Travel365

Travel services

Let Jennifer handle the heavy lifting.

From a single planning session to a fully booked trip with support while you're away — tailored to your goals, your pace and your budget.

The Travel365 edge

What you get that a search engine can't give you.

01

Curated, not generic

Jennifer sifts through countless reviews to find the best options for your preferences and budget.

02

Neighborhood intel

Street View checks for walkability, parking and the overall vibe before you book a place.

03

Dates & deals

Flexing your dates to land the best stays and prices across the whole itinerary.

04

One clear plan

A detailed itinerary with every booking and activity in one place, ready to travel.

Our advice is unbiased and based on genuine experience. We don't take kickbacks or commissions from travel providers — so you can trust the recommendations are only ever about your trip.

Packages

Pick your level of help.

Pay securely with Venmo. Add a note with your name and the package, and Jennifer follows up within one business day to start.

Get unstuck

Consultation

$189 / 45 minutes

  • Identify travel goals, destinations and how to work in your interests
  • Set (and stick to) a realistic budget
  • Choose transportation and accommodations
  • Work through travel fears
Pay $189 with Venmo

Note your name + "Consultation"

Most popular

Planning Package

$299 / per trip

  • Everything in Consultation, plus:
  • A personalized itinerary with activities and attractions
  • Accommodation and transportation recommendations
  • Help with an International Driving Permit
  • Trip-insurance guidance
Pay $299 with Venmo

Note your name + "Planning"

Hands-free

Booking Package

$499 / trip · 2 travelers

  • Everything in Planning, plus:
  • We book your main transport: flight, train or cruise
  • We book your accommodations
  • Excursion recommendations for your interests
  • Email support during your trip
Pay $499 with Venmo

Note your name + "Booking"

Add-on

Additional Traveler

Ask / added to a package

Traveling as a bigger group? Add travelers to a Planning or Booking package and we'll size everything to your party.

Ask about group pricing

Prefer to talk first? Send a message and we'll figure out the right fit.

How it works

Four steps to "all booked."

Step 01

Pay for your package via Venmo, with your name and package in the note.

Step 02

Tell us your trip. Jennifer sends a short intake to capture your goals, dates and budget.

Step 03

Get your plan. A tailored itinerary you can take as-is or refine together.

Step 04

Travel. With Booking, we make the reservations — and stay on email while you're away.