3 Days on Amelia Island

We are on the hunt for new digs in the South. Now don’t get your panties in a bunch, we will always maintain roots on Cape Ann, but these dang winters are KILLING me slowly. First stop on our tour of exploration, Amelia Island, Florida.

It is not much of a secret; Rich and I have plans to relocate to a warmer climate sometime in the future. With each passing year, the desire becomes stronger, and we get closer to making that goal a reality. This year, we decided to have some fun with it and make it a mission to explore our options. Our plan: to hit one of our potential relocation destinations per year until we find ‘the one”. Bonus, with each of these explorations is a promise of one long weekend away as a couple and a lot of fun opportunities to dream about our future together.

This is what we are looking for in our “someday” down-home, southern community:

1. Warm climate with the hint of seasonal changes
2. Proximity to the ocean
3. A warm, welcoming community with annual festivals and gatherings
4. Treelined streets with close-knit neighborhoods but houses that are not on top of each other
5. A town rich in history and houses reflecting that history
6. A travel destination where all my northern loved ones will want to visit

Basically, I am look for our current residence of Gloucester, Massachusetts with a dash of southern charm. Not much to ask, right?

Somewhere along my endless virtual searching, I fell upon the Amelia Island/ Fernandina Beach community. The moment I began scrolling through pictures on the internet, I knew this tiny beach community was a contender in the hunt. Dreamy images and insightful blog posts flooded my Google search, revealing an idealistic town full of all the historical charm and beauty I had been hoping for. From the quaint downtown area, expansive white beaches and streets flanked with strong oak trees draped romantically in Spanish moss, I instantly fell in love with what I saw and began planning our trip to experience it in person.

Located on the northeastern corner of Florida (literally, as far north as you can get in the sunshine state), Amelia Island is 13 miles long and two miles wide, with preserved park lands at each end. To my delight, it is super easy to get to at only 30 miles from Jacksonville. Everywhere we went on the island, we were surrounded by the natural beauty of mature trees creating romantic canopies over the roads and sightings of coastal vistas – whether ocean or river side.

As typical of most beach destinations, the options for lodging were abundant. From quaint Victorian bed and breakfasts to condominium rentals, beach motels to luxurious resorts, Amelia Island offers it all. There is even an inn on the main drag made from an old schoolhouse with a bar appropriately named “The Principal’s Office” (love it and plan to stay there in the future). For this trip, we were looking for a little pampering and ocean views. 2020 was a long, long year. On top of the relocation hunt, Rich and I wanted a place to unwind and stare off into the horizon from a balcony. I instantly fell in love with The Omni Amelia Island.

The Omni is located on 1350 acres of the southern point of the barrier island. The entire property is blanketed with lush green foliage including everything from tropical palms to those great big oak trees. It is home to numerous restaurants, shops, a golf course, spa, and a ton of entertainment options from paddle boarding to horseback riding. It was a great place for a relaxing stay with my husband and with all the activities offered, would have been great for the kids too.

During the planning, I looked at reviews of restaurants and activities; making a “must do” list of all I wanted to see. In the end, we took each day as they came and had a blast scoping out this beautiful corner of the world.

Day One: We Have Arrived

We arrived at the Omni Amelia Island at 6pm after a full day of traveling from Boston. Me, the super planner, thought that since we were traveling without children, I would be able to handle flying on a 1 stop flight. Yeah, I was wrong. (Rookie or spoiled… you decide). Not only did we arrive tired and hungry but to 50 degrees, overcast weather. I was disappointed in the anticlimactic arrival to what could be a new home for us and started to second guess our reasoning for taking this trip in the first place. Rich tried showing me the menus from the resort’s restaurants on his phone, however nothing was sparking any interest. I knew what I was looking for, an outdoor beach bar with fruity cocktails and local seafood of some sort. That was my idea of a perfect kick off to our weekend. When we realized we were not getting anywhere with the digital menus, we decided to just go for a walk and explore the resort.

And wouldn’t you know it, we arrived at Oceanside, an outdoor casual restaurant overlooking the beach and pool (ahhh). We sat at the bar like grownups without a gaggle of kids, ordered a specialty cocktail containing pure delicious fruitiness and filled our bellies with seafood dishes made of local shrimp. Just when I thought it could not get any better, a musician began to play his guitar and sing chilled out beach vibe music. Live music. Now remember, this is at the tail end of COVID. Live music had been removed from our life for over a year and I missed it immensely. Just hearing the singer strum to Jimmy Buffet tunes while I sipped on my “Amelia Margarita” brought everything right in the world and suddenly this trip was the best decision I ever made.

Day Two: Give Me All You Got AI

Long, long ago, in another lifetime, Rich and I took a trip to Cape Canaveral. The trip was intended to be a birthday present to Rich, my boyfriend for over a year. I planned it around the space shuttle launch, something I knew he had always wanted to see. Rich had another idea and proposed to me in our hotel room at Cocoa Beach. Just like the Omni, our room during that 2001 trip had a balcony overlooking the Atlantic Ocean. Not able to sleep the night of my engagement, I was up to watch the sun rise over the horizon. We took a picture as the sun seemingly glided from the depths of the ocean in all its golden glory. The picture of that monumental sunrise still sits on a shelf in our bedroom. With a similar view from our room in Amelia Island, I was determined to replay that moment again.

I set my alarm early and perched myself on the balcony with a hot cup of coffee at 6 am. The sky had cleared from the night before and the air was warm and balmy (as it should be for this Boston girl escaping the cold in April). As Rich and I sat on our balcony, watching the sun slowly make its way above the horizon, it felt just as symbolic as it had 20 years ago. I could not wait to tackle this fun filled day of exploration.

First stop, Downtown Fernandina Beach. One of the things that caught my eye while researching the area was the immense diversity in its history. The seaport village’s architecture and preservation reveal past occupancy of pirates, Gilded Age millionaires, bootleggers, and shrimpers. The shops on and around Centre Street are quaint and browsable with sweet gifts, antiques and boutique clothing. We explored our surroundings, dined al fresco for lunch and dinner, indulged in treats and wandered through the sun filled streets. It was instantly apparent that Amelia Island attracted people of all ages, from older couples in retirement to families on vacation to young adults shopping the boutiques. Rich and I began to envision our future on the island as we acquainted ourselves with the farmer’s market and coffee shops. We imagined bringing our children here and speculated what they would love about Amelia Island. Agreeing that despite the varying ages of the four of them – each would find this to be a pretty cool place to be.

We headed back to the hotel late afternoon after a day beyond what I had hoped for. The weather had turned out perfect, the sunshine and warmth I felt all day made my heart happy. Rich and I had in-depth conversations of what we wanted in our future together. Was this something for retirement or was this something we were willing to make a more immediate move on? We tried to determine what in the actual hell we were doing and where this little island fit into the picture. One thing was for sure, we both saw it as a contender.

And then came the reminder that we were in Florida.

As we stepped out of the hotel to return to town for dinner, the sky opened. Rain came pouring down on us in torrid streams. The wind began to whip the pelts of water at our face and my freshly curled hair fell dripping at my shoulder. Slightly disappointed but also struck in the amusement of our comical timing, we pivoted back into our dry room and witnessed an impressive lightning display that lasted approximately 30 minutes. The thunder and lightning storms of coastal southeastern towns are my favorite. I love watching the weather appear out of nowhere, move up the coast and dissipate just as abruptly. With our slight delay behind us, we headed into town to Pepper’s Cocina Mexicana & Tequila Bar. The fajita’s, margaritas and cleared up skies instantly brought us back to our happy island vibes. We sat on the outside deck and observed our fellow patrons also venturing out to enjoy the evening post-storm. After dinner, we again explored the downtown streets. Local bands performed on small stages and porches of outdoor bars tucked neatly between other establishments, music spilling into the streets. Rock music filling the sultry air with a summer vibe of normalcy. The atmosphere felt alive and a lot like home.

It was official, I had fallen in love with Amelia Island.

Day Three: Rain, Rain… Go Away

We had so much planned for day three. A hike in Fort Clinch Park. A guided boat tour on Amelia River Cruise. A walk on the beach and through the canopy tree trail at the Omni. More Al Fresco dining. Even more cocktail sipping… but alas… then came the rain. Just a glance at our weather app told us none of that was happening.

I was so bummed to not have the opportunity to explore and learn more about the area’s rich history.  We will just have to go back to Amelia Island and fulfill those empty checkboxes on my list. Possibly with the kids. Twist my arm 😊

Due to the wash out of our plans, we spent the day venturing by car, ruling out some neighborhoods and highlighting the possibility of others. Once we had exhausted our self-led island tour (remember, we only really had 13 miles to drive), we took a short excursion north to see what was on the other side of the river in Southern Georgia. Quickly determining there wasn’t much to see, we returned to the happy little island of Amelia.

We had a great lunch at The Tavern at AIBC (Amelia Island Brewing Company) where this gluten-free chick was able to partake in the brew company experience by enjoying a flight of cider. And followed the deliciousness with souvenir shopping for our 4 kids at home.

With the idea of a very early morning flight, we decided on pizza in our hotel room for dinner. Rich found Arte Pizza, a downtown wood-fired pizza establishment who make the most delicious cauliflower crust pizza (score 2 for GF girl and bonus to the hubby for hunting them down).

All in all, this was a fantastic weekend away with Rich. Although we were not able to do all we had planned due to the unfavorable weather, we plan to revisit Amelia Island soon. Neither of us left with the thought that it is the be all and end all in what we can see as our future home, however, the potential is there. For now, that is all we need.

Next stop, I think we will make plans to visit South Carolina in 2022 for some low-country living.

Stay tuned…