* This is the only date I found, and there only appear to be a few seats at this price.…
SFO > Kralendijk, Caribbean Netherlands: Flight & 8 nights: $990 (Aug-Oct)
* This is a “fare dump” with a few alternate dates available. San Francisco to Kralendijk, Caribbean Netherlands: 8 night…
SJC > Piarco, Trinidad and Tobago: Flight & 8 nights: $877 (Oct-Dec)
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
SFO > Kingston, Jamaica: Flight & 8 nights: $662 (Sep-Nov)
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
SFO > St. John’s, Antigua and Barbuda: $385 round-trip (Aug-Oct) [SOLD OUT]
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
SFO > Grenada, Grenada: Flight & 4 nights: $729 (May-Jul) [SOLD OUT]
* This is a “fare dump” with a few alternate dates available. San Francisco to Grenada, Grenada: 4 night trip.…
SJC > Aguadilla, Puerto Rico: Flight & 10 nights: $927 (Oct-Dec)
* This is a “fare dump” with a few alternate dates available. San Jose to Aguadilla, Puerto Rico: 10 night…
SFO > George Town, Cayman Islands: Flight & 8 nights: $805 (Nov-Jan) [SOLD OUT]
* This is a “fare dump” with a few alternate dates available. San Francisco to George Town, Cayman Islands: 8…
OAK > San Juan, Puerto Rico: Flight & 12 nights: $843 (Aug-Oct)
* This is a “fare dump” with a few alternate dates available. Oakland to San Juan, Puerto Rico: 12 night…
SFO > Piarco, Trinidad and Tobago: Flight & 8 nights: $697 (Oct-Dec)
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
SFO > Grenada, Grenada: $393 round-trip (May-Jul) [SOLD OUT]
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
SFO > Kingston, Jamaica: Flight & 5 nights: $558 (Oct-Dec)
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
SFO > Aguadilla, Puerto Rico: Flight & 6 nights: $605 (Apr-Jun) [SOLD OUT]
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
SFO > Piarco, Trinidad and Tobago: $434 round-trip (Apr-Jun) [SOLD OUT]
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
SFO > St. John’s, Antigua and Barbuda: $385 round-trip Aug-Oct [SOLD OUT]
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
Summer Break Trips: SJC > George Town, Cayman Islands: $381 round-trip [SOLD OUT]
* This is a “fare dump” with a few alternate dates available. San Jose to George Town, Cayman Islands: 8…
SJC > Montego Bay, Jamaica: Flight & 4 nights: $612
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
Summer Break Trips: OAK > Bridgetown, Barbados: $764 including flight & 7 nights lodging [SOLD OUT]
* This is a “fare dump” with a few alternate dates available. Oakland to Bridgetown, Barbados: 7 night trip. Flight…
SFO > Grenada, Grenada: $383 round-trip
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
Fall Break Trip: SFO > St. John’s, Antigua and Barbuda: $841 including flight & 7 nights lodging
* This is a “fare dump” with a few alternate dates available. San Francisco to St. John’s, Antigua and Barbuda:…
SJC > George Town, Cayman Islands: $662 including flight & 3 nights lodging [SOLD OUT]
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
OAK > Hamilton, Bermuda: $994 including flight & 4 nights lodging [SOLD OUT]
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
OAK > Oranjestad, Aruba: $705 including flight & 8 nights lodging
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
Summer Trips: SFO > Aguadilla, Puerto Rico: $918 including flight & 7 nights lodging [SOLD OUT]
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
SJC > San Juan, Puerto Rico: $314 round-trip [SOLD OUT]
San Jose to San Juan, Puerto Rico: 11 night trip. Flight Options Flight Alone: $314. Dates I found this fare:…
SFO > Piarco, Trinidad and Tobago: $720 including flight & 9 nights lodging [SOLD OUT]
San Francisco to Piarco, Trinidad and Tobago: 9 night trip. Flight Options Flight Alone: $404. Dates I found this fare:…
SFO > Saint Thomas Island, U.S. Virgin Islands: $721 including flight & 8 nights lodging
San Francisco to Saint Thomas Island, U.S. Virgin Islands: 8 night trip. Flight Options Flight Alone: $342. Dates I found…
SJC > George Town, Cayman Islands: $834 including flight & 7 nights lodging
San Jose to George Town, Cayman Islands: 7 night trip. Flight Options Flight Alone: $371. Dates I found this fare:…
SJC > Grenada, Grenada: $794 including flight & 8 nights lodging
San Jose to Grenada, Grenada: 8 night trip. Flight Options Flight Alone: $386. Dates I found this fare: Wed, Sep…
SJC > San Juan, Puerto Rico: $621 including flight & 8 nights lodging [SOLD OUT]
San Jose to San Juan, Puerto Rico: 8 night trip. Flight Options Flight Alone: $314. Dates I found this fare:…
SJC > Kingston, Jamaica: $420 round-trip [SOLD OUT]
San Jose to Kingston, Jamaica: 11 night trip. Flight Options Flight Alone: $420. Dates I found this fare: Sat, Apr…
Spring Break Trip: SFO > San Juan, Puerto Rico: $365 round-trip [SOLD OUT]
San Francisco to San Juan, Puerto Rico: 8 night trip. Flight Options Flight Alone: $365. Dates I found this fare:…
SFO > Piarco, Trinidad and Tobago: $364 round-trip [SOLD OUT]
San Francisco to Piarco, Trinidad and Tobago: 14 night trip. Flight Options Flight Alone: $388. Dates I found this fare:…
SFO > Grenada, Grenada: $363 round-trip
San Francisco to Grenada, Grenada: 8 night trip. Flight Options Flight Alone: $363. Dates I found this fare: Tue, Sep…
SJC > Kingston, Jamaica: $460 round-trip
San Jose to Kingston, Jamaica: 7 night trip. Flight Options Flight Alone: $460. Dates I found this fare: Tue, Nov…
SJC > George Town, Cayman Islands: $371 round-trip [SOLD OUT]
San Jose to George Town, Cayman Islands: 12 night trip. Flight Options Flight Alone: $371. Dates I found this fare:…
SFO > Ponce, Puerto Rico: $335 round-trip [SOLD OUT]
San Francisco to Ponce, Puerto Rico: 6 night trip. Flight Options Flight Alone: $335. Dates I found this fare: Tue,…
SFO > Piarco, Trinidad and Tobago: $712 including flight & 6 nights lodging
San Francisco to Piarco, Trinidad and Tobago: 6 night trip. Flight Options Flight Alone: $398. Dates I found this fare:…
SFO > Ponce, Puerto Rico: $684 including flight & 7 nights lodging [SOLD OUT]
San Francisco to Ponce, Puerto Rico: 7 night trip. Flight Options Flight Alone: $326. Dates I found this fare: Tue,…
SJC > George Town, Cayman Islands: $368 round-trip [SOLD OUT]
San Jose to George Town, Cayman Islands: 14 night trip. Flight Options Flight Alone: $368. Dates I found this fare:…