The Caribbean is a year-round destination, but the experience and cost vary quite a bit depending on when you go.

December through April is dry season: warm temperatures in the low to mid twenties Celsius, lower humidity, and reliably beautiful weather. It is also peak season, so expect higher prices and more competition for rooms, particularly over the Christmas and New Year holiday period.

Mid-April through May is a lovely shoulder period, sitting between dry and wet season. Prices begin to ease and it remains a wonderful time to experience the islands before the summer heat sets in.

June through November is wet season, aka hurricane season. Rates during this period can be forty to fifty percent lower than peak, making it the best value window for Caribbean travel. It is also a quieter, more relaxed time to visit.

October and November offer lovely rates and fewer crowds but are some of the most humid months of the year.

Worth knowing: some properties close temporarily for renovations or upgrades during August, September or October, so it is always worth checking ahead.

It depends on when you want to travel and what you are planning. One thing worth knowing upfront: the Caribbean has one of the highest repeat visitor rates in the world, which means at the most sought-after properties, availability moves faster than most people expect.

For festive season (mid-December through early January), this really matters. Many guests love these islands so much they rebook the same property, sometimes even the same room, for the following year before they have even checked out. The closer you can get to twelve months in advance, the better. Twelve to fifteen months is not too early at all. Even if a hotel's room rates are not yet published, I can put in requests on your behalf as most properties fill spots in the order they receive them.

For peak season (January through April), six to twelve months in advance gives you solid options, with closer to twelve being ideal. Prices tend to dip across most islands once the Easter holiday wraps up.

For summer travel (mid-April through October), three to six months generally works, though earlier is always better on smaller islands where inventory is ultimately limited.

For weddings, room blocks, and large group events, twelve to fifteen months in advance is strongly recommended regardless of time of year. Again, even if rates are not yet published, I can put in requests on your behalf. The earlier you are on a hotel's radar, the better your chances of securing exactly what you need.

For carnival travel, if experiencing a specific island's carnival is part of your plan, book ahead regardless of when it falls in the calendar. Even if it lands during a quieter month, demand and prices around carnival period can spike.

If you are reading this and feel like you might be coming to me too late, please still reach out. The timelines above are ideal scenarios, not hard rules. Depending on when you want to travel, there may be some limitations on availability, but I will always be honest with you about what is possible and do everything I can to make it work.

Hurricane season officially runs from June through November. Hurricanes are genuinely unpredictable. As your travel advisor, I cannot tell you which months within that window carry more risk than others. Some years activity is concentrated later in the season, some years earlier. It is simply impossible to forecast.

What I can tell you is that many people travel during hurricane season every year and have a wonderful time. Rates are significantly lower, it is quieter, and the islands are just as beautiful. If you are considering this period, travel insurance is something I always recommend regardless of season. It gives you real peace of mind if anything unexpected comes up.

For timing, the best starting point is the FAQ above on how far in advance you should book. The time of year you want to travel will give you a good sense of when to get in touch.

Beyond that, the most important thing is that you feel ready to start planning. Once we start working together, there will be real timelines on your end too: proposals to review, decisions to make, feedback to send within agreed timeframes. If life is hectic right now and you know you will not be able to show up fully, it is absolutely fine to hold off and come back when you are. This works best when we are both committed to keeping things moving.

Not quite ready to start planning but curious about working together? That is absolutely fine too. Just flag it on your inquiry form and I will structure our consultation call as more of an introductory conversation. It is a great opportunity to ask questions, get a feel for my process, and figure out the right time to properly dive in.

Not at all, but the closer you can get to at least a target month and year, the better. If you are traveling during peak or festive season in particular, the FAQ above on how far in advance to book is worth a read.

Even once we are working together, when I go to check hotel availability or reach out to partners, I need to put in specific dates. Availability from the 5th to the 10th of a given month can be completely different from the 10th to the 15th. So while you absolutely do not need exact dates before reaching out, the closer we can get to those specifics, the better your options will be.

If you are completely flexible on timing, we can work through it together on your consultation call.

It depends on the package and the complexity of your trip.

For standard trips, you can typically expect an initial proposal within five to seven business days of your signed contract and planning fee being received, sometimes even sooner.

For more complex trips or larger group bookings, that may extend to seven to fourteen business days. All timelines will be clearly outlined in your planning contract so there are no grey areas on either side.

Yes, completely separate. The planning fee covers my time, expertise, and everything I do on your behalf throughout the planning process. Your actual travel costs such as accommodation, flights, activities, and transfers are presented to you separately for your approval before anything is booked. You will never be charged for a travel cost without seeing it and agreeing to it first.

Planning fees are non-refundable once planning has commenced. By paying your planning fee, you have my full commitment: my time, energy, expertise, and resources dedicated to making your trip as close to perfect as possible. That is the promise behind the fee.

It is also worth knowing that payment plans are available for planning fees if that helps. Please note that payment plans apply to planning fees only. Any payments due to hotels, villas, experiences, or other travel vendors are handled separately and are subject to each vendor's own payment terms.

Yes! Payment plans are available for planning fees across select packages. If applicable, I will bring this up on your consultation call. Please note that payment plans apply to planning fees only. Payments for accommodation, experiences, flights, and other travel costs are handled separately and subject to each vendor's own terms.

Rum & Roots works exclusively with four, five, and six-star properties, from hotels to vetted villas across the Caribbean. This is a deliberate quality standard. As a travel advisor, part of my job is making sure you are placed somewhere that genuinely delivers on comfort, service, and experience. Below four stars, that becomes harder to consistently guarantee, and the last thing I want is to put you somewhere that does not meet the standard you deserve.

That is not to say that three-star hotels cannot be lovely. They absolutely can. It is simply that the quality assurance I can provide as your advisor is strongest at the four-star level and above. If a three-star property is what you are after, I would genuinely recommend exploring those options independently.

Sadly, no. Airbnb does not work with travel advisors or offer commissions, which is a core part of how I operate as a business.

Alternatively, I do work with select VRBO listings and primarily trusted villa rental companies across the Caribbean. It is worth knowing that many Caribbean villas are listed on Airbnb or VRBO, but booking directly through my villa partners can actually save you money since you avoid the third-party platform fees. You also get the added reassurance of working through a vetted professional partner.

Generally speaking, when it comes to both accommodation and flights, points bookings are not something I can assist with. Points are typically redeemed through your own personal loyalty or credit card accounts, whereas I book accommodation and other travel services through my partner portal systems. These two processes do not mix, which is why I am not able to help with points redemptions on either front. If using points is a priority for you, I would recommend handling those bookings independently.

Yes, I can help with routing advice, sourcing options, and booking flights as part of your overall trip planning. That said, there are a couple of considerations worth talking through on your consultation call, particularly around what level of ongoing support I can provide if any changes or disruptions come up on the day of travel. It is worth a quick conversation to make sure we are aligned before diving in.

The Caribbean is my specialty and where my deepest knowledge and supplier relationships live. That said, I do take on trips beyond the Caribbean for the right client, particularly destinations that share the same warmth and cultural spirit as, or historical connection to, the Caribbean. Africa and Latin America are two regions I have worked with and absolutely adore. If you have something specific in mind, reach out and we can chat about whether it is something I can take on.