Don't do THIS on your vacation - 10 Mistakes to Avoid During Your Trip to Clearwater Beach

Exploratory travel
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8 Video Views·Nov 1, 2025
In this video, we're sharing 10 things you should NOT do to make your trip to Clearwater Beach more organized, more fun, and more affordable. From avoiding rookie mistakes to money-saving tips and tricks, we're covering it all!
Okay, so you're planning your Clearwater Beach vacation and already know all the tips and tricks
about getting to the beach early to grab the best spots and remembering to reapply sunscreen every
couple of hours. But what about those sneaky tourist traps that suck up your precious time
in paradise and are so good at getting you to spend money on things you just don't need to?
Every vacation destination has them and we're here to help you avoid them on your next trip
to Clearwater Beach. Hey everyone, my name is Mandy and today we're sharing 10 things you should
not do to help make your trip to Clearwater Beach more organized, more fun, and more affordable.
Mistake number one, booking your excursions later in your stay. Just about everything to do here in
Clearwater Beach takes place outdoors. There's dolphin tours, fishing charters, parasailing,
the list goes on. If you plan on taking any of the boat tours or have some other must-do items
on your list, we recommend scheduling them in the first couple of days of your stay.
That way, in case of weather issues or other unexpected delays, you'll have time to reschedule
and still fit them into your trip. Little Toot Dolphin Tour, for example, offers a dolphin
sighting guarantee where on the rare chance that you don't get to see dolphins on your first outing,
you can take a second trip absolutely free. We've been on these tours many times and have
experienced not seeing dolphins and although it's rare, it does happen and scheduling these
tours later in your stay could prevent you from taking advantage of the complimentary second trip
should you need to. Another note on booking these boat trips, we recommend reserving them
several days in advance especially during peak times because they book up fast. Sunset tours
are usually the first to go so if you're hoping to snag one of those, you'll need to book even
earlier. Mistake number two, canceling your trip because of the weather. We know how it is, there's
nothing worse than seeing days of rain in the forecast during your upcoming vacation but don't
panic. Our rainy season lasts from June to September and it's not uncommon to see weather
forecasts like this one most weeks during the summer. Even though Clearwater Beach averages 361
days of sunshine a year, we do get an afternoon shower between 2 and 4 p.m. almost daily. The rain
and thunderstorms come and go quickly as do many rookie beachgoers leaving plenty of sunshine and a
much less crowded beach to enjoy. Another thing to consider if you plan on traveling here during this
time of year is that it is hurricane season. Hurricane season starts in June and runs through
November and can be one of the most affordable but also most nerve-wracking times to travel here.
If you're thinking of visiting Clearwater Beach during hurricane season, hit the subscribe button
now because we'll be telling you exactly what to expect and what you should do if you find
yourself on a Florida vacation as a hurricane is approaching. Mistake number three, buying your
supplies on the island. It's probably inevitable that you're going to need to grab something you
forgot, sunblocks, snacks, or something else you didn't think of. We all do it but if possible, try
to stock up on everything you may need during your vacation before making it to the beach.
As soon as you cross the bridge onto the island, you're going to be paying a premium for just about
everything. Things like sunblock, beach gear, and beer will all be a couple of dollars more once
you're on the beach. Lucky for you, there's a target right on Gulf to Bay which is likely the
road you're going to be traveling in on. A bit further down Gulf to Bay, you'll run into Missouri
Avenue where there's a Walmart as well as an ABC store which is where you'll find the lowest prices
on alcohol in the area. If you must do your shopping on the island, Publix on Island Way is
your best bet for groceries and you can likely find anything else you need at Walgreens. Just
expect to pay a few dollars more. If you're here without a car and you're wondering how you're
going to get to all of these stores, check out our video on getting around Clearwater Beach without a car
where all the methods of transportation we suggest will get you to some or all of the stores we just
mentioned. Mistake number four, talking to the timeshare people. If you're genuinely interested
in purchasing a timeshare, by all means go for it. But if you're not planning on purchasing and are
just looking to score some freebies, try to avoid being lured in by their offers. The free two nights
stay or whatever else they're offering typically comes with a lot of fine print that makes the
offer much less appealing than at first glance. Plus they will promise you that their presentation
only takes an hour but we have done them a few times and it's always been at least four hours.
One time we were there for six and we're not here to bash the timeshare industry but we do want you
to know what you're getting yourselves into with these presentations, especially if you're only here
for a limited time. If you don't want to spend hours of your precious vacation time stuck indoors
listening to a hardcore sales pitch, you'll definitely want to skip this one. Mistake number
five, missing the sunset. The sunsets here are truly stunning and are not to be missed.
Best of all, this amazing show happens nightly and is completely free. We've lived on Clearwater
Beach for over six years now and we still plan our evenings around the sunset as many locals do.
Rooftop bars like Jimmy's Crow's Nest pass out free sunset shots and even do a sunset countdown
nightly New Year's Eve style. Pier 60 hosts a sunset celebration seven nights a week that
features local artisans and craft vendors as well as buskers and of course the star of the show,
Mother Nature herself. Mistake number six, calling it the ocean. We're guessing we may
catch some flack for this one but we had to include it in this list because it is that
important. You may be surprised to know that the body of water surrounding Clearwater Beach is
considered the Gulf of Mexico, which is technically part of the Atlantic Ocean, although no one here
seems to care. It's the Gulf of Mexico and referring to it as anything other than that
is unacceptable. While calling it the ocean is a commonly mistaken label, it's one that
locals feel pretty passionately about. But why? Well, with roads like Gulf to Bay, Gulf Boulevard,
Gulf View, and Gulf Street, calling it the ocean just doesn't feel right. Keep this in mind the
time you reserve a hotel room and instead of asking for an ocean view room, ask for a gulf
view room. It's not the end of the world if you've been calling it the ocean, but we just wanted to
mention it because we're looking out for you and we don't want you to sound like a rookie,
at least not on our watch. Mistake number seven, overpacking. I think we're all guilty of this one
at one point or another. I know I am. Clearwater Beach, like many beach towns, is extremely laid
back. Now obviously what you pack is going to be determined by what time of year you're visiting
and even where you're visiting from. We see northerners out in shorts and flip-flops in the
middle of December when we're bundled up in our hoodies. 65 degrees to a Michigander is not the
same as 65 degrees to a Floridian. But one thing remains the same no matter where you're from and
what time of year you visit and that's that nothing in Clearwater Beach is particularly
dressy. Unless you're attending a wedding or other formal event, there's no need for fancy dresses or
high heels. Even in some of the more upscale hotels and restaurants, a sundress and sandals
or shorts and loafers are perfectly acceptable and expected. Mistake number eight, not paying
attention to beach flags. Beach flags fly above the lifeguard stands on Clearwater Beach and are
used by officials to communicate the current conditions of the water and any potential hazards
that may be present. Green flags indicate that the water is calm and safe for swimming. Other colored
flags are flown to warn beachgoers of changing conditions such as strong currents or dangerous
marine life. According to data from the United States Lifesaving Association, there were a total
of 98 reported drownings in Florida in 2020 with Pinellas County, where Clearwater Beach is located,
having had the highest number of beachgoer accidents in the entire state. If you see red
flags flying, do not enter the water under any circumstances as the conditions are considered to
be extremely hazardous. Yellow flags indicate moderate surf and currents and purple flags
signal that there is a dangerous marine animal such as a shark or jellyfish present in the water.
By taking the time to understand these flags, you can ensure a safe and enjoyable experience for
everyone. Mistake number nine, not checking online discount sites. If you're like most people,
especially in this economy, every dollar counts. Websites like Groupon, Travelzoo, and Living
Social offer some amazing discounts on everything from hotel accommodations and restaurants to boat
excursions and even spa treatments and are a great way to stretch your vacation budget.
At the time of filming this video, Travelzoo is offering a dolphin watching tour that is
discounted from a normal retail price of $68 per person down to only $40 per person.
That's a savings of around 40% that you'll miss if you don't take the time to check out
these websites during your planning and take advantage of the deals that they offer.
Mistake number 10, not budgeting for transportation costs. Now you may be thinking, but I have my own
car, why do I need to budget for transportation? Well, not so fast. If you plan on navigating the
beach by car, be sure to allocate funds for parking. Parking on the beach can get as high
as $60 a day and some hotels charge upwards of $40 a day for parking and that's in addition to
what you've already paid for your room and your resort fees. Just make sure to inquire about hotel
parking fees when you book and also remember to budget for other parking while visiting the beach.
If you're flying in and will be visiting the beach without a car, you can expect to pay anywhere
between $40 and $70 one way for airport runs from both Tampa International and St. Pete Clearwater
Airports. Once on the island, getting around is pretty affordable between the Jolly Trolley,
the Clearwater Ferry, ride shares and others, but it's still something you'll need to budget for in
your planning. We've created videos to help you no matter how you plan on getting around on your
vacation. Click either of the videos on the screen now to learn everything you need to know
about budgeting for transportation in Clearwater Beach. We hope this video has helped made your
trip planning a little bit easier. If you'd like to see more tips and tricks on how to make your
Clearwater Beach vacation an unforgettable one, hit that subscribe button now and let
us know in the comments what you'd like to see us cover next.
