Go anywhere, unhurried. Every day shaped around you.
Our itineraries are drawn around you: your pace, your appetite, your idea of a perfect day. Each trip is planned in Boston, looked after anywhere, and wholly yours.
Plan my trip today
See our journeys
Rated 4.9 by 380 travelers
On call 24/7 while you travel
Our approach
We don't sell packages. We sit down with you, listen to how you like to travel and draw the trip from a blank page. Then we stay on call until you're home.
15
years planning trips from Beacon Hill
2,400
trips planned, no two alike
64
countries our travelers have reached
4.9
stars from 380 reviews
Five ways to travel. None of them off the shelf.
Every trip starts as a conversation and a blank page. The fee covers the design; we never mark up the trip.
Planning fee $350
Custom journeys
Five to fourteen nights, up to three countries, drawn day by day around how you like to travel.
Planning fee $450
Honeymoons
Slow mornings, rooms with a view, and the surprises quietly arranged.
From $95 per traveler
Group trips
Weddings abroad, milestone birthdays and reunions for 8 to 40.
Planning fee from $350
Family trips
Kids' ages, nap times and connecting rooms, all thought through.
Planning fee $150
Long weekends
Up to four nights in one place, booked as if you lived there.
Where our travelers went last year
Amalfi Coast
Kyoto
Patagonia
Lisbon
Marrakech
The Azores
Tuscany
Cape Town
Bali
Scottish Highlands
A honeymoon we planned last spring
Ten nights. Two coasts, one honeymoon.
Amalfi and Sicily, ten nights
A room over the water, then the slow way south.
Days 1–3
Positano, a terrace room above the water
Day 4
A private boat to Capri, lunch on board
Days 5–7
Taormina, with a cooking class in the hills
Days 8–10
A farm stay near Noto, home through Rome
Trip from $9,800 for two
Planning fee $450
How it works
From first coffee to the flight home.
Four steps, one planner from start to finish, and no forms to fill in. The first conversation is free.
Book a first conversation
01
A conversation, not a form
An hour over coffee on Charles Street, or a video call wherever you are. We ask how you like to travel, not only where.
02
Your first draft in ten days
A day-by-day itinerary with the hotels, guides and tables we'd book, and what each one costs, laid out plainly.
03
We book and fine-tune
Flights, stays, drivers, tickets and tables. Change anything until it feels like yours; revisions are free.
04
On call while you're away
A planner's cell number for the whole trip, 24/7. A canceled train or a closed museum becomes our problem, not yours.
Planning fees
One fee to design it. No markup on the trip.
Hotels and partners pay us a commission, so the trip itself costs what it would if you booked it alone. Trips typically run $4,500 to $12,000 per person.
Long weekend
$150
planning fee
Up to four nights in one place, done properly.
A hotel chosen for you, not by an algorithm Transfers and two tables we love A one-page plan for your phone
Plan a weekend
Custom journey
$350
planning fee
Five to fourteen nights, up to three countries.
A day-by-day itinerary, revised free Private guides and drivers A planner on call 24/7 while you travel
Start a journey
Honeymoon
$450
planning fee
Any length, anywhere, with the surprises arranged.
Everything in a custom journey A honeymoon fund page for your guests Extras arranged quietly, before you arrive
Plan a honeymoon
Group trips for 8 to 40 travelers, from $95 per traveler.
Ask about a group
The people who plan your trip.
Four planners on Charles Street. One of them is yours from the first coffee to the flight home, with a cell number that answers.
Ines Kessler
Founder. Italy, Portugal and honeymoons; she has walked every hotel she books on the Amalfi Coast.
Dev Pryor
Planner since 2016. Japan, Southeast Asia and trips built around food.
Mara Quist
Planner since 2019. Weddings abroad, milestone birthdays and family reunions.
Postcards from our travelers.
Rated 4.9 from 380 reviews
“We gave Ines three words, slow, sea and pasta, and she gave us the best ten days of our lives. Our honeymoon still doesn't feel real.”
Priya, Jamaica Plain
“Mara moved twenty-two of us around Lisbon for my mom's seventieth without a single lost suitcase or a single argument.”
Tom, Somerville
“Our train out of Kyoto was canceled at 7am. Dev had us on the next one before we'd finished our coffee.”
Gail, Newton
Good questions, straight answers.
Anything else? Call or text (617) 555-0163. A planner answers, not a call center.
Call or text us
What does the planning fee cover?
The design of your trip: the first conversation, a day-by-day itinerary, every revision, the booking itself and a planner on call while you travel. Hotels and partners pay us a commission, so we never add a markup to the trip.
Do you book flights?
Yes, along with hotels, trains, drivers, guides, tickets and tables. If you'd rather use your own miles for the flights, we'll plan around them.
How far ahead should we start?
Three to six months for a custom journey, nine to twelve for a honeymoon in high season. We have done it in three weeks; it just narrows the choices.
Can you plan for a big group?
From 8 to 40 travelers, from $95 per traveler: weddings abroad, milestone birthdays and family reunions. Mara handles every group from the first call.
What if something goes wrong on the trip?
Text your planner, day or night. A canceled train, a lost reservation or a closed museum becomes our problem; we rebook and send you the new plan.
Do you sell travel insurance?
No. We'll recommend a policy that fits your trip and help you compare a few, but you buy it directly, so it's always yours.
Do you only plan for Boston travelers?
About a third of our travelers live elsewhere and plan with us by video. You only need a phone and an idea of where you'd like to be.
Start planning
Tell us where you're dreaming of.
Send a few lines and a planner will call or text within one business day to set up your first conversation. It's free, and so is changing your mind.
Call or text (617) 555-0163
hello@roamwelltravel.com
88 Charles St, Suite 2, Boston, MA 02114
Your trip, in a few lines
Send my trip idea