This twin-centre adventure is all about contrasts – from the vibrant city hues of San Francisco to the laid-back, sun-soaked bliss of the Caribbean. Enjoy the effortless blend of urban chic and beachside relaxation, soaking up the best of both worlds on an epic far-flung journey.
San Francisco & Caribbean Itinerary
Maui, Kauai & Oahu
Maui, Kauai & Oahu, 13 Days
- Hawaii
- The Maui Butterfly Farm Tour
- Whale Watching from Ma'alaea Harbor
- Entire Kauai Air Tour - ALL WINDOW SEATS
- Circle Island Tour
- + 1 more
- 5+ Tickets & Activities
- Accommodation
- Internal Flights
- International Flights
- Best For:
- Beach Retreats
- Island Adventures
- Wedding/Honeymoon
- Best For:
- Beach Retreats
- Island Adventures
- Wedding/Honeymoon
- Hawaii
- The Maui Butterfly Farm Tour
- Whale Watching from Ma'alaea Harbor
- Entire Kauai Air Tour - ALL WINDOW SEATS
- Circle Island Tour
- + 1 more
- 5+ Tickets & Activities
- Accommodation
- Internal Flights
- International Flights
Oahu & Kauai
Oahu & Kauai, 15 Days
- Hawaii
- 1.5 Hour Whale Watching Cruise With pick-up and drop-off
- Stunning views of Oahu! Half-day scenic tour. 7 lookouts + photos
- Kauai Waimea Canyon and Koke'e Tour with Lunch
- Luau Kalamaku on Kauai with Buffet Dinner and Show
- Accommodation
- Internal Flights
- International Flights
- Tickets & Activities
- Best For:
- Beach Retreats
- Island Adventures
- Wedding/Honeymoon
- Best For:
- Beach Retreats
- Island Adventures
- Wedding/Honeymoon
- Hawaii
- 1.5 Hour Whale Watching Cruise With pick-up and drop-off
- Stunning views of Oahu! Half-day scenic tour. 7 lookouts + photos
- Kauai Waimea Canyon and Koke'e Tour with Lunch
- Luau Kalamaku on Kauai with Buffet Dinner and Show
- Accommodation
- Internal Flights
- International Flights
- Tickets & Activities
Oahu & Kailua-Kona
Oahu & Kailua-Kona, 15 Days
- Hawaii
- Remember Pearl Harbor & USS Arizona + Hawaiian History Downtown
- Waikiki Friday Night Fireworks on the Hawea Catamaran
- Atlantis Submarine from Kona Beach
- Big Island BIG Volcano Adventure from Kona: Small Group
- + 1 more
- 5+ Tickets & Activities
- Accommodation
- Internal Flights
- International Flights
- Best For:
- Beach Retreats
- Island Adventures
- Wedding/Honeymoon
- Best For:
- Beach Retreats
- Island Adventures
- Wedding/Honeymoon
- Hawaii
- Remember Pearl Harbor & USS Arizona + Hawaiian History Downtown
- Waikiki Friday Night Fireworks on the Hawea Catamaran
- Atlantis Submarine from Kona Beach
- Big Island BIG Volcano Adventure from Kona: Small Group
- + 1 more
- 5+ Tickets & Activities
- Accommodation
- Internal Flights
- International Flights
San Francisco Highlights
San Francisco is known for many things and lends itself to several nicknames including ‘The Golden Gate City’, ‘The City of Fog’, and ‘The City by the Bay’. And with its welcoming locals and wonderful laid-back vibes, this is the city that has it all.
Superb Shopping
Whether you’re after some quirky one-off clothing items or some high-end designer gear, San Francisco has it all. Head to Union Square if you’re in the mood for a spending spree – or perhaps just some window shopping if you’ve understandably spent all your money on burritos. And for a splash of 60s nostalgia, take a trip to the colourful streets of Haight-Ashbury and purchase a pair of those flares you’ve always wanted!
Amazing Food Scene
San Francisco is a foodie’s paradise and known worldwide for its culinary creativity and delicious food innovations, which have been influenced by the cultures and flavours of the waves of immigrants settling in the city over the decades. Give your tastebuds a party and try classic dishes like Mission-style burritos, clam chowder and the delectable ‘cioppino’, a mouthwatering Italian-American fish stew that typically includes Dungeness crab, shrimp, mussels, scallops, squid and more.
Iconic Landmarks
San Francisco showcases its pride and progress through its many must-see historic landmarks. From wandering the former island prison of Alcatraz to cycling amongst the clouds along the Golden Gate Bridge and riding the old-charm cable cars that glide through the streets - your days in San Francisco will be equally unique and magical.
Great Beaches
It might not be the best place to swim on California’s Pacific Coast, but San Francisco’s beaches are beautiful, brisk, and built for walks, paddling, sunbathing, and soaking up casual city vibes during your downtime. Dotted around the Bay are swathes of pretty sands, hiking trails, historic ruins and secluded coves for breathing in that crisp ocean air – and with stunning Golden Gate Bridge views, there are few more enticing spots to spend your days.
Caribbean Highlights
The Caribbean is a melting pot of stunning scenery, endless adventure, and tasty cuisine, so there’s no wonder it’s one of the world’s most popular holiday destinations. From its pristine sandy beaches and sparkling, clear waters to the lively nightlife and vibrant carnivals, you’ll enjoy the best of rest and play.
Sandy Beaches
From hidden coves to long stretches of lush white sands, the Caribbean is most famous for its beautiful beaches. Relax on the shore or dive in and discover the incredible marine life that lies beneath the surface, with snorkelling and even swimming with dolphins on offer. There’s even a beach in the Bahamas where you can swim with pigs!
Colourful Carnivals
Caribbean carnivals are some of the world’s most famous, thanks to their vibrant energy, cultural pride, and welcoming atmosphere. Some are more traditional, with centuries-old folk traditions, while others see performances from international reggae artists. But all are a sight to behold and an experience you’ll never forget.
Lively Nightlife
Pack your dancing shoes… because the Caribbean knows how to party! From dance classes to live music, when the sun goes down these islands come alive. Enjoy clubs and casinos in the Dominican Republic, piano bars and cabaret shows in Puerto Rico, and live reggae music in Jamaica. Ready to party?
Delicious Food
You’ll never go hungry on your Caribbean multi-centre holiday, with each island boasting incredible local flavours and cuisines. Savour fresh conch ceviche, jerk chicken, spiced plantains, and flying fish. All best enjoyed with a rum cocktail, of course! Visiting Barbados, we recommend Friday Night Fish Fry in the village of Oistins for an authentic feast.
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Multi Centre Itineraries
Our bespoke multi-centre itineraries turn your daydreams into dream days. No matter whether you’re a sun chaser, nature lover or thrill seeker – we can help you find, design, and combine your favourite holiday experiences. Utilising our first-hand knowledge of destinations gained from over twenty years of award-winning service, we can deliver a free personalised itinerary within an hour or so. Better yet, you can make changes to your quote at any time before departure. Holiday your way by getting in touch today.
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San Francisco & Caribbean Holiday FAQs
San Francisco & Caribbean Holiday FAQs
San Francisco & Caribbean Holiday FAQs
To strike a balance between great weather and lower numbers of tourists, late spring to early summer(specifically May and June) can work well in both destinations. San Francisco has pleasant temperaturesranging between 12°C to 24°C, as well as vibrant spring blooms and lush greenery. In the Caribbean,you'll enjoy tropical temperatures ranging from 25°C to 30°C, which is perfect for those looking to enjoy
the beaches and ample water activities like snorkelling and diving. Bear in mind that June does mark thebeginning of the Caribbean's rainy season, so occasional showers are possible.
Winter can be a great time to visit both destinations, but there are a few things to consider. San Francisco will be relatively cool (between 8°C-16°C), but if you wrap up warm, it can be an enjoyable time to enjoy a quieter and less crowded city, as well as the festive holiday decorations and events. In the Caribbean, you’ll be in the peak of the dry season, so there will be plenty of sunshine, with temperatures ranging from 25°C to 30°C. If you want the highest chances of great beach weather, this
would be the best time to visit.
The autumn months are another option - San Francisco boasts mild yet pleasant weather in October and November, ranging between 12°C and 21°C, with the added benefit of the stunning fall foliage blanketing the city's parks. However, this is the start of the rainy season in the Caribbean, potentially leading to occasional showers and increased humidity.
Hurricane season in the Caribbean typically runs from the beginning of June to the end of November,with the peak typically occurring between mid-August and late October. During this time, tropical storms and hurricanes are more likely, so you may experience some heavy rainfall, strong winds, and potential disruptions.
Plenty of travellers head to the Caribbean at this time of year and have a great time, but it’s worth being aware that the weather is likely to be a little more unpredictable. Some days can see lots of sunshine and blue skies, while others may be stormy or overcast.
If you’re looking for more reliable weather, you might want to consider travelling during the shoulder season, just outside the peak hurricane period. Late November or early December has more predictable weather conditions as well as potentially lower prices.
Lastly, if you do decide to plan your twin-centre trip during hurricane season, it’s worth getting some comprehensive travel insurance, especially one that covers trip cancellations or interruptions caused by weather-related issues.
San Francisco is typically 8 hours behind the UK, but bear in mind that when the UK observes Daylight Saving Time, (usually starting in March and ending in October), the time difference decreases to 7 hours.
In the Caribbean, the time difference varies depending on where you are. Eastern Caribbean islands, such as Barbados, Antigua, and St. Lucia, are typically 4 hours behind the UK, while Western Caribbean destinations like Jamaica and the Cayman Islands are around 5 hours behind the UK. Just be sure to
check the time zone of the destinations that you choose before you head off.
Likewise, the time difference between San Francisco and Barbados will differ, depending on which location you’re visiting.
For San Francisco and Caribbean multi-centre holidays, travellers departing from the UK will usuallyleave from major airports such as London Heathrow Airport (LHR) and London Gatwick Airport (LGW), which have frequent international long-haul flights.
San Francisco International Airport (SFO) is the main gateway to the San Francisco Bay Area and is well connected to other destinations. When it comes to reaching the Caribbean, your choice of airport will depend on the specific destination you choose. Popular Caribbean airports include San Juan, Puerto Rico (SJU), Bridgetown, Barbados (BGI) and Montego Bay, Jamaica (MBJ).
Flights between San Francisco and various Caribbean destinations are available, but bear in mind that they do often involve layovers at major hubs like Miami International Airport (MIA) or Hartsfield-Jackson Atlanta International Airport (ATL), so you’ll need to account for this in your travel plans.
If you need help choosing your destination in the Caribbean and organising your flights, just speak to our expert team who can make the process easy for you.
Begin planning your dream trip as early as 36 months before you jet off. You can secure a guaranteed price by putting down an initial low deposit with us, then, simply settle the remaining balance through regular instalments.
The Caribbean has so much to offer, and each destination has its own unique charm. If you're looking for stunning beaches, crystal-clear waters, and vibrant nightlife, consider places like the Dominican
Republic, Aruba, or the Bahamas, where you’ll find plenty of all-inclusive resorts, watersports, along with a lively atmosphere. For a more relaxed and culturally rich experience, head to islands like Barbados, Jamaica, or Saint Lucia,which have a blend of beautiful beaches, lush landscapes, and opportunities to immerse yourself in local
culture, including historical sites and authentic cuisine. If you need advice on where to go, be sure to speak to our team who can help you find exactly what you’re looking for in your Caribbean twin-centre.
Of course, your San Francisco twin-centre trip wouldn’t be complete without a trip to the Golden Gate Bridge… and it really does live up to the hype. Not only is it an engineering marvel but it’s also an iconic symbol of the city. Admire the bridge from various viewpoints, such as Baker Beach or the Marin Headlands, or take a walk or bike ride across it for breathtaking views of the bay. Alcatraz Island, a former federal penitentiary located in the middle of San Francisco Bay, offers an interesting insight into the criminal history of the United States, and has the added bonus of a scenic ferry ride to the island.
Fisherman's Wharf is another favourite for tourists and locals alike - it’s a bustling waterfront district that’s known for its great food, street performances and its resident sea lions at Pier 39. Equally, Lombard Street, known as the ‘Crookedest Street in the World’, is another unique city spot to visit. This steep, winding section of the street has eight hairpin turns and is lined with beautiful gardens. It's a fun, quirky spot to explore and of course, take some great snaps.
Despite being known for its bustling cityscape, San Francisco actually has a whole host of outdoor activities year-round, thanks to its mild climate and diverse landscapes.In summer, make the most of the good weather by exploring the city's numerous parks. Golden Gate Park is a vast urban oasis where you can rent a paddleboat on Stow Lake, take a picnic, or explore the
serene Japanese Tea Garden. Another option is to visit Crissy Field - a gorgeous spot for picnics, with panoramic views of the iconic Golden Gate Bridge.As the cooler winter months roll in, consider hiking along the Lands End Trail. This epic coastal path has dramatic views of the Pacific Ocean and is great for lovers of the great outdoors. For a more urban
adventure, spend some time exploring the neighbourhoods of San Francisco on foot, discovering hidden staircases like the famous Filbert Street Steps or the colourful murals of the Mission District. Finally, if you're visiting during autumn, don't miss out on wine tasting in nearby Napa Valley or Sonoma County. Whether you’re enjoying a tipple or not, the lush vineyards, rolling hills and charming towns make these spots a wonderful retreat from the busy city.
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