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Award winner thanks to recommendations from couples on WeddingWire.com.
  • 2022
  • 2020
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  • 2017

Carefree Romantic Vacations

Destination Weddings
Honeymoons
Travel Insurance
Luxury Trips
Michael
Mark
Erika
Andrea
M

Recommended by 100% of couples

About this vendor

Based in Yucaipa, California, Carefree Romantic Vacations offers luxury honeymoons designed for couples who want an effortless, romantic, unforgettable start to forever.

Your honeymoon should feel seamless, meaningful, and completely stress-free — a once-in-a-lifetime beginning to your marriage filled with connection, joy, and unforgettable moments.

I’m Sheila Cannon, founder of Carefree Romantic Vacations and a multi-award-winning honeymoon specialist serving couples across the country. After 38 years of marriage — and visiting romantic destinations across all seven continents — I know how intentional, beautifully planned travel brings couples closer and creates memories you’ll cherish forever.

I design personalized, luxury honeymoons for busy couples who want expert guidance, curated recommendations, and a trip that feels elevated and effortless. If you’re dreaming of Bora Bora, Italy, Greece, St. Lucia, a private safari, or a boutique European escape, I handle every detail — flights, hotels, private transfers, curated tours, VIP perks, and special romantic touches.

My planning services include custom fees tailored to the scope and complexity of your honeymoon, ensuring a personalized and elevated experience from start to finish.

Planning your honeymoon? I’d love to help you create a romantic, stress-free luxury escape.

Click “Request Pricing” or “Message Vendor.”
Simply include your name, email, and event date, and feel free to personalize the message however you’d like.

Once I receive your inquiry, I’ll send you a link to complete my Honeymoon Planning Form, and then you’ll be able to schedule your complimentary consultation so we can begin designing your perfect honeymoon.

Specialties: Luxury honeymoons $10,000+, all-inclusive resorts, Europe (Italy & Greece), Bora Bora & Tahiti, cruises, Caribbean escapes, and bucket-list destinations worldwide.

Features

Woman-owned

Just me

Experience

  • 17 years in business

  • We speak English

Links

Visit website

FAQ

What types of travel do you specialize in?

Cruises
Destination Weddings
Honeymoons
Luxury Trips

What destinations do you specialize in?

Africa
Alaska
Asia
Australia / New Zealand
Caribbean
Dominican Republic
East Europe
Hawaii
Mexico
Pacific Islands
South America
West Europe

What travel services do you provide?

Travel Insurance

Still have questions?

Reach out about anything you didn't see answered here—no question is too small!

Wedding couple

Reviews of Carefree Romantic Vacations

Michael
Michael Sent on 07/07/2025
5 out of 5 rating

Amazing Belated Honeymoon!

We found Sheila and Carefree through a local google search of travel agents in our area. I'm so glad that we found her. We were looking for someone that was knowledgeable that could help us plan our belated honeymoon to Europe. Sheila was and did just that. She helped us plan our cruise, flights, drivers and hotels. She was also always available to talk to or email when we had a question. Were getting ready to plan our next trip with the kids and Sheila will be the first call I make. Thank you for all your help!
M
Madjany Sent on 12/21/2025
5 out of 5 rating

Sheila is Wonder Woman!

From start to finish, Sheila was absolutely amazing throughout the entire planning process. She was incredibly detailed, answered every question promptly, and always made me feel confident and supported.
When a severe hurricane hit the Caribbean island where my destination wedding was planned, I was devastated and close to canceling everything. Sheila remained calm, reassuring, and immediately jumped into action. She went completely above and beyond; finding multiple solutions, rebooking all 90 of my guests and transportation, and connecting me with a new wedding planner at the resort, all in literal record-breaking time. What felt impossible was handled with such care and professionalism.
During a very stressful time, Sheila was endlessly patient and kind with me and my family as we panicked. She truly understood how emotional the situation was and never once made us feel rushed or dismissed.
I’m very particular and was initially skeptical about moving to a new resort I had never been to, but the resort Sheila found ended up being even better than I ever imagined. I couldn’t have been happier with the outcome. It turned out to be the best vacation I’ve ever had. Over half of my guests had the same sentiments! 
I will always recommend Sheila to everyone I know and will absolutely be coming to her for all of my future travel needs no matter how big or small.
Thank you from the bottom of my heart, Sheila! 
L
Lindsey Sent on 01/17/2024
5 out of 5 rating

Amazing! Definitely recommend

Sheila was one of the best investments we made for our destination wedding. She helped us pick the hotel/venue, arranged all of our travel, and most importantly, helped arrange all the travel and hotel stays for our guests. It was invaluable having her as everyone's point of contact for those logistics, and it freed up our time for everything else we needed to plan for the wedding. She was available for any last minute issues that came up (even in the middle of the night), and gave us peace of mind we wouldn't have to worry about major issues on our wedding and honeymoon trip. Lastly, she sent us the cutest Christmas gift to commemorate our wedding. We would DEFINITELY recommend her 10/10!
Mark
Mark Sent on 02/23/2023
5 out of 5 rating

An AMAZING 25th Wedding Anniversary Trip!

Sheila is the absolute BEST AGENT you could ever find to help you plan the ultimate getaway! I wanted to plan something special for our 25th wedding anniversary on October 4, 2022. Both my wife and I have traveled abroad in the past to Europe in which we both planned our prior trips together. This time I wanted to surprise my wife with a trip we both would never forget and let me tell you, we were both taken back & totally impressed with our trip she planned to Croatia… absolutely FIRST CLASS all the way! I had a minor accident the second day we were in Zagreb where I tore my meniscus. We thought we had to quit and return home, however after our local tour guide contacted Sheila and explained my issue, Sheila immediately went into action modifying the remainder of our trip to accommodate my injury so we could enjoy the rest of our ten (10) day trip! Simply put, Sheila is amazing, We can’t wait to put together another trip using Sheila’s expertise!
A
Adrienne Sent on 02/19/2023
5 out of 5 rating

Best travel agent!

Sheila is our favorite and most knowledgeable Travel Agent. Our Clients become very excited about planning their honeymoon when they speak with her. Sheila does not only travel to great destinations like the Maldives and Croatia, Sheila shares her experiences with our Clients during their consultation. Our recent Client was wondering where to go for a “Romantic Honeymoon”. Sheila asks several detailed questions about their desired destinations, what the couple wants to experience and what they are truly looking for in a specific desired destination. With that information she bring selected destinations to fit the couples desires and plans everything for you from departure to transfers to hotel, to resort, activities and your return home. All you need to do is share your ideal “Romantic Honeymoon” with her and she will send you on your way to a wonderful “Romantic Honeymoon” destination. Our recent Client is headed to Croatia this fall and is very excited for both the land & sea itinerary she has created for them. Thank you Sheila for the detailed thought process and energy you give to our Clients. Keep traveling to wonderful romantic destination so you can continue to share your experience with your Clients!!
S
Stephanie Sent on 10/12/2022
5 out of 5 rating

Truly a Carefree Romantic Vacation

Quick points: Sheila was
very responsive,
kind and professional, and
very easy to work with.
She was like a matchmaker who helped us find the right resort that fit our many preferences for our destination wedding. She truly made our experience memorable and carefree, and we highly recommend her and her services. We plan to seek her help again for future travel plans. Feel free to continue reading below for more details about our experience.

We decided early that we wanted a destination wedding, but the world offers many options, and the task to pick a location seemed daunting. Even after we decided on a country (Mexico), the wedding planning task was still daunting to do on our own because there were so many options within that country, so we decided it would be best to seek the help of a professional. We found Sheila on The Knot, and after reading a little more about her, we decided to contact her. Part of requesting a consultation involved filling out a questionnaire that asked for several of our preferences, and during our first phone conversation, she asked us to elaborate on our responses to that questionnaire.

Some of our preferences included the following: 1) all-inclusive resort, 2) family-friendly, and 3) affordability for us and our guests. Following the phone conversation, she emailed a few suggestions based on our preferences, and we looked into the offerings of each by exploring their websites and YouTube reviews by other travelers. One of those resorts actually met all three of our major preferences, and as soon as we confirmed our choice, Sheila went into action. She immediately set up a website for us to share with our guests. After a round of feedback from us, the website was launched, and our guests used it to contact her, and she essentially served as their travel agent. She helped our guests book room reservations, flights, group transportation between the hotel and resort, and excursions (if desired by the guest). She helped all of our 75 guests, including accommodating families to be near each other at the resort (and this resort was VERY large).

Regarding our wedding, she helped us communicate with the appropriate wedding planning personnel at the resort. Whenever any issues arose, Sheila served as our advocate to help us communicate our needs with the resort. And throughout the trip, she threw in a few pleasant unexpected wedding surprises for us here and there. Our only criticism is that she could not join us as one of our wedding guests; she is such a pleasant person, and we wish she could have been there to enjoy the fruits of her labor.

The least we can do is thank her and recommend other couples to seek her assistance with destination wedding planning. We hope she'll consider helping us again for our next romantic getaway.
Erika
Erika Sent on 10/02/2022
5 out of 5 rating

Best honeymoon ever!!

I contacted Sheila when the time came to book our honeymoon for April 2022. We had an initial phone consultation during she really got to know my wants for the trip. I told Sheila that my future husband was not keen on traveling and I wanted a trip that he would love so much that it would make him want to travel more. I will say that my favorite thing about Sheila is that she made that a reality! The other great thing about her is that she has been all over the world and can tell you so much about so many places which really helps you decide where to book your trip to. We ended up deciding on Sandals Royal Plantation in Ocho Rios, Jamaica and we are so happy that we went there, it was the perfect honeymoon for us! The butler service, the food, the people, the beautiful scenery…everything was top notch and they really do treat you like royalty. Sheila let us know that we could go next door to the bigger Sandals resort with more amenities. We liked being able to have access to that as well but mostly enjoyed the calmer and more relaxed vibe at Royal Plantation. Sheila was very quick at communicating with me anytime I emailed her with questions. She booked two excursions for us: the bioluminescent blue lagoon and a day on the power boat, as well as a couples massage. We really enjoyed all of it and can’t wait to go back to Royal Plantation some day. If you are truly looking for a “carefree romantic vacation,” Sheila is the person to go to!
N
Naomi Sent on 09/06/2022
5 out of 5 rating

Sheila made planning an exciting vacation worry free!

Sheila planned our dream honeymoon for us! All we had to do was tell her what we wanted, and she made sure it happened. She was always available when we had questions and kept us on track and informed. We were able to relax and enjoy our vacation to the fullest because she was there to help us every step of the way.
Andrea
Andrea Sent on 11/30/2021
5 out of 5 rating

The perfect honeymoon

Sheila at Carefree Romantic Vacations is the best! She planned our perfect Honeymoon in Hawaii. First class tickets on the plane, an amazing hotel, transportation for all events, and fun attractions each day, every detail was perfectly planned. The best part was it was stress free. We didn’t have to do anything other than agree to some of the events. She also sends a link for a phone app that allows you to see the entire itinerary with special instructions for each event and all the necessary documentation. It was so nice to be able to check the app daily for step by step instructions to make sure the day went smooth. We never had to contact her while we were there because of this preparation. If you want a carefree vacation at the best prices available, Sheila will put the work in to make it happen. We really could not have asked for a better Honeymoon.
H
Holly Sent on 11/25/2021
5 out of 5 rating

Five stars

Sheila helped with our honeymoon and found customers for life! We give her five stars across the board! From handling flight details, schedules, and giving us her advice on things to do, we would have been lost without her! We will never vacation another way! Thank you, Sheila, for helping us have the stress free honeymoon of our DREAMS! We cannot wait to work with you again!
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Awards

64
WeddingWire Couples' Choice Awards 2022 Winner
WeddingWire Couples' Choice Awards 2020 Winner
WeddingWire Couples' Choice Awards 2019 Winner
WeddingWire Couples' Choice Awards 2018 Winner
WeddingWire Couples' Choice Awards 2017 Winner
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Sheila Cannon
Sheila Cannon
Chief Romance Designer

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