
Alyssa Chitwood
Based in Florida
English
Alyssa Chitwood
Ask me about
My Story
A foodie, lover of travel, and the planner of the group. With a background in hospitality, and an innate love for helping people, I’ve found myself here—helping couples discover romance, wherever their journey takes them!
Travel Style
Whether I’m discovering a new place or revisiting somewhere near and dear to my heart, I’m traveling in search of mouthwatering cuisine, once-in-a-lifetime experiences, and to make memories with loved ones. Now, I share that love with all my clients, allowing them to travel to all the beautiful pockets of the world they desire, without the stress of planning. From a simple weekend staycation through an elaborate anniversary celebration, I’m stepping in to handle research, bookings, itinerary build-outs, and everything in between. No trip is too big or small. Let’s write a love note to beautiful places together!
Reviews (12)
Cheryl M.
a month ago
Alyssa was the ultimate professional. She provided us with multiple resort options for our stay in Turks and Caicos. She listened to all of our wants and came up with multiple properties to support our wishes.
The attention to detail and the knowledge and information that she provided us on customs, transfers, restaurants etc made our stay easy and enjoyable from start to finish.
If you are looking to book a vacation I highly recommend Alyssa. She has a strong attention to detail and her follow through and responsiveness was exceptional. We were a party of 6 woman and there was not one complaint on our accomodations. She checked every box and exceeded our expectations in every way.
Sam L.
2 months ago
Amazing! Just a short trip but Alyssa made it so easy to book, with the best price possible. Put us right by our friends who were in the same hotel and got us an early check in from 4pm to 10am no extra charge! Checked in on us day of check in to make sure we knew she was available if needed. Warm, personable experience with Alyssa. Will absolutely be using her in the future for our bigger adventures.
Cheryl K.
3 months ago
We tend to book "things" last minute and Alyssa IS ALWAYS there to help. She goes above and beyond with her research to make sure that we are getting the best deal and with sharing her knowledge! I give Alyssa 10 STARS!
Chass C.
5 months ago
Alyssa was knowledgeable and attentive with all our questions and needs. Turn around time for any requests were insanely quick and well organized. If you need anything from A to Z, she will do it with speed and precision. She knew everything about anything and provided great detail and research. Using her as our travel advisor eliminated any and all hassles that comes with planning a trip yourself. I would give her 10 stars if I could. She made our vacation seamless and stress free. Will definitely be using her again in the future.
Lisa D.
5 months ago
Alyssa Chitwood was an amazing travel advisor who thoroughly researched everything I needed to know to have a wonderful vacation. She fulfilled my requests and I’m so glad she suggested the Fairmont Orchid. I would hire Alyssa in a flash for my next travel adventure.
Cheryl M.
a month ago
Alyssa was the ultimate professional. She provided us with multiple resort options for our stay in Turks and Caicos. She listened to all of our wants and came up with multiple properties to support our wishes.
The attention to detail and the knowledge and information that she provided us on customs, transfers, restaurants etc made our stay easy and enjoyable from start to finish.
If you are looking to book a vacation I highly recommend Alyssa. She has a strong attention to detail and her follow through and responsiveness was exceptional. We were a party of 6 woman and there was not one complaint on our accomodations. She checked every box and exceeded our expectations in every way.
Sam L.
2 months ago
Amazing! Just a short trip but Alyssa made it so easy to book, with the best price possible. Put us right by our friends who were in the same hotel and got us an early check in from 4pm to 10am no extra charge! Checked in on us day of check in to make sure we knew she was available if needed. Warm, personable experience with Alyssa. Will absolutely be using her in the future for our bigger adventures.
Cheryl K.
3 months ago
We tend to book "things" last minute and Alyssa IS ALWAYS there to help. She goes above and beyond with her research to make sure that we are getting the best deal and with sharing her knowledge! I give Alyssa 10 STARS!
Chass C.
5 months ago
Alyssa was knowledgeable and attentive with all our questions and needs. Turn around time for any requests were insanely quick and well organized. If you need anything from A to Z, she will do it with speed and precision. She knew everything about anything and provided great detail and research. Using her as our travel advisor eliminated any and all hassles that comes with planning a trip yourself. I would give her 10 stars if I could. She made our vacation seamless and stress free. Will definitely be using her again in the future.
Travel ideas (7)

Everything You Need To Know About MSC Seashore
MSC is an incredibly popular line among my clients for its accessibility here in Florida and outstanding value. I decided to give it a run for myself and am happy to report I absolutely loved the boat and am already looking at booking another voyage on this ship. Classy design, spacious, and numerous bars and eateries, and the Aurea experience that topped it all off.

Everything You Need To Know About MSC Seashore
MSC is an incredibly popular line among my clients for its accessibility here in Florida and outstanding value. I decided to give it a run for myself and am happy to report I absolutely loved the boat and am already looking at booking another voyage on this ship. Classy design, spacious, and numerous bars and eateries, and the Aurea experience that topped it all off.

The Tampa EDITION: Property Review
The Tampa EDITION is the first true luxury five-star property in the Tampa market, and it absolutely makes an impact.

The Tampa EDITION: Property Review
The Tampa EDITION is the first true luxury five-star property in the Tampa market, and it absolutely makes an impact.

Mountains, Brews & Beanies: Denver, Colorado
Denver has slowly become one my favorite cold-weather destinations, and trust me, there are not many. Having now spent a few weekends here in the late fall over the years, I’ve compiled a list of my favorite activities and places to inspire you to visit this always sunny city in Colorado—for something other than skiing and sipping hot toddies in a lodge.

Mountains, Brews & Beanies: Denver, Colorado
Denver has slowly become one my favorite cold-weather destinations, and trust me, there are not many. Having now spent a few weekends here in the late fall over the years, I’ve compiled a list of my favorite activities and places to inspire you to visit this always sunny city in Colorado—for something other than skiing and sipping hot toddies in a lodge.

The Historic Towns of Amelia Island & Fernandina Beach, Florida
Somewhat off the radar, about an hour north of Downtown Jacksonville is a quaint island with beach towns that gives all the coastal charm you need blended with rich history! It’s a bit of a trek to get there. It’s down one-lane, windy roads—but on a nice day the sun sits perfectly over the water as you cross multiple bridges, and this is the ideal location for a relaxing and romantic getaway. Amelia Island & Fernandina blend perfectly together for tons of fun on a weekend at the beach.

The Historic Towns of Amelia Island & Fernandina Beach, Florida
Somewhat off the radar, about an hour north of Downtown Jacksonville is a quaint island with beach towns that gives all the coastal charm you need blended with rich history! It’s a bit of a trek to get there. It’s down one-lane, windy roads—but on a nice day the sun sits perfectly over the water as you cross multiple bridges, and this is the ideal location for a relaxing and romantic getaway. Amelia Island & Fernandina blend perfectly together for tons of fun on a weekend at the beach.

A Bachelorette Weekend to Remember in Scottsdale
Scottsdale is a long-coveted bachelor and bachelorette destination, and I have finally learned why. Whether you opt for a hotel to be pampered as you so deserve, or you go the route of a private home rental, the city has so much to offer with chic accommodations and tons of activities that you won’t find just anywhere.

A Bachelorette Weekend to Remember in Scottsdale
Scottsdale is a long-coveted bachelor and bachelorette destination, and I have finally learned why. Whether you opt for a hotel to be pampered as you so deserve, or you go the route of a private home rental, the city has so much to offer with chic accommodations and tons of activities that you won’t find just anywhere.

7 Days on the Norwegian Epic
My husband had been dreaming of taking me on a cruise since we got together in 2020. Last year, he booked us a Wave Season deal on the Norwegian Epic—seven nights through St. Thomas, Tortola, Puerto Plata, and NCL’s private island, Great Stirrup Cay. With a balcony stateroom and plenty to celebrate, this trip completely changed my perception of cruising and ignited my passion for both sailing and selling cruises.

7 Days on the Norwegian Epic
My husband had been dreaming of taking me on a cruise since we got together in 2020. Last year, he booked us a Wave Season deal on the Norwegian Epic—seven nights through St. Thomas, Tortola, Puerto Plata, and NCL’s private island, Great Stirrup Cay. With a balcony stateroom and plenty to celebrate, this trip completely changed my perception of cruising and ignited my passion for both sailing and selling cruises.

A Day Trip From Barcelona to Sitges
Sitges is a historic port town known for its fishing and commercial port, and heavily influenced by late 19th century artists and writers. This town offers serene beaches, 17 to be exact, beautiful seafront walks, palm trees and architecture that holds centuries of stories. You can wander around the cobblestone streets and shop local vendors selling everything from hand woven clothing to Iberian ham. If you prefer, kick back in the sand enjoying the Mediterranean breeze away from the fast-moving excitement found in Barcelona. This coastal town is much better explored at your own pace, getting to navigate each winding road.
If you’re going to Barcelona for any extended period of time, chances are you’ve considered a day trip to a nearby city. Montserrat is commonly brought up in these conversations and you’ll find an abundance of excursions, guided tours, wine tastings and more among this mountainous city. Those opting for a more coastal break away from the big city, however, will be delighted to find Sitges just 35 minutes south by train.
I personally went on a cold overcast day in February as we stayed in Barcelona for three weeks out of the season. While it was chilly and at times rainy, the coastal town was still beautiful and the waterfront view has since become my phone screen wallpaper.

A Day Trip From Barcelona to Sitges
Sitges is a historic port town known for its fishing and commercial port, and heavily influenced by late 19th century artists and writers. This town offers serene beaches, 17 to be exact, beautiful seafront walks, palm trees and architecture that holds centuries of stories. You can wander around the cobblestone streets and shop local vendors selling everything from hand woven clothing to Iberian ham. If you prefer, kick back in the sand enjoying the Mediterranean breeze away from the fast-moving excitement found in Barcelona. This coastal town is much better explored at your own pace, getting to navigate each winding road.
If you’re going to Barcelona for any extended period of time, chances are you’ve considered a day trip to a nearby city. Montserrat is commonly brought up in these conversations and you’ll find an abundance of excursions, guided tours, wine tastings and more among this mountainous city. Those opting for a more coastal break away from the big city, however, will be delighted to find Sitges just 35 minutes south by train.
I personally went on a cold overcast day in February as we stayed in Barcelona for three weeks out of the season. While it was chilly and at times rainy, the coastal town was still beautiful and the waterfront view has since become my phone screen wallpaper.

Everything You Need To Know About MSC Seashore
MSC is an incredibly popular line among my clients for its accessibility here in Florida and outstanding value. I decided to give it a run for myself and am happy to report I absolutely loved the boat and am already looking at booking another voyage on this ship. Classy design, spacious, and numerous bars and eateries, and the Aurea experience that topped it all off.

Everything You Need To Know About MSC Seashore
MSC is an incredibly popular line among my clients for its accessibility here in Florida and outstanding value. I decided to give it a run for myself and am happy to report I absolutely loved the boat and am already looking at booking another voyage on this ship. Classy design, spacious, and numerous bars and eateries, and the Aurea experience that topped it all off.

The Tampa EDITION: Property Review
The Tampa EDITION is the first true luxury five-star property in the Tampa market, and it absolutely makes an impact.

The Tampa EDITION: Property Review
The Tampa EDITION is the first true luxury five-star property in the Tampa market, and it absolutely makes an impact.

Mountains, Brews & Beanies: Denver, Colorado
Denver has slowly become one my favorite cold-weather destinations, and trust me, there are not many. Having now spent a few weekends here in the late fall over the years, I’ve compiled a list of my favorite activities and places to inspire you to visit this always sunny city in Colorado—for something other than skiing and sipping hot toddies in a lodge.

Mountains, Brews & Beanies: Denver, Colorado
Denver has slowly become one my favorite cold-weather destinations, and trust me, there are not many. Having now spent a few weekends here in the late fall over the years, I’ve compiled a list of my favorite activities and places to inspire you to visit this always sunny city in Colorado—for something other than skiing and sipping hot toddies in a lodge.
Travel photos









