Dive beneath the surface in the Conch Republic in 48 hours…

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Where to stay:

Finding affordable accommodation in Key West can be a struggle. Most AirBnBs (in a decent price range) are on boats, which personally my sea sickness didn’t love that idea. For the best location and price value mix, it’s best to stay at an inn or bed and breakfast off Duval Street. I stayed at The Cabana Inn – a block away from Duval Street. This Inn is the perfect location, and walking distance from everything on the island. The architecture is very Key West style, with a pool, complimentary breakfast and happy hour. Other accommodation suggestion: The Mermaid and the Alligator.

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Transportation:

Flying: Key West International airport is about 15 minutes from the city center.

Ferry: Key West Express – there is a ferry from Ft. Myers and Marco Island to Key West.

Driving: From Miami, it’s a straight shot on Route 1 through the Keys, all the way down to the southernmost island, Key West. It’s a one way road, and if you don’t hit any traffic is about 3.5 hours. If your hotel doesn’t offer parking, there are a few parking garages on the northern side of Key West you can park in over night, which are about $15 per night.

Everything on the island is walking distance, so you won’t need your car. There are no Ubers, but there are plenty of car taxis and bike taxis when you want one.

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Day 1:

Glazed Donuts 

Debatably the best doughnut in Florida. This doughnut shop bakes new flavors daily, and also have great island flavors like key lime and pina colada(YUM!). It’s best to go earlier in the day because they do sell out.

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Fort Zachary Taylor State Park

In a town not known for its beaches, Fort Zachary Taylor Park is a beauty which sits on the western side of the island. It has the cleanest beach and clearest waters in Key West. Umbrella and chair rentals are available ($25 all day for 2 chairs and 1 umbrella). 

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Sunset pier

 Get there early to secure a front row seat to watch the sunset and sip on a pina colada. Try the conch fritters for some local eats.

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Garbos’ Grill

Featured on Diners Drive Ins and Dives on the food network, this food stand serves eclectic, inventive takes on tacos, burritos and burgers. Located behind a bar, Grunts. Perfect spot to have a drink and stuff your face with tacos.

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Better than Sex 

This dessert bar offers an extensive menu of decadent treats in an intimate environment. Be sure to indulge in the dipped wine glasses. With my champagne obsession, I ordered the Kiss Me Katie which is sparkling wine with a carmel sauce dipped glass(drooling just thinking about it). Be sure to make a reservation, this place fills up fast!

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Southernmost Point

This landmark marks 90 miles north of Cuba. Tip: Go at night to avoid the crowds and line of tourists waiting to snap a picture in front of it. It’s very peaceful sitting on the ledge overlooking the water.

Day 2:

Firefly Key West – delicious Southern restaurant, perfect for brunch and blood orange mimosas. If the heat is bearable, sit upstairs on the terrace.

Alternative spot: Blue Heaven

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Ernest Hemingway Home and Museum

Now a U.S. National Historic Landmark, this literary icon’s house is filled with his original furniture and memorabilia. The garden is remarkable, and one of my favorite parts. The house is swarmed with cats, have their own Instagram account(celeb status), @hemingwayhomecats. $13 admission for adults.

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Key West Light House

The light house is located right across the street from the Ernest Hemingway House. The climb up the 88 steps is steep and constricting. Although, the 365 degree views at the top are worth it. $10 admission for adults.

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Duvall Street

A street over a mile long filled with bars and restaurants. It’s definitely a tourist hot spot, but you can’t avoid going there. Tip: make your own bar crawl (day or night). My favorite spot is Fat Tuesday, a.k.a. frozen drink heaven. 

Bahia Honda State Park 

Add this beautiful state park to your list for some beach time and crystal clear waters.  It’s about an hour drive north from Duvall Street.

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What are some of your favorite Key West spots?!

Girl Bosses on the Go showcases gals who have a passion for traveling. This is an on-going series to showcase those women who deserve a girl boss stamp in their passport.

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The first of the Girl Bosses on the Go is my lovely friend, Rae, who has lived in Dubai for 3 years and currently works in business development. Read about her travel tips and tricks, life as a woman in the Middle East and favorite travel experiences after visiting 42 countries.

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(hiking Mount Kilimanjaro)

1. Tell us a little bit about yourself.

I am American, from Orlando, 28 years old, have completed 2 master’s degrees, lived on 3 continents, and traveled to 42 countries. Traveling is my oxygen, I itch to get out and explore the world – I want to see every country of the world – even the “forbidden” ones. Every country and culture is a new experience and I would hate to miss out on one.

2. What inspired you to start get your start your adventures living abroad?

My life has always been about chance… I read an article in Marie Claire magazine while on an airplane which highlighted this elite program at the International University of Monaco. I didn’t think much of it but my Mom encouraged me to apply. I didn’t tell anybody because I didn’t think I had a chance of gaining admission but when I got my acceptance letter, I was in awe. For a split second I had to think about what was happening, but then it just became a given that I was going because of the amazing opportunity awaiting me.

3. What made you decide to move to Dubai?

When I was living in Monaco, I was having the best time of my life. I always traveled here and there when I grew up in Florida… Bahamas or Mexico, always “far enough” but still close to home… but when I moved to Monaco is when I truly discovered my unquenchable thirst to explore the world. I suddenly found a new appreciation for history and cultural immersion, always seeking unique and authentic experiences. When I finished my degree, I knew I didn’t want to go back to the U.S. yet and Dubai just happened to have a great opportunity for me so as I always say in my life… “why not?”

4. What is life like as an American woman living in the Middle East? 

Before I moved to Dubai, I was buying sweaters, long dresses, one-piece bathing suits, and preparing myself to be ultra-conservative. Once I arrived is when I realized that the only people who dress like this (aside from the locals, of course), are the tourists because they don’t know any better. Being a woman in an Islamic country actually has its perks. We have ladies only taxis (driven by ladies wearing pink hijabs and the taxis are pink too!), ladies only check-out lines, ladies only gyms, and hundreds (yes, hundreds) of ladies nights all across Dubai every night of the week offering food and drinks specials – all of these are optional and nothing is forced. Ladies are always prioritized before men are – I often find myself being invited to skip lines.

Living here you learn to dress for the occasion and keep it appropriate… When I am going to the club, I wear the same as I would back home, when I go to the mall, I wear normal clothes (just not short shorts), and when I am going somewhere more conservative with locals (like a bank, government office, etc.) then I dress much more conservatively to show respect. Living in a country like this is all about finding the balance and maintaining respect.

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(Visiting Sheikh Zayed Grand Mosque in Abu Dhabi, United Arab Emirates never gets old – the opulence and details are simply stunning!)

5. What’s the hardest part about living in Dubai?

The hardest part about living in Dubai is obviously being so far away from my family and missing key moments. A few weeks after moving to Dubai my Grandfather passed away and it was very hard to get back for his funeral, but thank God I did. This past Christmas I missed my step-sister’s wedding. Living so far forces you to make tough decisions and learn to be independent while also making painful sacrifices.

In regards to Dubai specifically, the hardest thing about living here is respecting the laws for the Holy Month of Ramadan – especially when it’s in the dead middle of the summer and it’s 120 degrees Fahrenheit outside! I have experienced 3 Ramadan’s so far and it’s very hard to not eat in public, drink in public, no road rage, no cursing, no loud music, and basically just creating a “Stepford” style environment. Of course it’s a nice change to have everyone being so happy and nice, however, when it’s so hot outside and it’s illegal to drink water being seen, it definitely creates a challenge (I mean, who wants to sneak in a public bathroom just to sip the water you’re hiding in your purse!? Gross!).

6. What do you miss most about America?

Umm, totally Chik-Fil-A! Jokes. I mean, I do miss it but it’s not the number one thing I miss. The thing I really miss the most is special moments. I’ve had to pass up bridal showers, engagement parties, bachelorette parties, baby showers, funerals, weddings, American holidays and other monumental moments in the lives of my family and girlfriends. You would think that as the time goes on it gets easier but that’s never the case. Each one hurts just as much as the first time.

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(I’ve celebrated the 4th of July being abroad for the last 5 years – this year was my favorite celebrating in Dubai with fellow Americans.)

7. What advice can you give to people to make the leap to start traveling?

Americans get criticized a lot for having one of the most powerful passports in the world but not traveling enough. Once I moved abroad, I finally understood why… Traveling from the U.S. is not convenient as it often takes 24-hours each way to get anywhere vastly different from home. Given that most employees get a mere 2 weeks’ vacation, this does not make it easy to tempt someone to waste 2 days just for travel purposes. On the contrast, I wish more people would take the leap of faith and just go… go somewhere totally different, somewhere out of your comfort zone, so you can experience something completely new and at the same time, learn to appreciate where you are from.

8. What’s your best advice for someone who has never traveled abroad before?

Before booking a trip, if you want to go with someone, make sure they have the same traveling style as you. By “traveling style” I mean, find someone who has the same priorities. For me, I can’t stand wasting my time in museums. I spent 30 minutes in the Lourve and 20 of those minutes were spent battling crowds just to see the Mona Lisa, take my photo, and get back out. When people travel they have styles whether it be shopping, adventure, museums, city trips vs. nature trips, etc. I have been on a trip with someone who has a totally different approach to traveling than me and it doesn’t allow for a productive or enjoyable trip.

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(Hiking up the mountain to enjoy the beautiful views on Cat Bâ island in Vietnam.)

9. What are some of your traveling tips?

I have 3 goals when I travel: look for adventures, immerse yourself culturally, and give back.

When I go to a new city or country, I always try to book something adventurous (some examples of my adventures: climbing Mount Kilimanjaro in Tanzania, a hot air balloon ride over the Great Migration in Kenya, riding on an elephant bare-back in a river in Thailand, taking a private side-car tour in Spain, great-white shark diving in South Africa, and the list goes on). These moments to me were each unforgettable in their own ways.

For immersing yourself culturally, I always try to seek the most authentic moments possible… be spontaneous and see where you end up. Trust your gut. Talk to locals, hear their stories. Try to get off the beaten path and go where the tourists aren’t. Discover your own places and experiences.

When I travel, I naturally want to give back because many of the countries that I’ve been to are not thriving economies and I want to contribute as much as I can. Giving back doesn’t always mean volunteering but there are other ways, too. For example, when booking to climb Mount Kilimanjaro, I realized there are hundreds of companies to choose from, with many based out of the U.S. and U.K. Instead, I chose a local company based out of Moshi, Tanzania. I would much rather give a local company the business than some overpriced Western company.

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(After climbing Mount Kilimanjaro, all I wanted to do was go play with the kids at Amani Children’s home in Moshi, Tanzania.)

10. Where has been your favorite location to visit and what made it so special?

After conquering 42 countries, it’s really hard to narrow it down to one. I am in love with so many countries and places for reasons that were unique to each experience. 

Laos was definitely one of my favorite and life changing at the same time. While I was there, I learned of “The Secret War” which basically is a huge event in the history of the country, but no one knows about it – which is strange since the U.S. was the cause of all of it from 1964 to 1973 ☹ Basically during the Vietnam War, when the U.S. fighter planes had bombs that they didn’t drop, they couldn’t risk landing while still carrying them because of potential risks of self-explosion. Because of this, they would drop them over Laos, land safely back on base, and think nothing of it. The UXO’s (unexploded ordnances) would then sit there for years and still decades later and have caused detrimental damage to the country and people when they eventually develop the land. Because of the U.S.’s negligence, this beautiful country is still facing major, major challenges and deaths even today due to the presence of the UXO’s. Long story short, learning about this was embarrassing as it is indeed a secret (the U.S. finally acknowledged our role on May 15, 1997) but the most humbling moment was realizing that the Laotian people were so peaceful about it and so kind and welcoming to me.

It was a moving moment for me, so moving, that I got the word “Peace” tattooed in Lao language as the people represent the ultimate example of peace and how we should live. The fact that they don’t seek revenge or publicity, just peace, was absolutely mind blowing to me.

Catch Rae’s recent adventures on her travel blog or on IG @roamingrae. Comment below any questions you have for this traveling babe!

I present to you Santorini with #nofilter

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13876512_10154377303792442_5090453960512603888_n(A local Grecian’s home – aren’t those flowers to die for?!)

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13925024_10154377303682442_6120155666494157338_n(Lounged & pinacolodaed at Lioyerma Lounge Cafe Pool Bar)

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13932879_10154377303912442_7338207642662316431_n(This picture doesn’t do the Santorini sunsets justice)

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Couldn’t stop drinking, so sips and trips has continued!

 

1. Chateau Marmot in Los Angeles, CA

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2. Mango daquiri at The St. Regis Saadiyat, UAE

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3. Irene serving us a Sex on the Beach welcome drink in Markos Village, Ios, Greece

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4. Mint Lemonadae at Souq Waqif, Doha, Qatar

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5. Riesling in Mykonos, Greece

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6. Chai Tea Latte at Brew Urban Cafe, Fort Lauderdale, Florida

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7. Nutella Latte at Sambalatte in Las Vegas, NV13933355_10154365596292442_1583866673_n

8. Prosecco Pops at Loopy Doopy, New York City

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9. Merlot at Steak 954, Fort Lauderdale, Florida

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10. Fresh Orange Juice at Dubai Miracle Garden, Dubai, UAE

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Flights can be the largest chunk of your trip budget, but these sites make buying a flight a bit lighter on your wallet. There are two ways to do it: searching for a flight for specific location and time, or if you’re flexible. Tip: With flexibility comes greater savings.

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Here are the best kept airline secrets:

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(📷 by amwarman_)

Sky Scanner

 This is my first go to when looking for flights. It’s a flight search engine that shows the cheapest deal.

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Google Flights

More interactive user face including “Discover Trips” where eyou can set dates, places and interests. Google Flights allows you to include the “Multi-city” option when searching for flights. This means you can fly from different locations without having to buy one way tickets each place. For example, you can fly Orlando to Florence, and then from Rome to Orlando, and it’ll be within the same purchase.

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Airfarewatchdog 

A low airfare alert site that covers all airlines. You can sign up for email airfare alerts.

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Secret Flying 

If you’re dying to travel, but flexible on time and location, this is the site for you. How it works: This site offers details to the most incredible flight deals(I’m talking US to Asia for less than $500). When they find a great deal, it’s immediately posted it on the website. 

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Travel Pirates

 Similar to Secret Flying, Travel Pirates is a travel resource for posting the most affordable flight deals.

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Follow these on Twitter for instant knowledge of flight deals:

JetBlueCheeps

airefarewatchdog

SecretFlying

TravelPiratesUS