Most people don't realize that Florida is like multiple states in one. Even multiple countries. The panhandle and much of the north is kind of like the south, the west coast like the midwest, and the southeast like the north with a large latin influence. It's quite diverse in culture, people, nature, and climate. I spent quite a bit of time in southeast Florida growing up visiting family. I also took several subsequent trips to northeast Florida and South Beach, Miami in my 20s. My latest trip was spent exploring the rest of the state that I had not seen.

My Favorites

1. Orlando

Disney’s Hollywood Studios Star Wars Land

Highlights: Theme parks, golf, springs, swimming holes
Suggest Staying: 3-7 days
Stay Around: Lake Eola or Winter Park
Internet: Strong
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Probably best known for Walt Disney World and the various theme parks in the area, Orlando has a variety of other activities including parks, springs, kayaking, and golf. Orlando to my surprise was also very hip with some cool tea and coffee shops with plenty of great restaurants. Other than Disney, the city is also more chill than other big cities in Florida, making it much easier to get around and to relax.

See & Do

  • Lake Eola & Thornton Park. Beautiful lake and park area right downtown.
  • Disney World. Famed theme park. Here’s a great planning resource.
  • Universal Studios. Famed theme park. Here’s a great planning resource.
  • Winter Park. Nice upscale area with great food and shops. Find the hidden olive oil shop in the alley.
  • Mills 50. Artsy neighborhood.
  • Milk District. Artsy neighborhood.
  • SODO Shopping Center. Shops.
  • Lake Nona. Upscale area.

Food & Drink

  • East Garden Chinese Restaurant. Dim sum and plenty of other dishes.
  • TooJays Deli. Jewish delicatessen and bakery.
  • Infusion Tea. Great selection of teas and snacks.
  • Stardust Video & Coffee. Hipster coffee spot with live events and a bar.


  • Kennedy Space Center & Cape Canaveral. Space information and activities.
  • Wekiwa Springs State Park. Beautiful swimming hole with kayaking and camping.
  • Juniper Springs. Emerald green clear springs for swimming. Be sure to see both springs.


  • Disney World. Plan ahead! Disney is huge and you need to prioritize and plan your day(s). It could easily take 1-2 days for a single park. Pricing is per day per park. You can add a park hopper if you want to do multiple parks in a single day which is awesome if you have the stamina. It also easier if it’s not too crowded and you aren’t going on all of the rides, resulting in a lot of time waiting in lines. Use the above resource to help plan. Consider using the Disney app as well. You can make arrangements on the app and use your phone to hold and scan your tickets.

2. St. Augustine

St. Augustine

Highlights: Fortresses, pirates
Suggest Staying: 1-2 days
Stay Around: Historical Downtown
Internet: Strong
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The oldest city in the United States, this very cool small city is a must visit. Historical charm, a fortress, and pirates.

See & Do

  • Historical Downtown. Shops and restaurants.
  • St. Augustine Pirate & Treasure Museum. Awesome spot you can learn about pirate history, figures, and pirate movies.
  • Castillo de San Marcos National Monument. Fortress you can tour.


  • Palm Coast. Golf and beaches.
  • Daytona Beach. Popular spring break destination and raceway.
  • Jacksonville. Major city in the area.

3. The Florida Keys

Boyd’s Campground

Highlights: Snorkeling, scuba diving, fishing, boating
Suggest Staying: 1-3 days
Stay Around: Boyd’s Campground
Internet: Good
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The Keys are beautiful. My favorite thing is the drive through them. You feel like you’re driving on the water which is this beautiful crystal clear shades of blue and green. Each key has its own charm and set of activities, though most of the fun is on the water, with the exception of Key West.

See & Do

  • Key West. The most popular, very touristy, very unique place. It’s kind of like New Orleans meets Savannah established by pirates. Certainly there are wonderful nearby water activities from glass bottom boat tours to snorkeling to scuba diving. There are also tons of shops, restaurants, bars, and live music. Winter and spring sees a lot of tourists and can feel quite busy. Duval St. is the main drag.
  • Key Largo. Very close to Miami with opportunities for snorkeling, diving, and a dip into the keys if you have less time available to explore further. John Pennekamp Coral Reef State Park is cool, go early.
  • Islamorada. Variety of activities and one of the more developed keys. Theater of the Sea and Rain Barrel Village are two interesting spots.
  • Marathon. Half way point that serves as a great home base for exploring more of the keys.
  • Big Pine Key. Mostly a nature preserve which is cool for exploring wildlife. There are small deer, the size of a small dog, that inhabits the island. I couldn’t get a good story on how they got there. The Blue Hole is kind of neat for an off the beaten path stop where you might see an alligator or two and to escape the crowds. Ramrod Swimming Hole is a lovely relatively hidden spot you can wade around in the clear shallow water. People bring their dogs.
  • Anne’s Beach. The magic of this place is late afternoon when the tide goes out. The area turns into a series of tide pools that trap small fish and crabs, and you can walk pretty far out where it was previously covered in water. One of my favorite gems. Just past Islamorada.
  • 7 Mile Bridge. Long stretch that’s a great vista point.
  • Bahia Honda State Park. Area with some small beaches and nature. Nice spot to hang out if you’re seeking land based activities, though it can get crowded, so go early.

Food & Drink

  • The Fish House. Market and restaurant with fresh fish among other seafood and food options in Key Largo.
  • The Stoned Crab. Great spot for fish and seafood with nice ambiance. Also good spot if you’re wanting something outside of downtown Key West.


  • Dry Tortugas National Park. I didn’t actually make it here, but it looks to be a fun adventure. Most of the park is water and reefs. You will take a boat tour that includes some time at the fort and for snorkeling. You can also camp on the island which I can imagine would be quite peaceful. It’s about 2.5 hours each way from Key West, so you would need to budget a full day for this excursion. If you get seasick, I read that winter has more choppy water, so take some precautions.


  • Getting There. Most people fly into Key West. You can also drive from Miami. A third option is a ferry from Fort Myers.
  • Getting Around. If you want to explore, rent a car. If you are just hanging out in Key West, rent a bike.
  • Lodging. One option is to stay around Miami if you only want to make day trips, but going all the way out to Key West is quite far for a day trip. Islamorada and Key Largo are good options and have many places to stay. Just note that the keys are really expensive. I stayed at Boyd’s Campground which offers RV and tent spots. It’s a cool place, but can be a bit loud since it’s right under the airport’s flight path and near a naval air force base. Spaces are pretty crammed together. Overnight while sleeping it’s quiet and there are spots right on the water. There is an added benefit being a few miles outside of Key West with less hustle & bustle, and much cheaper. There are some companies where you can rent an RV down there, some even will deliver and set it up for you at your destination.
  • Crowds & Traffic. Because most of the highway through is 2 lanes and also sees a lot of visitors throughout the year, even people working from the mainland, traffic can be brutal. Research events happening when you plan on visiting, if you’re driving. Rush hour is a thing so leaving earlier in the morning or in the evening will be less crowded. Of course if you only plan on visiting Key West, it’s less of a problem. In normal traffic conditions it will take between 3-4 hours from Miami to Key West, depending from which part, to give you an idea. About an hour to Key Largo, another hour or so to Marathon, and another hour to Key West. You’ll likely move slower through the towns and want to hop out from time to time for pictures or exploring.
  • Seasickness. I’m very prone to motion sickness which only seems to get worse as I get older. Here are some things I have found success with. Dramamine (my go to, though it can make you drowsy), Transderm Scop (prescription required), ReliefBand (still experimenting with this, but so far pretty great). With Transderm Scop I would only recommend for a live aboard situation where you will be on a boat for multiple days. I used this in the Galapagos Islands for 3 days on a boat and it was great, but there are side effects, though they may vary for different individuals. You will be more sensitive to the sun, so cover up, potential for blurred vision and eye sensitivity, so wear sunglasses, and you may get sick after you take it off (or it could be a result of reverse seasickness), I was for 24 hours. Check with your doctor!

4. Fort Lauderdale

Morikami Museum and Japanese Gardens

Highlights: Beaches
Suggest Staying: 1-3 days
Stay Around: Las Olas
Internet: Strong
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Well know as a popular spring break destination, Ft. Lauderdale has some of the best beaches in Florida along with some fantastic restaurants. I don’t have a lot of specific recommendations other than just go to the beach. If you’re interested in exploring, there are also some other nearby beach and golf towns.


  • Hollywood. Nice beach and boardwalk. Pachamanka Authentic Peruvian Cuisine is very good, and there are tons of other restaurants.
  • Boca Raton. Upscale area good for golf and beaches.
  • Delray Beach. Upscale area good for golf and beaches.
  • Boynton Beach. Upscale area good for golf and beaches.
  • Palm Beach and West Palm Beach. Upscale area good for golf and beaches. The Morikami Museum and Japanese Gardens is lovely. Peanut Island is also quite fun.

5. Tampa Area


Highlights: Beaches
Suggest Staying: 3-5 days
Stay Around: St. Petersburg or Sarasota
Internet: Strong
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Tampa is an area of several great cities, most of which offers beautiful soft white sand beaches along the gulf coast. Some of the best in the country like Clearwater Beach and Siesta Key. A popular area for snowbirds looking to the west coast. The area gives off a bit of a midwest vibe compared to other parts of the state.

See & Do

  • Ybor City Historical District. Very cool artsy, hip historical district where restaurants and nightlife live.
  • Riverwalk. Nice walk along the river.
  • Oxford Exchange. Bookstore, boutique shops, tea, restaurant.
  • Clearwater. Beach.
  • St. Petersburg. Chill, artsy town, home to the Dali Museum and the James Museum of Western & Wildlife Art. Don’t miss the St. Pete Pier and Vinoy Park.
  • Anna Maria Island. Beach.
  • Sarasota. Another chill artsy city with beautiful white sand beaches nearby. Although I didn’t get to it, the John & Mable Ringling Museum of Art looks great.
  • Lido Key Beach. Somewhat less crowded beach, especially the county park beach.
  • Siesta Key. Beach.
  • Myakka River State Park. Forest, wetlands, kayaking, canopy walkway, camping

Food & Drink

  • Armature Works. Very cool upscale food hall and restaurants along the water with a great outdoor space.
  • Columbia Restaurant. Tampa staple that’s a mix of Cuban and Spanish food. Live performances some days. Make a reservation.


  • Crystal River. Swim with manatees.
  • Fort Myers. Downtown commericial district and beaches.
  • Naples. Healthy town and beaches.


  • Lodging. St. Petersburg and Sarasota are the nicest and less busy places to stay, but Tampa will be much cheaper and is not that far from the surrounding beach cities, unless you want to be nearest to the beach. Clearwater is very popular, busy, and difficult to park unless you’re staying at a hotel along the beach.

Other Considerations



Miami is by far the most diverse city in Florida, hosting people from not only all over the country, but also from the caribbean, central, and south america. Even many Europeans visit or even call Miami their home. There are many different neighborhoods, cultures, business opportunities, beaches, art districts, shops, restaurants, live music, and nightlife. It’s a very bustling town which can be overwhelming like any major city, so do your research, plan ahead, find your niche, and explore!

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See & Do

  • Wynwood. Arts district with murals all along the shops and restaurants.
  • Miami Design District. Design area.
  • Midtown. Shops and restaurants.
  • Brickell. Business area with some restaurants.
  • MiMo. Small strip hipster area.
  • Little Haiti. Latin restaurants.
  • South Beach. Beautiful beaches and nightlife. Popular spring break spot.
  • Coconut Grove. Shops and restaurants.
  • Coral Gables. University area.

Food & Drink

  • The Citadel. Upscale food hall with a rooftop bar.
  • Wynwood Marketplace. Open air market for food and drinks surrounded by painted shipping containers.


  • Hollywood Beach. Less crowded than Miami’s beaches with a nice, long boardwalk of shops and restaurants from all cuisines.
  • Biscayne National Park. Essentially part of Miami, this national park is ideal for snorkeling or scuba diving. You won’t see much or have much to do unless you’re out on the water.
  • Everglades National Park. The park is huge, much of the popular areas can be reached on the east side. Definitely look into airboat rides through the everglades where you can observe all kinds of wildlife from birds to alligators up close. There are some other tours and kayaking available as well.


  • Lodging. I would recommend staying around Wynwood or MiMo. The former is very artsy and popular, plenty of access to things within walking distance. The latter is much calmer and more chill, with less going on but a small strip of boutique stores and restaurants.


A small growing hipster city that houses a major university. Very much a college town but well balanced in terms of college madness yet plenty of places to relax and to explore. The main downtown area is along University Ave. between 13th and Main streets. For exploring you'll find a few nature based activities including, Kanapaha Botanical Gardens, Devil's Den Prehistoric Spring (scuba diving in a cenote), Ginnie Springs (swimming hole), Ichetucknee Springs, and Bolen Bluff (bison).


Panama City Beach

I was pleasantly surprised by the panhandle, the northwestern part of Florida that has a more southern vibe to it, which often gets overlooked. It still sees its fair share of visitors and tourists, but for me felt a bit less busy. Of course Panama City is a popular spring break destination and is very busy, and the beaches are nice. Along the gulf coast you’ll also find Pensacola, Watercolor, Rosemary Beach, and Destin which are nice little beach towns. Rosemary Beach in particular felt very European. The weather is noticeably cooler in this part of Florida compared to what people typically think of with Miami or Fort Lauderdale. En route to the capital city of Tallahassee, you can stop at Falling Waters State Park for a waterfall, depending on the time of year. The capital is very clean and nicely laid out, my favorite part of which is the hipster Railroad Arts District that is a must see. Nearby you can find Madison Blue Hole that offers swimming and kayaking.

General Tips

  • Weather. The jetstream splits Florida so you will definitely notice cooler temperatures up north, more variablity in the center, and warmer more temperate weather along the coasts. Florida is pretty humid everywhere. Best time to go is late fall (November) through early spring (March).

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