Traveling with Olivia

11/02/2026

Girls Group Trip announcement! 📣 💃

This one’s for the girlies looking for an easy getaway in paradise! 💅🏼🥰🏝️🍹

Want to jump on this trip?! Here is the info:

📅 July 9–13th, 2026
📍 Secrets Cap Cana, Punta Cana

☀️ Adults-only, All-inclusive, Luxury vibes only
☀️ Prices start at $1262 per person (2 in a room)
☀️ only $100 deposit! Final payment due May 25th
☀️ Flights can be packaged depending on location! If you choose this option, then you’ll pay $250 deposit.

👯‍♀️ TAG your bestie girl!
💌 SEND this to your travel friends!

MESSAGE ME to sign up for this summer vacay! 💖

The Adventure Awaits Vacations 💙🏝️💛✈️

10/02/2026

✍️ Write this down on your list of anniversary trip ideas (If you’re like me, I know you’ve got one running in your head 😉)

➡️ Caribbean cruise on the Carnival Celebration 🥳

Throwing it back to when we cruised on this ship and had the best time exploring all the restaurants, pools, activities, and hidden corners on this massive ship!

On this sailing we did…
• Beach day in Grand Turk
• UTV + waterfall + hiking excursion in Amber Cove
• Met sea lions at Blue Lagoon Island in the Bahamas 🦭

By the end of our 6-day cruise, we had barely scratched the surface of everything this ship has to offer! Need to go again now to fully enjoy it all tbh, haha! 😆

✨ Favorite spots onboard:
• Patio Pool + Guy’s Pig & Anchor for lunch on the stern
• Latitude’s Bar, where the featured menu changes every hour
• Live music in the Atrium, which spans multiple levels of the ship

Anniversary trips should feel like this 💙

🚢 Curious if a Caribbean cruise could be your perfect anniversary trip? MESSAGE me and I’ll help you find the right ship, itinerary, and cabin!

08/02/2026

OHHH this one was fun to book 😍🌴

Just booked a luxury Hawaii honeymoon in Maui for a couple who wants to fully relax after saying “I do.”

They’re heading to Wailea Beach Resort by Marriott this summer—one of the nicest areas to stay in Maui ✨

• Stunning beach + calm waters perfect for swimming & snorkeling
• Walkable to amazing restaurants & shops
• 4 pools (including the Nalu Adventure Pool w/ waterslides + the adults-only Maluhia Serenity Pool)
• 2 hot tubs
• Daily 2-hour bike rentals
• Fitness classes, intro scuba lessons & even a movie house 🎬

Right now I’m working behind the scenes on their custom itinerary, comparing flight options, rental cars, and curating restaurant + activity recommendations so all they have to do is show up and enjoy!

If a stress-free, luxury Maui getaway sounds like your vibe and you want someone to handle all the researching, planning, and details ➡️➡️➡️MESSAGE me today and let’s get your trip on the books 💌✈️

BookedByMe

07/02/2026

Lmk if this needs to be your next getaway 👀

07/02/2026

Forever & Always planning vacations in my brain 🥰🤔💭 —> A look into my research for a Disney trip through screenshots!

When you ask me to plan a trip (or when I am curious about a destination for funsies🤪), there’s alllll kinds of factors that I check out before even pitching options to you (or my husband, hehe 🙃)!

This almost every time includes:
💭 flight times & prices
💭 best areas to stay/explore
💭 how to get around (rental car? Ride share?)
💭 weather & holidays & special events

Want me to think about all of these details for you? Chances are, I’ve already thought it all out!

MESSAGE me and I will gladly book & plan your trip for you!

https://linktr.ee/travelingwitholiviaaa

03/02/2026

Why I fell in love with Disneyland 😍🏰 As someone who went to Disney World multiple times first before even thinking about going to Disneyland!

💖 it’s the original park and you can feel it when you’re there! From the “little” castle, antique buildings on Main Street, and retired ticket booths still standing, it’s all so classic feeling!

💖 park hopping is a breeze! Disneyland, California Adventure Park, and Downtown Disney are all connected through one walkway called the esplanade, and all you have to do to go from one to the other is… walk a few more steps. No bus, no Skyliner, no boat, no ride share needed (don’t get me wrong, I love alllll the transportation at Disney World, too!)

💖 truly a “theme park” — meaning that the parks have multiple very different themes within the same park and are so creatively & thoughtfully built within/around each other! Yes, Disney World also has this feeling, but the fact that Disneyland does it all in such a small amount of acreage AND also in the middle of very populated & built-up Anaheim, California? So incredibly impressive honestly!

I could go on and on about all the things that blew my mind and opened my mind to another realm of Disney magic!

✨Want to experience this classic Disney magic yourself? MESSAGE me to start talking about your trip!

https://linktr.ee/travelingwitholiviaaa

02/02/2026

What are you doing for Memorial Day Weekend? 👀🇺🇸 Because I found a getaway you’ll fall in love with! 😍

🌺 MAUI, HAWAII
Stay at the luxurious Westin Maui Resort & Spa — Ka’anapali and enjoy your weekend in paradise! Trip details below:

✈️ May 22 – May 27, 2026
👫 2 adults | 5 nights
💰 $3,982.85 TOTAL
(Only $400 deposit due today)

✔️ Hotel + round-trip flights from LAX included

🌊 Resort Highlights:
• Oceanfront resort on iconic Ka’anapali Beach
• Six stunning pools, including a serene adults-only pool deck
• Infinity pool & hot tub
• Snorkeling
• Water slide
• Walking distance to local shopping & restaurants

Memorial Day weekend in paradise hits different 🌴
📩 Contact me today to put your name on this trip! All I need is your $400 deposit!

Interested in this destination but not these dates? Let me know and I’ll give you a complimentary quote!

https://linktr.ee/travelingwitholiviaaa

**All prices & dates are subject to change based on availability, demand, and pricing increases.

HawaiiVacation

01/02/2026

This!! I’m here to share my expertise & help make your trip the best! Why not have someone who is passionate about travel plan your trip for you??? 😃

Is it cheaper to use a travel agent and do travel agents get better deals on cruises? Travel agents are an incredible resource for planning your first...

01/02/2026

If cold weather isn’t your love language… 🌞🌴

These getaways are warm, romantic, and EASY. Perfect for an anniversary trip or a gift for your Valentine!💌

✨ Beachfront resorts
✨ Sunset dinners
✨ Zero stress planning

Want help booking one of these destinations?
💌 Message me TODAY for a quote! I plan it, you live it!

📍Maui
📍Cancun
📍Aruba
📍Key West