VACATION PLANNING

Vacation Help That Fits

Plan your trip with clear calls, custom itineraries, hotel and resort picks, local activity ideas, and airport transfer help for couples, families, and friend groups.

Luxury villa terrace at dawn with suitcase, linen, straw hat, sandals and a waiting transfer sedan.

Metric 01

250+

trips planned

Metric 02

4.9/5

client rating

Metric 03

48 hrs

first draft ready

HOW IT WORKS

Four Clear Steps

A 60-minute call to map dates, budget, and trip goals.

Open suitcase with swimwear, straw hat, limes, and a sea-view lounge chair on a balcony.

60-min call

Vacation Consults

From $149

A 60-minute call to map dates, budget, and trip goals.

Travel-day essentials on pale stone steps in a warm resort alcove, lit by late-afternoon sun.

3-day draft

Custom Itineraries

From $349

Luxury oceanfront suite with made bed, folded robes, and a welcome tray by open balcony doors.

Stay match

Hotel & Resort Booking

From $279

Villa entry console with carry-ons, blank key sleeves, and stacked totes in warm daylight.
01Up to 12 guests

Group Trip Planning

From $499

Room blocks, shared plans, and guest updates for friend groups.

Snorkel fins, towel, shoes, umbrella and citrus on a stone ledge in dramatic tropical light.
02By destination

Local Activity Picks

From $129

Food spots, tours, beach days, and rainy-day plans.

Open trunk sedan with two suitcases at a curb lantern under warm evening haze.
03One-way or return

Airport Transfer Help

From $89

Ride plans from airport to hotel or resort on arrival day.

PLANNING SERVICES

Trip Help For Real Life

Share dates, places, group size, and budget in a quick intake form.

Top-down still life of travel booking essentials on a stone tray with soft daylight
01

Book a Call

Share dates, places, group size, and budget in a quick intake form.

Overhead travel flatlay with compass, key sleeve, canvas pouch and route tokens on stone tray.
02

Plan the Trip

We match hotels, routes, rides, and things to do with your goals.

Itinerary folios, pencil, and brass paperweight on a linen console in soft daylight.
03

Review Your Plan

You get a clear draft to check, trim, or change before booking.

Tan travel folio with key card, luggage tag and brass clasp on pale travertine in soft sunlight.
04

Book With Support

We help you lock in stays, transfers, and key activities.

TRIP STORIES

Plans That Saved Time

One consult call 7-day custom itinerary Hotel shortlist Local activity list Booking checklist

One trip planOne trip plan

Starter

From $499

  • One consult call
  • 7-day custom itinerary
  • Hotel shortlist
  • Local activity list
  • Booking checklist
Most popularPriority support

Signature

From $1,250

  • Everything in Starter
  • Two planning calls
  • Hotel or resort booking
  • Airport transfer setup
  • Group trip coordination
  • Day plan updates
Quoted by scopeQuoted by scope

Scale

From $2,750

  • All Signature items
  • Multi-room trip planning
  • Private villa and resort search
  • Guest schedule updates
  • Airport rides for groups
  • Final prep call

WHAT CLIENTS SAY

Words From Travelers

Four nights, two resort picks, and rides set before takeoff.

Folded robes and a welcome tray on a Cancun balcony with pool and sea beyond at golden hour.

Couples

Cancun Couple Week

Four nights, two resort picks, and rides set before takeoff.

Dawn-ready family hotel suite with two queen beds, backpacks, a folded stroller, and breakfast set out.

Family

Orlando Family Week

Empty Jamaica resort beach at sunset with pier, loungers, palms and glowing surf.

Resorts

Jamaica Resort Plan

San Diego hotel balcony with surfboards, carry-on, and an SUV over the bay.

Weekend

San Diego Weekend

Leather itinerary folio, brass compass, and hotel key sleeve on a dark stone tray.

Couples and honeymoons

Nina Torres

Stacked room-key sleeves, luggage bands and a luggage scale on brushed metal under dramatic light.

Friend groups

Derek Shaw

Top-down close-up of booking tools on pale wood: smartphone, earbuds, handset and leather wallet.

Hotels and resorts

Maya Patel

Flat lay of steel bottle, power bank, coiled cable and citrus wedges on slate.

Rides and activities

Luis Alvarez

Golden-hour South Florida skyline over calm bay water with palms and hazy sunset light

South Florida

Proof

Customer notes

Verified

“Nina took our dates and turned them into a clean plan fast.”

Stacked room-key sleeves, luggage bands and a luggage scale on brushed metal under dramatic light.

Janelle Moore

Couple traveler, Miami

Verified

“Our family trip had hotel choices, rides, and a day plan in one place.”

Top-down close-up of booking tools on pale wood: smartphone, earbuds, handset and leather wallet.

Marcus Hill

Parent, Orlando

Verified

“The group chat got much easier after Connect Vacay stepped in.”

Flat lay of steel bottle, power bank, coiled cable and citrus wedges on slate.

Tanya Brooks

Group host, Tampa

Service area

Central Florida

Orlando, Kissimmee, Tampa, Clearwater

Golden-hour Orlando lake country with distant resort towers above calm mist and still water.

Area 01

Central Florida

Orlando, Kissimmee, Tampa, Clearwater

Naples Gulf shoreline with pier, sandbar, sea oats, and hazy golden light

Area 02

Florida Coast

Naples, Fort Myers, Sarasota, St. Petersburg

Rain-lit Caribbean cove with turquoise water, coral rock, and open calm sea for copy

Area 03

Caribbean Trips

Cancún, Montego Bay, Punta Cana, Nassau

The Map

Questions

Common Questions

Quick answers before visitors choose a product, service, or next step.

01How soon should I start planning?+

Six to twelve weeks works for many trips. For holidays, cruises, and big groups, start sooner if you can.

02Can you book hotels and resorts?+

Yes. We can suggest places, compare options, and help you book the hotel or resort that fits your dates and budget.

03Do you help with group trips?+

Yes. We help with room blocks, guest lists, shared plans, and simple updates so one person is not stuck doing all the work.

04What do I get in the plan?+

You get a trip outline, hotel picks, ride notes, and a list of local things to do. We keep it clear and easy to use.

05Do you work with couples and families?+

Yes. We plan trips for couples, families, and friend groups, and we shape the plan around your pace, budget, and must-do spots.

06Can you help with airport rides?+

Yes. We can line up airport transfer options and tell you which ride fits your flight time, hotel, and group size.

Trip Tips By Email

Get short notes on stays, rides, and group trip timing from Connect Vacay.