Key West Holidays: Best Resorts for Baby Boomers

December 3, 2020

Best ever resorts for baby boomers in the Keys
key west holidays

The Stoned Crab restaurant at Ibis Bay in Key West

Overflowing with its own blend of bohemian-tropical charm, the Florida Keys are one of the few U.S. destinations that wield a magnetic appeal on the Baby Boomer generation. Key West holidays are some of the most popular in the US and for good reason!

The Florida Keys is a string of small islands floating in an ideal seaside location between the Atlantic Ocean and the Gulf of Mexico. With Key West containing the southernmost point in the United States, the temperature ranges from Caribbean sultry to relatively mild, making it a popular and easy tropical vacation spot for Americans to travel without a passport.

Like its island neighbors just south in the Caribbean Sea, Key West holidays offer many of the same amenities that baby boomers seek, such as snorkeling, sailing, kayaking, fishing, eco-tours, and lots of one-of-a-kind restaurants and bars.

Unlike the Caribbean, though, you won’t find a lot of high-rise, all-inclusive party resorts in the Keys – which is something appealing to baby boomers that are looking for a more personal kind of escape. The Keys have a kind of “throw-back” charm reminiscent of their childhood memories.

According to TravelPulse, Baby Boomers – not Millennials – “are the driving force in travel for the foreseeable future; a future that could span the next two decades.”

And the Florida Keys are paying attention. What baby boomers will find there – much to their delight – are three distinctly different resorts that provide not just accommodation, but an entire experience.

Because they have the luxury of time, many Baby Boomers enjoy traveling by recreational vehicles. If that’s your preferred mode of transportation/accommodation, here are some amazing RV parks in the Florida Keys.

Cheeka Lodge

View of the beach from the atrium of Cheeca Lodge.

Upper Keys: Cheeca Lodge and Spa, Islamorada

If you’re looking for a place to pamper yourself in the Keys, look no further than the luxurious Cheeca Lodge. The resort rests on the shore of an idyllic palm-lined, turquoise beach where you can relax with a cold drink at the beachfront Tiki Bar, walk or fish from the longest pier in the Keys, or try a new activity like kiteboarding in the tropical breeze.   Inside, the oversized bedroom suites are beautifully appointed with casually elegant Caribbean-Colonial style furniture, a furnished sitting area with a wet bar, and a balcony complete with a luxurious outdoor hot tub and a view of the Jack Nicklaus par 3 golf course or beach. The resort also has three restaurants, a spa, and adult and family pools.

key west holidays

Fish or walk on the Key’s longest pier at Cheeca Lodge

Best boomer activities on Islamorada

  • John Pennekamp Coral Reef State Park is just a short drive in Key Largo. From the park, you can take a catamaran out to America’s first undersea park where you can snorkel, scuba, or take a glass-bottom boat to view the multitude of vibrant tropical fish, colorful reefs, and underwater Christ sculpture.
  • The mangrove swamps are well-visited by boomers who want to experience a short canoe or kayak trip.
  • World-class fishing for bonefish and sailfish and seasonal tournaments draw anglers from all over the world.
key west holidays

The beach at Tranquility Bay

Middle Keys: Tranquility Bay, Marathon

Serenity is abundant in the two or three-bedroom beach house rentals overlooking the white sandy beach of the Gulf of Mexico in the heart of the Florida Keys. Who wouldn’t want to sit on your own private balcony to watch one of the Keys’ glorious sunsets? The beach houses are just steps from the shoreline in a quiet, secluded area. The houses have a full kitchen, but there’s also the Butterfly Café restaurant on the resort property as well as a beach Tiki bar, three pools, extensive gardens, and water sports.

Another plus is the abundance of great places to eat in Marathon!

key west holidays

Serenity and privacy on your own balcony at Tranquility Bay

Best boomer activities in Marathon

  • Baby boomers appreciate the eco-sensitivity and work of the Turtle Hospital where the public can take guided tours to meet and see the rehab in process
  • A few minutes’ drive south to Bahia Honda State Park is a must for a bathwater-warm swim in the impossibly iridescent seafoam green waters of Sandspur Beach.
Ibis Bay

The quirky, fun, Bohemian lobby at Ibis Bay

Lower Keys: Ibis Bay Beach Resort, Key West

Imagine an intoxicating bohemian retro vibe but with modern amenities, and you’ve arrived at Ibis Bay – Key West’s original 1956 beachfront resort. From the moment you walk into the vibrant, quirky lobby and are greeted by their talking macaw, you’ll feel fun saturating into your bones. The coral rock cottages have cheerfully decorated rooms that open onto a private terrace with palm-strung hammocks overlooking the bay. The onsite Stoned Crab restaurant overlooks the channel where fresh fish is caught and delivered on their own dock daily. Every element at Ibis Bay is infused with amusement, including their complimentary “Life is Too Short” short yellow bus that transports guests to Mallory Square every hour.

Ibis Bay

Each colorful room is unique and has its own hammock and view at Ibis Bay

Best boomer activities

  • The Conch Train Tour is a narrated trolley ride that crisscrosses through Old Town giving an informative – and often humorous – overview of the architecture and sights of historic Key West. It’s a great introduction to places like the Hemingway Home and Fort Zachary State Park which may pique interest for a more in-depth visit.
  • Key West is known for having some of the most vibrant sunsets in the world. One of the best viewing spots is on Mallory Square – a festive, sometimes raucous spot on the pier with live performances and is close to restaurants and bars. A quieter but more active sunset viewing can be had by sailing out into the sea with Danger Cruises.

The laid-back charm of days gone by is a characteristic the Keys recognizes and has taken steps to protect. There are few chain restaurants, another appealing feature to boomers who want to assimilate into the culture and feast on local seafood like stone crab and conch fritters…. and of course, the to-die-for Key Lime pie.

Are you ready for your Key West holidays?

Want more Baby Boomer inspiration? Check these out!

You may also be interested in:

10 Photos That Prove the Florida Keys is the #1 US Destination

Beyond Disney: Take Your Kids to the Florida Keys

Three Hands Fish: The Keys Best Seafood

For more information on the Florida Keys, visit Keys Tourism.

Disclosure: The author was honored to be the guest of Key West Tourism and the resorts during her stay in the Keys, but as always, the opinions, reviews, and experiences are solely her own.

About the Author

Patti MorrowPatti Morrow is a freelance travel writer and founder of the award-winning international blog Luggage and Lipstick and southern travel blog Gone to Carolinas. TripAdvisor called her one of “20 Baby Boomer Travel Bloggers Having More Fun Than Millennials” and she was named one of the “Top 35 Travel Blogs” in the world.

She is also the star of the upcoming TV series “Destination Takeover” which is scheduled to premiere in the new few months.

Patti is the author of the book “Girls Go Solo: Tips for Women Traveling Alone,” and has over 150 bylines in 40 print and online publications, including The Huffington Post, International Living Magazine, Washington Post Sunday Travel, Travel Girl, Travel Play Live Magazine, and Ladies Home Journal.  She has traveled extensively through six continents looking for fabulous destinations, exotic beaches, and adventure activities for her Baby Boomer tribe.


  1. Comment by Mary Mack

    Mary Mack Reply March 2, 2016 at 9:48 pm

    Hi Patti, just discovered your blog on the Trip Advisor Top Baby Boomer Travel Blogs Article. Congrats! We are planning/hoping to have a South Florida, Key West trip later this year. I was happy to find your article, it’s filled with great information and tips.

    • Comment by luggageandlipstick

      luggageandlipstick Reply March 3, 2016 at 8:23 am

      Glad you found that article, Mary! You are going to love Key West!

  2. Comment by Beth Smith

    Beth Smith Reply April 29, 2018 at 9:40 pm

    Hey Patti!! Loved this article! My mother (85y/o) and I (53y/o) are staying at Ibis Bay next week! Neither of us have ever been to the Keys. Thank you for this write-up!

  3. Comment by luggageandlipstick

    luggageandlipstick Reply April 30, 2018 at 12:08 pm

    So glad you liked it Beth! Enjoy Ibis Bay, it is a really fun place! Tell them you read about it here. 🙂

  4. Pingback: Boat Rentals Naples FL: How About a Houseboat? - Luggage and Lipstick

Leave a reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Go top