Last Updated on January 7, 2025 by Marybeth
What a year it was! How about yours? I think this was the most we’ve ever traveled in one year, and it was mainly fun, sometimes eye-popping (it is Florida, after all) and occasionally annoying. As all travel is, right? If we’re being honest.
We also have a new granddaughter: Ellis is a big sister! Rhoda is three months old. She received a terrifying diagnosis in utero, which somehow resolved itself over time. This experience has no description I can give you. No words are sufficient, none are needed. She’s here, and she’s fine. Wow, and yay! These two precious granddaughters are bringing us so much happiness, and I’m grateful to be a big part of their lives.
Amidst the angst and the joy, we traveled to all the farthest corners (and yes, I looked it up, it is ‘farthest‘ for this instance, not ‘furthest’) of Florida and many points in between. SO much adventure, including getting rear-ended on our way home from Key West (eye-popping! And swear-worthy! We were fine, the car not so much) that at our lowest energy moments (my husband and I both had the flu for a month) we wondered if we should just, from now on, STAY HOME.
But no. I do understand better now that feeling of needing to hunker down, just get through the day, focusing on health and well-being. But exploring is a form of self-care, and many travelers are jumping on a trend called glowbirding (as tired as some of us are of the word trend, this one sounds pretty cool and I’m here for it) prioritizing wellness and physical activities while traveling. Most of these glowbirds are looking for warm destinations and places where they can spend time outdoors in nature.
The Sunshine State! Naturally.
North Westernmost Florida: Pensacola
Perdido Key is geographically snugged right up to the Alabama border, but as it is unincorporated, and the westernmost bar – Flora-Bama – is there and its address is Pensacola, we’re declaring we visited the north westernmost town in Florida.
Why visit Pensacola?
- The vibrant downtown area surrounding Palafox Street.
- The multitude of locally owned shops and award-winning restaurants.
- The close proximity of downtown to one of the best beaches in Florida.
Stay: Two stand-out, independently owned boutique hotels are right downtown:
Oyster Bay Boutique Hotel’s site was originally The Lee House built in 1866, razed after damage from a fire and Hurricane Ivan in 2004. Rebuilt in 2007 with architectural reference to the original home, and completely renovated by its current owners in 2021, this eco-friendly boutique hotel’s mission is to empower their community and promote sustainable tourism. The soothing natural tones and materials used in the rooms and gathering spaces will encourage you to stay a good long while. With views of the bay right out front, and Palafox St. just blocks away, this location is ideal for exploring Pensacola.
Lily Hall Boutique Hotel was originally a church, Mt. Olive Baptist, built in 1928. Also damaged by a fire and Hurricane Ivan, the abandoned building was saved by the John Sunday Society, a non-profit named in honor of Pensacola’s first Black state legislator. The interior was gutted but the historic façade remained, to become this luxurious but affordable lodging experience, with award-winning on site Brother Fox, and speakeasy Sister Hen (no secret password needed!)
Play: by which we always mean drink/dine, and you’ll find so many options on and within a few blocks of Palafox (see photo, above.)
Read our full article about Pensacola, here.
North Easternmost Florida: Fernandina Beach / Amelia Island
Fernandina Beach is a historic town located on Amelia Island, the North Easternmost region of Florida. You can see Georgia from here!
Why visit Fernandina Beach?
- The welcoming local owners of the shops, restaurants, and lodging in this true southern town. Florida is mostly a mishmash of residents who come from all over the country and the world (yay, diversity!) but you’ll hear real southern accents in Fernandina Beach, along with good manners handed down through the generations.
- This town is truly the best of both worlds: a stroll-able riverside main street area with a ton of history, and a beach town all in one.
- The small-town feel. Fernandina Beach will envelope you with that true getaway atmosphere: lots to see and do, but no need to do it all at once. Sit down in a fold-up easy chair (from Zac Brown Band.)
Our collaboration with Discover Florida Channel brought us here in 2024 (we’ve visited Fernandina Beach numerous times, it’s one of our favorite Florida towns) for the Beaches, Bars, and Bungalows travel TV series, episode 3. Watch it, here. Our recommended spots to stay and to play are:
Stay: Sea Cottages of Amelia
The summer cabin-like vibe here will have you wondering how far away is the beach from these woods? The contrast of the massive shade trees, raised boardwalks, peace and birdsong, with the beach just a five minute walk away may feel other-worldly. And that’s a win-win in our book!
Play: The Principal’s Office Bar
With a motto of Being sent to the Principal’s Office has never been so fun you know you’re in for a good time! The Principal’s Office Bar is located in the renovated historic Amelia Schoolhouse Inn (another excellent option for lodging.) The original schoolhouse was the island’s first, built in 1886. The bar plays up the Principal’s office theme with a photo op dunce corner, and drinks with names like Loud Mouth, Paper Airplane, and Study Buddy. Hang out in the courtyard by the putting green, listen to live music every Thursday (weather permitting.)
Southernmost Florida: Key West
The history, the festivals, the crowds. One of Florida’s most popular destinations, Key West may or may not be on your Must Visit list. We recommend you go to Key West at least once. It is truly like no other town in Florida. If crowds aren’t your thing (they aren’t ours) just scope out when the big events are, like Fantasy Fest, Hemingway Days, Key West Brew Fest, and approximately 12 others, and plan to go in between the big crowd-magnet parties.
Why visit Key West?
- The free-spirited viewpoint of locals and visitors.
- The plethora of activities: Duval crawl (so many bars!), water sports, historic tours, dozens of boutiques and art galleries, sunset at Mallory Square, charters to the Dry Tortugas, outstanding restaurants, and so much more.
- The architecture: make sure to explore nearby Bahama Village and the tucked-away alleys throughout Key West to see Conch, Bahamian, Victorian, and Queen Anne styles.
Stay: Two of our favorite places to stay in Key West:
It wasn’t JUST that the name included ‘Bungalows,’ but also the resort feel of the extensive grounds, the lush landscaping, and the worlds-away peaceful setting that won us over. Also the three swimming pools, and the Bungalow Bar that has the perfect All are welcome here atmosphere, and a bartender (Keith) and chef (Michael) who felt like good friends by the time we left. The homemade breakfasts by Michael are top-notch, and one of the big reasons we want to go back, soon! Part of Key West Historic Inns collection; choose your ideal lodging style, here.
“For those who like to wander… and for those who crave comfort in a destination… our accommodations offer solace and community” is part of {verdigreen} hotels mission statement. The small boutique hotel brand’s owner and designer engineered a top-to-bottom overhaul of this historic property with intuitive creativity. For travelers seeking elevated and inspiring design, Marrero’s Guest Mansion is the place. Serenity lives here alongside a visual feast everywhere you turn. All 12 guest rooms are inspired by the whimsical individuality that is Key West. Chill by the pool after a day of exploring, gather for Happy Hour in the colorful parlor: relax and restore.
Read our full article about Winslow’s Bungalows, here, and Marrero’s Guest Mansion, here.
Play: Key West’s waterfront wharf area, Duval Street, Bahama Village, Mallory Square, Stock Island – explore them all! Some of our favorites, in no particular order:
- Schooner Wharf Bar. Touristy, yes, but we love it. Water views, good food, and live music.
- Garbo’s Grill. Cute food truck famous for their Korean BBQ tacos. Shares the spot with Hank’s Hair of the Dog. Go for food, drinks, live music and the happy visitors all around you.
- Green Parrot. Since 1890! A not-to-miss watering hole.
- Moondog Café. Tucked just off the main drag, a cute cottage, shady garden, great food.
- Matt’s Stock Island Kitchen & Bar. American coastal comfort cuisine, located in the Perry Key West (another beautiful place to stay!) Delightful views of the harbor, super cool vibe, amazing food.
- The Docks Restaurant & Raw Bar. Lesser-known waterfront restaurant with a modern feel, locally sourced seafood.
All the Points in Between We Recommend for Sunshine State Travel in 2025
A quick rundown for the points in between the farthermost corners of Florida, beginning in the Panhandle:
Apalachicola
Apalachicola has one of the most picturesque small town scenes in Florida. Steeped in history and full of friendly locals, the walkability and charm are stand-out reasons to visit.
Stay: The Gibson Inn
Built in 1907 and impressively renovated by the current owners in 2018, The Gibson Inn is the place to stay in Apalachicola. Settle in on a bar stool at The Parlor Bar, dine at The Franklin Café, or sit outside on one of the expansive porches and watch the world go by.
Play: Apalachicola Yacht Club
There are dozens of fun restaurants, breweries, bars and places to have a meal by the water in Apalachicola. Visit them all! We especially enjoyed the camaraderie at the Apalachicola Yacht Club.
Places we recommend you visit on Florida’s east coast:
Vero Beach
Vero Beach not only has a oceanfront town to explore, but just across the bridge is Vero Beach’s historic main street area. Visit both, for the true flavors of culture, history, diverse natural sanctuaries, and sophistication but also down-home hospitality this destination offers.
Stay: South Beach Place
As a Consulting Producer for the Discover Florida Channel I recommended South Beach Place, a tucked away hidden gem. South Beach Place is a mid-century modern oasis located in a quiet, mostly residential and historic neighborhood – Riomar – and just across a quiet lane from South Beach Park with its shady winding pathways to a wide, uncrowded beach.
Play: Heaton’s Vero Beach
Open, airy and upscale Heaton’s overlooks the ocean and gets the breezes and sunshine and stellar bar service from Lead Bartender, Jacob, pictured above. This guy is totally devoted – he has tattoos of drinks on his arms! Watch this fun episode on Discover Florida Channel.
Read more about our collaboration with Discover Florida Channel, and how we’re still shouting with excitement about it, here.
If you choose to stay close to the historic mainland downtown Vero Beach, we’ve detailed our experience in a gorgeous Casita on lush tropical grounds, perfect for your own ‘extreme relaxing event.’ (It’s an actual contest!)
Delray Beach
Bustling Delray Beach checks many boxes for travelers looking for something more than a quiet little surfer town: dynamic downtown, upscale eateries, luxury shopping, art districts, fashionable visitors wearing on-trend styles, and a vibrant nightlife. The beaches here have been awarded some of the cleanest, and the sidewalks, pedestrian pathways, beachfront promenade, and pavilion are all sparkling and well kept. During our visit we saw more fit people – including old, fit people – in one square mile than perhaps in any other Florida town. #Goals!
Stay: Crane’s Beach House Boutique Hotel & Luxury Villas
Locally owned and operated Crane’s Beach House is our top pick because of its location – close to everything but off the beaten path – and the tropical, peaceful nature.
Related: We always choose independently owned, small properties and *never* stay at chain hotels. But this once, in Delray… We Never Stay at Chain Hotels. This One Time We Did: Here’s What Happened.
Play: The Sandbar
With glimpses of the ocean and a quintessential beach bar ambiance, this was our go-to fun spot for lunch and tropical drinks two days in a row!
Pompano Beach
Pompano Beach has had an amazing transformation on its waterfront and pier, with a $181 million redevelopment initiative. The oceanfront park promenade winds its way past shade trees and palms, joining gorgeous waterfront dining opportunities, shops, parks, playgrounds and the completely overhauled Fisher Family Pier. The whole place just glows; as if with pride in itself – as it should. You have to experience it yourself, if you haven’t been yet.
Stay: Floasis by Sunvibes Rentals
Our visit’s oasis was this beautifully renovated 1949 bungalow which can accommodate five guests. A 2/1 just a short six-minute drive to the beach, we highly recommend this stellar retreat.
For a locally owned guesthouse/hotel stay we recommend Seahorse Guesthouse, a clean and comfy (pink!) updated property within a 2 minute walk to the beach.
Play: Lucky Fish Beach Bar & Grill
Lucky Fish is open for breakfast, lunch and dinner with direct beach and ocean views, located on the Fisher Family Pier. I took this photo early one morning right before they opened.
Read about our experience in Pompano Beach, here.
Places we recommend you visit on Florida’s Gulf Coast:
Holmes Beach / Bradenton Beach on Anna Maria Island
Impacted by Hurricanes Helene and Milton, the island towns on Anna Maria are coming back and businesses are mostly reopened. When we were married on Anna Maria Island 18 years ago it was truly a best kept secret. The secret is out, but this destination remains one of Florida’s best, retaining its small-town charm.
The Discover Florida Channel Episode 2 of the Beaches, Bars, and Bungalows travel TV series was created with our recommendations. Watching this Emmy award-winning talented team create a ‘moving picture’ in this town, full of nostalgia for us 18 years after tying the knot, was an experience beyond our wildest imagination. We have a cameo in this episode, watch it here. Not just to see us, but because the show is super fun, with a vibrant invisible host who has all the insider info.
Stay: Mello on the Beach
Located mid-island in Holmes Beach with ocean views – and hidden down a tiny side street – Mello on the Beach blends a relaxing Palm Springs vibe with amazing design details down to the retro phones and neon-bright coffee table books. As an aesthetics enthusiast (putting this mildly; I am obsessed with good design) my eyes were popping and my camera was flashing our entire visit. Recently reopened after the hurricanes, Mello on the Beach is an ideal spot for your Anna Maria vacation.
Play: Beach House Waterfront Restaurant
“Sips, Eats & Fun” since 1993! The atmosphere here is always celebratory and the staff is so friendly. Enjoy excellent food on the covered deck, outdoor bar, indoors or toes in the sand.
Dunedin
Dunedin – also nicknamed Dogedin for its plethora of dog-friendly businesses and dog murals all over town – has one of Florida’s most quaint Main Streets. Art galleries, shops, restaurants and breweries line the shady sidewalks.
The Pinellas Trail, a former rail trail, runs right through downtown Dunedin and is a protected greenspace perfect for walking, biking, jogging and skating.
Caladesi Island State Park is worth the ferry ride (the only way to visit) for a beach day, or drive to nearby Honeymoon Island State Park. Both have restrooms, picnic pavillions, and a café.
Stay: Meranova Guest Inn
Historic and completely renovated (some of my favorite words as a travel writer), built in 1910, Meranova Guest Inn’s perfect location is just off Main Street. Explore, dine out, or stay in and make a meal in your fully stocked kitchen – the suites’ kitchens range from efficiency to full-size. Designed with lovely understated coastal decor, the Inn offers lush gardens and a private heated swimming pool.
Play: Dunedin Mix
With its fresh take on the old food hall concept, Dunedin Mix includes Circle 1852, one of the few rotating bars in the United States. Various food vendors, boutique shops, a speakeasy, event spaces, and the open air dining area combine to make this destination a must-experience.
Part 2 of Episode 2 of our collab with Discover Florida Channel was set in Dunedin: in case you missed it, download the app and start watching today! Discover Florida Channel, Beaches, Bars and Bungalows travel TV series.
And the other important 2024 update for us:
Our granddaughters Ellis and Rhoda! I couldn’t talk about our year without introducing Rhoda (I wrote about Ellis, born during Covid, here.) These two cuties have my heart, my focus, and my time. When not being Pop and Wawee (so very happily!) my husband and I are traveling, gardening, cooking, sailing, volunteering, bicycling, renovating, reading, writing, drinking wine, and spending time with the rest of our family.
