4 of the Best Places to Stop on a Solo East Coast Road Trip

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Prior to the launch of this website, I decided to look back at some of my favorite moments spent traveling alone in 2015. One of the most memorable solo trips was my Miami to Maine solo driving adventure which took nearly seven weeks to complete with a quick break for a flight home to attend a wedding in between. In late April, 2015 I took off on this lengthy solo driving adventure beginning in the Miami and working my way up the East Coast ending in Maine.

12 Cities Visited

Over the course of the trip, I visited 12 solo friendly cities. My destinations included Palm Beach, Miami, St. Augustine, Jekyll Island, Savannah, Charleston, The Hamptons, Newport, Provincetown, Salem, Portsmouth and Kennebunkport.

Gardens at Magnolia Plantation in Charleston

In a previous blog post, I shared, “Countless hours have been put into the research for this trip. In addition, my media team gathered input from various tourist bureaus and I had scoured hundreds of websites and YouTube videos deciding on what to do, where to eat and stay, where to shop and bottomline, how to experience what makes each place special.”

My 4 Favorite East-Coast Destinations

While each location is unique, I kept an eye out for a few main themes throughout my trip. Culture, history, art, architecture and shopping were key things I explored in the various locations.

Yes, special this road trip certainly was! Some highlights of the road trip were at the Miami Design District, Kennebunkport, Savannah, and The Hamptons. I’ve recapped some of these key moments and memories below.

1. Miami Design District

The most impressive aspect of the MDD was the overall revitalization concept of this extremely rundown, impoverished area of Miami. The aesthetically minded developers have transformed the area into an ultra-modern, multicultural center for people from all walks of life. A modern lifestyle community is the essence of this cutting-edge development which offers top designer brand shopping venues, cutting edge art galleries, modern interior design emporiums, famed restaurants and a wide variety of contemporary living options designed by some of today’s most internationally renowned architects. Read my Miami Design District blog to give you a more in depth understanding for this ultra-cool area. The MDD is a happening, international place to live, work, play or visit. I was so taken by this well-conceived development; it made me consider moving there one day!

2. Kennebunkport, Maine

Schooner Sailing in Kennebunkport, Maine

Happy Place, Happy People is the feeling I experienced in Kennebunkport, Maine because everyone I encountered there was friendly, laid back, and the small town environment felt ultra safe. Nobody seemed to lock the doors of their well-maintained, picturesque homes most of which had a beautiful manicured yard with flower filled gardens. Kennebunkport’s weather was crisp and the air was ultra clean and fresh. Likewise, the breezes off of the Atlantic were delightful. Watching the memorable sunsets was a daily treat. This special Maine small town had the feeling of the Ozzie and Harriet days of the 1960’s when American life was still simple and wholesome. Kennebunkport’s character is polar opposite from the super trendy vibe of Miami but just as appealing in its own way. Anyone traveling alone to Kennebunkport would be comfortable and would enjoy a relaxing, rejuvenating week here sailing or exploring this quaint New England town.

3. Savannah, Georgia

My third solo, road trip highlight was the sultry, mysterious charm found in Savannah, Georgia. For starters, the many beautiful town squares throughout historic downtown make it a fabulous place in which to walk and leisurely explore, especially as a solo traveler. The city has a rich history to absorb, beautiful gardens to visit, many historic homes to tour, stellar antique stores to shop and delicious Southern food to savor.

Savannah is a relaxing solo destination with a classic Southern essence which can be discovered by visiting some its outstanding historical architectural gems. The transformative catalyst of the Savannah’s Historic District was the acclaimed Savannah School of Art and Design. SCAD is credited with starting the the push to save city’s magnificent historic architecture and is currently, directly involved in spearheading the District’s complete restoration. The school continues to train some of America’s leading historic architectural restorers. SCAD’s primary focus is all about saving Savannah’s unique southern culture through historic renovation.

The Hamptons Wine Vineyards

4. The Hamptons

My fourth solo trip highlight was the time I spent exploring the famed Hamptons on Long Island in New York. The week spent here was my favorite of the 12 solo friendly stops I visited. I l fell in love with everything about this area; it is earthy sophistication with a focus on living, eating and drinking well, largely due to the organic food movement that had its beginnings there. Ina Garten is one of the Hamptons famed residents! I was surprised to find so many farms and vineyards thriving here, as well as the many fantastic, farm to table restaurants that source their food ingredients from the local farms in the area. One of my most memorable meals- the best sandwich I’ve ever eaten, a lobster club- was enjoyed at the historic and elegant American Hotel in Sag Harbor.

The Maidstone Inn

Beyond the food, The Hamptons is special because each village has its own unique character and flair. From the clothing boutiques offering the latest in casual, elegant apparel and accessories, to the thriving bookstores that have famed writers signing there tomes regularly, the Hamptons offers some of the the best shopping experiences on the East Coast.

The Hamptons personifies everything I love- classy, sophisticated, earthy, good food, good wine, good books, posh, and fun-loving. The best of the best is here and can be savored in this small, unique, special place.

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