This post contains references to products from one or more of our advertisers. We may receive compensation when you click on links to those products. For an explanation of our Advertising Policy, visit this page.

For today’s Destination of the Week, TPG contributor Nick Ewen takes us down to Florida to the southernmost tip of the continental United States as we visit the Conch Republic also known as Key West.  


Key West
Key West is located at the southernmost tip of the continental United States.

Key West is the final stopping point along the 120+ mile stretch of highway that runs the length of the Florida Keys. It is said that the archipelago was first happened upon by Ponce De Leon in the 1500’s, but it wasn’t until the early 1800’s that Key West first appears in the formal records: a land grant for the island of “Cayo Hueso” (literally: “bone island”). Many believe that the name Key West resulted from the Anglicization of the original Spanish name. Nevertheless, the island retained much of its Spanish influence while simultaneously emerging as a wonderful spot for a relaxing, Caribbean-style vacation. While certainly subject to the occasional tropical storm, the island benefits from the trade winds that consistently blow across it, carrying away much of the heat and humidity for which South Florida is reviled.

Since Key West is the southernmost point in the continental United States, one tourist trap (but must-visit site!) in town is the Southernmost Point marker, located at the corner of Whitehead and South Streets. The line to take a picture can snake up South Street, but for a quick snapshot, it’s worth the wait. Nowhere else in the country can you stand just 90 miles from Cuba. You’ll also notice that the picture below includes our puppy, and fortunately, Key West is incredibly pet-friendly. Many of the hotels and bed & breakfasts in town accept pets; however, make sure you understand the policy, restrictions, and fees prior to arrival. To keep your own pet happy and energized, you can visit Key West’s only dog beach (at the intersection of Waddell and Vernon Avenues, near Louie’s Backyard) or Higgs Beach Dog Park.

Me, my wife, and our pup pose (sort of!) in front of the Southermost Point marker.
Me, my wife, and our pup pose (sort of!) in front of the Southermost Point marker.

Just a block away from the marker is the southern tip of Duval Street, the main entertainment, shopping, and dining thoroughfare in the town. Running the length of the island, Duval Street has spots for visitors of all persuasions: high-end boutiques, casual cafes, attractions (such as the relatively new Butterfly & Nature Conservatory), fine dining, bars of varying levels of repute, and even numerous drag shows sure to impress even the most conservative member of your traveling party! (My recommendation: Aqua…just beware of the “Fireball” drink!) TPG’s parents also recommend a popular dive bar called the Green Parrot, which they call “a truly fine drinking establishment.”

TPG’s Dad enjoying the Green Parrot.

During the height of spring break, the nightlife comes alive, as college-age visitors flock to spots such as the Hog’s Breath and The Bull & Whistle Bar. Even if your hotel isn’t quite walking distance from these hot spots, pedicabs roam the city, offering simple and affordable transportation back to your accommodations.

The Bull (downstairs) and Whistle (upstairs) Bar along Duval Street comes alive at night.
The Bull (downstairs) and Whistle (upstairs) Bar along Duval Street comes alive at night.

TPG’s parents also suggest a few must-stop restaurants for visitors. Blue Heaven is great for breakfast and a popular spot with locals that often gets quite crowded. Louie’s Backyard has an upstairs deck with ocean views that’s the perfect spot for sunset drinks, and Salute! On The Beach is a sister restaurant to Blue Heaven located near the Casa Marina and serves fresh fish for lunch and dinner.

Key West is also paradise for adventurers, as the island provides numerous ways to pass the time out on the open water. The Florida Keys are renowned for the diving they offer, and Key West is no exception. Many different companies offer tours to shipwrecks and coral reefs just off the coast, including Dive Key West and Adventure Watersport Charters. The marina area also provides a plethora of boat excursions off shore to whet the appetite of even the most avid mariner out there. TripAdvisor is full of reviews of various charter boat operators, with some offering full-fledged fishing outings and others providing a relaxing sunset sail along the waterfront.

Grab a charter boat for a memorable snorkeling or diving experience in or around Key West.
Grab a charter boat for a memorable snorkeling or diving experience in or around Key West.

One excursion deserves special mention: making the 70-mile journey west to the Dry Tortugas National Park. The park covers roughly 100 square miles and consists of seven small islands and the coastal waters around them. Accessible only by boat or seaplane, the park contracts with many licensed vendors out of Key West who provide chartered fishing, diving, or snorkeling trips to take in the breathtaking beauty of the area. Fort Jefferson, the largest all-masonry fort in the United States, was built to protect the Gulf of Mexico shipping channels in the 1800’s and occupies one of the islands; guided and self-paced tours are available upon arrival. Visitors can also take advantage of overnight camping on Garden Key (the same island as Fort Jefferson). Entrance fees are only $5 and cover 7 days in the park.

Consider taking a trip to the Dry Tortugas National Park, just 70 miles west of Key West.
Consider taking a trip to the Dry Tortugas National Park, just 70 miles west of Key West.

For the more academically-inclined, the city itself offers many ways to immerse yourself in history and literature. Harry Truman’s Little White House, located at 111 Front Street on the west side of town, served as the naval station’s command headquarters in the Spanish-American War as well as both world wars. Beginning in 1946, Harry Truman frequented the house during his winter vacations, and numerous visitors’ logs document his everyday duties as Commander-in-Chief. Guided tours of both the house and surrounding botanical gardens are available and included with the admission fee.

The Ernest Hemingway House.
The Ernest Hemingway House.

Literary aficionados can visit the Ernest Hemingway Home & Museum. Located at 907 Whitehead Street (just down the road from the Little White House), the house was Hemingway’s home for more than 10 years. While living in Key West, the Nobel Prize-winning author penned numerous classics, including The Snows of Kilimanjaro and For Whom The Bell Tolls. The estate today remains the single largest residential property on the island, and visitors can take part in a guided tour of the house, stroll through the lush gardens, or marvel at the 40-50 resident cats, some of whom are direct descendants of Ernest Hemingway’s original cat Snowball.

TPG’s parents also recommend renting a bike to get around the island like the locals – they even saw famous local Jimmy Buffett out for a spin during one of their trips.

Destination of the Week pieces are not meant to be comprehensive guides to destinations since we don’t have the time or funds to visit all these places in person and report back to you. Nor are they endorsements of all the hotels we mention. They are simply roundups of top destinations that we have specifically pinpointed for the opportunity they present to use your miles and points to get to and stay there. As always, we welcome your comments to help enrich the content here, provide opinions and first-hand experiences of these destinations.

Key West International Airport (EYW) is located just two mile east of the central business district of Key West, offering easy access to the city’s attractions and lodging options. Each major alliance serves the airport with daily flights, offering a myriad of ways for mile collectors to redeem their hard-earned currencies for free transportation. United Express offers flights from Tampa, Fort Lauderdale and Ft. Myers (all of which are operated by Silver Airways), while US Airways provides flights from both Charlotte and Washington-Reagan airports. Delta serves Key West from their Atlanta hub, while American Eagle uses their Miami hub for the short flight down to the Keys. Southwest and AirTran, meanwhile, provide regular service from Orlando, Tampa, and New Orleans.


As you walk the streets of Key West, you will undoubtedly encounter many quaint and charming bed & breakfasts, but sadly, these do not offer any point redemption opportunities. Fortunately, most of the major hotel chains have properties on Key West for you to take advantage of.


The gorgeous pool area at Casa Marina.
The gorgeous pool area at Casa Marina.

Key West is home to two Waldorf Astoria-flagged properties: The Reach, A Waldorf Astoria Resort and Casa Marina, A Waldorf Astoria Resort. The two hotels are separated by just a few blocks along the southern coast of the island. The Reach is just steps from the southern end of Duval Street and offers 150 stylish guestrooms, each with a private balcony. Catch a sunset from the resort’s private beach (the only natural one on the island) or relax in a chaise lounge by the pool. More active guests can take advantage of unlimited watersports or visit the on-site fitness center, while all visitors can indulge in fine dining at the Strip House, the property’s signature steakhouse.

Casa Marina, originally opened in 1920, combines the Old World charm of Key West with the contemporary luxury expected at a Waldorf Astoria property. The resort also boasts a large stretch of private beach along with two oceanfront pools; guests can relax even further in the on-site Spa al Mare. The 311 guestrooms and suites provide at least 350 square feets. TPG’s folks love the Casa Marina’s grounds, which they say “takes it to a whole new level versus the Sheraton, but the rooms felt inferior.” In fact, TPG’s mom rates the rooms here at just a 3/10 with small bathrooms and no balconies – plus service was less than friendly.

Both resorts have rates starting at $236 per night in May, but they both charge resort fees of $25/day. Both are Category 9 properties requiring 80,000 points/night from December to May. The Reach drops to 70,000 points per night from June to November, while Casa Marina drops to 60,000 points per night during that off-season. The Casa Marina is also part of the American Express Fine Hotels & Resorts.

The other Hilton property on the island is the DoubleTree Key West; even though it is away from the action, a complimentary shuttle takes guests to Duval Street, the marina, and other top spots in town.

The Hyatt Key West Resort & Spa offers luxurious oceanfront accommodations on the northern edge of the island.
The Hyatt Key West Resort & Spa offers luxurious oceanfront accommodations on the northern edge of the island.


Hyatt Key West Resort & Spa: Located on the north edge of the island, just a couple of blocks from the main pier, this oceanfront property blends the architectural features of old Key West with the modern luxury of the Hyatt brand. The 118 guest rooms start at 460 square feet and include modern amenities such as flatscreen TV’s, private balconies and mini-fridges. After a day of touring, guests can cool off in the outdoor pool while sipping a drink at the Blue Mojito Pool Bar & Grill, or they can indulge in a treatment at the Jala Spa. The on-property Shor American Seafood Grill provides bay views and freshly caught fish in a relaxed yet elegant environment, a perfect spot to end the day. Rates in May start at $305/night. As a Category 6 property, free nights are available for 22,000 points per night.

Hyatt also offers three residence club properties in Key West, ideal for family accommodations: Hyatt Sunset Harbor, Hyatt Windward Pointe, and Hyatt Beach House. Redemption details are available here.


The oceanfront Marriott Beachside Hotel.
The oceanfront Marriott Beachside Hotel.

Key West Marriott Beachside Hotel: Away from the hustle and bustle of Duval Street, this hotel is located just across the bridge onto the island. The seven-acre property features lush gardens, a private beach, and an oceanfront pool. Each guestroom is fitted with luxury furnishings such as marble flooring and LCD TV’s, while most suites offer oversized balconies with great water views. The Tavern N Town restaurant offers a fine dining option, while guests desiring a more casual experience can grab a drink or small bite at the poolside Blue Bar. Staying away from town doesn’t mean isolation; the resort offers complimentary transportation to and from Duval Street to ensure that guests can take advantage of all that Key West has to offer. Rates in May start at $188/night. As a Category 7 hotel, free nights will set you back 35,000 points/night.

Other Marriott options in Key West are the Courtyard Key West Waterfront and the Fairfield Inn & Suites Key West, both Category 6 properties requiring 30,000 points/night.

Priority Club

King guest room at the Crowne Plaza Key West La Concha.
King guest room at the Crowne Plaza Key West La Concha.

Crowne Plaza Key West La Concha: If you prefer to be smack in the middle of things, you certainly can’t go wrong with this hotel, which recently completed a multi-million dollar renovation, is located right on Duval Street, offering easy access to all of Key West’s attractions and nightlife. Each guestroom features flatscreen TV’s, mini-fridges, and Crowne Plaza’s signature Sleep Advantage bed. The sun deck and swimming pool offer a respite from the noise and crowds of Duval Street, and guests can grab a drink or bite to each poolside as they take in another spectacular Key West sunset or venture downstairs to Jack’s Seafood Shack for a large & creative menu in a historical setting frequented by the likes of Hemingway and Truman. Rates in May start at $189 per night. Free nights at this Category 8 property will set you back 45,000 points/night. Points & Cash rooms are also available for 40,000 points + $40 or 35,000 points + $70.


Oceanfront king guest room at the Westin Key West.
Oceanfront king guest room at the Westin Key West.

Westin Key West: Located on the northwest corner of the island just two blocks from Truman’s Little White House and a block from Duval Street, this hotel’s 178 guestrooms and suites include the Westin Heavenly Bed, signature bath amenities, and the usual appointments to keep guests pampered. The property includes an outdoor heated pool and Key West’s largest private marina, including casual bar & dining options with panoramic water views. For guests in search of more elegance, the on-property Bistro 245 serves American fare in a sophisticated setting with views over the nearby harbor. Rates in May start at $279 per night. As a Category 6 property, the Westin will set you back 20,000 – 25,000 points per night (depending on the season).

The other SPG option in town is the Sheraton Suites Key West; though it is away from the main drag, the property does offer complimentary shuttle service downtown, and TPG’s parents liked the rooms here and the location across from Smathers Beach, where you can rent chairs for the day cheaply. They also liked the lunch service and ambiance on the patio at the hotel’s Coral Crab Cafe. Ask for a room at the front of the property with a balcony for the best experience.

American Express Fine Hotels & Resorts
Fine Hotels & Resorts is a program exclusively for American Express Platinum Card cardholders, who are eligible for extra benefits such as room upgrades, free continental breakfast, early check-in and late check-out, dining and spa credits and more.

Sunset Key Guest Cottages, A Westin Resort.
Sunset Key Guest Cottages, A Westin Resort.

Sunset Key Guest Cottages, A Westin Resort: This resort occupies seven acres of the 27-acre Sunset Key, a secluded island just off the coast of Key West. Guests can choose from one- to four-bedroom villas, each offering terrific views of the ocean or lush gardens surrounding the property. Every villa includes flatscreen TV’s, living room, dining room, and fully-equipped kitchen pre-stocked with select food & beverages. Property amenities include a spacious white sand beach, swimming pool with two whirlpools, two tennis courts, and a board game & literary library. Guests can rejuvenate with a treatment at The Spa at Sunset Key or dine in style (or alfresco!) at Latitudes. Even though the resort is bookable through, they have limited participation in the program and thus require more points for a free night. One-bedroom cottages start at $850 per night in May. This is also a SPG Category 7 property with limited SPG participation.

Starwood Points are the most valuable points currency out there.
Starwood Preferred Guest® Credit Card from American Express
Apply Now
More Things to Know
  • Earn 75,000 Bonus Points after you use your new Card to make $3,000 in purchases within the first 3 months.
  • Earn 6 points for each dollar of eligible purchases at participating SPG® and Marriott Rewards® hotels and 2 points on all other eligible purchases.
  • No Foreign Transaction Fees on International purchases.
  • Receive 1 Free Night Award every year after your Card account anniversary. Award can be used for one night (redemption level at or under 35,000 points) at a participating hotel. Select hotels have resort fees.
  • Enjoy complimentary, unlimited Boingo Wi-Fi on up to four devices at more than 1,000,000 Boingo hotspots worldwide. Enrollment required.
  • $0 introductory annual fee for the first year, then $95.
  • Terms Apply.
  • See Rates & Fees
Intro APR on Purchases
Regular APR
17.74%-26.74% Variable
Annual Fee
$0 introductory annual fee for the first year, then $95.
Balance Transfer Fee
Either $5 or 3% of the amount of each transfer, whichever is greater.
Recommended Credit
Terms and restrictions apply. See rates & fees.

Editorial Disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

Disclaimer: The responses below are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser’s responsibility to ensure all posts and/or questions are answered.