Sail for the
festival.
Anyone can book a week in the Caribbean. The trick is landing on the one day the island throws its own party — and being ashore when it actually happens. Every festival below shows its real hours against a typical port call, so you know before you book whether you need a late departure, an overnight, or just a normal Tuesday. And when the answer is “get there a day early,” you already have the one thing nobody else on the ship has.
Where the bars don’t overlap, the sailing needs help. That’s what we’re for.
Fall 2026
Sailings are open and priced. Each entry shows the festival’s real hours against a typical port call, so you know before you book whether you need a late departure, an overnight, or just a normal Tuesday.
September
September Celebrations
All month · Independence Day Sept 21
Belize spends the whole month celebrating. Parades, live music and official ceremonies build toward Independence Day on the 21st, and a Carnival Road March sends costumed bands and revelers through the streets of Belize City — a short walk from where the tenders land.
Works on a normal port day. The Road March is daytime and downtown.
Curaçao Pride
Sept 30 – Oct 4 · Parade Thursday Oct 1
The 14th edition, with warm-up events starting the week before. The parade runs Thursday October 1 through Willemstad — one of the few Caribbean ports where the ship ties up close enough that you walk off into the middle of it.
Needs a late departure. Southern Caribbean sailings often hold Willemstad until 10 or 11 p.m. — confirm before booking.
Nonrev angleCUR has solid interline access from MIA and ATL, and Curaçao sits outside the hurricane belt. Easy week to build around a land stay if the sailing times don’t cooperate.
October
Taste of Bermuda
Oct 8–11 · City of Hamilton
The island’s largest food festival, in its thirteenth year. It opens with the TasteMakers series hosted across Bermuda’s best hotels, runs a Bacardi mixology showcase on the 9th, and stages Tabletop at Pier Six on the 10th — a projection-mapped dinner built around Bermudian ingredients. Bermuda’s advantage: ships stay two and three nights. This is the easiest festival on the list to actually attend.
Built for cruisers. Multi-night calls put the evening events fully in reach — the ferry from Dockyard into Hamilton takes 20 minutes.
Fantasy Fest
Oct 16–25 · Parade Saturday Oct 24, 7 p.m.
Ten days of costuming, themed this year “Musical Icons and Iconic Musicals.” The Bahama Village Goombay Festival on the 17th and 18th is the family-friendly stretch; the rest skews firmly adult. The parade down Duval on Saturday the 24th is the whole point, and it starts at seven in the evening.
Doesn’t fit a standard call. A daytime Key West stop catches the street fair and Goombay, not the parade.
Nonrev angleThe one on this list that’s easiest to do without a ship at all. Nonstop into EYW is tight, but MIA or FLL plus the drive down is a routine day — and interline hotel rates matter here, because Key West rooms triple during Fantasy Fest week.
BVI Restaurant Week
Oct 20–24 · part of BVI Food Fete
More than 37 restaurants running curated menus across the islands — traditional BVI cooking alongside newer kitchens. Lunch service means this one is genuinely reachable on a port day, which is rare for a food festival.
Works on a normal port day — book a lunch table in Road Town and walk to it.
Bahamas Culinary & Arts Festival
Oct 21–25 · Nassau
Five days of Bahamian cuisine and creative work. Nassau is the most heavily called port in the region, so the odds of a sailing landing inside this window are better here than anywhere else on the page.
Works on a normal port day, and better on sailings that hold Nassau past dinner.
Nonrev angleNAS is one of the easiest interline runs out of the Southeast, and a 3- or 4-night Bahamas sailing is the cheapest way onto this list. Good one for a last-minute week.
World Creole Music Festival
Oct 23–25 · Windsor Park Stadium, Roseau
Three nights at Windsor Park in the capital, headlined this year by Ne-Yo, Machel Montano and Maxi Priest, with bouyon, cadence-lypso, kompa, soukous and soca acts from across the Creole world. It runs during Dominica’s Independence season, which peaks November 3. The music starts late and ends later.
Not a port-day event. Sell this one as a land trip, or a pre-cruise stay in Roseau before boarding elsewhere in the islands.
Nonrev angleDOM takes a connection through SJU, BGI or ANU, so build in a buffer day. Roseau rooms tighten early during Independence season — don’t leave it to the week of.
Jounen Kwéyòl
Sunday Oct 25 · communities island-wide
Creole Day closes a full month of heritage programming. Villages across the island turn into open-air kitchens — roasted breadfruit, bouyon, coupe — with madras dress, music and dancing from breakfast onward. It’s a Sunday, and it’s a daytime affair, which makes it unusually cruise-friendly.
Works on a normal port day. Take a driver out of Castries to a village celebration rather than staying at the pier.
Hanal Pixán & Día de Muertos
Oct 25 – Nov 2 · Yucatán and Quintana Roo
The Yucatán’s version of Day of the Dead is called Hanal Pixán — “food of the souls.” Mérida runs the Festival de las Ánimas from October 25 through November 2: a monumental altar on the Plaza Grande, parades, and the candlelit Paseo de Ánimas from the General Cemetery to San Juan Park. Cancún and the Riviera Maya run their own programming October 30 to November 2. From Progreso, Mérida is about a 45-minute drive.
Partly reachable. Altars, markets and cemetery visits run all day; the Paseo de Ánimas is at dusk and needs a late departure or a night in Mérida.
Nonrev angleMID has good interline access from DFW, IAH and MIA, and Mérida hotels are a fraction of Cancún’s. The strongest play on this page: fly in, do the Paseo de Ánimas properly, and pick up a Western Caribbean sailing on either end.
Dive & Conservation Festival
End of October · Grenada
Expert-led dives, underwater photography workshops, and hands-on conservation work — coral restoration, debris cleanups, mangrove planting. Built for divers who’d rather do something with the water than look at it.
Works on a normal port day for the dive sessions — confirm exact dates, they move slightly each year.
November
Barbados Food & Rum Festival
Nov 5–8 · island-wide
The island that claims to have invented rum spends four days proving it — chefs, mixologists and producers running collaborations, tastings and demonstrations. Second reason to go this year: Barbados marks 60 years of independence on November 30, and the whole month runs warmer than usual.
Strongest as a turnaround. Barbados is a homeport — fly in early and the evening events are yours.
Nonrev angleBGI is one of the better interline runs in the eastern Caribbean and doubles as a cruise homeport, so the fly-in-early plan costs you almost nothing extra.
Pirates Week Festival
Grand Cayman Nov 6–14 · Brac Oct 30–31 · Little Cayman Nov 20–21
The national festival, themed this year “Spirits, Gold and Glory.” A flotilla storms George Town harbour, costumed pirates come ashore to capture the Governor, and a float parade and street party follow — plus district heritage days, a night parade and fireworks across eleven days. This is the one major Caribbean festival event that happens in broad daylight, in the middle of a cruise port.
The best fit on this page. A standard tender day drops you right into it.
Grenada Flower & Garden Festival
Nov 8–15 · first edition
Brand new this year. Growers and designers stage gardens and floral installations across the island, with guided tours, workshops and beautification projects open to visitors. On the Spice Island, less of a stretch than it sounds.
Works on a normal port day. Pair it with a nutmeg estate or the Grand Etang rainforest.
Festival de la Gastronomie
Nov 11–22 · French St. Martin
Twelve days of French-Caribbean cooking on the northern half of the island, drawing chefs who compete around a designated local ingredient. Marigot and Grand Case are the centers of it — and Grand Case is where you want dinner regardless.
Needs a late departure for the dinners; lunch events and markets fit a normal call.
Nonrev angleSXM is a strong interline destination in its own right and the runway approach alone justifies the trip for most of this list’s readers. Twelve days of programming means you don’t need to hit an exact date.
Anegada Lobster Festival
Nov 27–29 · Anegada
Locally caught spiny lobster, cooked every way the island’s restaurants can think of — fritters, salads, pizza, and the straightforward grilled version. Anegada is flat, remote and reached by ferry from Tortola, which is exactly why the people who go keep going back.
Needs a land night on Tortola or Anegada — the ferry schedule won’t fit inside a single port call.
The Mexican Riviera
Different ocean, different ships, opposite season. These sailings leave from Los Angeles, San Diego, Long Beach and San Francisco, and the Mexican Riviera season runs October through April — so the months that are thin in the Caribbean are the busy ones here. The festivals below sit in Mazatlán, Puerto Vallarta, Los Cabos and Acapulco, and the same rule applies: the bars show real hours against a real port call.
October 2026
Vallarta Nayarit Gastronómica
Oct 4–7 · 18th edition
Mexico’s largest chef-to-chef congress, and it runs in daylight — showcookings, tastings and workshops rather than a street party. The 2026 roster brings Michelin-starred Spaniards Benito Gómez, Kisko García and Rubén Sánchez alongside Carlos Gaytán and Rodrigo Rivera Rio. It is ticketed and it is an industry event, which is exactly why the sessions are worth sitting in on.
Works on a normal port day. The Sheraton Buganvilias is eight minutes from the terminal and the sessions run through the afternoon.
Día de San Lucas
Sunday Oct 18 · Cabo San Lucas’ patron saint day
The cape took its name in 1541, when the navigator Francisco Bolaños sheltered from a storm in this bay on the feast of St. Luke and called it San Lucas. October 18 is still the town’s patron saint day, and it is the best day of the year to be standing on the marina. The town sings las mañanitas at the parish at 4:30 a.m., then carries the image of San Lucas Evangelista by boat around the entire bay, followed by a horseback cabalgata, a fair and evening performances. You can watch the boat procession from the ship at anchor.
The most cruise-friendly festival on the Pacific side. Everything is within a ten-minute walk of the tender landing, and the water procession comes to you.
Bisbee’s Black & Blue
Oct 19–24 · fishing Oct 21–23 · weigh station 2–9 p.m.
The richest fishing tournament on earth — a record 11.5 million dollar purse in 2026, decided by a handful of fish. Only qualifying blue, black and striped marlin cross the scale, so one animal can move millions in a single afternoon. The weigh station sits at Puerto Paraíso Mall on the marina, a two-minute walk from where the tenders land, and it is free to stand and watch. The smaller Los Cabos Offshore runs the week before, Oct 12–17, and weighs tuna and dorado too — far more scale action.
Works on a normal port day if you plan around it. The scale opens at 2 p.m.; be there by three and you will see fish.
Nonrev angleSJD has strong interline access out of LAX, PHX and DFW, and tournament week is the one week Cabo rooms actually sell out. If you want the evening weigh-ins and the awards night, fly in.
Día de Muertos on the Pacific
Oct 30 – Nov 2 · Puerto Vallarta, Mazatlán, Los Cabos, Acapulco
The Pacific coast does Day of the Dead differently in each port, and one of them is built for daylight. Puerto Vallarta stages a Guinness-record catrina skull — over 27 metres — on the Malecón, ringed by dozens of giant decorated calaveras commissioned from local businesses; it stands for days and photographs beautifully at noon. Mazatlán’s callejoneada leaves Plazuela Machado at 8 p.m. behind a giant catrina with 500 costumed performers. Los Cabos floats Altares en el Mar — illuminated boats processing through the marina after dark. Acapulco’s procession of altars starts at the maritime terminal and walks to the Zócalo.
Puerto Vallarta works on a normal port day — the installations are up all day. The three processions are all after dark and need a late departure.
Nonrev anglePVR and MZT both run well from the Southwest, and this is the week the coast is at its most photogenic. Two land nights in Vallarta gets you the Malecón by day and the parade at dusk.
November 2026
Los Cabos Tuna Jackpot
Nov 3–7 · fishing Nov 5–6 · weigh-ins 3–6:30 p.m.
A 1.47 million dollar yellowfin tournament that opens with the Green Hair Party — a genuine local tradition in which several hundred people dye their hair green at Tesoro Resort on the marina and then go fishing. The weigh-ins happen at the cruise-ship pier area, which is to say directly where your tender drops you.
Tight but doable. The scale opens at 3 p.m., so this only works if your ship holds Cabo past five.
World Wide Technology Championship
Tournament week Nov 2–8 · rounds Nov 5–8 · El Cardonal at Diamante
The PGA TOUR’s Mexico stop, in its 20th year and its second in Los Cabos. 120 professionals play El Cardonal — Tiger Woods’ first course design — on the Pacific side of the cape, broadcast to 220 countries. Past champions include Viktor Hovland twice and Russell Henley. Grounds passes are sold to the public.
Works on a normal port day. Fifteen to twenty minutes from the marina by road, and the golf runs sunrise to late afternoon — but buy tickets before you sail.
Torneo Internacional de Pesca Marlin y Atún
Nov 11–14 · Marina Vallarta
One of the oldest sportfishing tournaments in Mexico, running since the 1950s, with more than a million pesos on the line. Boats leave at dawn and the daily weigh-ins draw a crowd onto the marina docks in the afternoon — last year’s winner took it with a 181-kilo marlin. The scale is a five-minute walk from the cruise terminal.
Works on a normal port day, and it is the shortest walk to a festival anywhere on this page.
Festival Gourmet International
Nov 12–22 · 31st edition
Mexico’s longest-running culinary festival, and the format is unusual: around thirty host restaurants each import a guest chef who cooks in that kitchen for the run of the festival — 60-plus visiting chefs and 20-plus wineries across Puerto Vallarta, Riviera Nayarit and Tepic. You book directly with the restaurant. Eleven days means you do not need to hit an exact date.
Lunch service fits a normal call; the gala dinners and the Chefs’ Table need a late departure or a night ashore.
Nonrev anglePVR is one of the easiest interline runs on the Pacific coast and November is shoulder season for rooms. Three nights here buys you dinners the ship-day crowd cannot get to.
Festival Internacional La Nao
November · 19th edition · Philippines as guest nation
Acapulco’s flagship cultural festival commemorates the Nao de China — the Manila galleon that ran between this bay and the Philippines for 250 years. For 2026 the Philippines has been confirmed as guest nation of honour, which is the whole point of the thing. Fifty-plus events across concerts, dance, theatre, film and children’s workshops, all of it free, staged at the Zócalo, the Fuerte de San Diego and the Sinfonía del Mar.
The venues are 400 metres from the ship — but the concerts start around seven in the evening. Needs a late departure.
Nonrev angleRead the note at the top of this section before you plan around Acapulco. Calls are still thin while the port rebuilds, and a fly-in stay may be the only way to make this one work.
December 2026
Fiestas Guadalupanas
Dec 1–12 · Magna Peregrinación Dec 12, 11 a.m.
The biggest and most genuinely local event in the Vallarta year, and almost no visitor plans for it. For twelve straight nights, 350 to 400 separate pilgrimages — organised by neighbourhoods, taxi drivers, hotel staff, fishermen, schools — walk up Calle Juárez to the Parroquia de Guadalupe, one leaving every five minutes from 5 p.m. until past ten, each with its own banner, matachines dancers and banda. On December 12 there are mañanitas at midnight and the Magna Peregrinación at 11 a.m. with up to 20,000 people. It is also the city’s birthday.
The nightly processions need a late departure. December 12 is the exception — that one is late morning, and it is the largest of the twelve.
Nonrev angleIf you only fly one trip off this page, make it this one. PVR is an easy interline run, December rooms are bookable, and twelve consecutive nights means you cannot really miss it.
Gran Maratón Chevron Mazatlán
Dec 4–6 · races Dec 5–6 · 25th edition
Mazatlán’s biggest participatory sports weekend — about 9,000 athletes. Friday is expo and packet pickup; the racing is Saturday (triathlon at 7 a.m., then 5K and 10K) and Sunday (marathon and half at 6 a.m.). The course runs the whole length of the Malecón, straight past the cruise terminal and out to Playa Bruja. The 25th anniversary gets a special medal.
Works on a normal port day, but know that the Malecón closes to traffic on race mornings — walk, do not book a taxi.
Festival Internacional de Cine y Creatividad
Dec 9–13 · 14th edition
The Los Cabos film festival, back after a two-year hiatus with federal culture funding and a new name. Its two pillars are La Baja Inspira, a science and documentary platform, and the Fondo Fílmico Gabriel Figueroa, which funds first features from emerging Mexican directors and hands out its awards during the week. Recent editions have added open-air screenings on the beach. Note that it moved off November — it is a December festival now.
Mostly San José del Cabo, thirty to forty minutes away, and screenings run into the evening. Plan a night ashore.
February 2027 — the one to plan for
Carnaval Internacional de Mazatlán
Feb 4–9, 2027 · theme: Amamos Nuestras Tradiciones
Mazatlán claims the third-largest carnival in the world, and the numbers back it up — 157,000 visitors and 88% hotel occupancy in 2026. Six days of coronation galas at Estadio Teodoro Mariscal, giant papier-mâché monigotes lining Olas Altas for weeks beforehand, the Quema del Mal Humor (a giant effigy of Bad Mood, burned), and then the Combate Naval — a fireworks spectacle over the bay at Olas Altas honouring the city’s 1864 defence against the French corvette La Cordelière. Two float parades run the Malecón. The 2027 dates are confirmed; the day-by-day usually posts around December.
Not a port-day event. The Combate Naval and both parades are after dark, and Carnaval week is one of the few weeks Mazatlán actually sells out.
Nonrev angleThe strongest fly-in on the Pacific side of this page. Olas Altas is a fifteen-minute walk from the port, so a hotel in Centro Histórico puts you inside the whole thing on foot. Book by autumn 2026.
The 2027 Calendar
Further out, the picture changes. Some 2027 dates are locked, some are fixed by the calendar itself, and some won’t be announced until spring. Everything below is labeled so you know which is which — and we hold the sailings while organizers catch up. Pacific-coast entries carry their port code — MZT Mazatlán, PVR Puerto Vallarta, SJD Los Cabos, ACA Acapulco — and sail on Mexican Riviera itineraries, not Caribbean ones.
December 2026
Jamaica Jerk Championship
First edition, at The Cliff in Negril. Judges with James Beard, Michelin and Chopped credentials decide the island’s best jerk chicken. Tastings, demos, and a rum-and-rosé bar program.
Crucian Coconut Festival
St. Croix turns the coconut into a competition — culinary contests, artisans, and cultural demonstrations.
Hamilton Christmas Boat Parade
A flotilla of decorated boats competes in Hamilton Harbour, with entertainment at the Viewing Village. Bermuda’s cruise season is closed by December, so this is a fly-in.
St. Croix Christmas Boat Parade
Christiansted Harbour lights up after dark. Needs an overnight or a land stay.
Sugar Mas (St. Kitts Carnival)
Runs from mid-November into the first week of January. J’ouvert and the Grand Parade fall between Christmas and New Year’s — calypso and soca competitions, pageants, sunset cruises.
Junkanoo
The Bahamas’ signature event, and it starts in the small hours of Boxing Day — costumed groups, goatskin drums and cowbells down Bay Street until dawn. The single hardest event on this calendar to reach by ship, and the most worth flying for.
Maskanoo
Turks and Caicos’ Boxing Day street festival takes over the heart of Grace Bay in Providenciales — masqueraders, junkanoo rush, food and live music.
Crucian Christmas Festival
A full week of parades, food fairs, J’ouvert, pageants and nightly entertainment on St. Croix, running into the new year.
January 2027
New Year’s Day Junkanoo
The second and, for many, better parade. Same Bay Street route, same pre-dawn start, fresh costumes.
Bermuda Restaurant Weeks
Sixteenth year. A month-long run of prix-fixe lunches and dinners across dozens of restaurants — the cheapest month to eat well in Bermuda, and the quietest time to have the island to yourself.
Cayman Cookout
Eighteenth edition at the Ritz-Carlton, hosted by Eric Ripert with José Andrés, Daniel Boulud, Emeril Lagasse and Clare Smyth. Forty-plus experiences across four days. Tickets and packages sell out early.
Fiestas de la Calle San Sebastián
Old San Juan’s biggest street party closes out the holiday season — cabezudos, bomba y plena, artisan stalls and four days of crowds through the blue cobblestones.
Curaçao Carnival opens
Six weeks of build-up begin in January and run to the Gran Marcha in February. Tumba festival, jump-ups and children’s parades along the way.
Humpback season, Banderas Bay
Humpbacks calve in the bay and are legally protected from December 8 to March 23. Licensed three-hour boats leave from Marina Vallarta several times a day — the single easiest thing to do on a Vallarta port day all winter.
Maratón y Medio Maratón Cabo San Lucas
Marathon, half, 10K and 5K starting and finishing at Puerto Paraíso on the marina — effectively at the tender landing. Sold out in 2026. Expect marina road closures on race morning.
February – March 2027
Holetown Festival
Barbados marks the 1627 landing of the island’s first English settlers with a week of street fairs, music and heritage events along the west coast.
Gran Marcha, Curaçao
The grand parade through Willemstad draws up to 65,000 — feathers, sequins, and a fusion of Afro-Caribbean and Latin rhythms from early morning on. Farewell parades close things out February 9.
Aruba Carnival
The island’s biggest event of the year: tumba, steel pan, salsa and marching bands, building to the Grand Parade in Oranjestad the Sunday before Lent.
Trinidad Carnival
The one the rest of the region measures itself against. J’ouvert before dawn Monday, full mas on Tuesday. Book flights and rooms a year out — this is not an exaggeration.
Mas Domnik
Dominica’s carnival, and one of the most traditional in the Caribbean — sensay costumes, lapo kabwit drumming, and far smaller crowds than Trinidad.
Carnaval de Cozumel
One of Mexico’s oldest carnivals, running the week before Lent with nightly parades through San Miguel. Cozumel is a heavily called port, so a matching sailing is likely.
Martinique Carnival
French and African traditions blended into something that stands apart from the anglophone carnivals. Ends with the burning of Vaval on Ash Wednesday.
Montserrat St. Patrick’s Festival
The only place outside Ireland where St. Patrick’s Day is a public holiday — and here it also commemorates a 1768 slave uprising. Ten days of masquerade, freedom run and Irish-African heritage. Small-ship and charter territory.
Carnaval de Mazatlán
The third-largest carnival in the world: coronation galas, the Quema del Mal Humor, the Combate Naval fireworks battle over Olas Altas and two float parades down the Malecón. Full entry above.
Abierto Mexicano de Tenis
The ATP 500 at Arena GNP Seguros in the Diamante zone — the biggest annual event in Guerrero, broadcast to 180 countries. Marquee matches are night sessions that regularly run past midnight, and the arena is 20 km from the port.
Puerto Vallarta by UTMB
UTMB World Series trail racing from the coast up into the Sierra Madre — five distances from a 5K to the 81-kilometre Hikuri with 3,900 metres of climbing.
Spring Jazz Festival
Free beachfront jazz at Cuates y Cuetes on Playa Los Muertos, five bands a day from about four in the afternoon, ending in open jams. Musicians come from Mexico, the US and Canada. No admission — you buy lunch.
Fiesta de San José
San José del Cabo’s patron-saint festival and its biggest week: mañanitas at the mission at 5 a.m., a horseback procession at 8, a Guinness-attempt sashimi fest, the Juegos Florales poetry competition, and headline concerts at the Teatro del Pueblo that close with a burning pyrotechnic castle.
Semana Santa
Mexico’s largest domestic travel week, and the busiest days of the year in all four ports. Beaches at capacity, hotels near 100%, taxis scarce and transfers slow. Good Friday brings Vía Crucis processions. Plan for crowds rather than around them.
Semana Internacional de la Moto
Mexico’s largest motorcycle rally and Mazatlán’s second-biggest event after Carnaval — 13,000-plus riders, a welcome party at Olas Altas, a mass parade down the Malecón and free concerts. The whole waterfront is loud for four days.
Spring 2027
Carnival season moves north into the Virgin Islands and St. Maarten, Bermuda’s cruise season reopens, and the shoulder-season fares are the best of the year.
April 2027
Jamaica Carnival
Road March falls the Sunday after Easter. Kingston is the center of it, with soca fetes running for weeks beforehand.
St. Maarten Carnival
Three weeks of jump-ups on the Dutch side, centered on the Carnival Village in Philipsburg. J’ouvert and the Grand Parade land around Kingdom Day at the end of April.
Peppercorn Ceremony
St. George’s stages the annual payment of one peppercorn in rent to the Bermuda government, in full colonial ceremony — Bermuda Regiment, bearskins, cannon salute. Ninety minutes of pageantry that has run since 1816.
Conch Republic Independence Celebration
Key West’s ten-day celebration of the day it seceded from the United States in 1982. A mock naval battle in the harbour, a bed race, and a great deal of not taking itself seriously.
Fiesta de El Cedral
Cozumel’s oldest tradition, in the island’s inland village — Maya ceremony, bullfights, rodeo, and a fair that runs for five days.
Antigua Sailing Week
One of the great regattas, out of Nelson’s Dockyard and Falmouth Harbour, with a shoreside party scene to match the racing.
St. Thomas Carnival
Weeks of calypso tents, food fairs and a village on the waterfront, closing with the Adults’ Parade and fireworks over Charlotte Amalie harbour.
Dia di Rincon
Bonaire’s oldest village throws the island’s biggest party — folkloric dance, local food, and simadan harvest traditions.
IRONMAN 70.3 Los Cabos
A 1.9 km swim off Palmilla Beach, 90 km on the bike toward the Cerro Colorado hills and a half marathon. Corridor road closures on race day can badly snarl transfers between Cabo San Lucas and San José del Cabo.
Festival Internacional de Cine en Puerto Vallarta
Free public screenings run by the Universidad de Guadalajara across the university campus and the Los Mangos library, awarding the Golden Iguana and a Maguey Prize LGBTQ+ selection.
May – June 2027
Batabano Carnival
Grand Cayman’s carnival, named for the tracks turtles leave in the sand. Costume bands and a street parade through George Town — daytime, and right at the port.
Saint Lucia Jazz & Arts Festival
Stages at Pigeon Island and around the island, mixing international headliners with Caribbean acts. Evening shows, so plan for a stay.
Bermuda Day
The island’s national day and the unofficial start of summer: a parade through Hamilton, the half-marathon derby, fitted dinghy racing, and the first day locals will admit the water is warm enough. Cruise season is open by then.
Aruba Soul Beach Music Festival
Memorial Day weekend, with R&B and comedy headliners and beach parties across the island.
Bermuda Carnival / Heroes Weekend
Bermuda’s own carnival — J’ouvert, a Raft Up on the water, and the Parade of Bands in bright costume. The island’s biggest party after Cup Match.
Dia di San Juan
Bonaire’s harvest tradition: bonfires, the dera gai dance, and songs that predate the island’s tourism by centuries.
Belize Lobster Festivals
Three of them, in sequence: San Pedro, Caye Caulker and Placencia each open the lobster season with their own street festival. Grilled tails, live music, and a good excuse to stay past the ship.
Restaurant Week
Despite the name it runs almost four weeks. Around fifty restaurants across Banderas Bay serve a three-course prix fixe with three choices per course at one of three fixed prices. No pass, no ticket — you book and ask for the menu.
Fiestas de Mayo
Puerto Vallarta’s municipal fair on the Explanada Vallarta, three and a half kilometres from the terminal: rides, palenque concerts, fireworks, food stalls, lucha libre and a queen’s coronation, closing on the city’s May 31 anniversary.
Vallarta Pride
Parade along the Malecón at 4 p.m. followed by a block party on Calle Lázaro Cárdenas, plus a boat flotilla in the bay and a full circuit programme at Mantamar. Puerto Vallarta was named Best LGBTQ+ Destination at the 2025 Magellan Awards.
San José Jazz Weekend
Two evenings of jazz in San José del Cabo’s historic centre, thirty to forty minutes up the corridor.
Día de la Marina
National Navy Day, and both ports take it seriously. Puerto Vallarta’s ceremony is at Muelle 3 — the cruise terminal itself — followed by a flotilla carrying a floral offering out into the bay. Mazatlán’s is at the Obelisco de La Puntilla, a kilometre from the ship.
Summer 2027
Carnival season’s second act, and the busiest stretch on the calendar. Crop Over, Spicemas, Cup Match and Reggae Sumfest all land inside five weeks — this is when the region is at full volume.
July 2027
Reggae Sumfest
Montego Bay, and the biggest reggae and dancehall festival in the world. A week of events building to two all-night main-stage shows at Catherine Hall.
Saint Lucia Carnival
J’ouvert at dawn, then two days of Parade of Bands through Castries. The island’s calendar bends around it.
Junkanoo Summer Festival
Junkanoo in daylight, on consecutive summer Saturdays at Arawak Cay — the easiest way to see the tradition without a 3 a.m. start.
Nevis Culturama
Nevis’ emancipation festival: string band and calypso competitions, food fairs, and a Grand Parade through Charlestown.
Cup Match
Bermuda’s biggest event of the year and a two-day public holiday marking Emancipation Day and Mary Prince Day. Cricket between St. George’s and Somerset, plus Crown & Anchor tables, camping, and the Non-Mariners Raft-Up in Mangrove Bay to close it out. 2027 is an odd year, so the match goes to St. George’s.
Mifel Tennis Open
Mexico’s Pacific-coast ATP 250 on hard court at the Cabo Sports Complex, ten minutes from the marina. Past champions include Kyrgios, Medvedev and Tsitsipas. Deep low season for cruise calls, though.
August 2027
Grand Kadooment (Crop Over)
The finale of a two-month festival marking the end of the sugar cane harvest. Costume bands from the National Stadium to Spring Garden, then the beach. Barbados is a homeport, which makes this one of the more straightforward big carnivals to reach.
Antigua Carnival
Ten days of calypso monarch competitions, panorama and J’ouvert, closing with Last Lap through St. John’s on the first Tuesday of August.
BVI Emancipation Festival
Two weeks of festival village, horse racing at Sea Cows Bay, and the August Monday parade through Road Town.
Anguilla Summer Festival
Street parades, soca and calypso shows, beach parties and traditional boat racing — the island’s national sport — every day and night for a week.
Spicemas
Grenada’s carnival, and the one with the most distinctive traditions in the region: J’ouvert Jab Jab covered head to toe in used motor oil, then Pretty Mas through St. George’s the following day.
Curaçao North Sea Jazz Festival
The Caribbean edition of the Dutch institution — three stages, two nights, and a lineup that regularly mixes jazz, Latin and pop headliners.
Fall 2027
The same shape as fall 2026 — Creole season, the food weeks, and Pirates Week — one year on. Dates below follow each festival’s established pattern; organizers typically post firm dates between March and June.
September 2027
Bonaire Day
The island’s flag day, with folkloric performances, food stalls and island-wide celebration.
Mexican Independence
El Grito on the night of the 15th in every town square, parades on the 16th. Cozumel, Costa Maya and Progreso all mark it.
St. Kitts & Nevis Independence
National Heroes Day on the 16th, Independence on the 19th, with parades and cultural programming through the week in Basseterre.
Belize September Celebrations
A month of parades, live music and ceremonies building to Independence Day, plus the Carnival Road March through Belize City.
Curaçao Pride
Fifteenth edition. Beach parties, sunset sails, and a parade through Willemstad, with warm-up events the week before.
Caribbean Sea Jazz Festival
Two nights in Oranjestad mixing jazz, Latin and Caribbean acts with a visual arts market.
Fiestas Patrias / El Grito
Every port does its own. Mazatlán’s Gran Fiesta Mexicana fills Plazuela República from 6 p.m. with the Grito at 11; Acapulco’s is on the Zócalo, a five-minute walk from the ship; Cabo San Lucas starts at Plaza Amelia Wilkes around six. Civic-military parades the morning of the 16th.
HYROX Acapulco
Fitness racing — eight one-kilometre runs alternating with eight functional stations. Deliberately scheduled into Acapulco’s deadest month as post-hurricane stimulus; 13,000-plus competitors registered in 2026. Expo Mundo Imperial, 30 km from the port.
October 2027
Taste of Bermuda
Fourteenth edition of Hamilton’s food festival, and still the most cruise-friendly festival on this entire calendar thanks to Bermuda’s multi-night calls. October is also Bermuda Art Month, island-wide.
BVI Restaurant Week
Part of the BVI Food Fete series. Curated menus at nearly forty restaurants, with lunch service that fits a port call.
Bahamas Culinary & Arts Festival
Five days of Bahamian cuisine and creative work in Nassau — the most heavily called port in the region, so the odds of a matching sailing are excellent.
Fantasy Fest
Ten days of costuming, culminating in the Duval Street parade on the final Saturday. Runs the last full week of October every year, which puts it over Halloween in 2027.
Hanal Pixán & Día de Muertos
Mérida’s Festival de las Ánimas and the candlelit Paseo de Ánimas, plus official programming in Cancún and the Riviera Maya from October 30. Progreso is 45 minutes from Mérida.
World Creole Music Festival
Thirtieth edition. Three nights at Windsor Park Stadium in Roseau, on the last weekend of October, inside Dominica’s Independence season.
Jounen Kwéyòl
Creole Day falls on the last Sunday of October, so 2027 puts it on Halloween. Villages across St. Lucia become open-air kitchens from breakfast onward — daytime, and unusually cruise-friendly.
Dive & Conservation Festival
Expert-led dives, underwater photography workshops, coral restoration and mangrove planting off Grenada.
Butterfield Bermuda Championship
The PGA TOUR event at Port Royal in Southampton — four days of competition with ocean views from nearly every hole. Daily and weekly grounds passes.
Vallarta Nayarit Gastronómica
Mexico’s largest chef-to-chef congress, at the Sheraton Buganvilias eight minutes from the terminal. Ticketed, daytime, and worth sitting in on.
Los Cabos Billfish Tournament
The season opener for Cabo’s marlin fishery, with a purse north of 750,000 dollars and afternoon dockside weigh-ins at the marina.
Día de San Lucas
Cabo San Lucas’ patron saint day, with the image of San Lucas carried by boat around the whole bay — visible from a ship at anchor.
Bisbee’s Black & Blue
The richest fishing tournament in the world — an 11.5 million dollar purse in 2026 — with the weigh station on the marina, a two-minute walk from the tender landing. Scale opens at 2 p.m.
Día de Muertos on the Pacific
Puerto Vallarta’s Guinness-record catrina skull stands on the Malecón all day; Mazatlán’s callejoneada leaves Plazuela Machado at 8 p.m.; Los Cabos floats illuminated altars through the marina; Acapulco’s procession starts at the maritime terminal.
November 2027
Dominica Independence Day
The peak of Creole heritage season — national dress, traditional food, and celebrations that run either side of the day itself.
Barbados Food & Rum Festival
Chefs, mixologists and distillers across four days on the island that claims to have invented rum. Best done as a turnaround with a couple of pre-cruise nights.
Pirates Week Festival
Eleven days across all three islands, with the George Town landing pageant and float parade the centerpiece. Still the best daylight fit on the calendar for a standard port call.
Cartagena Independence
Colombia’s most exuberant independence celebration — parades, cabildo, music and street parties through the walled city. Relevant to Panama Canal and southern Caribbean itineraries.
Festival de la Gastronomie
Twelve days of French-Caribbean cooking centered on Marigot and Grand Case, with chefs competing around a designated local ingredient.
Garifuna Settlement Day
Belize marks the 1832 arrival of the Garifuna with a reenacted landing by dugout canoe at dawn in Dangriga, then drumming, punta and street celebration all day.
Caribbean Food and Wine Festival
Five days across the luxury resorts of Turks and Caicos, with Michelin- and James Beard–recognized chefs and top wine producers.
Anegada Lobster Festival
Spiny lobster caught that morning, cooked every way the island’s kitchens can manage. Ferry from Tortola; needs a land night.
Los Cabos Tuna Jackpot
A yellowfin tournament that opens with the Green Hair Party, and weighs in at the cruise pier area from 3 p.m.
World Wide Technology Championship
The PGA TOUR’s Mexico stop at El Cardonal — Tiger Woods’ first course design — fifteen minutes from the Cabo marina. Buy grounds passes before you sail.
Torneo Internacional de Pesca Marlin y Atún
One of Mexico’s oldest sportfishing tournaments, with afternoon weigh-ins a five-minute walk from the Vallarta cruise terminal.
Festival Gourmet International
Thirty host restaurants across Puerto Vallarta, Riviera Nayarit and Tepic, each importing a guest chef for the run of the festival. Lunch fits a port call; the galas do not.
Festival Internacional La Nao
Acapulco’s free cultural festival marking the 250-year Manila galleon route, staged at the Zócalo and the Fuerte de San Diego, 500 metres from the terminal. Evening-weighted.
Día de la Revolución
A civic-military parade of fifty-plus contingents — navy, charros on horseback, school bands, children in adelita dresses — steps off at 8 a.m. and marches north along the Malecón past Paseo Claussen.
Ciclotour Mazatlán
An international gran fondo drawing 2,500-plus riders over 70 and 140 kilometre coastal routes, starting and finishing on the Malecón.
The Holidays
The most festival-dense fortnight of the year in the Caribbean — and almost none of it is reachable on a port call. These are fly-in trips, and they’re worth planning a year out.
December 2027
Bermuda’s Christmas season
The Hamilton tree lighting in late November, the National Trust Christmas Walkabout in St. George’s, and the Christmas Boat Parade in Hamilton Harbour. Cruise season is closed — this is a flight and a hotel.
Sugar Mas
St. Kitts’ carnival runs from mid-November to the first week of January, with J’ouvert and the Grand Parade in the days after Christmas.
Junkanoo
Bay Street from the small hours of Boxing Day until dawn. Then again on New Year’s Day.
Maskanoo
Grace Bay’s Boxing Day street festival in Providenciales — junkanoo rush, masqueraders, food and live music.
Crucian Christmas Festival
St. Croix’s carnival: parades, food fairs, J’ouvert, pageants and nightly entertainment into the new year.
Fiestas Patronales de la Inmaculada Concepción
Mazatlán’s patron-saint novena at the twin-spired cathedral: nine nights of pilgrim processions from Parque Zaragoza, mañanitas with mariachi at 11 p.m. on the 7th, and a pontifical mass and fireworks on the 8th.
Fiestas Guadalupanas
Three hundred and fifty separate pilgrimages over twelve nights, one leaving every five minutes from 5 p.m. The Magna Peregrinación on December 12 is at 11 a.m. and draws 20,000 — the one piece that fits a port day.
Gran Maratón Chevron Mazatlán
The 26th edition. Marathon, half, triathlon, 5K and 10K over three days, on a course that runs the length of the Malecón past the cruise terminal.
Cabo San Lucas Nautical Christmas Parade
Yachts, sportfishers and pangas strung with Christmas lights parade through the marina after dark — at the tender landing, but well after most ships have sailed.
Festival Internacional de Cine y Creatividad
The Los Cabos film festival, now firmly a December event, centred on San José del Cabo with a second screening venue on the Cabo San Lucas marina.
Gala de Pirotecnia y Show de Drones
At 11:50 p.m. the whole arc of Bahía de Santa Lucía lights up for ten minutes of synchronised fireworks, drones and lasers. The bay’s amphitheatre shape makes the malecón by the terminal a genuinely good vantage point.
Tell us the festival. We’ll find the ship.
Some of these need an overnight, a late departure, or a night on land at either end — and that’s the part that’s impossible to see on a booking site. Tell us which one you want to be at, and we’ll come back with the sailings that actually put you there, at interline rates, with no booking fees.