Packing is one of those things that feels simple until you are standing in a hotel room in a different country realizing you brought four books and forgot your phone charger.
I have helped hundreds of families and couples prepare for trips to the Caribbean, Mexico, and Costa Rica, and the packing conversations are always revealing. The things people over-pack are predictable. So are the things they forget.
Here is the guide I give my clients. It covers what actually matters, what you can leave at home, and a few things that most packing lists never mention.
Start With What Not to Bring
Most people pack too much. Not slightly too much — genuinely too much, in ways that make travel harder.
Overpacking adds weight, slows down airport security, creates anxiety about checked bags, and results in half the suitcase coming home unworn. Before you think about what to add to your bag, think about what you actually do not need.
For a Caribbean or Mexico beach vacation:
You do not need an outfit for every possible social occasion. Resorts are casual. A beach cover-up doubles as a dinner look with sandals. You will repeat outfits and no one will notice or care.
You do not need a full makeup kit if you are going somewhere hot and humid. Lighter is better. Your vacation face is probably simpler than your daily face.
You do not need entertainment for every possible scenario. You brought yourself to a beautiful place — the entertainment is largely outside.
The Real Packing List for a Beach or All-Inclusive Trip
Documents and essentials (carry-on only)
- Passport and copies stored separately
- Trip confirmation documents, hotel info, transfer details — printed or downloaded offline
- Travel insurance information and emergency contacts
- Credit cards (more than one) and some local currency for small tips
- Any medications you need, packed in original containers, in quantities exceeding the length of your trip
Clothing (one week, tropical destination)
- Five to seven light bottoms: shorts, linen pants, casual skirts
- Five to seven tops in breathable fabrics
- Two or three dresses or cover-ups if relevant
- One nicer outfit for a dinner out if your destination warrants it — truly one
- Comfortable walking shoes or sandals for excursions
- Flip flops or slides for the resort
- A light layer for heavily air-conditioned restaurants and evening breezes
- Swimsuits: two or three so you always have a dry one
Toiletries and sun care
- Reef-safe sunscreen in adequate quantity — this is not optional, and running out is miserable
- Aloe vera gel for after sun
- Insect repellent if you are going to Costa Rica or anywhere with jungle, mangrove, or wetland access
- Your regular skincare and personal items in travel sizes
- Any prescription medications, clearly labeled
Gear and electronics
- Your phone and charger with a backup battery pack
- A universal adapter if traveling outside the Caribbean
- Earbuds or noise-canceling headphones for the flight
- A waterproof phone case or dry bag if you are doing water activities
- A lightweight daypack for excursions
- Apple AirTags for checked luggage — I recommend these to every client
For families traveling with kids
- One full change of clothes per child in your carry-on bag — flight delays and luggage delays happen
- Any comfort items or travel snacks that make the flight manageable
- Compact first aid kit with basics: bandages, pain reliever, antidiarrheal, antihistamine
- Your children's medications even if you do not expect to need them
- Small activities for the flight: downloaded shows, card games, a new small toy if your child is young
What to Leave Behind
- The hair dryer. Resorts almost always provide them.
- Multiple pairs of jeans. One at most, if your destination or season calls for them.
- Books you might read. Download everything. Paperbacks are heavy.
- A full medicine cabinet. The basics, yes. The whole cabinet, no.
- Anything valuable or irreplaceable that does not need to travel.
Packing for Costa Rica Specifically
Costa Rica deserves its own note because it is genuinely different from a beach resort destination.
The environment is wet, humid, muddy, and extraordinary. Add to your list:
- Closed-toe shoes or water shoes suitable for trails and river crossings
- A lightweight rain jacket you can compress easily
- Moisture-wicking clothing rather than cotton, which stays wet and heavy
- More insect repellent than you think you need
- A dry bag for electronics on water activities
Leave behind anything you would be upset to lose or get dirty. Dirt, humidity, and the occasional river crossing are part of what makes Costa Rica magical. Pack accordingly.
The One-Bag Carry-On Strategy
For trips up to a week, packing everything into a carry-on is genuinely achievable with the right approach. Roll clothing instead of folding. Use packing cubes to compress volume. Choose fabrics that are lightweight and do not wrinkle badly.
The advantages are significant: no checked bag fees, no waiting at baggage claim, no risk of lost luggage, faster airport navigation. For families with young children who are already managing a lot at the airport, eliminating the checked bag process makes travel days noticeably smoother.
If you need a checked bag, check it without guilt. But test the carry-on strategy at least once. Most people find they can pack lighter than they imagined.
The Day Before You Leave
Lay out everything you plan to pack. Look at it without putting it in the bag yet. Remove anything you have not used in the past two weeks that you are bringing "just in case." Remove one or two more clothing items. Now pack.
Also: charge every device, confirm your transfer and resort information, and make sure your passport location is known and your travel insurance paperwork is accessible.
Travel days go better when you are calm, organized, and not dragging a bag that weighs more than a child.
If you want a pre-trip consultation that covers destination-specific preparation, packing considerations, and what to actually expect when you arrive, I include that in my full planning service. Schedule a free consultation and let's make sure you arrive prepared.