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Key West: My Guide to the Conch Republic

If the craziness of Miami has you longing for more laid-back vibes, the Florida Keys are just a short drive away. Key West, the southernmost island, fits the bill nicely with Duval Street bars and gorgeous sunsets in Mallory Square. I highly recommend Key West if you prefer flip-flops over heels, beach coverups to slinky dresses, and dive bars to bottle service. You can easily do this place in a couple of days (perhaps tacked onto a Miami trip) or spend an entire week. Only 90 miles from Cuba (technically closer to Cuba than Miami), this island actually makes you feel like you are in the Caribbean when you're really still in the U.S. No passports needed which makes it a tad easier to access. But there are a couple of items I'd like to address:

  1. Key West is not known for its beaches. That doesn't mean you won't find any, they are there, they are just not the pristine white-sanded beaches you envision when you think of the Caribbean. And actually, you can find prettier beaches at other Florida destinations.
  2. Key West airport is very small so don't expect flights to be cheap. This is especially the case over holidays and school vacations, unfortunately.

But don't let the facts deter you. Simply opt for some quality pool lounging and rent a convertible and hit the road (for the most scenic drive in the U.S.) from Miami or Fort Lauderdale where flights are much, much cheaper. Once you've made it over the final bridge in the keys, here's what you should do:

 

SEE

Duval Street- This mile-long street is Key West's main street that's full of restaurants, bars, cafes and shops. Definitely take a few strolls up and down and bar hop along the way. No need to chug that beer though--with a lax open container policy you can bring it with you to your next watering hole (plastic cups only!).

Mallory Square- The best place to catch one of Key West's beautiful orange sunsets. Live performers, carts selling everything from drinks that light up to Christmas ornaments, and happy people out enjoying life makes this a perfect place to start your night. Be sure to Google the time of sunset and plan to arrive at least 30 minutes before to watch the bright orange circle get sucked into the sea.

Southernmost Point - A life-size buoy marks this spot. Must get a photo with the view in the background. On a clear day you can spot Cuba (just kidding, but you are only 90 miles away).

Ernest Hemingway House - If you don't mind lots of free-roaming cats, and 6-toed ones at that, then visit the famous American writer's home where he lived from 1931 to 1939 and arguably wrote some of his best work. (907 Whitehead St.)

 

EAT

La Creperie - Both the sweet and savory varieties abound on the menu at this cute little cafe. The owner is from Brittany, France so you can expect these to be as authentic as they get without going to France. (300 Petronia St.)

Margaritaville - I mean, When in Rome! This Jimmy Buffett outpost is the original and in my mind is therefore the best. It offers live music most nights starting at 8p so why not enjoy your Cheeseburger in Paradise and order that Boat Drink? (500 Duval St.)

Ana's Cuban Cafe - A little hole in the wall near the Southernmost point serving up delicious made-to-order sandwiches, Cuban delights and breakfast. (1330 Simonton St.)

Kelly's Caribbean Bar & Grill - For any fellow aviation enthusiasts this is the place to visit because it is the original Pan Am headquarters back when Pan Am was the first American airline to fly an international route - Key West to Havana. The casual restaurant is also the location of the Southernmost Brewery offering beers brewed on the premises. (301 Whitehead St.)

Glazed Donuts - The gourmet donut shop craze made its way to the southernmost point of the continental U.S. to bring you both classic flavors as its name suggests and more adventurous flavors like Key Lime Pie (of course) and candied bacon. Espresso drinks too. Closed Mondays. (420 Eaton St.)

La Te Da - A classic choice if you're looking for a more upscale dinner on a charming, candlelit patio. (1125 Duval St.)

 

DRINK

Sloppy Joe's Bar - If there's only one place you go to while you're in Key West make it this iconic establishment. Casual bar by day, live music and dancing by night. (201 Duval St.)

Captain Tony's Saloon - Jimmy Buffett fan or not, this dive bar is a must with bras hanging from the ceiling and business cards covering the walls. Sometimes you'll catch a one-man band and his guitar and other times you'll spend way too much time trying to toss a coin over your shoulder and into the mouth of the fish that rests on top of the sign outside. (428 Greene St.)

Hog's Breath Saloon - Another Key West icon with, you guessed it, live music. Belly up to the outdoor bar and feel like you're in a treehouse. Don't be surprised if you get pulled into a conga line; this place can get rowdy but in a good fun kinda way. (400 Front St.)

Louie's Backyard - For a more refined evening, opt for glass of wine with a gorgeous view of the water. Head upstairs for said view and ask for a table on the balcony. You won't regret it. (700 Waddell Ave.)

Sunset Pier - Head to this colorful dockside spot for an ice cold boat drink and sit back and enjoy the sunset. (0 Duval St.)

 

SLEEP

Casa Marina - Off the quieter end of Duval Street is this grand Waldorf Astoria resort. The pool/waterfront area is one of the prettiest on the island and you can go swimming off the dock into the ocean (a plus when the shore is protected by coral reef). You even get popsicles delivered to your lounge chair. If you're worried about being too far from the action, perhaps a pedicab ride will change your mind. (1500 Reynolds St.)

The Reach - Located next door to the Casa Marina is another lovely Waldorf Astoria resort. Much smaller than the Casa Marina, especially the pool and waterfront, so guests at this hotel are welcome to use the facilities at the Casa Marina if they so wish. (1435 Simonton St.)

The Westin Key West Resort & Marina -  Located steps away from Mallory Square, this hotel is a great option if you prefer to be close to all the action. There is no beach here, but the pool is inviting. Guests can choose to have breakfast dockside at the property's restaurant, Latitudes, and watch the ships pull in. (245 Front St.)

Southernmost on the Beach - If the above options are a little too pricey, try for this stylish hotel. From appearances, it looks more like an inn but offers hotel amenities. It is located, as the name suggests, on one of the few beaches on the island just steps from the Southernmost Point. (508 South St.)

 

Last but not least, if you're lucky enough to be able to visit Key West during the holidays, I highly recommend you do so. Flights and accommodations are pricey but you're guaranteed endless merriment. Palm trees are decked out with Christmas lights, lampposts are decorated to look like candy canes and there are numerous New Year's Eve countdown celebrations to choose from (a pirate sliding down the mast of a schooner....um, yes please). Plus, Duval Street shuts down to traffic to allow for a big party in the street. I promise, this experience will not disappoint.

Whether or not you visit during the holidays, Key West really makes you leave your worries behind and gives you a taste for Jimmy Buffett/Ernest Hemingway-inspired life. It is a crazy but amazing little place that should be on everyone's bucket list. I mean, who can turn down a boat drink while taking in the gorgeous sunset? After all, if we weren't all crazy we would go insane.

Views for days on the drive down to the Keys

Views for days on the drive down to the Keys

The Southernmost Point was getting a fresh paint job unfortunately!

The Southernmost Point was getting a fresh paint job unfortunately!

Gorgeous tropical views abound in Key West

Gorgeous tropical views abound in Key West

Cruise ships docked near Mallory Square
Cruise ships docked near Mallory Square
A Key West sunset
A Key West sunset
Key West decked out for the holidays
Key West decked out for the holidays
Sloppy Joe's on Duval Street is a true Key West tradition
Sloppy Joe's on Duval Street is a true Key West tradition
Captain Tony's for all you Jimmy Buffett fans out there

Captain Tony's for all you Jimmy Buffett fans out there

The original Pan Am headquarters, wow!

The original Pan Am headquarters, wow!

The beautiful Casa Marina Hotel

The beautiful Casa Marina Hotel

The grounds and pool area at the Casa Marina

The grounds and pool area at the Casa Marina

The pool area at the Reach Resort 

The pool area at the Reach Resort 

The Westin Key West Resort & Marina
The Westin Key West Resort & Marina

Save on SPG Hotels

I admit, I'm a little late for posting about Cyber Monday deals but this one is not over yet. Starwood hotels are on sale-- up to 25% off-- for travel through September 2016. So if you're planning a trip for next year (as you should be) this is an excellent chance to get a quality stay for less. What's even better is Starwood Preferred Guest members get an additional 5% off!

Incase you are not familiar with Starwood, this family of hotels includes St. Regis, Westin, Sheraton and many more including the Luxury Collection of unique boutique hotels.

Book now until December 6th to take advantage of these amazing deals.

westin_lagunamar

 

7 Places to See in Tuscany

Tuscany. One of the largest and most-visited regions in Italy. It is no wonder that it tops many people's bucket lists with land comprising of vast plains, gorgeous green rolling hills, hundreds of vineyards and lots of quaint, medieval hillside towns. It is such a beautiful place words cannot describe and that photos don't do justice topped off with some of the most delicious food and wine around. If this dreamy destination is not on your list, it should be. And for a decent chunk of time. There is so much to see and do in Tuscany that you really should plan to spend at least a week to get a taste of the wonderful culture. And then you should go back and do more. Better yet, you should just move there like Diane Lane does in Under the Tuscan Sun. But if that cannot happen well then here is a list of 7 places to see on your next trip to Tuscany that will have you longing for more.

A street in Florence

A street in Florence

PISA

Home of the Leaning Tower and pretty much nothing else. A half day is more than enough in this touristy city and trains run regularly here every day from Florence (about a 30 min ride). The Leaning Tower can be found in Piazza dei Miracoli. It is free to wander the grounds but you have to buy a ticket to climb it. I've never felt the need to do that. There are tons of tourists here so you will probably just want to get your picture and turn right around. Avoid eating or drinking near the Leaning Tower because those places tend to rip off tourists. Instead stop at Il Crudo in nearby Piazza Cairoli (Piazza Cairoli 8) for a delicious panino.

An obligatory picture with the Leaning Tower

An obligatory picture with the Leaning Tower

FIESOLE

Another great day trip from Florence, this charming little town is located up on the hills slightly north of the city so has a spectacular view and also has a cute little piazza with trattorias and gelaterias. Make sure you wander the side streets up the hill because there are spectacular views once you reach the top. If you are staying in Florence and unable to spend time exploring the Tuscan countryside but want a taste for it, this is the place to go. It is a quick 20 minutes on ATAF bus number 7 from Piazza San Marco. Purchase your tickets inside the tabaccheria. Make sure to validate (stamp) your ticket in the machine as soon as you board the bus.

Views from Fiesole

Views from Fiesole

SIENA

Another major city of Tuscany but smaller than Florence and a little over an hour south. You will want at least a full day to explore this city. Piazza del Campo is the main square full of places to eat and bustling with people. Definitely fun to wander around. For an amazing Tuscan meal off the beaten path in a super cute tiny square with a great outside patio, visit Enoteca I Terzi (Via dei Termini 7). Also, the Duomo (Piazza del Duomo 8) is supposedly one of the most beautiful cathedrals in Tuscany, especially the interior. Other than that have fun and get lost wandering the streets, my most favorite activity.

Lunch al fresco at Enoteca I Terzi

Lunch al fresco at Enoteca I Terzi

CERTALDO ALTO

Definitely a lesser known town in Tuscany, my husband and I stumbled upon this place when we were searching for a town with a city hall to get married. This one definitely fit the bill-- old and medieval, perched up high on a hill with gorgeous views of the rolling Tuscan countryside, quaint, and filled with cobblestone streets for strolling. Cars need a special permit to drive up here so visitors must park at the town below (Certaldo proper) and take the funiculare up the hill, which just adds to the charm. It is a really small town that you don't need a full day for but is a great place to relax outside with some wine and bruschetta at a cute little cafe like Enoteca Boccaccio (Via Boccaccio 37) taking in the scenery. It's about 45 min to an hour south of Florence.

The quaint town of Certaldo Alto

The quaint town of Certaldo Alto

SAN GIMIGNANO

Another quaint medieval town great for wandering around located about an hour south of Florence. A few hours are perfect for exploring the many cute streets lined with shops and places to grab a bite or drink. This town produces one of the few white wines in Tuscany, Vernaccia, and it's pretty good so make sure to have a glass! The views on the drive to town are so amazing and exactly how you would picture Tuscany. This town can get pretty crowded but escape the masses and have a delicious panino and glass of wine for lunch at dal Bertelli (Via Capassi 30), a cute little spot off the main tourist drag that offers local ingredients.

The towers of San Gimignano

The towers of San Gimignano

MONTERIGGIONI

This small, fortified medieval town still has its walls intact. Walk along the walls for amazing views of Tuscany and relax in its piazza with an espresso or prosecco. You don't need more than 2 hours here because it is so small. It's about an hour south of Florence and on the way to Siena.

The view from the walls of Monteriggioni 

The view from the walls of Monteriggioni 

Not mentioned in the list above but something everyone should include in their trip is a visit to a winery. There are literally hundreds in Tuscany to choose from whether it be a huge, well-established brand or a small, family-owned name. On my last trip, I visited the new Antinori Winery (Via Cassia per Siena 133, Bargino) which was down the street from where we were staying. Antinori is a huge production (some bottles can be found in the States) and the facilities were nothing short of spectacular. On my next trip, however, I plan to make it to some of the smaller, independently-owned wineries for a more intimate experience. Here is a helpful site that lists all the wineries in the Chianti region of Tuscany and here is another helpful resource that includes some other Tuscan wine regions as well. Be sure to check the winery's own website to make sure they are still in business and for more details on their hours.

The crew at Antinori Winery

The crew at Antinori Winery

Curious about where to stay? You could choose to stay in Florence which serves as a good home base and has plenty of hotels. For a splurge, stay at the Westin or St. Regis which are centrally-located, on the river Arno and housed in buildings with beautiful architecture that make you think for second you're in a museum. OR, you could opt to stay in the countryside in an agriturismo which is an excellent and affordable option (you will just need a car). What is an agriturismo you ask? Well, my next post will be all about it and the agriturismo that I stayed at, so check back soon or follow me to receive a notification.

Wondering about Florence? Read my post on that here.

Not on this list but a top priority for my next trip to Tuscany are the towns of Montalcino and Montepulciano for their exceptional wine-- Vino Nobile and Brunello. If you've been to either of these places, I'd love to hear all about it including any wineries you visited. Leave me a comment below, per favore!

And as always, if you have any specific questions about Tuscany I encourage you to ask away! Happy traveling :)