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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!
With over 20 years of vacation planning expertise in Key West, Key West Rebecca will serve as your dedicated travel agent, concierge, and local guide. Leveraging insider knowledge and a rich network of resources, I customize each aspect of your getaway for a personalized experience. From iconic landmarks to hidden gems, let me simplify your vacation planning, ensuring a stress-free, all-in-one Key West adventure tailored just for you.
Local Tips, Hidden Gems & Island News
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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, 2020Great sunset cruises. Great times.

Doreen Kilpatrick
December 28, 2019We 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 Boyles
March 19, 2021She is extremely knowledgeable in the island and the locals. Very Friendly

Aldo Hamilton
April 9, 2020Thank 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 Seely
July 27, 2021Fun, outgoing, friendly, professional!

Mike-Tara Kelly
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, 2019Rebecca’s team did a wonderful job at finding me the experiences I was looking for! Highly recommend!

Joanne Irene
September 14, 2022The 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 Bateman
April 30, 2023Our 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, 2022Delightful 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, 2019She's very informative. I would recommend her before getting a travel book.

Lyron Connor
September 14, 2018We 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 Vondrasek
December 7, 2019I 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, 2021Thank you so much for making sure our sunset cruise was awesome!

Lisa Gardner
October 26, 2019
great ambassador for my favorite place. key West

Lisa Landau
November 8, 2019Incredibly 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 Wetzel
December 15, 2021We 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 Vondrasek
December 7, 2019My 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, 2021Our 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, 2022Good experience very professional & knowledgeable.

Amy Campbell
September 29, 2021I 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 Ann
June 12, 2020Rebecca 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 Enlow
September 14, 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, 2021





