Alyssa Chitwood
Based in Florida
Speaks 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!
My 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!
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My reviews (9)
Chass C.
2 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.
2 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.
Bernard S.
4 months ago
Alyssa helped us plan our Barcelona trip and had great recommendations from the start. She listened to our interests, likes, and dislikes. She was able to secure an early check in at our hotel and our room was ready upon our mid morning arrival. Alyssa is very familiar with Barcelona and made great restaurant and sight seeing recommendations. Lastly, she provided an itinerary for our entire stay including helpful Catalan phrases, maps and local transport information. When the meeting place for one of our Viator tours changed she quickly emailed us to ensure we were aware of it. We will definitely be using Alyssa again! She’s already planning a sibling cruise for us next year.
Savannah R.
5 months ago
When I tell you I would give Alyssa 100 stars if I could, I would. She is truly so amazing to work with.
From our wedding to now our vacations, she has had us covered! Start to finish, it was stress-free, seamless, and the best part, FUN! Truly the BEST personality. We’ve recommended her to all of our friends and family and the ones that have had the privilege to work with her, have said the same amazing things!
If you’re looking for someone who listens to what you want and actually cares, Alyssa is the best choice. We can’t wait to book more vacations through her!
Staci C.
5 months ago
Having Alyssa as our travel advisor was a great decision and we will never travel without her input again! She provided us with several hotel options and helped us make a decision based on our needs and nailed it with Epic Sana.
She also us found us several excursions and local spots not to be missed and they were all excellent. Her efforts really helped take our vacation to another level and we just loved working with her.
But what actually was the most amazing part of working with Alyssa was learning how much she cares…..
On our second day, Alyssa had booked us a kayak trip through the Benagil caves which we were very excited about. All started out great and the directions to the meet and greet area and the tour guides were right where they said! We hit the water and within 5 minutes I realized that kayaking on the ocean is a bit different and got quite seasick to the point where the guide had to bring me back in to shore. There was a little confusion with the communication with rest of the tour team who were going to pick us up early but they were very nice and apologized for the problem and immediately refunded our money for the tour ( without asking)
But here is where I just knew we would always continue to work with Alyssa for any future travel plans -
Since we booked through Alyssa and Fora, as soon as the tour company ran the refund ( which was immediately after the issue ) Alyssa got a notification.
It could not have been more than 5 minutes since this all happened when I got a text from Alyssa asking if we were ok and what happened! And if we needed her to help rebook another tour Now that is a level of service and care that is just rare in this world. Hence - we will always reach out to Alyssa for all of our future travel plans!
Thank you Alyssa !
Chass C.
2 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.
2 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.
Bernard S.
4 months ago
Alyssa helped us plan our Barcelona trip and had great recommendations from the start. She listened to our interests, likes, and dislikes. She was able to secure an early check in at our hotel and our room was ready upon our mid morning arrival. Alyssa is very familiar with Barcelona and made great restaurant and sight seeing recommendations. Lastly, she provided an itinerary for our entire stay including helpful Catalan phrases, maps and local transport information. When the meeting place for one of our Viator tours changed she quickly emailed us to ensure we were aware of it. We will definitely be using Alyssa again! She’s already planning a sibling cruise for us next year.
Savannah R.
5 months ago
When I tell you I would give Alyssa 100 stars if I could, I would. She is truly so amazing to work with.
From our wedding to now our vacations, she has had us covered! Start to finish, it was stress-free, seamless, and the best part, FUN! Truly the BEST personality. We’ve recommended her to all of our friends and family and the ones that have had the privilege to work with her, have said the same amazing things!
If you’re looking for someone who listens to what you want and actually cares, Alyssa is the best choice. We can’t wait to book more vacations through her!
My travel ideas (5)
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.
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.
My travel photos
