Sunrise over ocean with stylized waves, above the text "Bobbi's Holidays" in red, rounded font.

turn your wanderlust into wonderful adventures.

Personalized vacations designed with care, clarity, and style.

A woman with long dark hair and glasses smiling

I’m a travel advisor who believes your vacation should feel effortless from the moment you start dreaming it. Whether you’re craving a relaxing resort stay, a custom getaway, or the perfect cruise; I’m here to create a trip that’s personal, seamless, and genuinely exciting to plan.

I focus on clear communication, transparent pricing, and thoughtful recommendations that fit your style- not just what’s trending.

Hi, I’m Bobbi.

Domestic & International Travel • Group Trips • Couples Retreats • Reunions • Solo Adventures • Milestones

Maine-based • Serving clients nationwide

Start Planning
  • Woman on a cruise ship at the rail looking out at the ocean

    Cruises

    Ocean • River • Family •
    Adults-Only • Theme

    Your perfect sailing- tailored to your style, pace, and budget.

  • Loungers on a deck in front of the ocean

    Resorts & All-Inclusives

    Caribbean • Mexico •
    DR • Beyond

    Relaxation made simple-
    clear pricing, curated recommendations, and
    stress-free planning.

  • Golden clouds out the window of an airplane overlooking the wing

    Custom Getaways

    USA • Europe •
    Asia • Anywhere

    Thoughtfully crafted itineraries with all the details handled- flights, stays, activities,
    and the extras.

  • Group of friends with arms around each other sitting in a line overlooking a ski lift and mountain

    Group Travel

    Celebrations • Reunions •
    Friends’ Trips • Retreats

    Bring everyone together- personalized planning and seamless coordination for trips meant to be shared.

Flexible Payment Options

Many of my trusted travel partners offer book-now, pay-over-time plans to help make your vacation more accessible and easier to plan.

Ask me which options fit your getaway.

Close-up view of sand with ripples on the beach at sunset, with the sun setting over the horizon and clouds in the sky.

Why Travelers Love Working With Me

Care

I take time to understand what you value most- your pace, comfort, and the kind of moments you want to remember.

A single yellow dandelion flower with a dark background and blurred surroundings.

Clarity

Simple communication, transparent pricing, and guidance that makes planning feel easy instead of overwhelming.

Autumn scene with a small waterfall flowing over layered rock formations into a dark pond, surrounded by colorful fall foliage in red, orange, and yellow.

Style

I use a curated, intentional approach to travel planning that makes your vacation feel polished and thoughtfully designed from day one.

Travel is personal- your planning experience should be too.

A narrow cobblestone street in a Mediterranean village lined with white buildings with blue doors and windows. There are outdoor seating with wooden tables and chairs, a flowering bougainvillea bush hanging overhead, and a black street lamp.
Night view of Dubai skyline featuring the Burj Khalifa, with illuminated skyscrapers and highways with streaks of light from moving vehicles.
Two blue Adirondack chairs face the ocean on a sandy beach under a clear blue sky.
A large white cruise ship named Norwegian Gem sailing on the ocean at sunset, with a colorful sky of clouds and the sun setting on the horizon.
Sun setting over a snowy mountain lake with a small island of trees, surrounded by snow-capped mountains, in a winter landscape.
Scene of a canal in Venice, Italy, with boats and gondolas, historic buildings along the water, and the dome of a church in the background under a blue sky.

Traveler Experiences

  • "I’ve worked with Bobbi and my trip was flawless and carefree she does the best for her customers and gets the best deals possible. If you have questions at any point she’s there to answer your questions. She checks in with you to see if everything going alright just to make sure things are smooth. I’d love to go back to Bobbi for our next family trip. Thanks Bobbi!"

    -CK

  • "you have definitely gone above and beyond to make sure my vacation experiences have been top notch!"

    -CS

  • "I want to give a HUGE shout out to our travel agent Bobbi Borrelli for helping us with this trip! She was soo incredibly helpful and knowledgeable, every time we had questions she answered them right away! 10/10 would recommend her for your future adventures 😊"

    -HK

Ready to start planning?

Let’s bring your next getaway to life.

Get Your Free Travel Quote →