Alyssa Chitwood
Based in Florida
English
Love Notes & Landmarks
Ask us about
Our 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 (17)
Lori C.
travel to France
25 days ago
Alyssa was amazing to work! She with informative, providing many options, pivoting with patience on changes to location, type of hotel and number of guests. We’ve always made our own travel plans in the past but had never been to the French Riviera before so all insights and support was appreciated! We had the best time and we’ll book through Alyssa again!
Bryce B.
travel to Tuscany
about 2 months ago
Alyssa is fantastic and helped curate what will most likely be one of my most memorable days ever. She sought out a wonderful private wine tour and tasting and set it up so that I could to turn into a surprise proposal for my now fiancée. Not only that she helped setup an incredible lunch reservation following the proposal which tied into a fantastic stay at a boutique hotel in Fiesole paired with a romantic dinner (one that will never be forgotten) into couples massages, etc. All this to say that Alyssa is elite and curating special experiences and I would/will recommend her to anyone in need.
Willard B.
travel to Venice
about 2 months ago
Alyssa is awesome to work with, extremely accommodating!
Madison M.
travel by cruise
about 2 months ago
We had an excellent experience working with Alyssa from start to finish. Planning a family vacation can be overwhelming, especially when traveling with a child who has additional sensory and support needs, but she made the entire process feel manageable and stress-free.
She took the time to understand our family’s unique needs, answered every question promptly, and provided thoughtful recommendations that helped us feel prepared and confident before our trip. Her guidance regarding accommodations and strategies to help our son have a successful vacation was especially appreciated. We will absolutely be using her services in the future!
Joe C.
travel to Mexico
about 2 months ago
Very good, not much else to say, I don't really have anything I would say to improve on. Couldn't have planned the trip without her.
Lori C.
travel to France
25 days ago
Alyssa was amazing to work! She with informative, providing many options, pivoting with patience on changes to location, type of hotel and number of guests. We’ve always made our own travel plans in the past but had never been to the French Riviera before so all insights and support was appreciated! We had the best time and we’ll book through Alyssa again!
Bryce B.
travel to Tuscany
about 2 months ago
Alyssa is fantastic and helped curate what will most likely be one of my most memorable days ever. She sought out a wonderful private wine tour and tasting and set it up so that I could to turn into a surprise proposal for my now fiancée. Not only that she helped setup an incredible lunch reservation following the proposal which tied into a fantastic stay at a boutique hotel in Fiesole paired with a romantic dinner (one that will never be forgotten) into couples massages, etc. All this to say that Alyssa is elite and curating special experiences and I would/will recommend her to anyone in need.
Willard B.
travel to Venice
about 2 months ago
Alyssa is awesome to work with, extremely accommodating!
Madison M.
travel by cruise
about 2 months ago
We had an excellent experience working with Alyssa from start to finish. Planning a family vacation can be overwhelming, especially when traveling with a child who has additional sensory and support needs, but she made the entire process feel manageable and stress-free.
She took the time to understand our family’s unique needs, answered every question promptly, and provided thoughtful recommendations that helped us feel prepared and confident before our trip. Her guidance regarding accommodations and strategies to help our son have a successful vacation was especially appreciated. We will absolutely be using her services in the future!
Travel ideas (7)

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.

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.

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.

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.

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.
Travel photos










