Accommodations, transportation, activities, dining and the details in between, thoughtfully planned to work together for your trip
30 years of first hand experience in Key West
Rebecca handles the details so you can enjoy the anticipation
Every vacation is designed around you
The best local partners for the best activities
Thoughtful touches that make your trip extraordinary
Ready to experience the laid-back charm of the Conch Republic for the very first time? Whether you’re planning a romantic escape, family getaway, or solo adventure, we’ve got your perfect itinerary covered. Start planning your dream trip today!
Welcome to our Fishing Headquarters, your ultimate guide to the best fishing charters in Key West!
With over 20 years of vacation planning expertise in Key West, Key West Rebecca serves as your dedicated travel agent, concierge, and local guide. From iconic landmarks to hidden gems, Rebecca simplifies your vacation planning, ensuring a stress-free, all-in-one Key West adventure tailored just for you.
The 4 events we did through KW Rebecca were top notch. without her help we never would have had such an enjoyable trip. Scott and cathy
Scott B.You can trust Key West Rebecca for your shared sandbar fun! She organized a shared trip for us with Island Tales Charters. We could not have gone without her coordination… read more
Trudy V.Rebecca’s team did a wonderful job at finding me the experiences I was looking for! Highly recommend!
Joanne I.Our party of 6 visited Key West in May of 2021. I ran across Key West Rebecca while researching things to do while on vacation there. I contacted her and… read more
Jason K.Incredibly helpful and has the best tour options to choose from!! Responds quickly and is truly the nicest!! If we ever return to the area, we will contact her to… read more
Jen W.My husband and I visited Key West for the first time. Rebecca was able to book us a dolphin, snorkel, sunset cruise that was absolutely amazing and also helped us… read more
April B.Good experience very professional & knowledgeable.
Amy C.Thank you again for an amazing trip. Arrangements for bikes for the week complete with free delivery and pickup. We went to Blue Moon kayak and had a blast!!!… read more
Ginger S.I can’t say enough about using Key West Rebecca. We had booked a deck boat and at the last minute (per the boat companies recommendation) we had to cancel. It… read more
Sherry G.We are first time visitors to Key West. Rebecca helped us with getting golf cart in a pinch . She was a life saver! She is upbeat and so easy… read more
Brenda B.My fiancé and I arrived in Key West on Feb 13th, the day before Valentine’s Day. I spoke with Rebecca a week or so before our arrival, I wanted some… read more
Walt M.We worked with Key West Rebecca for our trip over Thanksgiving and i am so glad we did. I contacted her and told her what we wanted to do… read more
Jolene W.Hooked me and my best friend up with scooter for the day and gave amazing suggestions for anything we needed!!! Thank you for making my first trip to the keys… read more
Dione B.She helped us book our snorkeling tour. She was awesome! Thank you!!
Cara R.Rebecca was a life saver on our vacay! She took care of booking all of our water adventures with sunset sports! All I did was tell her our interests and… read more
Christy T.I found Key West Rebecca on a fb group for Key West Locals and am so happy I found her! We booked a fishing trip she recommended and it was… read more
Mary A.She is extremely knowledgeable in the island and the locals. Very Friendly
Aldo H.Some of the people on this group are very hateful people wouldn’t recommend if you love nature or the beauty of the keys .
Suzanne E.Not sure what to do in Key West?? Contact Rebecca.. she will take care of all your traveling needs ❤️
Mary G.Key West Rebecca took all the stress out of planning events for our trip. She got us 2 day passes for the on-off trolley tour, tickets to the Hemingway house,… read more
Doni C.Great sunset cruises. Great times.
Doreen K.We’re from Chicago and I’m glad we found Key West Rebecca. She is very knowledgeable and provides excellent service. I would call her and say “Tomorrow we would like… read more
Doreen S.We are planning a trip for this upcoming March and I love reading her posts. I have sent her numerous questions and she has always replied quickly and with… read more
Beth V.Recently moved to KW and Rebecca is my go-to gal for everything from events around the island to a good oil change for my car!
Laurie J.great ambassador for my favorite place. key West
Lisa L.Thank you so much for making sure our sunset cruise was awesome!
Lisa G.Rebecca set up a cigar factory tour for my husband and two of his friends. They enjoyed it thoroughly and we appreciated her help in booking it for them.
Terri E.Rebecca is very knowledgable about the Keys, very friendly, pleasant to talk with.
Teresa R.Rebecca was amazing with helping me plan activities for our up coming vacation. Highly recommend her 🙂
Shelley S.Key West Rebecca you are amazing! Thank you so much for helping us with our last minute trip to Key West and hooking us up with so many great things… read more
Nicole K.We are planning a trip for this upcoming March and I love reading her posts. I have sent her numerous questions and she has always replied quickly and with... read more
Beth Vondrasekif you want a good..now you have the best ❤️ Rebecca has the know-how..... give her a try 😎🌴
Anthony Waynegreat ambassador for my favorite place. key West
Lisa LandauWe worked with Key West Rebecca for our trip over Thanksgiving and i am so glad we did. I contacted her and told her what we wanted to do... read more
Jolene WormleyDelightful lady, charming and witty, helpful and entertaining, and sexy as hell!
Timothy FosterRecently moved to KW and Rebecca is my go-to gal for everything from events around the island to a good oil change for my car!
Laurie JacobsmaOur party of 6 visited Key West in May of 2021. I ran across Key West Rebecca while researching things to do while on vacation there. I contacted her and... read more
Jason KempaShe is extremely knowledgeable in the island and the locals. Very Friendly
Aldo HamiltonRebecca was amazing with helping me plan activities for our up coming vacation. Highly recommend her 🙂
Shelley StowellIncredibly helpful and has the best tour options to choose from!! Responds quickly and is truly the nicest!! If we ever return to the area, we will contact her to... read more
Jen WetzelRebecca’s team did a wonderful job at finding me the experiences I was looking for! Highly recommend!
Joanne IreneKey West Rebecca you are amazing! Thank you so much for helping us with our last minute trip to Key West and hooking us up with so many great things... read more
Nicole KellyMy fiancé and I arrived in Key West on Feb 13th, the day before Valentine’s Day. I spoke with Rebecca a week or so before our arrival, I wanted some... read more
Walt MushlitzThe 4 events we did through KW Rebecca were top notch. without her help we never would have had such an enjoyable trip. Scott and cathy
Scott BatemanTop Notch gal! Knows all the fun things to do while in Key West!
Delayne HiottHooked me and my best friend up with scooter for the day and gave amazing suggestions for anything we needed!!! Thank you for making my first trip to the keys... read more
Dione BurkeTop Notch gal! Knows all the fun things to do while in Key West!
Delayne HiottIncredibly helpful and has the best tour options to choose from!! Responds quickly and is truly the nicest!! If we ever return to the area, we will contact her to... read more
Jen WetzelIf you’re not sure what to do when you get to Key West make Key West Rebecca your “Go To Guide!!” Her walking tours are Fun and Informative,not too tiring after... read more
Laels ArtCartShe's very informative. I would recommend her before getting a travel book.
Lyron ConnorGreat sunset cruises. Great times.
Doreen Kilpatrickshe's great. the sunset cruise she booked for us was great!
Annie MartinWe’re from Chicago and I’m glad we found Key West Rebecca. She is very knowledgeable and provides excellent service. I would call her and say “Tomorrow we would like... read more
Doreen SchwartzWe worked with Key West Rebecca for our trip over Thanksgiving and i am so glad we did. I contacted her and told her what we wanted to do... read more
Jolene Wormleyif you want a good..now you have the best ❤️ Rebecca has the know-how..... give her a try 😎🌴
Anthony WayneYou can trust Key West Rebecca for your shared sandbar fun! She organized a shared trip for us with Island Tales Charters. We could not have gone without her coordination... read more
Trudy VinceI didn’t plan to stay in Key West.
In 1995, I came down for what was supposed to be a simple seven day vacation… and somewhere between the salt air, the sunsets, and happy hours, I realized I wasn’t going back. What started as a visit turned into a life, and now, more than 30 years later, I’m still here.
Like many Key West stories, mine started out on Duval Street as a street barker, talking to visitors, learning what drew people here, and helping them figure out how to make the most of their time on the island. From there, I spent years working alongside local watersports companies, getting to know every corner of what makes Key West special, from snorkeling and scuba diving to sailing, kayaking, and everything in between.
I’ve always been an island girl at heart, and for many years I lived my own version of Boats, Beaches, Bars & Ballads. Days on the water, nights filled with music, and years spent experiencing the island the same way my clients dream about it.
Along the way, I started to notice something. Visitors were constantly trying to piece their vacations together on their own, booking accommodations in one place, activities in another, and hoping it would all come together as they imagined. There wasn’t one place they could go for real, personalized help planning a complete Key West vacation.
That’s where the idea for Key West Rebecca came from.
In 2019, I turned everything I had learned, every connection I had built, and every experience I had lived into a full service Key West travel agency designed to bring it all together in one place. This was not based on online reviews or generic recommendations, but on decades of firsthand experience and a deep understanding of what makes a trip here truly unforgettable.
Today, I help visitors plan their time in Key West in a way that feels easy and completely customized to them. Every trip is different, because every person is different, and that’s exactly how it should be.
Because for me, this island was never just a destination.
It became home.
And there’s nothing I love more than helping people experience it the way I did.
Thank you!
