Florida vacation for 55+ couple….

My sister and I are trying to plan a week long vacation for our Dad and step-mother to somewhere in Florida.  When we agreed to do this, I do not think we ever thought it would be this challenging but it is becoming quite apparent why it gets harder to travel once you get older.  For some folks, the adventure never leaves them but for the others familiarity and comfort is a necessity.
One one hand, we have our patient, ready to try anything, step-mom who would be fine taking longer commutes, navigating the area by herself, and lounging on a beach all day.  Then on the other hand is our sweet, loving, fair skinned dad who is semi-impatient that would die if he had to travel for more than five hours, drive himself to the hotel, couldn’t find an umbrella or shady tree throughout the day, and whose idea of a vacation is an oversized chair, overlooking the ocean, with someone cooking meals for him.

Starting to get the picture now???

The stipulations are as follows:

1.  Airfare with no more than one stop-both ways.

2. Flights need to depart mid-morning.

3. Pre-arranged transportation to take them to and from the airport.

4. Rentals cars are out.

4. They prefer all-inclusive.

6.  Shopping/dining that is within walking distance or a short taxi ride away.

7.  Quiet yet offers entertainment

8.  Accommodation needs to have a pool and spa.

Ok, with all that in mind we are thinking some island on the west coast…maybe Sanibel & Captiva, Amelia Island, or Anna Maria.  Why?  Read on to learn more about each destination….

Sanibel & Captiva Islands 

Escaping to the sister islands of Sanibel and Captiva is to escape much of the hustle and bustle that’s permeated so many of Florida’s beach towns and keys. On these tranquil barrier islands along Florida’s Gulf Coast, you won’t see stretches of cookie-cutter high-rise condominiums or the tacky amusement parks that litter so many other parts of Florida, and you most certainly won’t hear the annoying buzz of jet skis or other watercraft with engines; they aren’t allowed within 300 yards of the islands’ shores.
Sanibel & Captiva Islands
Instead you can blissfully stroll through the island’s charming main street, while under a shady sheath of palm tree fronds. The island’s shell-strewn beaches are stunning: Among the more popular is Turner Beach, which faces west and is a delightful place to watch the sunset. If searching for seashells by the seashore gets dull, visit the J. N. “Ding” Darling National Wildlife Refuge, which you can explore by bike, foot, canoe or kayak.

Amelia Island

Florida’s northernmost barrier island, tranquil Amelia Island, lures travelers seeking a quiet and charming seaport community far removed from city doldrums. Pack your sunscreen and sneakers, because when you aren’t exploring the quaint town of Fernandina Beach, you’ll want to spend much of your vacation enjoying Amelia Island’s copious outdoor activities. Thirteen miles of beaches will satisfy folks hoping to relax on the sands or hit the water for a swim. Amelia Island also offers excellent kayaking, fishing, biking and hiking along sand dunes or within the island’s interior parks.

Fernando Beach Shopping

Fernandina Beach Shopping

Once you’ve had your fix of basking in the sun, spend quality time wandering through Fernandina Beach. History buffs will find plenty to admire in the Victorian, Italianate and Queen Anne-style homes that line the town’s streets, while shoppers and foodies will be ecstatic to discover an array of delightful boutique shops and eclectic restaurants. Island accommodations suit all manner of travelers and tastes, from swanky beachfront resorts, like the Omni Amelia Island Plantation (which reopens in spring 2013, following an $85 million-renovation), to homey bed-and-breakfasts in the heart of the historic center.

Anna Maria Island

It’s easy to be enamored of an island where the preferred pastime is paying homage to the sunset. On 7-mile-long Anna Maria Island, you will, in fact, find both locals and tourists flocking to the island’s Gulf Coast beaches, bars and restaurants to watch the stunning daily spectacle. The ultra-laidback vibe of Anna Maria pays homage to “Old World” Florida, a time before glitzy resorts, glam high-rise condos and chain restaurants clogged so many of Florida’s beach town shores.
Anna MariaYou’ll want to join the locals at Anna Maria’s wide, sandy shores, such as Bradenton Beach or Bean Point; it’s easy to explore the various beaches via the island’s complimentary trolley. Kayakers, boaters and windsurfers will likely convene with other like-minded outdoors lovers at Palma Sola Causeway Beach. Whether you’re an Old Salty Dog who loves fishing or you could care less about baiting a hook, plan to hit the island’s Rod & Reel Pier, a fishing hot spot marked by a budget-friendly seafood restaurant at the pier’s end.  Source: Travel Channel 

Ok so lets see which island meets most of our needs:

Sanibel & Captiva Accommodations: 

South Seas Island Resort – Offers everything we need from rooms with a view, dining, shopping concierge service, location, and pool.  We will have to call about airport pick up.

** Tween Waters Inn Resort and Spa – Love this one because it offers a variety of dining options directly onsite which is super important to our dad.

Sanibel Harbour Marriott Resort and Spa – This one works for all the right reasons except our dad isn’t going to want to pay $25 pp for breakfast.  This is a huge draw back because it is one of his favorite meals of the day and he isn’t going to want to explore the town every time he wants to eat.  He needs convenient, affordable food.  This one is probably a no.

** Pink Shell Beach Resort and Marina – This one seems like the best fit but there is only one catcher.  It is in Fort Myers.  Which, actually may be ok.  There is an airport there so you can fly directly there and catch a short cab ride to the hotel.  This resort also offers free continental breakfast for two daily, a full service spa, waterfront dining, 3 heated pools, free beach chairs and umbrellas, and all other convinces you expect to find from a full service resort.

** Our favorites

Amelia Island

I just looked around and I didn’t see anything I liked so I am not going to waste my time and yours going over the different resorts.

Anna Maria Island

After researching, it seems Anna Maria does not offer any full service resorts.  They do have “resorts” but they are more like condominiums which more than likely would require our folks to cook and that wouldn’t happen.


Well folks, I think after all this we have narrowed it down to Sanibel & Captiva Islands or Fort Myers.  In order to plan a vacation, the best thing to do it make a list of everybody’s wants and needs.  From there, just research, research, research.  It will become a matching game but do not discouraged and always try to compromise!  Now, to sell the idea to our folks!  Wish us luck!

United Military Travel

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