Key West: sightseeing, partying and shopping

By Tom Jacobs, a Travel Professional

Read more on Key West.

Overall rating:4.0 out of 5 (based on 2 votes)
Recommended for:
Beach, Food and Drink, Nightlife, Budget, Expensive, Mid-range

Key West offers the perfect island life. From serene coffee shops to lively nightlife, crazy street performers to welcoming locals, it is a place everyone must visit at least once

The first time I reached Key West I fell in love with the place immediately. I hope to share my passion for the island with you.

Where to stay

You might not get much sleep if you’re partying on Duval Street every night. But for somewhere to stay my top choice is the Key West Bed & Breakfast - The Popular House. The house was built by Bahamian shipbuilders and is on the National Historic Register. It is situated right in the heart of the Old Town and the owners are wonderful hosts who offer excellent advice about the island. The house is beautifully decorated and the breakfast with fresh banana loaf and juice is a great start to any day. Rooms start from $80 a night so for value and experience this cannot be beaten.

If you want something with more facilities, or are celebrating something special, then The Westin Key West Resort & Marina offers a great location, right on the waterfront and only one block from Duval St.

If you can't get a good deal at the Westin then try the Hyatt Key West Resort and Spa which is also on the waterfront and offers a similar standard.

To still get that old Key West feel without sacrificing luxury then go for the Marquesa Hotel. It’s an old converted conch house in a fantastic location just two blocks from Duval St. The hotel, while full of modern facilities, still feels very "old Key West" and offers a wonderful experience in exquisite surroundings. It also has vacation rentals in three bedroom cottages, which is great for families or large groups although, unfortunately, the hotel will not accept guests under the age of 14.

What to do

There are plenty of well known attractions on Key West but I want to tell you about some hidden gems worth visiting.

The first of these surprised me. After settling into Key West life I was told that I could become a citizen of the Conch Republic and receive a passport! This is an interesting visit and you get to hear some interesting stories about how the passports have been used (

The next must see is Nancy Forrester's Secret Garden. Nancy is an eco artist and her garden is a masterpiece with shaded palms and parrots. True to its name the garden can be hard to find but this is part of the fun! Head to the 500 Block on Simonton Street and the garden is just off here at One Free School Lane (

Another attraction well worth a visit is the Pirate Soul Museum, which boasts the largest and most authentic collection of pirate artifacts under one roof. It is especially good for the kids with their 'Please Touch' rules (

If you’re doing a boat trip, forget the short snorkelling ones, the best boat trip is to the Dry Tortugas. Whilst expensive (around $160 per person) and a long day it’s one of those once in a lifetime trips and worth every penny. It gives the chance to see excellent wildlife including turtles and wonderful scenery. To make it even more special it’s possible to travel by seaplane and camp overnight. The two main operators to the Dry Tortugas are Sunny Days ( and Yankee Freedom ( There is not much difference between the two companies. However, if you are prone to sea sickness, I would recommend Sunny Days as they use a catamaran which is more stable in rougher seas.

Eating, drinking and partying

Key West is renowned for its good, fun and laid-back nightlife and, of course, the infamous Duval Street bar-crawl. To get through the late nights you’re going to need a good coffee so make sure you stop by The Coffee Plantation at 713 Caroline Street for a morning pick me up. They boast "the best tasting coffee in Key West" and, after having quite a few myself, I agree so it’s well worth a visit (

For lunch I’d recommend the Southernmost Beach Café & Bar. To find it head south to the very bottom of Duval Street. The café and bar is to the left on the beach. It’s a very relaxed place with a good beach vibe and the reason I love it so much is that you can enjoy some sunbathing there too. My favourite dish is the Blackened Catch of the Day served with a tasty Caribbean Vinaigrette and spinach salad (

Before dinner do as everyone else does and head for Sunset Pier. The sunset celebrations are famous for their street performers, some of which are fun and quirky others just weird! Watch the sunset and enjoy a cocktail from the 'Mojito Man' he’s easy to spot at the end of the pier. If you fancy a pre-dinner snack then try something different and have conch fritters from one of the stalls.

For dinner my personal favourite is Turtle Kraals which does excellent seafood and the southern style BBQ they offer is to die for ( - 305-294-2640).

For a good Mexican meal head to Salsa Loca on Duval Street - but bear in mind it’s closed on Mondays ( - Tel: 305-292-1865).

For some good classic well cooked food then Caroline's is also a good restaurant on Duval Street with reasonable prices. They also offer the island's biggest burger! ( - 305-294-7511).

For a special occasion The Commodore serves excellent food and has great panoramic views. It offers a lovely dining experience and serves mainly seafood and steaks. Due to the ambience and location the prices are obviously a little higher than other places ( - 305-294-9191).

After dinner it’s time for that Duval Street crawl. Sloppy Joe's ( is a Key West institution now and is always very busy. There’s often good live music at Willie T's ( but Captain Tony's Saloon ( is my top choice with excellent bands and a good crowd. The building also has an illustrious history dating from 1851 and was actually the location of Sloppy Joe's during most of Hemmingway’s time on the island. The Bull and Whistle ( is also good and the second floor balconies are great for people watching on Duval Street.


There are plenty of tourist shops that line Duval Street. However, for a change, why not visit the Sunset Cigar Company, where you can watch cigars being rolled by hand (, and also Kermit’s Key Lime Shoppe which sells some great salsas, jellies and BBQ sauces all, of course, made with Key Lime. Kermit himself is normally there and is happy to give ideas on recipes and you can have a taste of anything in the shop. (

For something very different, and if you like photography and art, then visit Peter Lik's Gallery. I have followed his work since 2002 and his photography skills are truly amazing. Even if you don’t purchase one of his expensive prints the gallery is still worth a visit (

I hope you enjoy the laid-back lifestyle of Key West and visit some of the above during your stay. I love the island and am now proud to show off my Conch Republic passport.

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More information on Key West: sightseeing, partying and shopping:

Tom Jacobs
Traveller type:
Travel Professional
Guide rating:
Average: 4 (2 votes)
Total views:
First uploaded:
11 November 2009
Last updated:
5 years 22 weeks 5 days 7 hours 18 min 50 sec ago
Destinations featured:
Trip types:
Beach, Food and Drink, Nightlife
Budget level:
Budget, Mid-range, Expensive
Free tags / Keywords:
sightseeing, hopping, Best Restaurants

Tom recommends


Price from Rating
(out of 5)
1. The Westin Key West Resort & Marina
2. Marquesa Hotel
3. Hyatt Key West Resort And Spa
4. Key West Bed & Breakfast - the Popular House

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Community comments (4)

1 of 1 people found the following comment helpful.

This brings back some good memories, Key West is awesome.

There are some good tips in here, particularly for those who may only stopping off for the day on their cruise itinerary.

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Hi Rick,

Cheers for the comments, Key West is indeed an awesome place :-)

1 of 1 people found the following comment helpful.

Tom, thank you for all of the hard work that you have put into this guide. You offer a good overview of Key West and all of your links and addresses are really useful. To nitpick, I would have liked to see prices after your restaurant recommendations as the statement "prices are obviously a little higher than other places " isn't very useful when you don't give any prices. However, the structure of this guide works and I like your personal touches. Thanks.

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Cathy, I appreciate your kind comments. I would happily include more details although I was conscious of your 1200 word limit and didnt want to sacrifice, places to stay or visits to include lots of addresses or costs. Moving forward with my new guides I will certainly take your comments onboard