We guide you through two days spent in Florida’s southernmost outpost – one reserved for living up luxuries on-resort at Sunset Key, and the other consumed with the can’t-miss things to do in nearby Key West.

The beauty of staying at Sunset Key Cottages, a 27-acre island just seven minutes by boat from Key West, is that you can easily submerge yourself in your own private island for a day and then resurface to get back to civilization in nearby Key West.

Day On at Sunset Key Cottages

Breakfast to Your Porch

Start the day stress-free with the delivered-to-your-doorstep “Rise, Dine, and Sunshine” breakfast basket, filled with just-baked muffins, croissants, and fresh fruit. Kick back on your cottage’s private veranda and enjoy the views while you welcome the day as you dine.

Yoga on the Beach

On Saturday mornings at 8:30 a.m., the resort offers a complimentary, first-come, first-serve yoga class at The Point, a stretch of the island’s beach protected by a rock sea wall and known for its soft sand and spectacular views. If you can’t make the Saturday morning time, additional sessions are available upon request.


In addition to diving and snorkeling excursions, fishing charters, and sailing adventures, the resort also runs its own parasailing service. Get picked up directly on Sunset Key’s dock and glide away on an adventure you won’t find like this at home. The exhilarating ride will give you a view normally reserved for birds.

Sunset Key Cottages Pool

Relax at the Pool

If you’re ready to kick back and relax a little bit, head to the resort’s zero-entry pool. Accented with a waterfall and enveloped by a mass of palm trees, the private oasis is the ideal place to sit in the shade and nap or read in the chaise lounge chairs. When you work up an appetite, grab a light lunch at Flipper’s Pool Bar.


You don’t need to be a pro (or have any experience at all) to spend some time on the tennis courts at Sunset Key. Rackets and balls are complimentary, but it’s up to you to bring the talent (although lessons can be arranged through the concierge, too).

Dinner at Latitudes

Dinner at Latitudes

Cap the night with dinner at Latitudes. Between the jaw-dropping, panoramic views of the Gulf of Mexico and the delectable island cuisine comprised of fresh fish and tropical fruits, it’s no wonder why Latitudes was named the “Best Overall Restaurant in Key West” in 2016 and one of the “100 Most Romantic Restaurants in America” for 2017 both by OpenTable. But make sure you book a reservation at least a couple days in advance.

Day Off in Key West

Breakfast at Cuban Coffee Queen

The lively counter-service coffee stand of the colorful Cuban Coffee Queen is a classic Key West destination in itself. The breakfast menu has a modern Cuban twist and is full of delicious choices, but the real challenge will be picking a type of coffee. Most are fun Cuban blends – like the Cafe Con Leche and Cuban Chocolate Mocha – though if you want to stay traditionally American, they offer something called the Gringo Coffee, too (your regular American-style java).

Cuban Coffee Queen in Key West

Harry S. Truman Little White House

Get a little dose of American history by taking the Harry S. Truman Little White House tour. Serving as the winter White House for Harry Truman from 1946–1952 and later used by other American presidents, the location is known for its Truman Annex, where visitors can get an intimate look at where the 33rd president retreated to during the cloud of the Cold War.

Lunch at La Grignote

You may not think “French bakery” when you’re in Key West, but you haven’t been to La Grignote. Opened in fall of 2016, the rustic little bistro brings a European flair to Duval Street and is overseen by a French duo who bakes their own breads and pastries daily on-site. We suggest the chicken pesto panini served on conch bread.

Looe Key Snorkeling Tours

Head to Bahia Honda State Park (a 45-minute drive northeast of Key West) to embark on one of the Looe Key Snorkeling Tours, departing at 1:30 p.m. sharp for a one-and-a-half-hour tour. If this is your first time snorkeling, fair warning: Not all reefs are this beautiful. This quiet, tranquil experience will give you a whole new view of the ocean and bring you up close and personal with the plentiful Elkhorn and massive Star corals that call this spot home.

Snorkeling at Bahia Honda State Park

Dinner at Louie’s Backyard

A Key West staple since 1971 and listed in the National Register of Historic Places, Louie’s Backyard is a Caribbean-American restaurant, known for its beautiful backyard view – to the ocean. With a menu that is a fusion of classic dishes with new interesting twists – think sesame-crusted King salmon with yuzu syrup over a coconut rice cake – it’s easy to see why Louie’s has been a mainstay here for over four decades.

Key West Ghost & Mysteries Tour

As Florida’s second-oldest city, Key West has a history unlike any other. Learn about it first-hand during a 90-minute Key West Ghost & Mysteries Tour, where experienced guides walk you through the city as they narrative eerie stories and legends tied to specific sites.

Where to Stay Sunset Key Cottages