A pink sign shaped like a room key with the words 'Checking In with Jess' and a small illustration of a beach umbrella.

Travel, thoughtfully planned.

Let's Start Planning

You know that feeling when you find the perfect hotel? The restaurant you can't wait to try? The little experience that ends up being everyone's favorite part of the trip?

Those are the details I love finding.

I create thoughtfully planned, personalized trips around the way you actually like to travel - from the right hotel and room to memorable restaurants, private guides, seamless transportation, and experiences that are worth making time for.

You tell me where you want to go, what matters most, and how you want your trip to feel. I’ll take care of the rest.

A pink beach umbrella with a beach chair and a tote bag in front of it.

Meet Jess

I’m a planner by nature, so I genuinely love figuring out the details. The ideal resort, the best dinner reservations, the guide who knows all the good spots, and how to get from one place to the next without wasting precious vacation time. I believe thoughtful planning makes a trip better - not because every minute needs to be scheduled, but because when the important details are taken care of, you’re free to actually enjoy where you are and who you’re with.

To me, that’s what Checking In is all about. Making sure you’re in the right place, at the right time, with the details taken care of so once you arrive, you can settle in, relax, and enjoy the experience.

Read My Story

  • "Every detail was perfectly curated yet not over scheduled. Truly felt like such a vacation with her at the helm of our planning!"

    - Elizabeth B.

  • "This was my first time using a travel advisor and Jess made everything exponentially easier. We were travelling with a group and had a lot of moving parts and Jess helped streamline everything. From getting us deals to local insight and keeping our itineraries all together in one place, she was wonderful from the beginning to end."

    - Alexandra C.

  • "Jess is simply the best to work with. I never have any hesitation that what I need won't be accommodated when working with Jess. She's accountable, listens to and takes time to understand your needs, and ultimately makes great recommendations. I know I'm in good hand and my trip will be smooth when I book with Jess."

    -Britt M.

From the perfect stay to every detail in between.

  • A luxury hotel with a swimming pool on a beachfront property, with palm trees, lounge chairs, and a cloudy sunset sky.

    Hotels & Resorts

    From boutique hideaways to iconic luxury resorts, I’ll help you find the right place to stay based on how you actually like to travel, from the location and room to the amenities and little extras that make a stay feel special.

  • Transportation

    Flights, trains, private drivers, transfers, and all the in-between details that keep a trip moving smoothly.

  • A person skiing down a snowy mountainside surrounded by snow-covered trees during winter.

    Experiences & Tours

    Private guides, food tours, boat days, cooking classes, cultural experiences, and the things you'll still be talking about when you're home.

  • A large cruise ship sailing in the ocean with a clear sky and scattered clouds above.

    Cruising

    Whether you’re sailing the Caribbean, cruising the rivers of Europe, or exploring Alaska by ship, I’ll help you find the right cruise, cabin, itinerary, and experiences to make the most of your time on board and ashore.

  • Street view of a café and brasserie named 'Le Saint Jean' with outdoor seating, people walking by, and a building with multiple windows in the background.

    Dining Reservations

    From the buzzy new spot everyone’s talking about to the little neighborhood restaurant you’d never find on your own, I’ll help you find the right places to eat and secure the reservations worth planning your trip around.

  • Close-up of a handwritten note on a piece of paper with the words 'Enjoy your day!' written in black ink.

    The Details

    Room requests, special occasions, timing, logistics, and all the little things that make a trip feel seamless.

A woman is relaxing on a lounge chair at a beachfront poolside restaurant, with a table of food and drinks in front of her. There are palm trees, a swimming pool, and the beach with umbrellas and lounge chairs in the background, under a partly cloudy sky.

Your trip planning starts here.

Every itinerary is thoughtfully designed around your travel style, preferences, and priorities. My goal is to make the planning process just as seamless as the vacation itself.

  • Complete the inquiry form or send me an email and tell me about your travel dreams. If needed, we'll schedule a consultation call to discuss your vision, priorities, and travel style.

  • Once we’ve aligned on your trip, I get to work. I’ll begin researching and collaborating with trusted partners, destination experts, and luxury suppliers to create a personalized proposal tailored specifically to you.

  • We'll review your itinerary together and make any adjustments until everything feels just right. Once approved, I'll secure your reservations and manage all of the booking details.

  • As your departure approaches, I'll coordinate the details that make your trip exceptional, from dining reservations and private experiences to transportation and concierge requests. You'll receive your final digital itinerary and travel documents before you leave.

  • Now comes the best part - you simply show up and enjoy. While you're traveling, I'm just a message away should you need assistance, so you can relax knowing someone is looking out for you every step of the journey.

Start Planning Your Trip

Your Questions, Answered.

  • Because your time is valuable and planning a great trip takes more than finding a hotel and clicking “book.” I bring the research, experience, relationships, and attention to detail that help turn a good trip into a great one. I’ll help you find the right hotels and rooms, navigate the options, coordinate the moving pieces, and be your advocate before and during your trip if something doesn’t go according to plan.

    As an independent affiliate of Fora Travel and a Virtuoso member, I also have access to preferred partnerships with many of the world’s leading hotels, cruise lines, and travel suppliers. When available, those relationships can translate into benefits such as room upgrades, complimentary breakfast, resort or hotel credits, early check-in, late checkout, and other VIP amenities.

    But the perks are just part of the value. You’re also getting someone who knows the questions to ask, the details to look for, and the people to call when you need help. You get to enjoy the trip. I’ll handle the work behind it.

  • A little bit of everything! Family vacations, romantic getaways, girls’ trips, milestone celebrations, cruises, group travel, weekend escapes, and multi-stop adventures. Whether you know exactly where you want to go or need help figuring that out, I can help.

  • It starts with a conversation. Tell me where you’re headed or what you’re dreaming about and what you already know about the trip. I’ll get to know your travel style, priorities, and budget, then take it from there.

    For a simple hotel or cruise booking, I’ll curate the right options, handle the booking, and make sure you’re set up with any available preferred partner perks. For a more involved trip, I’ll build a personalized itinerary and coordinate the hotels, transportation, tours, dining, and experiences that bring it all together.

    Once everything is booked, you’ll have an organized itinerary and a travel advisor in your corner from planning through your trip.

  • There’s no magic number, but earlier is generally better - especially for peak travel dates, popular hotels, villas, cruises, and larger groups.

    A good rule of thumb is at least 3 months in advance for domestic travel, and 6 to 9 months out for international travel. Some cruise lines book 1 year out.

    That said, I’m always happy to see what’s possible for a last-minute trip. Sometimes, there are still great options hiding out there!

  • I plan and book the pieces that bring a trip together - from hotels and resorts to cruises, transportation, tours, experiences, and dining reservations.

    I can help with everything from a simple hotel booking to a fully customized, multi-stop itinerary, including special occasions, family trips, group travel, and those once-in-a-lifetime adventures.

  • In most cases, I’m paid a commission by the hotel, cruise line, tour operator, or other travel partner when you book through me. You generally pay the same rate (or lower) that you would booking directly, while getting the benefit of my expertise, planning, and access to preferred partner perks when available.

    For more complex trips that require extensive research and hands-on planning, I may charge a separate planning fee. I’ll always let you know upfront if a fee applies, so there are no surprises.

  • Some travel planning is complimentary, while more complex trips may include a planning fee.

    Simple hotel and cruise bookings can often be handled through my complimentary planning service, while multi-stop itineraries, groups, and more research-intensive trips typically fall under my full-service planning. I’ll always let you know what applies before we get started.

  • I can book premium economy, business, and first class flights, as well as private jets. Sometimes, I book economy flights as part of a package with a resort or cruise.

  • I am able to book some VRBOs but no Airbnbs.

    I also have fantastic partners (ex. Plum Guide, HVN, local Villa companies) with highly vetted villas and apartments that I can book.

  • All major cruise lines, including AmaWaterways, Viking, Royal Caribbean, Princess, Disney, Silversea, Regent Seven Seas, Seabourn, Explora, Oceania, and Four Seasons.

  • Absolutely! Hotel only bookings are complimentary and many times I can secure preferred rates and perks like breakfast, hotel credits, priority check-in and upgrades (when available).