Top Ten Chicago (Top Ten Things to do and see in Chicago, Illinois)

Top Ten Chicago

  1. Go on an Architecture River Tour. The best way to tour the city is from the water on a river and lake architecture tour.  While the Chicago Architecture Foundation Tour is probably the best known, all the tours are very similar and other companies offer the tour on discount sites such as Groupon. If you’re doing the tour in fall or spring, choose a company that offers enclosed seating to ensure you don’t freeze.
  2. Ride the Navy Pier Ferris wheel. Catch some great views of Chicago from the Ferris wheel at Navy Pier for less than half the price of other popular viewing spots such as Hancock and Willis Tower, plus the added fun of an amusement park ride.
  3. Dine on deep dish pizza. Getting some deep dish pizza in Chicago is a must. Try the locals’ favorite, Lou Malnati’s or the well known Giordino’s.
  4. Visit the Signature Lounge. Skip the $18 fee for the 360 at Hancock Tower and head two floors up to the Signature Lounge on the 96th floor for drinks and appetizers instead. If you go right before sunset you can catch great day and nighttime views of the city.
  5. Experience The Wiener Circle. Not for the easily offended, The Wiener Circle is a popular hot dog stand that becomes very colorful late at night. The surprisingly delicious hot dog spot is famous for insulting and frequently cursing at rambunctious customers, though the customers are encouraged to give it right back to the employees.  If you would like some nudity with your hot dog, be sure to order the famous “chocolate milkshake”.
  6. Get a drink on the Trump Tower Terrace- Right on the river, the Trump Tower Terrace bar offers great views of the city. Walk along the canals then stop here for drink or bite to eat. Fair warning, you pay for the stunning vistas with drink prices here, but it’s well worth it.
  7. Feast at Eataly. I previously mentioned the food market chain in the Top Ten: Rome post, but if you aren’t visiting Italy soon, stop by one of the few U.S. locations in Chicago. A great, unique spot to grab lunch or dinner at one of the restaurant stands on the top floor. They also have a bar and wine tasting spots. Be sure to save room for dessert though, on the bottom floor is a Nutella bar, full of different desserts made with Nutella.
  8. Ride bikes along the lake front. Some of the best views of Chicago come from the walking and biking paths along the lake between Lincoln Park and Navy Pier.  You can grab a Groupon for Divvy bikes, which you can rent by the hour at many convenient locations throughout the city.
  9. Get some laughs with Second City Comedy Club. The Chicago based comedy club is famous for starting the careers of an impressive amount of SNL cast members and other famous comedians including Tina Fey, Chris Farley, and Steve Carrell, to name just a few. Opt for the revue or classic improv over tickets to a scripted show.
  10. Catch a Buckingham Fountain show. The well known fountain near Millennium Park has fountain shows each evening including lights and music, starting at dusk then every hour on the hour with the last show beginning at 10:35 P.M.

Key West Itinerary (4 Days in Key West, Florida)

Key West is a town full of character and charm where deals are not difficult to find.  Flying directly to Key West is often not the most cost effective way to get to the Keys. Check out the ferry from Ft. Myers or drive along the famous Overseas Highway US 1 from Fort Lauderdale or Miami.


Key West Itinerary 1

We started our trip in Fort Lauderdale, rented a red Mustang convertible, and drove south to the Florida Keys.  If you take this route and pass through Key Largo, I highly recommend The Conch House.  Awesome food and drinks with the best key lime pie we had on our trip.  We timed our drive to get to Key West right as the sun was setting, providing some beautiful scenery. Fair warning, I do think the Overseas Highway has a little too much hype around it. If it works well to save you money, go for it, but I wouldn’t go out of my way to make the drive.  We ended our night with some slushy adult beverages at the Flying Monkey. Be sure to check with your hotel for coupons.  Most restaurants and bars we went to offered deals and promos for tourists and our hotel offered us buy one, get one drink vouchers for most of the bars.


Key West Itinerary 2

Started the day at Harpoon Harry’s, a 50’s style diner then picked up some bikes from the shop next door. Key West is a very bike friendly town and bikes are a great way to see the town. Aimlessly Riding around looking at all the houses and landscapes was a fun way to spend the morning.  We then stopped by the famous Kermit’s for some chocolate dipped key lime pie. Kermit’s offers just about anything you can imagine in key lime, cookie mixes, coffee syrup, wine, etc.  and is a perfect place to pick up interesting by usable Key West souvenirs for your family and friends.  After dinner we ended the evening with a sunset party cruise which leaves the dock just before sunset then offers drinks and dancing as the sun sets.


Key West Itinerary 3


Started day three checking out the harbor which offers some great restaurants on the water to grab lunch or breakfast at. Again, check for special offers, you can likely get them for the restaurants here too. Then we headed to the not so typical tourist attraction, the Key West Cemetery.  Touring a cemetery is weird you say? Well the Key West cemetery has the typical Key West character and is a bit quirkier than other cemeteries. Here you can find gravestones with inscriptions such as “I told you I was sick” and “I’m just resting my eyes”.  Next we went out on the water to view some sharks. If you find sharks at all interesting, you will really enjoy this tour.  Finally we ended the evening at the dessert restaurant Better Than Sex.  I highly, highly recommend dining on desserts at Better Than Sex. They offer a great dessert menu and serve glasses of wine with chocolate or caramel dipped rims. Absolute heaven.


Key West Itinerary 4


Day four we spent exploring the more classic attractions of Key West. Stopped my Hemingway’s house and toured Truman’s annex. Then stopped by the Southernmost Point and took a picture (expect a line to take a picture with the famous statue any time you go).  Finally we climbed to the top of the Key West Lighthouse to enjoy a view of the city from above before our journey home. Definitely recommend checking out the lighthouse, they offer student and AAA discounts on the fee to get to the top.

Overall Key West is a very interesting town with plenty to do and see and great deals if you look for them.


Top Ten Amsterdam (Best Things to Do and See in Amsterdam, The Netherlands)

Top Ten Amsterdam

1. Cruise the Canals.  Amsterdam is home to 165 canals.  Viewing the city from the water is a must whether it be by a public boat or a private one.

2.  See the city by bicycle.  Bicycles are widely used in Amsterdam and it is incredibly easy to find a rental.  Riding around the city on bike is great way to experience the town.  Biking in Amsterdam should only be for those comfortable on a bike though.  Locals often express their annoyance at tourists who don’t know how to bike and who do not follow the rules of the road.

3.  Dine on Pannekoeken or Poffertjes.  When you think of Amsterdam, the cuisine is not likely to be one of the things that comes to mind.  Dutch Pannekoeken, or pancakes, are well worth a try though.  Similar to French crepes, but you can get fillings like meat and cheese in addition to dessert flavors.  Check out The Pancake Brewery for some good and unusual pancakes.

4. Visit the Markets. Amsterdam has a variety of markets to explode, some specializing in one particular thing such as fabric or flowers.  Dappermart was voted one of the top 10 shopping streets in the world by National Geographic and is worth a look.

5. Try local beer. The Heinken tour is a well known attraction in Amsterdam, but there are plenty of interesting pubs and micro-breweries that are likely cheaper and definitely less touristy than Heineken.  Check out this post for some ideas of where to get local beers:, alternatively try a pub crawl.

6. Visit the tulip fields.  Every spring 1,000s of neatly planted tulips bloom in Holland.  One of the most famous spots to view the flowers is Keukenhof Gardens, which is just under an hour outside of Amsterdam.  Spend a day going to see the famous fields.

7. Experience a Coffee Shop.  Amsterdam is well known for its acceptance of cannibis, which has become a huge part of the essence of the city.  You should definitely stop by a “coffee shop” to see what the hype is about, no participation necessary.

8. Tour the Red Light District.  The Red Light District is much more than a sex symbol, the area is full of interesting culture and is a big part of Amsterdam.  Try a guided tour of the district to learn about the secrets that are often overlooked.  You should also visit during day and then again at night, it will seem like a completely different place.

9.  See Anne Frank’s House.  Arguably the top must see in Amsterdam, Anne Frank’s House is an incredibly sobering and interesting reflection on WW2.  Be sure to order your tickets online ahead of time and either go early or late in the day to avoid crowds as much as possible.

10.  Day Trip to a Surrounding Town.  There are a number of smaller towns outside of Amsterdam easily accessible by train.  Perhaps the most quintessential, Zaanse Schans is less than a half hour from the city and ofters a wooden shoe workshop, multiple windmills, and the famous Dutch blue ceramics.

See more pictures and things to do in Amsterdam here.

Top Ten: San Juan Puerto Rico (Top Ten Things to Do and See in Puerto Rico)

An island getaway whose old charm has lasted the test of time, Puerto Rico has become a hotbed for tourism.   Much like Cuba, the fourth most populated Caribbean island has been able to keep its idyllic heritage and culture while still catering to its many admirers.  Here are the top ten things to do in Puerto Rico:

Top Ten Puerto Rico

1. Climb to the top of Castillo San Felipe del Morro.  The old fort hosts some awesome views of San Juan. Bring a snack and enjoy the sights.

2. Follow the trails in El Yunque.  The only rain-forest in the U.S. National Park system, El Yunque National Forest is about an hour outside of San Juan.  Many tour companies offer day or half day trips or you can rent a car and drive yourself. El Yunque is on the way to Farjardo where many Bio Bay tours are, so try a tour that offers a combo of both.

3. Check out Pamela’s Caribbean Cuisine.  Pamela’s is literally set up on the beach, so you can dine with sand under your toes and listen to the waves hit the shore with a pretty view of downtown San Juan. Dine at night and enjoy the sunset or during the day and you can get beach chairs and umbrellas to lounge on after your meal.  You must get the coconut creme brulee for dessert.

4.  Eat Monfongo. Ask a local what’s in the monfongo and you’re likely to get a different answer each time.  A signature dish of Puerto Rico, monfongo is based on plaintains and typically includes one type of meat or another.

5. Relax on a beach. You’re in the Caribbean, so this should be an obvious thing to do.  There are many beaches around San Juan, the best beach access is found on the hotel properties where you’ll have access to chairs.  Many hotels have partnerships for beach access in San Juan, so check with your concierge to see where you can stake a spot in the sand if you hotel isn’t on the beach or you want to try out a different spot.

6. Try a Zipline Adventure. There are many places offering zipline tours around San Juan that have day trips from the city.  Check out Toro Verde which has a zipline called The Beast at almost a mile long with a harness where you lay belly down instead of hanging from your waist.

7.  Experience the Bio Bay.  One of the most unique things in Puerto Rico is the Bio Bay, or Bioluminescent Bay.  The water in these bays is home to tiny plankton which illuminate when the water around them moves.  It is like kayaking through stars. The best place to experience this is on Vieques, an island off the coast.  However, the bay in Fajardo is more easily accessible and has a wide variety of tours to choose from.

8. Wander through Old Town San Juan. Spend some time walking around Old Town to see the beautiful buildings and bright colors. Stop and grab a mojito and enjoy the atmosphere and friendly people of San Juan.

9. Take a trip to Vieques or Culebra. While getting there may not be the easiest thing to do, the islands host some of the best beaches in the world. Drive an hour and a half to the coast then jump on an early ferry to Culebra or Vieques for the day. The ferries can get packed, so the earlier the better. Vieques is quickly becoming the ‘it’ place to visitIt is also home to the top Bio Bay in Puerto Rico, which makes staying a few days ideal.

10. Eat Lechon from the “Pig Highway”.  Another specialty of Puerto Rico, roast pig stands.  Along the side of the highway you can find Lechoneras which sell cuts of pork.  One of the more authentic experiences you can have in Puerto Rico.

Check out our other guides to Caribbean locations here.