The 7 Best Key West Sunset Dinner Cruises🌅[2022 Reviews]

Key West is one of the most beautiful places not only in the United States, but in the entire world. It makes sense, then, that tons of tourists flock here every year.

The natural beauty and incredible climate that stays consistent pretty much year-round makes it a great place to hang out outdoors. The natural landscape, ocean, and electric sun come together for gorgeous sunsets every night, and there are many great places to watch them.

However, nothing compares to one of the top Key West sunset cruises, which we’re here to bring you today!

Best Sunset Cruises in Key West

 Key West Sunset Sail Aboard SchoonerSmall-Group Key West Sunset Sail with WineKey West: Sunset Cruise with Buffet Dinner and Open Bar
editors choice
Key West Sunset Sail Aboard SchoonerSmall-Group Key West Sunset Sail with WineSunset Cruise with Buffet Dinner and Open Bar Key West
Departure Point:202 William St, Key West255 Front St, Key West201 William St, Key West
Departure Time:Varies by time of yearVaries by time of yearVaries by time of year
Duration:2 hours2 hours2 hours
Includes:Complimentary beer, wine, champagne, soda, individually-plated hors d'oeuvresUnlimited beer, wine and soft drinks, wine tasting, light refreshmentsBuffet dinner, open bar, live music, sunset cruise

Tour Information & Booking

Tour Information & Booking

Tour Information & Booking

Quick Answer: The 7 Best Rated Key West Sunset Sails For 2022

  1. Key West Sunset Sail Aboard Schooner
  2. Small-Group Key West Sunset Sail with Wine
  3. Key West: Sunset Cruise with Buffet Dinner and Open Bar
  4. Key West Sunset Sail with Full Bar, Live Music & Hors D’oeuvres
  5. Key West Sunset Cruise with Live Island Music
  6. Sunset Sail Cruise in Key West
  7. Key West Sushi Sunset Cruise

Key West Sunset Cruise Reviews

1. Key West Sunset Sail Aboard Schooner

Key West Sunset Sail Aboard Schooner

Tour Highlights:

  • Duration: 2 hours
  • Departure: 202 William St, Key West
  • Departure Time: Varies by time of year
  • Includes: 2-hour sailing experience aboard America 2.0, complimentary beer, wine, champagne, soda, individually-plated hors d’oeuvres

If you want to feel like you’ve gone back in time almost 200 years, then you have to check out first tour out! The Key West Sunset Sail Aboard Schooner tour will take you over the beautiful ocean on a replica of the 1851 Schooner America.

This smooth ride is luxurious, a load of fun, and one of the best ways to watch the sun go down on the island. Meet up around 4 pm along with the rest of your group to board the ship. You’re immediately greeted by the crew, who are super friendly and make the experience that much better.

Once you take a seat (or stand if you prefer), you’ll be served with complimentary hors d’oeuvres along with a nice selection of alcoholic and non-alcoholic drinks.

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This is a great way to meet other tourists or locals, bring the entire family on board, or simply experience it with your significant other.

Set sail, enjoying the sounds of the water underneath the ship as you head towards Mallory Square. There are a ton of people who come to the square to watch the sunset – wave to them from the ship!

Next, you’ll sail by the famous Fort Zachary Historic State Park, which has its own unique history and looks impressive from the water! At this point, the sun will start going down. However, not before you reach the incredible views that Sunset Pier has to offer!

The neon orange reflects wonderfully off the water, and the music and other people nearby just makes it that much more magical.


Tour Information & Booking

100% refund for cancellations within 24 hours of tour experience

2. Small-Group Key West Sunset Sail with Wine

Small-Group Key West Sunset Sail with Wine

Tour Highlights:

  • Duration: 2 hours
  • Departure: 255 Front St, Key West
  • Departure Time: Varies by time of year
  • Includes: Unlimited beer, wine and soft drinks, wine tasting, light refreshments

Are you a lover of wine and/or beautiful sunsets on the water? If you are, then you’re the perfect guest for the Small-Group Key West Sunset Sail with Wine Tour! This is a bit more of an intimate cruise, where the one prior to this was made for the larger crowds of people.

Make sure to check in approximately 30 minutes before the departure time the crew advises you of, ensuring everyone gets on board and comfortable. We found the crew to have incredible attention to detail, and were very friendly, putting safety at the forefront of the operation.

Once you board the 65-foot schooner, you’ll realize that there’s plenty of seating room, and you won’t be squashed in with other passengers.

Once you set sail, you’ll be served a choice of wine, 4 different kinds of beers, along with delicious charcuterie selections such as a wonderful cheese, cracker, meat, and olives plate.

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Rest assured the crew will keep the wine flowing with 8 different selections available! We personally enjoyed the summer sausages, brie, and green apples with honey, however, there really is something to suit any taste.

If you’re looking to plan a fantastic date night with your other half, this is really the way to go due to the smaller group sizes and alcoholic beverage selections against a stunning background.

Watch the sun go down over the horizon of endless shimmering water, with the sun reflecting off of it. This creates an orange glow that looks almost unreal at times. Make sure to take out the camera for some excellent photo ops!


Tour Information & Booking

100% refund for cancellations within 24 hours of tour experience

3. Key West: Sunset Cruise with Buffet Dinner and Open Bar

Sunset Cruise with Buffet Dinner and Open Bar Key West

Tour Highlights:

  • Duration: 2 hours
  • Departure: 201 William St, Key West
  • Departure Time: Varies by time of year
  • Includes: Buffet dinner, open bar, live music, sunset cruise

Who doesn’t love endless food and drinks? If you’re enjoying a wonderful vacation in Key West, you shouldn’t have to limit yourself and try everything that catches your eye. On the Key West: Sunset Cruise with Buffet Dinner and Open Bar tour, you don’t have to!

This is yet another 2-hour, intimate cruise with smaller group sizes. With that being said, if you’re going with a significant other, it’s a great date night option. However, just as well, it’s a fun time for the entire family though it tends to lean more towards adults.

Are you looking for a calm, relaxing cruise tour instead of a party cruise? There are plenty of both in Key West, and this one falls into the category of the former, despite the ship being called “The Party Cat”.

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The smooth ride on the ship along with the chill music makes for a serene way to enjoy the afternoon.

Once you board, enjoy a buffet comprised of fresh tropical fruit and dishes. You can expect options such as: roast pulled-pork in mojo sauce, deep-fried sweet plantains, black beans and rice, grilled chicken, friend fish, mixed veggies, pasta with mini shrimp, along with Cuban bread and butter.

Drinks are also delicious, with endless margaritas, rum runners, champagne, beer, wine, and spirits. After dinner, head upstairs to the upper deck to groove the night away to some live music!

The local musicians are very talented and entertaining, setting the tone for a fun evening as you watch the sun set with the electric colors spreading across the sky.


Tour Information & Booking

100% refund for cancellations within 24 hours of tour experience

4. Key West Sunset Sail with Full Bar, Live Music & Hors D’oeuvres

Key West Sunset Sail with Full Bar, Live Music & Hors D'oeuvres

Tour Highlights:

  • Duration: 2 hours
  • Departure: 205 Elizabeth St , 205 Elizabeth St, Key West
  • Departure Time: Varies by time of year
  • Includes:Beer, wine, champagne, sangria and soft drinks, chef’s selection of hors d’oeuvres, full liquor bar included, live music from local Key West musicians

If you’re on the hunt for an amazing sunset cruise but are on a budget, put this one at the top of your list! The Key West Sunset Sail with Full Bar, Live Music & Hors D’oeuvres is all that and more.

Oh, but it’s not just a cruise! It’s a 2-hour excursion where you get to try a little bit of southern flavor with peel-and-eat shrimp and an upscale twist with fresh hors d’oeuvres. If you want to escape the crowds that gather on shore to watch the sunsets, we can’t think of a better way to do it!

Meet up at the tour office located between Conch Republic and Schooner Wharf 30 minutes before the departure time (around 4 pm). Board the sleek, 60-foot catamaran that sports a whopping 1,500 feet of deck space!

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With smaller group sizes, everyone has more than enough room to walk around and mingle, or kick back and relax.

The crew is incredibly friendly, and always attentive and there to make sure everyone has a great time. Once you board, you’ll be able to revel in amazing live entertainment, and all-you-can-eat drinks and snacks.

Yep, you read that correctly! The music does vary, but typically you’ll have some jazz and smooth music to accompany you. Drinks consist of beer, soft drinks, sangria, full liquor bar, wine, champagne, and more.

As the sky starts changing colors, you’ll cruise by important landmarks along the coast, such as Mallory Square, Navy Mole Fort Zachary Taylor Historic State Park, and more. Make sure to take your camera out to take some photos of the blue waters meeting the orange sky!


Tour Information & Booking

100% refund for cancellations within 24 hours of tour experience

5. Key West Sunset Cruise with Live Island Music

Key West Sunset Cruise with Live Island Music

Tour Highlights:

  • Duration: 2 hours
  • Departure: 631 Greene St , 631 Greene St, Key West
  • Departure Time: 4 pm
  • Includes: Appetizers, dishes, alcoholic beverages, soft drinks

Does dancing to some island grooves from local musicians while you eat, drink, and enjoy a beautiful sunset on the water sound like a good time to you? Then give the Key West Sunset Cruise with Live Island Music a good look! This is yet another cruise that’s easy on the wallet and a couple of hours of good vibes.

From the very get-go, it’s an awesome experience thanks to the attentive and friendly staff, and positivity all-around. We should let you know that this is kind of a more upbeat experience than the others, which have a more relaxing setting.

The band plays everything from reggae to rock, and the crowd can get a bit lively! However, it’s a ton of fun! The crew will escort you onto the spacious catamaran, which is clean, and looks to be quite new.

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There’s ample seating everywhere, aside from the large dance floor so you can bust a move without worrying about anyone getting in your way!

Enjoy unlimited appetizers, beer, margaritas, wine, sangria, champagne – whatever you feel like having! There are plenty of soft drinks and water available as well, if you don’t want any of the other options.

Enjoy cruising along the calm waters as the sky turns pink, orange, and yellow, reflecting off of the ocean. You’ll get to see Mallory Square, Sunset Key, and Key West Harbor as you sail along.

This is a very welcoming experience, with a lively atmosphere that’s perfect for guests of all ages! However, it may not be ideal for children who do not like loud music as this is a live band. It’s a great way to dance a little, enjoy cruising along, and have some appetizers while being back just in time for dinner!


Tour Information & Booking

100% refund for cancellations within 24 hours of tour experience

6. Sunset Sail Cruise in Key West

Sunset Sail Cruise in Key West

Tour Highlights:

  • Duration: 2 hours
  • Departure: 631 Greene St , 631 Greene St, Key West
  • Departure Time: 4:00 pm
  • Includes: Sunset sail, snacks, coolers of ice with cups and bottled water

Next up, we bring you the Sunset Sail Cruise in Key West, which is a crowd favorite. Have you ever thought that being a pirate may be fun? Well, then this tour should immediately hit the top of your list because you’re about to get as close as possible to that!

We’re sure there’s no other Key West sunset cruise like this one, as you’ll be riding on the island’s most photographed ship? Why does it hold this title?

Because the Schooner Jolly II Rover is the only squared-rigged, topsail schooner in the Historic Seaport! You may have heard of it referred to as the island’s famous “Red Sails in the Sunset” tall ship!

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If sailing catches your interest, you’ll love how interactive this cruise is. You’ll be able to help raise the sails, steer the ship, and “shoot the cannons”. However, it’s never obligatory. You can be as involved as you want, no pressure.

The crew is one of the friendliest we’ve encounters, which is really saying something! It’s not uncommon for the ship’s owner to come out and visit with everyone, either. The crew will give an interesting historical account of the ship, the area, and much more.

As you sail, make sure to take advantage of the unlimited snacks and ice-cold water onboard. On here, you won’t be hearing any music or rowdy environments. This tour is designed to be peaceful and allow you to take in the experience of sailing while enjoying the natural beauty around you.

You’ll cruise into Man O’ War Harbor, see Christmas Tree Island, mansions on Sunset Key, Mallory Square, Navy Mole, and Fort Zachary Taylor!


Tour Information & Booking

100% refund for cancellations within 24 hours of tour experience

7. Key West Sushi Sunset Cruise

Key West Sushi Sunset Cruise

Tour Highlights:

  • Duration: 2 hours
  • Departure: Barefoot Billy’s Boat Cruises – Garrison Bight Marina , 719 Palm Ave, Key West
  • Departure Time: Varies by time of year
  • Includes: Alcoholic beverages, bottled water, soda, snacks, restroom on board

You’re probably already aware of the fact that Key West has some of the best seafood in the United States. This means that there’s a ton of good sushi offered on the island as well. If you want to enjoy some delicious sushi rolls while watching the pink sunset electrify the water and sky, check out the Key West Sushi Sunset Cruise!

This boat is one of the smallest ones of any sunset cruise we’ve seen in Key West, however, this offers a more intimate experience that’s great for sharing with your loved one(s). The captain and crew do a great job of keeping you entertained while making sure everyone is tended to properly.

Once on board, you’ll be served platters of sushi so make sure you save some room! This is a great way to get to try different types of rolls that you haven’t had before. There are plenty of other snacks and many beverages available as well, just in case someone in your group isn’t a sushi fan.

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Even if you are bringing the entire family, there’s enough fresh food for everyone with everything cooked to perfection!

While the captain tours you around, they’ll share many stories, personal anecdotes, and historical accounts that will have you at the seat of your chair!

Cruise by Mallory Square, Fort Zachary Taylor Historic State Park, Key West Lighthouse and Keeper’s Quarters Museum (seemed to be most peoples’ favorite), and the incredible Southernmost Point.

This is the lowest latitude land in the contiguous North American States so make sure to get a photo or two!


Tour Information & Booking

100% refund for cancellations within 24 hours of tour experience

Key West Travel Guide

Best Sunset Cruises in Key West

Getting There

Air – Getting to Key West is really simple from just about anywhere within the United States. Most major airlines (national and foreign) serve Key West, such as American Airlines, Delta, Allegiant, United, JetBlue, and many others. If you prefer traveling without dealing with crazy packed commercial flights, you can opt for one of the many charters that serve Key West.

Alternatively, you can head to Miami International Airport, and just drive to Key West by taking LeJeune Road heading south to 836 West. Take the Florida Turnpike South toward Key West, then follow US 1 South until you get to Key West.

Train – The Amtrak can take you as far south as Fort Lauderdale from just about any major city in the country (but make sure to revise). Once you get to Ft. Lauderdale, you can hop on a transfer to the Keys Shuttle.

Shuttle – There are many shuttle services with daily stops from the mainland and the Keys. The Keys Shuttle is the best-rated, thanks to their door-to-door services to and from both Miami and Ft. Lauderdale airports. Their staff is incredibly helpful, and if you have a large group they can really make things a lot more convenient.

The Florida Keys Express Shuttle can also get you to/from Fort Lauderdale-Hollywood International and MIA airports. Select either a Mercedes Benz van or SUV limo, and you’re riding in style! It’ll be more expensive, but if you want to relax in a more opulent mode of transport, you have it.

Water – As you probably already figured, accessing Key West by water is quite common. The Key West Express features high-speed ferries operating from Ft. Myers Beach and Marco Island. The ferries pull into the Key West Bight Ferry Terminal placed in the middle of the Historic Seaport Terminal which is easy to access from just about any point of the island.

Getting Around

Getting around Key West is incredibly simple, thanks to the island’s compact size. Driving is easy and isn’t much different from mainland US. Don’t feel like you need to drive here though, as there are tons of options that are more affordable and just as easy.

Walking – As Key West is pretty flat, you don’t have to worry about ascending hills nor about “sketchy” parts of town. On the contrary, the communities here are very well-kept, with charming homes and nice gardens. If you really want to get to know the island, it’s arguably the best way to do so. With the climate being one of the best in the US, rainfall or cold weather isn’t usually a big threat.

Taxis – Taxis serve the entire island, and are best to hire by calling ahead rather than hailing from the street. However, if you’re at the airport, you’ll see a line of taxis waiting for arrivals for tourists trying to get to their hotels or other accommodations.

Ride Sharing – There are now Uber and LYFT operating on the island, which tends to be more convenient for many non-locals who are already familiar to the apps. Not to mention, it gives some people an increased sense of security knowing that there is a paper trail of where they’ve gone and who’s driving them.

Cycling – Aside from walking, biking is another excellent way to get to know the city. It’s a nice way to get in a bit of exercise, and you can rent one for just 50 bucks a week! There are rental places aplenty, and if they don’t already tell you, it’s a good idea to ask about local rules.

Mopeds – Mopeds are also common among locals, however, they can be quite dangerous. There’s no helmet law in Florida, and they can get up to some pretty high speeds. Not to mention, you need to watch out for motor vehicles, other mopeds, and more. Not only that, but you have to follow the laws of the road, too.

Local Transportation – You have buses and trolleys all over the place in Key West, and both have day passes available. You can check out schedules online, and if you’re on a budget, they’re both highly-recommended options.

Where to Stay

Key West seems to have a perfect balance of modern and historic. Old Town is where most people will hang out, particularly if it’s your first time on the island. In a way, it’s like hopping back in time, with beautiful architecture and historic sites (including the seaport) to explore. With clean, large streets, it’s perfect for strolling around with the entire family.  However, you can also opt for a more luxurious experience in downtown or Casa Marina resort.

Duval Street is ultra-popular, with its colorful vibes, endless restaurants, shops, bars, and so on. It’s located in the center of Old Town, but you can easily walk to downtown from here, too. Are you really into sea sports and seafood? Then give The Historic Seaport a go. Not to mention, it’s a beautiful place!

Truman Annex is named such due to the fact that former president, Harry Truman, had a residence here. The house includes a gift shop for history aficionados. If you head towards the Historic Seaport, you’ll also see the original Pan Am airlines headquarters, which is now the First Flight Island Restaurant and Brewery, an aquarium, the Mel Fisher Maritime Museum, and much more. If you’re into nightlife and bars, then you have to check out Downtown/Duval Street. This is where you’ll find all the fun: all types of cocktails, parties of all kinds, and so much more.

Restaurants and Eating Out

If you’re a seafood lover, you’re in the right place. Even if you aren’t, there really is something for everyone here.

Glazed Donuts – Glazed Donuts is the perfect breakfast for first-thing in the morning before a tour, or if you have a packed schedule and don’t have time for a sit-down breakfast.Grab a freshly-brewed café accompanied with their famous key lime pie doughnut finished off with torched meringue or other delicacies.

Blue Heaven – Hanging out on the corner of Petronia and Thomas street, you’ll find Blue Heaven. It’s not just a place for some delicious Caribbean/American fusion dishes, but will supply you with live music, ping pong, and a laidback vibe with friendly locals. Don’t forget to try their legendary “Mile-High” Key Lime Pie! If anything, at least go for the pie!

A&B Lobster House – If you’re on the hunt for a more upscale place to take a date, you’ll love this restaurant that’s managed to perfect their vibe since 1947. With a beautiful wraparound balcony and extensive marina views, it sets the tone for a relaxing night full of great conversation and food. Just a few notable items from the menu include: Caribbean lobster thermidor, strip steak au poivre, and an impressive classic cocktail selection and wine menu.

Smoked BBQ – We all love the calm vibes of Key West, and you have it concentrated in a large supply at Smoked BBQ. Sure, it has some lovely marine views, but has a more “fisherman” kind of scene that people from all ages and backgrounds seem to love. Pulled pork sandwiches with a sweet BBQ sauce are the crowd favorite, though it also has some delicious seafood options like fish and chips.

Café Marquesa – This gorgeous restaurant is located inside the Marquesa Hotel, which is sophisticated with a hometown twist. Fresh Key West seafood is in large supply, and everything is cooked to perfection. Their desserts are housemade, and have a kind of Southern feel which is consistent with the friendly service.

Nightlife and Entertainment

Key West has some booming nightlife, and you’re about to experience it! If you thought the daytime was fun, you’ll really enjoy when the sun sets.

Duval Crawl – You haven’t lived if you haven’t gone bar hopping on Duval Street. Lined with all kinds of bars and nightclubs, you can see why it’s one of the top spots in Key West. Sloppy Joe’s is a top pick among locals and tourists, while Upper Duval is a bit more “upscale” with an array of romantic wine bars, craft cocktail hangouts, and more refined options. There’s always something along the spectrum of sophisticated and unruly entertainment.

Key West Theater – If you aren’t in the mood to down some cocktails or beers, head out for an evening at the Key West Theater. Placed in the center of Old Town, it hosts top-notch comedians, musicians, and bands. It also features community theater productions, exclusive film screenings, and more.

Hauntings Ghost Tour – Did you know that Key West is supposed to be one of the most haunted places in the US? If you didn’t, you sure will after participating in this ghost tour! It’ll cover the Hemingway House, lighthouse, as well as their local resident: the “Typhoid Mary” ghost. The Ghosts & Gravestones tour is another fascinating ghost tour if that’s your cup of tea. This tour takes place on a trolley with a narrated tour of the island’s old wooden home history, a Civil War fort and barracks, the haunted East Martello Tower, and much more.

Galleon Tiki Bar – Key West is simply too beautiful to not enjoy all its waterfront options! This tiki bar is located at the Galleon Resort and Marina, though you don’t have to be a guest to enjoy it. Locals head here often to watch the sunset, accompanied by one of their many delicious happy hour drinks and dishes!


As we mentioned briefly, you don’t typically have to worry too much about weather conditions in Key West, unless perfectly warm, sunny days aren’t your thing. Yep, even in the winter you won’t find it drop below 65 degrees. August is the hottest, and even then it doesn’t usually get over 90 degrees so it’s not blisteringly scorching.


As you’re probably already sick of hearing, the place to be is Duval Street. No matter when you’re out and about, you’ll always find something fun and interesting in this area. Extending from Mallory Square to the Southernmost Point marker, it sports beautiful homes, pretty gift shops, mouth-watering restaurants, lively bars, clubs, and much more.

The Ernest Hemingway Home and Museum was inhabited by the legendary writer from 1931 until 1940, more or less. Featuring a lush tropical garden, saltwater pool, and beautifully timeless furniture, it is apparently the place in which he created various infamous novels.

If you’re the kind of person who loves exploring Mother Nature and all she has to offer, you have to give the Key West Butterfly and Nature Conservatory a visit. As home to over 50 species of butterflies and over 20 species of exotic birds, it’s perfect for visitors of all ages. If you have kids along, it’s one of the top sights we recommend taking them to.

Mallory Square is one of the most popular places in the city, with live musical performers, street performers, art, vendors, delicious street food, and more. It’s hard to miss! Not to mention, if you can swing it, watching the sunsets here is highly recommended.

Mel Fisher Maritime Museum houses an array of rich artifacts, along with historical accounts that are sure to give you a different perspective on the area. One of which, is the Henrietta Marie, which was a slave ship that also transported tons of historic artifacts. The Spanish Santa Margarita is another, which dates back all the way to the 17th century.

The Martello Towers were constructed back in the mid-1800’s, and were made to protect Fort Zachary Taylor. Though it was never fully finished, it is made of impressive, 8-foot-thick granite walls! Take a casual stroll through the grounds, which are romantic and serene.


While Key West has some fantastic weather the vast majority of the time, hurricane season that run from June 1st to November 30th. However, from August to October, you’re likely to see the strongest storms. While they’re not typically the dangerous sort, it can still dampen your plans as a lot of Key West activities take place outdoors.

If you’re planning on driving, know that finding parking near Duval Street can be really difficult at times. You’re better off hailing a rideshare or taxi in these times, especially if you’re going out a night on the weekends. It’s not a bad idea to ask your hotel if they have a shuttle that can take you to/from the area. If you’re close enough, renting a bike or walking over there is a great option as well.

Driving to Key West is a wonderful experience in itself, as you get to drive over the Overseas Highway. It’s exhilarating, yet somehow it’ll completely clear your mind of any stress or worry – perfect for preparing you for a great time on the Island.

Key West is home to the only living barrier reef in the entire continental United States. Located about 6-7 miles offshore, snorkeling the Key West Reef can’t be missed while on the island!

Sites Seen

The Key West Sunset Sail Aboard a Schooner is our Editors Choice for the best Key West sunset cruise

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Robert Baker

Robert is a content writer and editor at World Guides to Travel where he shares his love for the great outdoors. He also writes in-depth travel blogs for other websites around the world. Robert is passionate about the environment and uses his writing to educate people about the advantages and importance of sustainable living. Robert enjoys creative writing. In 2009, his children’s novel Sally Hemings & the Good Associates won the Children’s Fiction section of the You Write On Book of the Year Award.
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