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5 Second Summer Destinations to Visit This Year

5 Second Summer Destinations to Visit this Year - Sun Air Jets

Who says that summer has to end with fall making its appearance? Just because you are holding a pumpkin spice latte in one hand and a warm apple fritter in another doesn’t mean you can’t plan a getaway. Why not consider fall your second summer?

If you aren’t ready to dive head first into the holiday season and would like to pretend it is summer for a little bit longer, we’ve got five second-summer destinations to visit this year. 

1. Second Summer in Catskills, New York

Imagine sitting around a lake, letting the minutes pass you by while you take in the quiet surroundings and the breathtaking fall foliage. That’s what you will find in the Catskills. 

This area is full of rolling hills, crisp temperatures, and shades of fall. Just looking around will make you feel warm and cozy. There are a ton of amenities in the surrounding area, including fall festivals, taking strolls and drives, visits to cideries and breweries, theaters and museums, and so much more. 

A visit to this classic destination is sure to be peaceful and memorable.

2. Lexington, Kentucky

A little off the beaten path, Lexington, KY, has become quite the go-to destination for fall (or second summer) travel. Not only are the landscapes beautiful and incredibly colorful this time of year, but there is a lot for you to do while here, too. 

Lexington doesn’t get its nickname of Horse Country for nothing. It is an important equestrian center consisting of many farms. Do you know what that means? Yep – horseback riding tours through the fall foliage for an unforgettable experience. 

A few other must-do stops include touring (and sampling) the many bourbon makers, visiting art galleries in downtown Lexington, shopping antiques, and indulging in some excellent cuisine. You will also have access to boat river tours, zip-lining, and hiking along limestone cliffs and caves. 

You may be surprised at what Lexington, KY, can offer you. 

3. Anna Maria Island, Florida

Sometimes you want the beach. And sometimes, you want that beach to symbolize solitude and stillness rather than not being able to see all the sand because there are too many beach-goers. 

At Anna Maria Island, you get a paradise of white sandy beaches and light emerald waters crashing into the coast. This barrier island is located along the Gulf coast just south of Tampa. It’s quiet and unlike other beach experiences in Florida. And fall is the perfect time to visit because the weather is still warm, but the crowds are few. 

While relaxing on the beach is one thing you are sure to enjoy while here, it isn’t the only thing to do. You can go kayaking through the mangrove tunnels, visit the Anna Maria Island Historical Museum, shop along Bridge Street and dine at local restaurants that will delight your taste buds. Take a stroll with homemade ice cream, or even take a sunset cruise. Rumor is that you will see some of the most incredible sunsets from Anna Maria Island. See for yourself!

4. South Padre Island, Texas

South Padre may be a huge spring break destination – but in the fall? It is awaiting your arrival. The rowdy crowds are gone, leaving you with laid-back experiences you won’t want to miss. For instance, horseback riding along the shore, jet skiing, paddle boarding, fishing, dolphin cruises, or even learning about rehabilitating injured sea turtles at Sea Turtle, Inc. If you are daring, you can give parasailing a try, too. 

Believe it or not, this destination is more about relaxing and enjoying life than partying – despite its reputation. There are so many ways to relax while here. Watch the magnificent sunset and then the fireworks overhead after dark. 

You are sure to find that this is a destination you will want to revisit time and time. 

5. Second Summer in Turks and Caicos

If you want to take your second summer vacation destination to a new level, visiting the Turks and Caicos is warranted.

It doesn’t matter what time of year you come, the weather is always beautiful and warm – and there is always something to do. Depending on what you are looking for, relaxing on the beach with a good book while listening to the waves crash could be all you need. But if you are looking for more, you will have to try: 

  • Snorkeling through the reefs or just off the ocean
  • Whale watching
  • Kiteboarding
  • Kayaking
  • Paddleboarding
  • Parasailing
  • Fishing 
  • Cruising

Do some dining and shopping, and then finish off your days with the local nightlife. You are sure to have a second summer vacation you won’t want to miss. 

6. Portland, Oregon

Another excellent place you won’t want to miss is Portland, OR. As if the fall colors surrounding you aren’t enough, there is always the opportunity to explore and create new memories. 

Go hiking through Washing Park, Forest Park, or even Witches Castle Hike. Corn mazes are always exciting, whether haunted or not – but they are sure to bring a lot of fun. Apple picking in Hood River is always a delight. 

You are dining on comfort foods, sipping hot coffee from one of the many coffee shops you will find here, enjoying live music and patio fires, and delighting your tastebuds with local wines. Whether you are looking for indoor or outdoor fall activities, you will find them here in Portland. 

Flying Private to Your Second Summer Destination

If you want to get to (and from) your second summer destination in style and comfort, then you need to book a private jet charter. There are so many reasons that flying personal can enhance your vacation that choosing any other travel method doesn’t make sense. 

  • You get to choose your travel times.
  • Non-stop travel
  • Luxurious and comfortable seating and accommodations
  • Inflight entertainment
  • A private experience
  • The ease and enjoyment of an FBO experience

When you opt for a private jet charter, you miss out on all the frustrations of flying commercial in a bustling airport. Instead, your second summer vacation truly feels like a vacation. All you have to do is decide where to go this fall. 

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