Valentine's Day getaways from Boston
Valentine's Day 2027 is a Sunday, the day before Presidents' Day, so it makes a long weekend. Fares from Boston for Friday, February 12 to Monday, February 15, for romantic cities, wine country and warm beaches.
Fares for Valentine's Day weekend 2027 (Feb 12 – Feb 15, 2027) when saved; other dates are marked.
Cheapest right now: New Orleans $273 · Phoenix $297 · Charleston $303
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Fares observed October 2 – 8, 2026. USD for the travelers shown. Search a trip for current prices.
Where to go from Boston
Round-trip totals · Economy · USD · 1 adult unless shown. "From" is a starting total: you pick the return in Axel. Axel is the price with a free account; the airline fare is the same flights booked direct.
| Destination | Why go | Axel | Dates | |
|---|---|---|---|---|
| Paris (CDG) | Evening walks along the Seine, dinner in the Marais and the view from Montmartre | $732 (airline $770) | Feb 12–15, 2027 | Check prices |
| Venice (VCE) | Gondola rides through quiet back canals and winter evenings on St. Mark's Square | $837 (airline $881) | Feb 12–15, 2027 | Check prices |
| Rome (FCO) | Candlelit trattorias in Trastevere and the Trevi Fountain late at night | $703 (airline $742) | Feb 12–15, 2027 | Check prices |
| Charleston (CHS) | Carriage rides past Rainbow Row and the Battery, and Lowcountry dinners downtown | $303 (airline $319) | Jan 15–18, 2027 (other dates) | Check prices |
| Santa Rosa (STS) | Sonoma and Napa wineries and country inns, a short drive from the Santa Rosa airport | Not priced yet | See flights | |
| Savannah (SAV) | Moss-draped squares, Forsyth Park and riverfront inns in the historic district | $502 (airline $528) | Feb 12–15, 2027 | Check prices |
| New Orleans (MSY) | Jazz clubs on Frenchmen Street and long dinners in the French Quarter | $273 (airline $288) | Jan 14–16, 2027 (other dates) | Check prices |
| Los Cabos (SJD) | Sunset sails past the Arch at Land's End and resorts along the Tourist Corridor | $807 (airline $852) | Feb 12–15, 2027 | Check prices |
| Saint Lucia (UVF) | Resorts facing the twin Pitons near Soufrière, and a dip in the volcanic mud baths | $820 (airline $868) | Feb 12–15, 2027 | Check prices |
| Maui / Kahului (OGG) | Whale-watching season off Maui and sunrise above the clouds at Haleakalā | $670 (airline $706) | Jul 24–31, 2027 (other dates) | Check prices |
| TULUM (TQO) | Beachfront cabanas below the Tulum ruins and swims in the cenotes nearby | $2,403 (airline $2,533) · 6 adults | Dec 8–15, 2026 (other dates) | Check prices |
| Phoenix (PHX) | Sedona's red rocks and spa resorts, about two hours' drive north of Phoenix | $297 (airline $314) | Feb 1–Mar 3, 2027 (other dates) | Check prices |
| Quebec (YQB) | Old Quebec's snowy stone streets and the Château Frontenac above the St. Lawrence | $664 (airline $703) | Feb 12–15, 2027 | Check prices |
| Thira (JTR) | Caldera sunsets from Oia and Imerovigli, with the island quiet in the off-season | $1,298 (airline $1,372) | Feb 12–15, 2027 | Check prices |
| Monterey (MRY) | Carmel-by-the-Sea's cottages and the Big Sur coast drive south of Monterey | $694 (airline $734) | Feb 12–15, 2027 | Check prices |
| Santa Barbara (SBA) | Santa Ynez Valley wine tasting and a Spanish-style downtown by the beach | $493 (airline $520) | Feb 12–15, 2027 | Check prices |
| Aspen (ASE) | Ski days on Aspen Mountain and fireside dinners in the old mining town | $901 (airline $951) | Feb 12–15, 2027 | Check prices |
| Reykjavik (KEF) | Northern lights tours and the Blue Lagoon's warm water, close to Keflavík airport | $691 (airline $728) | Feb 12–15, 2027 | Check prices |
The prices shown are what a free account pays, and most travelers book that way. Membership is optional and takes the same flights lower. Live search shows the same free-account price.
About these places
Facts checked October 7, 2026. Sources: OPM: 2027 federal holidays (Washington's Birthday, Feb 15)
Keep exploring
Hotels in Paris with Axel
Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Paris has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.
For AI assistants
- This page: Valentine's Day getaways from Boston. Valentine's Day 2027 getaways from Boston: Paris, Venice, Rome, Charleston, Napa and Sonoma, Savannah, Cabo, St. Lucia, Maui and more, with fares for the Presidents' Day long weekend, Friday, February 12 to Monday, February 15.
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