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Beginners Guide to Key West
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!
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Check Out Endless Hours of Fun and Excitement Key West Has to Offer

fishing headquarters
Welcome to our Fishing Headquarters, your ultimate guide to the best fishing charters in Key West!
How I Became
Key West Rebecca
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.
Local Tips, Hidden Gems & Island News
Leave us a review
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 with other couples. Best Day!

Trudy V.
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 scheduled parasailing, a sunset dinner cruise, and a sandbar /snorkeling excursion. We had a blast!!! Everything went off without a hitch. I highly recommend Key West Rebecca for any and all of your vacation excursions. She is very knowledgeable and friendly to deal with. I will definitely be contacting her again when the time comes for another trip to paradise.

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 schedule more fun before we arrive!! Thank you!!

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 with a Jeep rental so we could drive up the Keys one day! Very friendly and I would recommend her for all things Key West!!

April B.
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 Will see you again!!!

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 took a bit on her part to get our refund, but she went all out. If we make it to the Keys again I would def give her a call to book any of our outings!!

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 to work with. So very helpful with booking what we needed. It has been a great experience. She took a lot of stress off of us so we could enjoy our vacation.

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 flowers to be in our room when we got there. Not only were the flowers very beautiful but Rebecca also left a welcome package for us filled with great coupons!!! She also kept in contact with me letting me know that the flowers were delivered. I very highly recommend her for anything related to Key West!!!

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 and she gave us some ideas as well. She booked us on a private charter to a sandbar which was absolutely amazing and also on a snorkeling trip. She took care of everything for us so we didn’t have to worry. We had so much fun on our excursions. She definitely has the best contacts in the Keys for providing fun. I highly recommend Rebecca for all your fun in the sun and she was always so easy to contact with immediate responses. We will definitely use her again when we return to Key West. Thanks Rebecca!

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 amazing! I will be back!!

Dione B.
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 she took care of the rest! She even drove to ibis bay resort and left us an envelope of coupons and such! Not to mention just gave us all types of tips and suggestions. Choose Rebecca for your vacay plans!

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 AMAZING-the boat, the crew, the company was all stellar. She also gave us some great restaurant recommendations and coupons. We will definitely be hitting her up next time we come back.

Mary A.
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 jet ski tour tickets, sunset cruise buffet dinner tickets and a reservation at the perfect time for Latitudes. Not to mention a welcome package with tons of coupons for drinks and desserts. Highly recommend her. Thank you so much. Our trip was amazing.

Doni C.
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 to…….” and she would find our activity at a great price. We booked our snorkeling/dolphin/sunset trip, parasailing, mopeds, and jet skis with Rebecca. I HIGHLY recommend working with her.

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 such zest. She has offered to leave us a welcome package at our hotel when we arrive. She is a gem.

Beth V.
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 to do, see and enjoy. Can’t wait for our next visit and see what other great things we didn’t get to do. One day was just not enough. Although we crammed in everything from visiting the beaches, parasailing, riding around town in a golf cart eating and drinking and enjoying the night life:) Thank you so so much! xoxo Stay warm…

Nicole K.
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 she took care of the rest! She even drove to ibis bay resort and left us an envelope of coupons and such! Not to mention just gave us all types of tips and suggestions. Choose Rebecca for your vacay plans!

Christy Tucker
July 7, 2020Top Notch gal! Knows all the fun things to do while in Key West!

Delayne Hiott
September 5, 2018We’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 to.......” and she would find our activity at a great price. We booked our snorkeling/dolphin/sunset trip, parasailing, mopeds, and jet skis with Rebecca. I HIGHLY recommend working with her.

Doreen Schwartz
December 20, 2019Great sunset cruises. Great times.

Doreen Kilpatrick
December 28, 2019She's very informative. I would recommend her before getting a travel book.

Lyron Connor
September 14, 2018Delightful lady, charming and witty, helpful and entertaining, and sexy as hell!

Timothy Foster
September 5, 2018she's great. the sunset cruise she booked for us was great!

Annie Martin
May 19, 2019My 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 flowers to be in our room when we got there. Not only were the flowers very beautiful but Rebecca also left a welcome package for us filled with great coupons!!! She also kept in contact with me letting me know that the flowers were delivered. I very highly recommend her for anything related to Key West!!!

Walt Mushlitz
February 14, 2021If 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 partying all night on the Cruise & Quite Tasty!!😋

Laels ArtCart
February 17, 2019Rebecca’s team did a wonderful job at finding me the experiences I was looking for! Highly recommend!

Joanne Irene
September 14, 2022Rebecca is very knowledgable about the Keys, very friendly, pleasant to talk with.

Teresa Renfro
August 3, 2019We 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 and she gave us some ideas as well. She booked us on a private charter to a sandbar which was absolutely amazing and also on a snorkeling trip. She took care of everything for us so we didn't have to worry. We had so much fun on our excursions. She definitely has the best contacts in the Keys for providing fun. I highly recommend Rebecca for all your fun in the sun and she was always so easy to contact with immediate responses. We will definitely use her again when we return to Key West. Thanks Rebecca!

Jolene Wormley
December 19, 2020I 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 took a bit on her part to get our refund, but she went all out. If we make it to the Keys again I would def give her a call to book any of our outings!!

Sherry Gerth-Montgomery
March 23, 2021My 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 with a Jeep rental so we could drive up the Keys one day! Very friendly and I would recommend her for all things Key West!!

April Bostik
October 17, 2021Not sure what to do in Key West?? Contact Rebecca.. she will take care of all your traveling needs ❤️

Mary Gruba
March 8, 2020Key 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 jet ski tour tickets, sunset cruise buffet dinner tickets and a reservation at the perfect time for Latitudes. Not to mention a welcome package with tons of coupons for drinks and desserts. Highly recommend her. Thank you so much. Our trip was amazing.

Doni Cody
February 16, 2020
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 with a Jeep rental so we could drive up the Keys one day! Very friendly and I would recommend her for all things Key West!!

April Bostik
October 17, 2021Thank you so much for making sure our sunset cruise was awesome!

Lisa Gardner
October 26, 2019She's very informative. I would recommend her before getting a travel book.

Lyron Connor
September 14, 2018Our 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 scheduled parasailing, a sunset dinner cruise, and a sandbar /snorkeling excursion. We had a blast!!! Everything went off without a hitch. I highly recommend Key West Rebecca for any and all of your vacation excursions. She is very knowledgeable and friendly to deal with. I will definitely be contacting her again when the time comes for another trip to paradise.

Jason Kempa
January 19, 2022Top Notch gal! Knows all the fun things to do while in Key West!

Delayne Hiott
September 5, 2018if you want a good..now you have the best ❤️ Rebecca has the know-how..... give her a try 😎🌴

Anthony Wayne
February 18, 2019Good experience very professional & knowledgeable.

Amy Campbell
September 29, 2021Recently 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 Jacobsma
December 7, 2019Great sunset cruises. Great times.

Doreen Kilpatrick
December 28, 2019Not sure what to do in Key West?? Contact Rebecca.. she will take care of all your traveling needs ❤️

Mary Gruba
March 8, 2020





