Four Summer Trips Worth Booking Right Now

There is a version of summer that most people plan in theory and never quite execute. The long weekend they have been meaning to do. The boy’s trip that keeps getting pushed. The beach escape that always sounds better in January than it does in July, when the calendar is already full.

These are four of those unforgettable summer trips. The ones that once you book, they are unforgettable. And the flight, in every case, is the easiest part.

Search, compare prices up to 15% below market rate, and book directly from the Elevate Jet app. No hold music. No forms to submit. Your price is locked the moment you book.

Polo in the Hamptons

The Bridgehampton polo fields sit at the intersection of sport and social calendar in a way that almost nothing else in the Hamptons does. On match days, the atmosphere shifts. The rolling fields of Bridgehampton fill with a crowd that takes the sport seriously and the afternoon even more so. It is one of those events where the game itself is genuinely worth watching and the scene around it is equally worth being part of.

Match dates this summer are July 18th and July 25th. Both weekends sell through early. If you are planning to attend, your travel should be sorted before the field fills.

Insider tip:

East Hampton Airport (HTO) sits roughly 15 minutes from the Bridgehampton polo fields. It is one of the most efficient summer arrivals in the Northeast — you land, you clear the ramp, and you are at the match. Most commercial travelers are still sitting in Hampton Jitney traffic. Flying private into HTO on a polo weekend is one of the clearest time arbitrage plays in private aviation.

The New York to Hamptons route starts at $8,338. For a group, a light jet handles the hop with ease — short runway, efficient cabin, and no wasted aircraft for a 45-minute flight. Search the route in the Elevate app and your price is locked before you close the screen.

The Aspen Summer Reset

Aspen in winter is well documented. Aspen in summer is something different — quieter, greener, and in many ways more compelling. The crowd thins, the pace shifts, and the mountain opens up in a way that rewards people who know to show up before fall. Privacy is easier to find. The social calendar is strong but not overwhelming. And if you want a strong social calendar, the ArtCrush gala on July 31st is one of the most coveted invitations of the summer arts season.

The Aspen Art Museum's annual ArtCrush event draws collectors, artists, and a crowd that moves between the auction, the parties, and the mountain with the kind of ease that defines the Aspen summer. If you can get a ticket, the trip builds itself around it.

Insider tip:

Aspen Pitkin County Airport (ASE) sits at 7,820 feet elevation, making it one of the most operationally complex airports for private aviation in the continental United States. Aircraft performance calculations change at altitude, and not all aircraft in the charter market are well-suited for ASE arrivals — particularly with full passenger loads in summer heat. When you search for Aspen in the Elevate app, Ruby accounts for these conditions in the price and aircraft it returns. You are not guessing at which aircraft can make the approach. The answer is already baked in.

Routes into Aspen from New York, Miami, and Dallas are all live in the app. A super midsize jet is the preferred category for longer hauls into ASE — the range and cabin volume work well for the trip, and the aircraft performance profile handles altitude with margin to spare.

Paradise in Todos Santos

Baja California Sur has been having a moment for a few years now, and Todos Santos sits at the center of it. The town itself is small — a handful of streets, a UNESCO-recognized historic center, a gallery scene that punches well above its size. But the draw is the combination: Pacific coastline, desert terrain, creative culture, and a pace of life that is entirely removed from the resort corridor of Los Cabos.

Todos Santos is not a mass tourism destination. It is the kind of place that rewards travelers who find it before it becomes obvious. That window is still open, but not indefinitely.

Insider tip:

Los Cabos International Airport (SJD) is the standard arrival point for the Baja Peninsula, but private aviation travelers flying into Todos Santos have a closer option: Ciudad Constitución Airport (CNA), a smaller general aviation field that eliminates the two-hour coastal drive from Cabo entirely. Not all charter operators price or route through CNA — but in the Elevate app, Ruby evaluates available options across the network and returns the most efficient routing for your itinerary. Worth searching both before you commit.

The New York to Cabo San Lucas route starts at $34,397. From the West Coast, the Los Angeles to Cabo San Lucas route starts at $22,087. For international routing, a midsize jet or heavy jet handles the range comfortably. Search both options in the Elevate app and Ruby returns a locked price based on current market conditions, aircraft positioning, and your specific routing.

The Montecito Long Weekend

Montecito occupies a specific position in the California coastal hierarchy. It is not Santa Barbara — it is quieter, more private, and considerably more concentrated in terms of who lives there and what the hospitality infrastructure looks like. The main draw is a pace of life that feels genuinely separated from the city. You arrive, the urgency drops, and the weekend extends itself naturally.

This is a destination that rewards staying a day longer than planned. The restaurants are worth the reservation lead time. The beach access is worth the morning walk. And the drive back to the airport is the hardest part of the trip.

Insider tip:

Santa Barbara Airport (SBA) is the closest field to Montecito and handles private aircraft without the congestion of LAX. The drive from SBA to the main Montecito corridor is under ten minutes. If you are flying from the East Coast, the 

New York to Santa Barbara route starts at $40,524. For transcontinental range at that comfort level, an ultra-long-range jet or heavy jet is the right category. Flying from the West Coast? The route is short enough that a light jet or turboprop handles the hop with ease. Open the Elevate app and Ruby will surface the right aircraft for your route automatically.

Frequently Asked Questions

How do I book a flight to one of these destinations?

Download the Elevate Jet app, enter your route, date, and passenger count, and Ruby returns a locked price instantly. No follow-up calls required. What you see is what you pay.

What aircraft should I book for a summer trip?

It depends on your route, group size, and destination airport. Short hops like New York to the Hamptons work well on a light jet. Transcontinental trips to California call for a heavy jet or ultra-long-range jet. International routes to Mexico favor a midsize or super midsize jet. The Elevate app recommends the right category automatically based on your specific search. Browse all aircraft types here.

Are prices on the app final?

Yes. Ruby returns a locked price based on aircraft positioning, fuel, crew, airport conditions, and current market rates. The price you see in the app is the price you pay.

How does Elevate Jet verify safety for the aircraft I book?

Every aircraft in the Elevate network is reviewed for safety and compliance history, crew qualifications, maintenance records, insurance, and operator financial stability before a booking is confirmed. Elevate Jet operates under FAA Air Carrier Certificate #B8MA127H and holds Argus Platinum and Wyvern Wingman safety ratings. Full details on safety standards are available here.

Do you offer jet cards or memberships for frequent summer travelers?

Yes. The Azurite Jet Card is built for travelers who fly regularly and want transparent pricing without the overhead of aircraft ownership. Elevate also offers membership options designed around frequency, flexibility, and better terms per flight.

Can I search routes to see pricing before I commit?

Yes. The Elevate app lets you search any route and see live pricing before booking. You can also browse popular routes with starting prices directly on the website.

I have never flown private before. Where do I start?

Start with the Elevate app. Enter your route and travel dates and the app walks you through aircraft options, pricing, and booking in a single flow. If you prefer to speak with someone first, Elevate specialists are available through the contact page.

Summer books fast. Search your route now in the Elevate Jet app, compare prices up to 15% below market rate, and be wheels up this weekend.