Waterfront homes on Long Island Sound seen from Greenwich Point

GREENWICH · CONNECTICUT · WORLDWIDE

Best Travel Agent in Greenwich, CT

You live in Belle Haven, Round Hill or Old Greenwich, a short drive from Westchester and an hour from the city. Justkeeps Travel plans the trips that take you away from both, with air, hotels, villas, private aviation and every change handled by one advisor.

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FAMILY CALENDARS · PRIVATE DEPARTURES

A Greenwich travel agent who knows the calendar.

Greenwich families travel on a familiar rhythm. February in Palm Beach or the islands, spring break somewhere warm, summer in Nantucket or Europe, and the holidays in the mountains or the Caribbean.

We plan around the Greenwich Academy, Brunswick, Greenwich Country Day and public school calendars, so those weeks are booked early and the rooms fit the whole family. You work directly with Justin, so the preferences and the history stay with one person.

WHAT JUSTKEEPS COORDINATES

What we plan for Greenwich clients

01

Winter escapes

St. Barths, Anguilla, Palm Beach and the mountains for the coldest weeks, with the best villas and rooms held well ahead of the holidays.

Explore leisure travel

02

School breaks, done properly

Spring break, Presidents Week, the holidays and summer booked early, with connecting rooms, kids clubs and flights that suit the family.

Explore concierge support

03

Executive and family office travel

Board meetings, deal travel and family trips under one relationship, for principals, assistants and private offices.

Explore executive travel

Hotel benefits depend on the property, booking channel, dates and confirmed eligibility. They are never assumed.

Also serving clients in Westport, Purchase and Long Island.

GREENWICH, DOOR TO DOOR

The local details we plan around

Leaving Greenwich well is half the trip. Which airport, what time to leave and what to book before everyone else does.

Private aviation

Westchester, fifteen minutes away

Westchester County Airport has several private terminals and is the usual choice for private flights from Greenwich. We coordinate the aircraft, the car and the arrival on the other end.

Long haul

JFK and Newark for Europe and beyond

JFK and Newark carry the long haul nonstops. We pick the airport by airline and schedule, and time the car around the Merritt and I-95 so the day starts well.

School calendars

Breaks planned a season ahead

Greenwich Academy, Brunswick, Greenwich Country Day and the public schools set the dates. We hold rooms for those weeks early, before the best options fill.

Holiday villas

St. Barths books by spring

The best villas in St. Barths and Anguilla for Christmas and New Year are often gone by summer. We start the search early and hold the right house while plans settle.

Justin Keeperman, founder of Justkeeps Travel, luxury travel advisor for Greenwich

WHY WORK WITH JUSTIN

Why Greenwich clients work with Justin

Justin has planned luxury travel since 2011. He works with Greenwich families, executives and private offices by phone, text and email, and he stays involved from the first conversation through the flight home.

Justkeeps Travel is based in Boca Raton, on the same time zone as Greenwich, and many Greenwich families already spend part of the winter in Palm Beach. The value is continuity: one advisor who knows the travelers, the school calendar and what needs to happen when plans change.

More about Justin

TRIP IDEAS

Trips we plan from Greenwich

Examples of how a trip comes together. Every plan is built around the travelers, the dates and the budget.

Private villa terrace overlooking a turquoise bay in St. Barths

7 to 10 nights · Christmas to New Year

The holidays in St. Barths

A villa with staff or a suite at a hotel such as Eden Rock or Le Toiny, flights through St. Maarten with the short hop across, a boat for the week and New Year's Eve dinner booked months ahead.

St. Barths guide
Empty stretch of white sand along calm water in Anguilla

5 nights · February break

A quiet week in Anguilla

A beachfront resort such as Cap Juluca or Malliouhana, a private boat transfer from St. Maarten, long beach days and a table at the best lunch spots on the island.

Anguilla guide
Snow-covered Gstaad chalet village beneath the Swiss Alps

7 nights · Presidents Week

Skiing in Gstaad

An overnight to Geneva, a private transfer into the mountains, a hotel such as The Alpina Gstaad or a chalet, ski instructors booked for every level and fondue nights in the village.

Gstaad guide

CLEAR ANSWERS

How to choose the best travel agent in Greenwich

Questions from Greenwich clients

How do I choose the best travel agent in Greenwich?

Choose an advisor who understands school breaks, winter escapes and private departures from Westchester. Justkeeps Travel is IATAN accredited, registered as Florida Seller of Travel ST150047, and has planned luxury travel since 2011. You work directly with Justin from the first call until you are home.

Which airport works best for Greenwich travelers?

Westchester County Airport is about fifteen minutes away and works well for private flights and many domestic trips. JFK and Newark carry the long haul nonstops, and we time the drive around the Merritt and I-95 so the day starts well.

Can I fly private from Westchester?

Yes. Westchester is the usual private departure point for Greenwich and has several private terminals. We coordinate the aircraft with the car, the hotel and the arrival on the other end.

When should we book the holidays in St. Barths?

Book by spring for Christmas and New Year. The best villas are often gone by summer and the top hotels fill soon after. Read our St. Barths guide.

How do you plan around Greenwich school breaks?

We plan around the Greenwich Academy, Brunswick, Greenwich Country Day and public school calendars. Spring break, Presidents Week, Thanksgiving and the holidays are held early, before the rooms that fit a family are gone.

Where do Greenwich families go in February?

Palm Beach, St. Barths, Anguilla and the mountains are the usual February choices. Each books early for the school break, so we start in the fall. Read our Anguilla guide.

Can you handle executive and family office travel too?

Yes. Board meetings, deal travel and family trips can sit under one relationship, with one advisor for principals, assistants and private offices. See executive and family office travel.

Can you plan for the whole family, including grandparents?

Yes. We plan multi generation trips with travelers flying in from different cities, with connecting rooms, kids clubs and one itinerary everyone can follow.

Do I need a travel advisor who lives in Greenwich?

No. What matters is fast answers, good judgment and strong relationships with the hotels you use. Justin works with Greenwich clients by phone, text and email on the same time zone, from Boca Raton near Palm Beach.

How much does a luxury travel advisor in Greenwich cost?

Planning fees are set by scope and confirmed before any planning begins. Many hotel, resort and cruise bookings carry no planning fee, and air only tickets are $35 domestic or $50 international. Read what a luxury travel advisor costs.

Planning from Greenwich

SERVING GREENWICH AND FAIRFIELD COUNTY

Plan your next trip from Greenwich

Tell us when you want to get away and who is coming. We will come back with a clear plan and one point of contact. Serving Greenwich, Old Greenwich, Riverside, Cos Cob and Belle Haven.

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Justkeeps Travel, LLC561-300-3540hello@justkeepstravel.comFlorida Seller of Travel Registration No. ST150047