Plan A Couples Vacation To Clearwater Beach

Gulf of Mexico at Clearwater Beach

Update December 21, 2022: No red tide reported in Clearwater Beach. Planning a vacation is exciting when you're visiting a Gulf beach destination on the west coast of Florida. We've done the work for you: hotels, fun activities, and more. There's nothing like having a Florida local help you out with your itinerary!

Why is Clearwater Beach so popular?

Photo: Clearwater Beach by Drew Dau

There are many activities for tourists to enjoy in Florida. You can go fishing, swimming, or snorkeling at any beach. There are countless restaurants, bars, and events happening in and around Clearwater Beach. It can be mind-boggling! As a couple, we know you'd rather focus on fun and romance. That's why we've prepared a 5-day trip itinerary for the perfect couples' vacation in Clearwater Beach. Keep in mind these are suggestions only. You can modify your trip activities or choose your own as you go along.

Photo: Ethan Walsweer

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:

• Sheraton Sand Key Resort
• Wyndham Grand Clearwater Beach
• Barefoot Bay Resort & Marina
• Holiday Inn & Suites Clearwater Beach

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

Salty's Island Bar & Grille

The first thing any couple should do upon arrival at their hotel in Clearwater Beach is walk on the beach! There's nothing more beautiful than a white sand beach on the Gulf of Mexico. Most of us don't get to see that every day, even when we live in Florida. You may have spent most of the day traveling on a plane or car, so it's time to stretch your legs before dinner. Don't forget your sunscreen. 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: Beach-related Activities

Photo: Clearwater dolphins by Mike Ash

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

Photo: Ken Cheung Clearwater Beach Pier

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?

Captain Memo's Pirate Cruise

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! Today its the day for a pirate cruise. This is not just for kids. Captain Memo's Pirate Cruise is a special treat for adults, especially at sunset with complimentary beverages. It's famous in Clearwater and a fun experience. If you're not married yet, you can have your Florida wedding on the pirate ship! They don't feed you on the pirate ship so Italian food can be enjoyed at Cesare's On The Beach. Watch the sun go down on Pier 60. They have a variety of crafts and entertainment from 6-9 p.m. each night. 

Vacation Day Five: Water Activities

Swimming at Clearwater Beach

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

Clearwater Beach shore

This final morning enjoy breakfast on the balcony of your oceanfront room. Even though it's hard to leave Clearwater Beach, you can always come back. There's always more to do: we didn't even cover activities in Tampa Bay or nearby Orlando. So enjoy that stroll on the white sand and book next year's trip when you get home.

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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