2026 Quick Trips and Staycations for a Fantastic Memorial Day Weekend
Looking to just sneak away for the day? Check out some of our top staycations and getaways!
Let’s be real – we all need a getaway or staycation more often than we would like to admit. We hear you! Flroida (and especially Tampa Bay) is home to beautiful beaches and endless resorts and activities – which means there are so many options for a quick escape from reality.

Looking to just sneak away for the day? Check out some of our top staycations and getaways!

One of our favorite things to do in Tampa Bay involves the best hotels, without staying the night! You can take advantage of a hotel day pass with ResortPass. It’s an easy way to feel like you’re on vacation for the day. This special pass gives you access to local hotels and resorts for a…

John’s Pass Village and Boardwalk is a semi-large shopping area perfect for a day date. Despite having over 100 merchants within its boundaries, it has quite a quaint feel. Located just across the street from Madeira Beach, John’s Pass provides tourists and locals with plenty of activities and opportunities for fun, while the boardwalk offers…

Here in Tampa, choosing the perfect hotel for Valentine’s Day can be difficult, especially with so many options across the bay! Luckily, the Tampa area is home to plenty of romantic hotels with a smaller, boutique feel that will set your Valentine’s Day apart from the big chains and their hundreds of rooms. Typically, boutique…

Christmas at Gaylord Palms is an amazing series of experiences that need to be seen (and felt) to really grasp. Here’s what to expect.

We’ve officially made it to the holidays! And it’s a great time of year to have a romantic getaway with the love of your life. Tampa Bay has many wonderful hotels and resorts perfect for a staycation to escape the hustle and bustle of everyday life. Below you’ll find a list of Tampa Bay hotel…

Situated between Tampa and Orlando in Lake Wales lies a special place that’s always worth the drive: Bok Tower Gardens. The iconic 205-foot Singing Tower, winding paths lined with flowers and lush greenery, secret hideaways, Mediterranean estate, and the cute on-site café combine to make Bok Tower Gardens the perfect destination for a date day…

For couples in Tampa looking for romance without the hassle of long travel days, Conrad Orlando offers the perfect blend of convenience and luxury. Nestled just around the bend from Walt Disney World, this stunning resort combines luxury accommodations, world-class dining, and serene amenities—making it a dream destination for a romantic getaway. Conrad Orlando: Convenient…

Sometimes, the best dates happen away from home. If you have a day to spare, consider an Orlando day trip for your next rendezvous. Orlando is about an hour from Tampa, so you won’t lose much of the day to travel. Spend the day reveling in everything Orlando has to offer. Here are some options…

Calling all foodies! The beloved Walt Disney World Swan and Dolphin Food & Wine Classic returns for its 15th year, Friday and Saturday, November 14-15, 2025. The event offers guests unlimited tastings at outdoor stations featuring culinary and beverage selections amidst a festive backdrop of live entertainment on the hotel’s scenic causeway. The menu lineup…

In need of a staycation? Check out the hip and eclectic The Hollander Hotel in St. Petersburg!

Plan an overnight getaway to Orlando for Magical Dining, with three-course meals for $40/person and $60 per person – 2025 details here

Enough with the ho-hum and the three hour traffic getting to Orlando. Enough with the white-knuckle driving and awful drivers. Take the train! Amtrak has been running routes between Orlando and Tampa for decades, and no one really takes advantage of it enough, in my opinion. It’s not as glamorous as European train travel, but…

Head south to St. Armands Circle in Sarasota for a day trip filled with shopping, dining, and beautiful scenery. This popular destination, established in 1926, is located on St. Armands Key in the Sarasota area and has been enchanting guests and locals for years with its incredible charm and timeless feel. Bring the kids for…

Day trips and staycations are a great option for adventurous souls. Lucky for us, the “Theme Park Capital of the World” is our next-door neighbor. If you’re craving a little novelty, hit the road (aka I-4) and travel to Orlando for a day trip. A handful of Orlando resorts offer day passes through ResortPass, a…

Besides the typical fun of living in Tampa, I love living here because there are so many amazing destinations that are only 1-2 hours away from us. From beaches, to springs, the sponge docks, to the Space Coast, there’s something for everyone within easy driving access of the Bay. For us in Tampa, Orlando may…

Getting away from it all as a couple is so important and beneficial. But getting away from it all doesn’t have to mean roughing it. Timberline Glamping in Tampa makes it possible to enjoy comfortable and thoughtful glamping in the middle of a glorious state park—think of it like the fabulous cousin of traditional tent…

Summer is here and now is the time to plan a getaway to the corners of Florida you’ve yet to explore, including the scenic beaches along the Gulf Coast in Florida’s Panhandle! Visualize a place where bright blue skies and puffy clouds hang over brilliant turquoise water and pure white sand. When the sun dips…

Three days at the beach? You deserve it! For those looking for romance, family time, or a bit of one-on-one with nature, head south to Sanibel and Captiva Island. These islands are perfect for everything and offer local hotels, dining, shopping, and entertainment. Plus, tons of outdoor delights as well, not to mention 15 miles of…

It’s time to party like a pirate at the 5th Annual Bucs Beach Bash held April 24 – 26, 2025, at the TradeWinds Resort – the Official Beach Resort of the Tampa Bay Buccaneers! Celebrate all weekend long with live music, drinks, prizes, cornhole tournament, Kids Zone, and more! Plus fan favorites, like the Bucs Cheerleaders,…