4 Florida Vacations That Need To be on Every Middle-Class Retiree’s Bucket List
Written by
Ashley Donohoe
Edited by
Amen Oyiboke
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Florida is not only a popular place for relocating retirees, but also the country’s most popular vacation destination. If you’re a middle-class retiree who wants to spend your well-deserved free time taking memorable trips, the Sunshine State has a lot to offer that you likely won’t find back home. Plus, you won’t even have to drain your retirement savings to enjoy yourself.
Whether you prefer the beach life, theme park thrills, historical places or unique luxuries, these four Florida vacation destinations should have a place on your retirement bucket list.
Orlando
If you’re a theme park lover, Orlando might end up being your favorite destination. You can check out the four diverse parks at the popular Walt Disney World Resort to enjoy some rides, see your beloved characters and eat themed meals. While Disney doesn’t offer senior discounts for its tickets, which can widely vary in price, you can get up to $60 off a three-day ticket if you’re an AARP member.
Other popular parks in Orlando include Sea World (as low as $50 per day) and Universal Studios (starting at $119 per day). When you want to get away from the action, consider hiking the famous Lake Tibet-Butler Nature Preserve (free), exploring butterflies and native plants at Harry P. Leu Gardens ($15) and enjoying nearby Wekiva Island’s water activities.
While theme park resorts can easily set you back several hundred per night, Kayak lists a more modest average nightly hotel cost of $221, with some basic inns and motels costing less than $60. Kayak’s Summer Travel Check-in also reported a reasonable average airfare cost of $293 in 2025.
Naples
Like its Italian counterpart, Florida’s city of Naples stands out for luxuries that any retiree is likely to enjoy. For you, that might look like spending hours browsing the luxury shops, enjoying rounds of golf, going sailing and taking in the scenery. You might also like that it’s easier to go at a slow pace than in the action-packed Orlando.
If you’re a nature lover, you’ll want to add Naples Botanical Garden ($27), the Naples Pier (free), and the Corkscrew Swamp Sanctuary ($17) to your to-do list. Other worthy stops include the Historic Palm Cottage Museum ($16) for history buffs, Revs Institute ($25) for car enthusiasts, and Naples Zoo ($25.95 for seniors) for animal lovers.
Although Naples is considered an upscale Florida travel destination, Kayak listed an average nightly hotel room cost of only $179 in August 2025, with several basic stays costing under $80. While Naples does have a small airport, many travelers fly in from Fort Myers, where the average airfare costs $289 in 2025, per Kayak.
St. Augustine
Often cited as the nation’s oldest city, St. Augustine is a unique vacation spot that is ideal for retirees who enjoy learning about history and want to experience the town’s unique Spanish architecture. It also offers lovely beaches where you can relax.
You can plan for many free activities, such as checking out the art galleries and shops on St. George Street, visiting the Fort Matanzas watchtower (via ferry) and walking through the historical Fort Mose Historic State Park. You also won’t want to miss budget-friendly fee-based attractions, like the St. Augustine Lighthouse ($15.95 for seniors), the Old Town Trolley Tour (starting at $35.14) and the Castillo de San Marcos National Monument (as low as $15).
St. Augustine also stands out for its affordable hotel options. According to Kayak, the average nightly rate for a room in August 2025 was $141, and you can find more luxurious beach hotels for around $250 per night. Many tourists fly in from nearby Orlando or Jacksonville (average airfare of $344 in 2025, according to Kayak) and reach the city via bus or car.
Key West
The island city of Key West is a worthy bucket list destination where you can experience the vibes of a Caribbean-style vacation while staying closer to home. You can enjoy a more laid-back life on this highly walkable island with many opportunities to lounge on the beach, go snorkeling or sign up for one of many cruises where you can see dolphins.
Some popular attractions you can check out include the Ernest Hemingway Home and Museum ($19), Key West Butterfly and Nature Conservatory ($14.50 for seniors) and Fort Zachary Taylor Historical State Park (as low as $2.50). You can also get some rest and enjoy a tour of the city’s famous spots aboard a ride on the Conch Tour Train (as low as $40.80) or Old Town Trolley (starting at $55.05).
While this city is pricier than the other destinations, you can make it work on a middle-class budget if you forego some luxuries. Kayak lists an average nightly room price of $309, which is more in line with the town’s resorts, but you can find basic motel and guesthouse rooms starting at around $100. The travel site also noted that an average flight costs $428 in 2025.
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