed specifically for couples looking for a fun and romantic vacation. Enjoy fishing, swimming, and snorkeling on the beach, explore the countless restaurants, bars, and events in the area, and make unforgettable memories together. Keep in mind that our itinerary is just a suggestion - feel free to modify your trip or add your own activities as you go along.
You may already be thinking about a hotel to stay at in Clearwater Beach. There are many choices. One important tip is to choose a hotel on the Gulf of Mexico beachfront, or within walking distance. Otherwise, you will have to deal with beach parking issues which can cause a lot of grief. Here are some Clearwater Beach hotels that have good reviews:
One of the best things about Clearwater Beach is how close it is to Tampa International Airport. Find the lowest airfare prices by booking your Florida trip online at Lowest Flight Fares.
Day One: Arrival in Clearwater Beach
Upon arrival at your hotel in Clearwater Beach, the first thing you should do as a couple is take a walk on the beach. There's nothing more breathtaking than the beautiful white sand beach on the Gulf of Mexico. Even if you live in Florida, chances are you don't get to see such beauty every day. After a day of traveling on a plane or in a car, it's important to stretch your legs before dinner. Be sure to pack your sunscreen as the sun is strong all year round.
Afterward, you will be hungry. We recommend staying on the beach to enjoy the sea breeze and tropical atmosphere. Try Salty's Island Bar & Grille. This casual, outdoor dining will be what you need after a day of travel. Try the MahiMahi grilled or blackened. Don't forget to have some "Killer Key Lime Pie" while live music plays. It's delicious! Stay for an island cocktail and watch the spectacular Gulf coast sunset.
Vacation Day Two: Enjoy Beach-related Activities
Rise and shine for your first full day of Florida adventure. Breakfast on the deck or the outside space of your hotel during the morning is a special thing. At this time of day it is warm, but not too hot. You can both relax and enjoy the views of people taking a morning swim in the Gulf of Mexico. After you are done eating, it's your turn on the beach with another walk and dip in the warm, emerald water. There's nothing like seeing fish swim by in crystal clear water.
There are a few choices on your Florida itinerary today. Take a dolphin boat tour, Tiki cruise that's BYOB or visit the Clearwater Marine Aquarium. When you break for lunch (or dinner) you can grab some Mexican food at the famous Taco Bus. It's not too far from the Holiday Inn & Suites Clearwater Beach so you can walk there from the beach. Is it really a bus? Well, that's how they started the restaurant. You will find the bus inside the store with all their Mexican food delights. Afterward, enjoy a late date playing Mini Golf at Captain Bligh's Landing just down the street. The dolphin boat tour (Tropics Boat tours) also offers a sunset cruise. We like the sound of that!
Vacation Day Three: Food and Wine Day in Clearwater
Sunning and swimming are again the best way to start a Clearwater Beach day. Today might be a great day for a winery tour at Aspirations Winery. Yes, Florida has wineries! It's about 30 minutes inland and worth the drive. It's been named the number one winery in the state of Florida. You will need reservations for the Tour and Tasting experience. There are several times during the day you can choose. Tarpon Springs is another great way to spend the day. It offers a sponge cruise, kayaking and Greek dining (locals love Mama's Greek Cuisine). If it's raining, you can take in a movie at Westfield Countryside Mall after eating at the Cheesecake Factory. If staying at the beach is what you crave...it's okay you're on island time! Get some romantic time away from the Clearwater Beach crowds by spending the day at Sand Key Park. As one of our favorite Florida beaches, we personally recommend it. Sand Key beach has an exposed sandbar that offers pretty consistent waves for surfing too. There's also a Columbia Restaurant in Sand Key with intracoastal waterway views. Reservations are needed. Make sure you catch the stunning Clearwater Beach sunset.
Vacation Day Four: Pirate Cruise Anyone?
You can start this vacation day by going out for breakfast at Another Broken Egg Cafe. Climb aboard the Jolley Trolley to avoid taking your vehicle. The Cafe serves omelettes, pancakes, grits and biscuits get you ready for another exciting day in Clearwater Beach!
Experience some pirate fun on your vacation by joining the Captain Memo's Pirate Cruise, which is not just limited to kids but is also perfect for adults. Don't miss the opportunity to enjoy complimentary beverages while watching the sunset on this famous pirate ship cruise in Clearwater. It's even possible to have your Florida wedding on the pirate ship! However, keep in mind that they don't provide food, so head to Cesare's On The Beach for some delicious Italian cuisine. As the sun goes down, head to Pier 60 for craft displays and entertainment from 6-9 p.m. every night.
Vacation Day Five: Clearwater Beach Water Activities
It's impossible to ignore the beauty of the Gulf of Mexico in Clearwater Beach. That's why this final day of your Florida vacation is focused on watersports and fishing. After your daily walk and swim on the white sand beach, consider a half day fishing charter. Beginning at 12:30, the two of you can enjoy some calm water fishing in the bay and nearshore waters. Snook, trout and flounder are easy catches near Tampa Bay. You don't have to be an expert fisherman to experience this tour run by Fisheye Sport Fishing.
Fishing is not everybody's thing, but nearly everyone loves to ride a jet ski. Located behind Shepherd's Beach Resort, you can rent a jet ski for 30 minutes of more at Makin' Waves Rentals. Your final evening can be spent at Cabana's Coastal Grill. Dine outside in the tropical breeze under the covered patio. We love the beer battered fish tenders. For island music head over to Shepherd's Tiki Beach Bar at sunset. Shepherd's has been around forever and are known to have the best entertainment on the Clearwater Beachfront. We first visited Shepherd's almost 30 years ago!
Time To Go Home
Before departing, savor your last morning by having breakfast on the balcony of your oceanfront hotel room. While leaving Clearwater Beach might be tough, rest assured that you can always come back. With plenty of other activities to explore in Tampa Bay and nearby Orlando, there's always more to see and do. Take one last stroll on the white sand, and start planning your next trip to this beautiful Gulf beach destination.
DISCLAIMER: These are activity suggestions only. The views and opinions expressed in the Truck That Beach blog and on this page are purely the bloggers’ own. Any claim, quote or other representation about a product or service should be verified with the manufacturer, service provider or party in question. We make no guarantees regarding the results from using the information provided. While all information is true to our best knowledge, information may change at any time and without notice. Call providers ahead of your trip to be sure.
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Susan and Bruno are travel bloggers. We write about Florida beaches on every coast. Our opinions only.