Aloha. Let's plan your next escape.
I'm Courtney, a travel agent for Caribbean, Hawaii and Mexico vacations, cruises, and Disney and Universal trips. Tell me what you're picturing and I'll find the resort, the rate and the perks, then handle the booking. It costs you nothing: the resorts and cruise lines pay me, so you pay the same as booking direct.
Price your trip in under a minute.
The first question every travel agent hears is "how much would this cost?" These calculators answer it with current seasonal pricing for flights, lodging, dining and extras. When you're ready, send the estimate to Courtney and she'll turn it into a real quote.
Vacation package
Flights, hotel or all-inclusive resort, dining and extras for 45 destinations in the Caribbean, Hawaii, Mexico and Orlando.
Cruise
Eight major lines. Pick a cabin and a length and see the fare with port fees, taxes and gratuities included.
Walt Disney World
Resort tier, park tickets, dining plan and Lightning Lane, all in, before you commit to dates.
Universal Orlando
Hotel tier, Park-to-Park tickets and Express Pass, including the Premier-hotel "free Express" math.
Premier hotels include Express Unlimited for everyone in the room. Pick an Express option to compare.
Where should we take you?
Pick a region to see when to go, how long the flight is, what you need to bring and what a trip typically costs.
Short flights, long beaches, all-inclusive ease.
From Punta Cana’s palm-lined all-inclusives to the Pitons of St. Lucia and the shallow blues of Turks and Caicos, the Caribbean is the easiest warm-weather trip to pull off from the Midwest and the East Coast. Thirty islands and resort towns are covered here, and most of them are all-inclusive country.
Book winter and spring break four to six months out. Late April through June gives you the same beaches at shoulder prices, and southern islands like Aruba sit mostly outside the hurricane belt if you want late summer.
When to go
Know before you go
- Best time
- December through April: dry, breezy and about 80 °F. May, June and November are the sweet spot for value.
- Watch for
- Hurricane season runs June 1 to November 30 and peaks August through October. Aruba, Bonaire, Curaçao and Barbados sit mostly outside the belt.
- Flight time
- About 4 to 5 hours from the Midwest, 3½ to 4½ from the East Coast, 3 to 4 from the South, 1½ to 3 from the Southeast, and 6 to 8 from the West Coast, usually with one stop.
- Passport
- Required, except for Puerto Rico and the U.S. Virgin Islands, where U.S. citizens only need a government photo ID.
- Money
- U.S. dollars are accepted almost everywhere. Bring small bills for tips and taxis.
- Time zone
- Eastern or Atlantic time: the same as the East Coast, or one hour ahead.
- Weather
- Highs of 78 to 88 °F all year; water 79 to 84 °F.
- Lodging
- All-inclusive country. Standard resorts run roughly $180 to $450 per person per night with meals and drinks included.
- Good for
- Honeymoons, families who want zero decisions, and quick escapes from the Midwest and East Coast.
Volcanoes, rainforests and the gentlest surf in the Pacific.
Each island has its own personality: Maui for sunrise and whales, Oahu for Waikiki and Pearl Harbor, Kauai for cliffs and canyons, the Big Island for lava and Kona coffee. It is a long flight, but nothing about the trip needs a passport.
A week is the minimum worth the flight; ten days lets you pair two islands. Oceanfront rooms and the Road to Hana sell out first, and the Haleakalā sunrise needs a reservation.
When to go
Know before you go
- Best time
- April to May and September to October: fewer crowds, lower rates, perfect weather. Humpback whales visit Maui from December to April.
- Watch for
- Peak pricing from mid-December through March and all summer. Windward coasts see more rain from November to March, though showers pass quickly.
- Flight time
- About 5½ to 6 hours from the West Coast, 8 from the South, 9 from the Midwest (nonstop to Honolulu; one stop for Maui, Kauai and Kona) and 10 to 11 from the East Coast.
- Passport
- None: it’s a U.S. state. The agricultural inspection on the way home is the only extra step.
- Money
- U.S. dollars. Budget more for meals; all-inclusive resorts are rare here.
- Time zone
- Hawaii Standard Time, with no daylight saving: five to six hours behind the East Coast.
- Weather
- Highs of 75 to 88 °F year-round; water 75 to 80 °F.
- Lodging
- Resorts and condos, mostly room-only. Standard oceanfront runs about $300 to $600 a night, plus roughly $100 a day per person for food.
- Good for
- Honeymoons, bucket-list nature, multi-island itineraries and long-haul trips with no passport.
Caribbean beaches on a four-hour flight, at the best all-inclusive prices anywhere.
Cancun and the Riviera Maya deliver turquoise water, cenotes and Mayan ruins; Cabo and Puerto Vallarta trade them for desert sunsets, whales and old-town charm on the Pacific. Eight beach destinations are covered here.
Cancun is the easiest nonstop from most of the country, and Tulum and Playa del Carmen are 45 to 90 minutes south of the same airport. For a quieter Pacific trip, Puerto Vallarta from November to April is hard to beat.
When to go
Know before you go
- Best time
- December to April on the Caribbean side (Cancun, Riviera Maya, Cozumel); October to May for Cabo and Puerto Vallarta, with whales off Baja from December to April.
- Watch for
- Rainy season from June to October on the Caribbean coast, with the hurricane peak in September and October. Sargassum seaweed can reach east-facing beaches from April to August. The Pacific coast gets showers from July to September.
- Flight time
- About 2½ hours from the South, 4 to 5 from the Midwest, 3½ to 4 from the East Coast and 1½ from the Southeast. From the West Coast it is 2½ to 3 hours to Cabo and Vallarta and 4½ to 5 to Cancun.
- Passport
- Required: a passport book for air travel. Allow 30 to 60 minutes for immigration at Cancun on busy weekends.
- Money
- Mexican pesos. Resorts and tours take U.S. dollars, but pesos are cheaper for taxis, markets and tips.
- Time zone
- Cancun and the Riviera Maya stay on Eastern Standard Time year-round, so one hour behind the East Coast in summer. Puerto Vallarta is Central; Los Cabos is Mountain.
- Weather
- Highs of 80 to 90 °F; Caribbean water 78 to 84 °F. Baja is drier with cooler winter seas.
- Lodging
- The best all-inclusive value anywhere: standard resorts run about $150 to $400 per person per night with meals and drinks included.
- Good for
- All-inclusive families, couples’ and friends’ getaways, bachelor and bachelorette groups, and anyone who wants Caribbean water without the Caribbean price.
Short flight, no passport, a lot of moving parts.
Walt Disney World has four theme parks, two water parks and dozens of resorts; Universal Orlando now has three theme parks with Epic Universe. The trick is picking dates, resort tier, tickets and line-skipping so the trip fits the budget, which is where a planner earns her keep.
On-property guests get early park entry at both resorts. At Universal, Premier hotels include Express Unlimited for everyone in the room, which is usually the biggest single saving on the trip.
When to go
Know before you go
- Best time
- Late January to early March, late April to May, and September through early November: lighter crowds and lower resort rates.
- Watch for
- Spring break, summer, Thanksgiving week and mid-December through New Year’s are the busiest and priciest. June to September brings 90 °F days and afternoon thunderstorms; hurricane season is June to November.
- Flight time
- About 2½ to 3 hours from the East Coast and the Midwest, 2 to 2½ from the South and 5 from the West Coast. From the Southeast it is a short hop or a drive.
- Passport
- None: it’s Florida.
- Money
- U.S. dollars. Disney resort guests park free at the theme parks; everyone else pays daily parking.
- Time zone
- Eastern.
- Weather
- January highs near 72 °F; July near 92 °F with humidity and daily afternoon storms. Pack ponchos.
- Lodging
- Disney has Value, Moderate, Deluxe and Deluxe Villa resorts, each a different price tier. Universal has Value, Preferred and Premier hotels, with Express Unlimited included at Premier.
- Good for
- Families and multi-generation trips, first-timers who want everything handled, and long weekends on a short flight.
Four islands, one unpack.
Carnival, Celebrity, Disney Cruise Line, Holland America, MSC, Norwegian, Princess and Royal Caribbean sail the Caribbean and the Bahamas from Florida, Texas and the Northeast, and the Mexican Riviera from California.
Fares change weekly, and a good agent re-fares your cabin if the price drops before final payment. Mid-ship, mid-deck cabins ride smoothest; avoid rooms under the pool deck or beside the laundry.
When to go
Know before you go
- Best time
- January to April, after New Year’s: calm seas, great weather, moderate fares. Late August to October is cheapest; it is hurricane season, and ships reroute around storms.
- Watch for
- Spring break, summer and holiday sailings book early and cost the most. Final payment is usually 75 to 90 days before sailing.
- Home ports
- Miami, Fort Lauderdale, Port Canaveral near Orlando, Tampa, Galveston, New Orleans, Baltimore, and New York and Cape Liberty. Los Angeles and San Diego for the Mexican Riviera.
- Documents
- A passport is strongly recommended. On closed-loop cruises (the same U.S. port out and back) U.S. citizens can sail with a birth certificate plus a government photo ID, but you need a passport to fly home from a foreign port if you miss the ship.
- Money
- U.S. dollars onboard and in most Caribbean ports. Gratuities of roughly $16 to $21 per person per day are added automatically, and port fees and taxes add about $100 to $300 per person.
- Cabins
- Inside cabins are the cheapest and ocean view adds a window. A balcony adds a private deck and is the most popular choice; suites add space, priority boarding and perks.
- Weather
- Caribbean and Bahamas sailings run 78 to 88 °F year-round, with the calmest seas from January to April. Mexican Riviera winters are drier and a little cooler.
- Fly in early
- Arrive the day before: a missed ship is the one thing a travel agent can’t fix. A pre-cruise hotel night runs about $200.
- Good for
- Multi-generation groups, first-timers (start with three or four nights to the Bahamas) and seeing several islands with one unpack.
Popular destinations
Tap a destination to explore the area.
Maui, Hawaii
From the sunrise at Haleakala to the Road to Hana, Maui offers dramatic landscapes and laid-back island vibes. Perfect for couples, families, and adventure seekers alike. Discover world-class snorkeling, lush rainforests, and unforgettable sunsets.
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Cancun, Mexico
Turquoise waters meet ancient ruins in Mexico's most popular resort destination. World-class beaches, vibrant nightlife, and easy access to Mayan archaeological sites. The perfect blend of relaxation and adventure for every traveler.
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Montego Bay, Jamaica
Reggae rhythms, jerk cuisine, and stunning north coast beaches define this vibrant Jamaican city. Rich culture meets world-class resorts along the famous Hip Strip. Explore Dunn's River Falls, Blue Hole, and warm island hospitality.
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Punta Cana, Dominican Republic
Miles of palm-lined beaches and all-inclusive resorts make Punta Cana a top Caribbean getaway. Warm hospitality and great value keep travelers coming back year after year. Enjoy zip-lining, catamaran tours, and crystal-clear cenotes.
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Oahu, Hawaii
Home to Waikiki Beach and the North Shore's legendary surf, Oahu blends city energy with island paradise. Explore Pearl Harbor, hike Diamond Head, and savor fresh poke by the shore. The heart of Hawaii with something for everyone.
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Kauai, Hawaii
Hawaii's greenest island is all dramatic scenery: the Na Pali Coast, Waimea Canyon, and the sun-soaked Poipu shore. Hike, kayak, or fly over emerald cliffs by helicopter. Laid-back Kauai rewards travelers who love the outdoors.
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Big Island, Hawaii
From Volcanoes National Park's lava fields to snow-dusted Mauna Kea, Hawaii's Big Island packs every climate into one. Sip Kona coffee, snorkel Kealakekua Bay, and relax on black-sand beaches. The most geologically dramatic island in the chain.
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Walt Disney World, Florida
Four theme parks, two water parks, and dozens of resorts make Orlando's Walt Disney World the ultimate family trip. Master Lightning Lane, dining plans, and park-hopping with a little planning. Pure magic for kids and grown-ups alike.
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Playa del Carmen, Mexico
Buzzing Fifth Avenue, Riviera Maya beaches, and easy cenote swims make Playa del Carmen a Caribbean-coast favorite. Ferry to Cozumel, tour Tulum's ruins, or unwind at an all-inclusive. Walkable, lively, and endlessly convenient.
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Cabo San Lucas, Mexico
Where the desert meets the sea, Los Cabos pairs the iconic El Arco with Medano Beach energy and world-class golf. Watch whales in winter, sport-fish year-round, and dine along the marina. Baja's most glamorous resort escape.
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Puerto Vallarta, Mexico
The Malecon boardwalk, cobblestone Zona Romantica, and Banderas Bay beaches give Puerto Vallarta real Mexican charm. Snorkel hidden coves, savor the food scene, and catch a Pacific sunset. Warm, walkable, and welcoming to every traveler.
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Tulum, Mexico
Cliffside Mayan ruins, jungle cenotes, and boho beach clubs give Tulum its one-of-a-kind vibe on the Riviera Maya. Stay at an eco-chic resort, bike the beach road, and swim in crystal sinkholes. Bohemian style meets ancient history.
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Hi, I'm Courtney.
Planning a vacation should be exciting, not exhausting. I do the research, compare the resorts, find the perks and handle the booking from start to finish, so you just get the vacation.
I've walked the beaches and toured the resorts, and the supplier relationships behind this site are what get you upgrades, unpublished rates and extras you won't find on booking sites. I plan all-inclusive beach trips, honeymoons, family Disney and Universal vacations, cruises on eight lines, group trips and destination weddings.
Independent travel advisor with Pineapple Escapes Travel, LLC. Free, no obligation, and she replies within a day.
Mahalo, Courtney
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Not sure where to start?
Tell me what you're picturing: a destination, a budget, a week in March, or just somewhere warm. I'll come back with a few options, real pricing and the trade-offs, and handle the booking if you want to go ahead. Free, no obligation.